BE CREATIVE

11 Future Pen
51TourdeH
10 Grungevet
50Patience,
09 Tragic Sans
49TheGame
08 Spray Paint
48CheckMe
07
Gridlocked
47
SeeingWhat
06
Mr.Blue
46
PosterbyNum
05
I’m Drawing a Blan
45
RobotArmyMail-
04
One Line Logo
44
RecordStorePuppetT
03
Time Machine
43
PrintedandSewn
02
Easy asABC
42
Reduce,Reuse,Redecorate
01
Hello,MyNam
eIs
41
JustMyPrototype
80
Well,inMyBook…
40
CranePromotion
79
WhatDoIKnow?
39
OutdoorWedding
78
BendingGeography
38
IHeartPlaidCandles
77
CanYouHearMeNow?
37
TrompeL’OhWow
76
SniffTest
36
NeverTearUsApart
75TouchScreenofDeafRock
35LickItGood
74BlindedbytheLight
34TypeFace
73FreeTibetBlog
33Let’sTakeaNap
72Paper,Plastic,Glass,Vapor
32SellMeaBridge
71ThisIsforYourHealth
31GoingtoSeed
70Future-Casting
30FlappingintheWind
69OutofGamut
29I’veGotaGoldenTicket
68UrbanDiapers
28Ten-SecondFilmFestival
67
What’sinStore?
27
CreatureFeature
66
I’dBuyThatForaDollar
26
ImaginaryFilm
65
ListenUp,WriteItOff
25
TotallyCereal
64
Let’sDish
24
HeShaves,SheShaves
63
ReadyWhenYouAre
23
BookReport
62
IThink,ThereforeIShop
22
OppositesAttract
61
TechnoYoga
21
Dead Philosphers Rock
60
E.V.O.O.toGo
20
Storybook Ending
59
Veni,Vidi,Vino
19
It Sounds Better on Viny
58
MoreIsLess
18
I’m Feeling Really,R
57
Biodegradable
17
Free Association
56
iPhoneAmeri
16
Hey,You Made
55CD,LP,EP,D
15 Sixty-Second
54ThinkingO
14 10 x 10
53ExcuseM
13 Three in O
52WackyVe
12 Strange C
FOUNDATION
EXECUTIONMATERIALITY
INSTRUCTIONOBSERVATION
INNOVATIO
N
INTERPRETATION
WORKSHOP
creative
teacher’s guide
DAVID SHERWIN &
MARY PAYNTER SHERWIN

CONTENTS
build upon this work! ............... 3
INTRODUCTION: what DO
design students need? .............. 5
Using creative workshop
in a classroom setting ............ 13
Teaching the challenges:
Foundation ............................... 21
Execution .................................. 30
Materiality............................... 42
Instruction ............................... 49
Observation ............................... 52
innovation ................................ 55
interpretation......................... 62
about the authors .................... 71
GET THE BOOK ............................. 72
layout based on a design by Grace Ring, HOW Design Press

3Build Upon this Work!
This e-book is an accompaniment to Creative
Workshop: 80 Challenges to Sharpen Your Design Skills,
published in November 2010 by HOW Design Press.
The print book contains 80 creative challenges that
will help any designer reach a breadth of stronger
design solutions, in various media, within any set time
period. Exercises range from creating a typeface in
an hour, to designing a paper robot in an afternoon,
to designing web pages and other interactive
experiences. Each exercise includes compelling
visual solutions from other designers and background
stories to help designers increase their capacity
to innovate.
This e-book was written to work in concert with
Creative Workshop. It is a work in progress, intended
for teachers of design & creative thinking, but it may
also be helpful for designers and creative managers.
If you have any updates or improvements to the ideas
contained here—or if we made a mistake—we’d love
to incorporate your input and promote your thinking
to the greater design community. And if you’ve
created a challenge and tried it out with others, we’d
love to consider it for a future Creative Workshop book.
Write us at david@changeorderblog.com.
Build Upon this Work!
Creative Commons License Info
The material contained in this eBook is
©2011 David and Mary Sherwin. It is offered
under a Creative Commons Attribution-
NonCommercial-ShareAlike 3.0 Unported
License for use internationally. The full details
of the license can be found here: http://
creativecommons.org/licenses/by-nc-sa/3.0/
To quickly summarize the license:
You are free to…
Share: To copy, distribute, and transmit
the work
Remix: To adapt the work
Under the following conditions…
Attribution: You must attribute the work in the
manner specified by the author or licensor
(but not in any way that suggests that they
endorse you or your use of the work). Please
provide attribution back to the authors as
follows: “From Creative Workshop: A Teacher’s
Guide by David and Mary Sherwin, http://
www.CreativeWorkshopTheBook.com”
Noncommercial: You may not use this
work for commercial purposes. If you’d
like to, you’ll need to contact us at david@
changeorderblog.com for permission.
Share Alike: If you alter, transform, or build
upon this work, you may distribute the
resulting work only under the same or similar
license to this one.
To order copies or have
Creative Workshop supplied
to your university bookstore,
call 1-800-289-0963. You can
also buy copies online at
http://bit.ly/CWTheBook

5Introduction: What Do Design Students Need?
Introduction: What Do
Design Students Need?
When considering the skills that today’s designers
need to be successful in today’s job market, we often
focus on job requirements, which are listed in tidy
bullet points on recruitment requests:
• Experience working in Adobe Creative Suite
version du jour
• Knows Flash, Dreamweaver, HTML5/CSS3,
Javascript, and more esoteric flavors of script-
ing languages (and theoretically knows how
to create an interactive experience)
• 3-5+ years of “related” design experience
Creative Workshop, both the book and the class,
was inspired by a survey we conducted in 2008 with
designers and creative directors with whom David
had worked in the past, as well as creative leaders in
the American design community whose paths we had
crossed. Specifically, we wanted to know what today’s
creative directors and designers sought in students
emerging from design school—what skills students
weren’t learning that could be infused back into their
course curriculum.
The questions in the survey were open-ended, such
as: When working with or managing other designers,
what skills do you most actively cultivate? We also
asked for anecdotes regarding how they overcame
a difficult design challenge, thereby stretching their
talent and growing a practical design skill.
“If you want to study something, it’s better
not to know what the answer is.”
—Shunryu Suzuki, “Find Out for Yourself”
The answers we received back were surprisingly
consistent, and distressingly integral to the success of
any designer working today. The majority of them fell
into the following four categories:
1. Big-Picture Ideation Planning
the Execution
Strong conceptual thinking is the root of any well-
crafted design execution—and the skill of creating
concepts through focused brainstorming is often
learned through mentorship or brute repetition on
the job. Additionally, most designers discover that an
idea is meaningless if it isn’t delivered on time and
executed well. So, effective ideation requires strict
time management and structure. Otherwise, we’re just
creating napkin sketches.
“My experience working with young designers is
that they are excited and interested in present-
ing a technique. Often there is little thought
behind it other than it looks cool. I prefer to
have the cool as the topping for a carefully
planned design.”
—Wendy Quesinberry, creative director and
principal of Quesinberry Associates
“Idea generation has become increasingly
important to me. That means no computer!
Just sketches and notes and scribbles and
mood boards. These all help keep ideas from

6 Introduction: What Do Design Students Need?
becoming too precious, and encourages
exploration of ideas. There’s something about
sitting down and finessing an idea on the
computer that can make it harder to let go of
an idea that’s just not working. Even when you
know it’s not!”
—Michel Vrana, book designer
2. Collaboration Communication
Even for solo designers, collaboration is the lifeblood
of any professional creative endeavor—with your
clients, with fellow designers, and with vendors that
support fulfilling your work. But to collaborate well, you
have to squelch your ego, speak your mind, bring in
partners from other disciplines beyond design, and
know the business problems you’re trying to solve.
“Sharing your thoughts isn’t a risk, it’s an asset.
Creative kinships with people from a wide
variety of skill sets serve to expand your views
of what’s possible. Whether designers, pro-
grammers, motion graphics artists, illustrators,
copywriters, or photographers, the result will
be a mix of cultural, economic, and creative
energy that can offer true originality while test-
ing your assumptions of how things are done…
I love to watch the sparks fly when creative
individuals meet, match wits, and inspire each
other. I also thoroughly enjoy participating in
these exchanges myself. These relationships
require honesty and a lack of ego combined
with a willingness to share and help each
other… It just doesn’t feel like work when you’re
doing it right.”
—Duane King, principal of BBDK and creator of
the design blog Thinking for a Living
“Trust is by far the most important thing. It’s
fragile and takes time to build, but only with
trust can there be collaboration. And only with
collaboration will people help each other to
make the best ideas in the group surface.”
—Scott Berkun, author of The Myths of
Innovation and Making Things Happen
3. Sketching Ideas
Out of all the tools available to a working designer, the
humble pencil is often the quickest method to access
one’s intuition. It’s often not listed as a requirement
in a job listing, but creative directors and designers
looking to hire you will listen not only to what comes
out of your mouth, but also the quality of thought
that you render through design sketching. Only after
considering a sketch can the design execution take
place, whether via Photoshop, code, or tempera paint.
“The ability to sketch an idea before executing
it is fundamental to any work environment and
to any economy. Sketching affords designers
the ability to suggest without committing to
marks or grids or any element of design. By
quickly sketching out ideas, the poor ones
fade quickly from priority without wasting pre-
cious time to execute them. The discerning
designer uses sketching to rule out as well as
rule in dominant ideas about the formal ele-
ments of any communication. It is the domain
of the sketch where the concept is nailed
down as well, instead of massaging more aes-
thetic details, which don’t matter one iota if
the big idea doesn’t work.”
—Carrie Byrne, Creative Director, Worktank
“Technology and tools should not get in the
way of your ideas. The second this happens,
you’re screwed.”
—David Conrad, Studio Director,
Design Commission
“Technology and
tools should not get in
the way of your ideas.
The second this happens,
you’re screwed.”
—David Conrad

4. Resilience Under Pressure
To quote Scott Berkun: “There is nothing like the
impossible and the unfair to stretch your talents.”
Designers who focus their energies on untangling
extraordinary and seemingly intractable problems
learn design fundamentals more quickly, while
exposing new domains for future exploration. However,
these kinds of “stretch” projects must be balanced
with time for reflection, or designers will burn out.
“There was a time in my career when I worked
for an individual who directed a department
of a well-known agency. This was a person
of questionable character who overstepped
boundaries in every way possible. This Devil
wore Prada. The years spent at that place
were my second college education. My but-
tons were pushed. My ego was battered and
bruised. Because of this, my creativity/problem
solving was stretched to new levels. This was
the most tortuous yet rewarding experience of
my career. Although it may not seem like it at
the time, being pushed beyond what you think
is possible is the best education available.”
—Jon Lindstrand, designer
“I had been studying how to design and devel-
op web pages without using tables for layout,
instead using divs and CSS entirely, but found
it quite difficult. I always had to abandon my
effort and go back to table-layout as I butted
up against my knowledge and skill limitations.
Shortly after starting my first job at an agency, I
had a client discovery session where I looked
across the table and told the client that ‘this
site will be designed and developed with a
modern, CSS-based format.’ I had no clue
if I’d be able to pull it off. With the added
pressure of having given my word I threw
myself into the project and succeeded where
before I had not. I’ve never gone back to
table-based work since. Pressure and fear is
an excellent motivator.”
—Andy Rutledge, Principal and Chief Design
Strategist, Unit Interactive
How Can Students Acquire
These Skills More Quickly?
Why aren’t more students graduating with these skills?
Can these skills be taught in that setting at all?
In the classroom, there may be a desire to focus on
deep study of design fundamentals, such as typog-
raphy, layout, and the use of computer programs,
rather than exploring various domains of design. But
in analyzing the survey we’d sent out more thoroughly,
we realized that developing a fast-paced sequence of
quick design challenges would force designers to ide-
ate in an improvisational manner. They could illustrate
their ideas in collaboration with fellow designers, and
communicate them to a client or teacher.
Recent thinking by design educators in America is
echoing this desire to create:
“curricula characterized by flux rather than
stability; classrooms that are open and perme-
able rather than closed and finite; teaching
materials understood as participatory plat-
forms that are modular and extensible; and
pedagogical practices founded on perceiving
the larger system rather than isolated entities
within that system.”
—Holly Willis, “Embracing Flux,” New Contexts/
New Practices: Six Views of the AIGA Design
Educators Conference, edited by Julie Lasky
It can be just as hard to effectively learn the skills I’d
identified in two- and four-year design schools as it is
in the workplace. But not all of this knowledge must
come from doing graphic design projects. We’ve
been following ongoing discussions on the Interaction
Design Association’s website regarding this subject.
Diversion Media, when queried by a graduating
“There is nothing like
the impossible and
the unfair to stretch
your talents.”
—Scott Berkun

student about work experience requirements for
becoming an entry-level interaction designer,
said this:
“The only way to acquire all these skills is to do
projects… However they don’t all need to be
UX projects. If you’ve been a carpenter, short
order cook, or theater designer you probably
have a lot of them already. Plus, of course,
you need to demonstrate killer deliverables,
mastery of several software programs, and
familiarity with the development process. I’d
also like to know that you’ve been on at least
one successful software project through the
full lifecycle (from whiteboard to launch). All
of the above is much more important than an
arbitrary number of years...”
So, every student must master new software technolo-
gies, old-school design theory, and production meth-
odologies, while fulfilling more projects. But we think
the dirty secret is not in that a designer should spend
weeks or months on those projects. The projects
should be unfair in their construction, and limited to
an hour or two at a time, not days or weeks.
creative overload as a
pedagogical approach
To prove this theory, David taught two quarter-long
classes where recent graduates from design school
were tasked with solving 80 creative challenges
across all disciplines of design—many of extraordinary
complexity and difficulty. Most of the people in the
class were also working full-time as designers. Most of
them had tool-based skills with the latest and greatest
software. The only stipulation was that for each chal-
lenge in the class, they would need to turn in a pencil-
based sketch of their solution, unless a computer
execution was required.
The structure of the class was not invented whole-
sale by the two of us. One of our first roommates
post-college was a graduate student in poetry. In
the summer of 1999, he took a class called “Instant
Thesis, or 80 Works in 7 Weeks,” which was being
taught by the poet Peter Klappert. The class explored
collage methods, blot-outs, concrete poetry, metric/
fixed forms, linked verse, anaphora, dialogue, satire,
visual shape, collaborative writing, fixed and loose
rhyme schemes, musicality, tone, and dozens of other
approaches. Each student was responsible for fulfilling
in-class and take-home exercises, as well as coming
up with their own exercises that could be shared with
the class. Many students found the class to be one
a transformative creative experience far beyond any
other classes they had ever taken in college or gradu-
ate school.
With a little research, we discovered that Peter’s class
was adapted from a course taught at the Corcoran
School of Art—one where students were only allowed
two weeks for creating 80 artistic works! The artist
Angie Drakopoulos said this about her experience in
the Corcoran class:
“The Corcoran encouraged students to work
with many different media and explore new
ideas. What I really learned was a way of think-
ing about art, not necessarily how to make it,
but how to think about making it. One of my
favorite exercises, in my junior year, was a proj-
ect to make 80 works in two weeks. We were
given specific instructions on different media
that had to be used, or an idea to be incorpo-
rated, or a color, or words for a piece to refer
to. It was exhilarating; it really opened my mind
to the possibilities of making art. Also, because
of the project’s size and deadline, you couldn’t
spend too much time on any individual work;
so you achieved a certain degree of detach-
ment from the end result, which allowed a lot
of latent ideas and tendencies to surface. I
“Without rules, you’ve
got no target to aim for.
Without flexibility, you
haven’t the freedom to
redefine the target.”
—Duane King

Almost everyone knows what the Olympics are, so a
design brief isn’t required to understand what charac-
teristics may comprise a great logo for the event.
What made this a difficult challenge was the con-
straint around how you exercise a critical, almost
commonplace skill for any designer: sketching.
Becoming more mindful of what ideas flow out of
a set of intuitive pencil gestures, and using those
gestures as finished material rather than polishing
and refining identity concepts with tighter sketches
helped students begin to trust their initial ideas and
their hand-crafted nature.
We also had students try out a variant where teams
of people had to create Olympic logo ideas with a
different constraint:
take it further
Get into a team of four people. Together, you will
sketch a new logo for the upcoming Olympics. The
design will be passed from one person to the next.
Each person, using a permanent-ink marker or col-
ored pencil, can contribute one element to the design
at a time. If you’re crafting type, you can dot an i or
cross a t, but only one word can be written per person
(unless it’s a run-on, if you really want to bend the
rules). Altering the paper in any way can also consti-
tute an element of your design. Keep in mind: once
you’ve started, you can’t crumple it up and start over
again. And when you’re done, your team will share
your work with the class.
think that was the first time I experienced art
as a mind-game.”
Designing Structures for Improvisation
Could design be approached as a similar sort of mind
game, fostering a similar sense of detachment, allow-
ing intuition to bubble up from the margins? Would
it possible to cram a set of wildly divergent design
exercises into the course of short time frame, forcing
designers to exercise the full breadth of their abili-
ties in a finite period of time—learning critical skills
more quickly? Would people in such an environment
become better designers at an exponentially faster
rate, with substantially better output?
During 2009, we worked to construct the challenges
that would serve as the foundation of this “80 Works”
class for designers.
When considering what would comprise these
design challenges, one of Duane King’s responses to
our survey best summarized the spirit of our approach:
“There are various factors in creating an ade-
quate space for a creative team to work within,
but I tend to focus on the definition of struc-
tures for improvisation, simplicity in complex-
ity and freedom of will. Without rules, you’ve
got no target to aim for. Without flexibility, you
haven’t the freedom to redefine the target.”
We loved the notion of “structures of improvisation”
and how it encouraged a push and pull between
rules and flexibility. We knew that each challenge
would have to combine open-ended flexibility with
rigid rules. The time limit for each challenge would
also have to force an immediate confrontation of the
problem at hand, rather than letting solutions rumble
around in the subconscious for a few days.
As an example, one of the first challenges David
taught in the class was “One Line Logo,” which has a
30-minute time limit:
challenge
You’ve been asked to submit an
identity design for the 2012 Olympic
Games in London. The initial sketch
of your logo must be composed
from a single, unbroken line. Once
you’ve placed your pen or pencil
down on the paper, you can’t take it
off the page until the logo is complete. Don’t
go back for corrections—embrace mistakes!

This is the opposite of the previous constraint: instead
of completing an idea in one gesture, the idea must
be painstakingly communicated or collaboratively
created. And with only one shot to put the idea down
on paper, the students had to be clever about inte-
grating any mistakes into their final identity sketch.
This is only one example of how we constructed
the challenges. In the last section of this e-book,
“Teaching the Challenges,” we provide further
thoughts around what makes the challenges
in Creative Workshop so, for lack of a better
word, challenging.
Structuring the Design Process
Through Timeboxing
In the process of brainstorming the challenges,
we realized the following: If a designer knew which skill
they want to learn, almost any kind of problem could
be designed to help them acquire it. But the way stu-
dents tried to solve the challenges, and the specific
processes they used to arrive at a solution quickly,
would require an explicit structure if they were going
to succeed in the time frames they were provided.
And this structure needed to start with a designer
identifying strong ideas, before she or he became
lost in the flow of polishing an executed design.
In researching and testing different design processes,
the one that stood out as an exemplary model for the
class was timeboxing. This technique is often used in
the world of software development, but it’s just as use-
ful when creating design solutions. It also keeps design-
ers from moving too quickly into a design execution,
before they’ve brainstormed a broad range of ideas.
Throughout each class, the students learned to
use timeboxing both in solving individual challenges
and in team collaboration, working in short sprints
tempered by pauses for evaluation and reflection.
When solving design problems, the students
would use the first timebox as a place to use
unorthodox brainstorming methods to kickstart
their creative process.
By repeating this process over and over again—
sometimes in as little as 15 to 20 minutes—students
had a chance not only to exercise their own talents
under pressure, but to also gain an appreciation of
the ways fellow designers solved the same problems.
Needless to say, during the first few weeks the stu-
dents struggled. They were putting in sleepless nights
perfecting design executions instead of following the
provided class instruction and focusing on simple
pencil sketches of their ideas. By the end of the class,
however, they were exploring strong design ideas from
sketchbooks filled with possible design directions and
spending less time sweating under their deadlines
in class and at work. They learned to collaborate
with each other effectively; with such short deadlines,
there wasn’t time for ego. And, most importantly, they
explored domains of design they had never experi-
enced before, which redirected many of their career
paths dramatically.
You can read more about timeboxing and using light-
weight brainstorming methods beginning on page 4
of Creative Workshop.
“Pretending you know what you’re doing is almost
the same as knowing what you are doing, so just
accept that you know what you’re doing even if you
don’t and do it.”
—Bre Pettis and Kyo Stark, “Cult of Done Manifesto”

Designing (and Teaching) with
Dirty Hands
When design curricula is slow to change, and it
requires great effort to learn and understand the
new and ever-changing technologies we must use
as designers and teachers of design, it’s tempting to
cling to what we’ve learned and “what works” as the
end-all, be-all of design practice. Yet in schools, we’re
seeking to keep our students’ hands dirty all the time.
Perhaps we’re just turning over the same plot of land.
In having taught the 80 Works class twice, and in
having solved all of the challenges in the Creative
Workshop book—some multiple times—we’ve dealt
with a lot of ambiguity in the design process, as
well as many blind spots in training and working as
a designer. It would be impossible for us to profess
expertise in many of the focus areas we tackled in
class. In many cases, constructing a challenge and
placing it in the hands of multiple designers has been
a leap of faith: sometimes leading to highly successful
and exciting design thinking, and sometimes fizzling
into a muted failure.
But in all cases, we noticed that as the class (and
by extension, the teachers) settled into not knowing
where the next turn would take us, we became more
creative and more willing to take risks. “Pretending you
know what you’re doing is almost the same as know-
ing what you are doing, so just accept that you know
what you’re doing even if you don’t and do it,” say Bre
Pettis and Kyo Stark in their “Cult of Done Manifesto.”
They add: “People without dirty hands are wrong.
Doing something makes you right.”
Flipping our fear of doing something wrong into a
desire to experiment and take risks is what we think
our student’s employers truly desire from the designers
that they hire. We should be even more purposeful in
how we cultivate these next generations of designers
with the right thinking tools.
This requires us to surprise ourselves, and by extension
our students and co-workers. Time spent teaching
tools and craft must be balanced with the time neces-
sary for students to gain tacit knowledge in ideation,
collaboration, sketching, and remaining nimble and
creative under pressure. That is, if we want students
to be employable and successful in their first roles as
designers, out in the world.
The rest of this e-book outlines how this more agile
philosophy for design instruction was implemented in
a classroom setting. It’s our hope that there is mate-
rial from this text that you can adapt, explore, and
improve as part of your teaching efforts.

13Using Creative Workshop in a Classroom Setting
Using Creative Workshop
in a Classroom Setting
The core of a Creative Workshop class is a set of
instructor-provided challenges, which is then supple-
mented by a set of student-created challenges.
The teacher then constructs “story arcs” out of the
challenges for each class (and its accompanying
homework assignments), conveying larger lessons
about creativity, craft, teamwork, process, and other
fundamental skills.
What Makes a Great Creative Challenge?
For a challenge to succeed, it needs to contain the
following attributes:
An Area of Focus
When considering which challenges to use in a
class—or creating your own challenges—make sure
there is a clear, stated area of focus as part of the
challenge statement. This ranges across the various
domains of design, from branding to packaging to
advertising to user interface design. This will help the
class gauge what kinds of design outputs are neces-
sary while solving the challenge. A list of focus areas is
included in the Creative Workshop book.
Tangible Creative Output
Each challenge requires tangible output, from a
design sketch to a high-fidelity design execution.
Sharing an idea verbally when time is up does not
count for credit.
An (Almost) Impossible Time Limit
In class, the time limits for challenges from Creative
Workshop can be cut in half, or even shorter. If stu-
dents aren’t rushing to the last second to complete
the stated deliverables required at the end of a
challenge, you’ve given them too much time. Your
students will become faster and faster at solving chal-
lenges, so you’ll need to further shorten their dead-
lines or increase the number of deliverables required
as you progress.
No challenge should have a time limit longer than
two hours—especially for take-home assignments,
where students will be tempted to lavish days on pol-
ishing design executions. They can do that when the
class is over.
True Goals for Growth
There’s what you’re asking your classes to create in
a focus area, and then there’s what you want them
to learn.
For example: Challenge #3, “Time Machine,” requires
students to take an old advertisement and execute
it as if it had been published in a modern magazine.
While this is the goal for class output, what the chal-
lenge is actually teaching students is how to assess
the strategy behind an advertisement, analyze the
societal and artistic trends that helped to shape its
execution, and translate all of those details into a
modern design execution.
This is no small feat—especially in 90 minutes.
SITS Outside Everyone’s Comfort Zone
(Including Yours)
Truly inspiring creative challenges aren’t bread-and-
butter design problems. When constructing a chal-
lenge, think about how you can add variables or
unusual constraints to an everyday project to push
your class (and the teacher) into uncharted and
risky territory.
If you don’t feel comfortable leading an exercise in
an area of design you haven’t explored before, invite

14 Using Creative Workshop in a Classroom Setting
in other instructors or working professionals to help
facilitate those challenges.
Contains Content Your Students
Care About
Each time we taught a Creative Workshop class,
we provided the students with a brief survey at the
beginning where we asked them what types of proj-
ects and what kinds of clients they’d like to work with
in the future. This information was incorporated into
many of the class challenges and increased
student engagement.
In addition, we asked for each student to provide at
the start of every class period a challenge that they’d
created. This can be for credit, or for students to
have input into the class content. Depending on how
you’ve structured the class, you can select the
student-suggested challenges that fit the arc of
upcoming classes and incorporate them.
Based on student suggestion, we’ve included at least
20% student-inspired challenges over the life of each
class we’ve taught.
VARYING LEVELS OF DIFFICULTY
The challenges in Creative Workshop are ordered from
craft-oriented problems that hone making skills to
design problems that are open-ended, highly compli-
cated, and fraught with ambiguity. When brainstorm-
ing challenges for the class and the book, Mary hit
upon the following categories for the different types of
problems designers solve in their daily work, indepen-
dent of disciipline:
Foundation: The fundamentals of being a designer
from a craft-based perspective. This includes typog-
raphy, layout, grid systems, design history, research,
illustration, and sketching.
Execution: Moving from fundamentals to real-world
design deliverables, while being forced to explore a
range of design solutions in a faster timeframe than
they may have attempted in the past.
Materiality: The tangible act of making things as
part of the design process—often without comput-
ers—yielding design executions that rely on the hand-
made touch for their power.
Instruction: Cultivating the crucial skill of breaking
real-world situations down into their constituent com-
ponents, then analyzing them for ways in which they
can be reconstructed and improved.
Observation: Requiring students to step outside the
classroom and their studio into the real world, using
their senses to observe and reflect on how other
people behave—then using this insight as the fuel for
design solutions.
Innovation: Working with design problems specifically
in the domain of product design, service delivery,
and social innovation—forcing designers to grapple
with how to reinvent businesses and reshape human
behavior.
Interpretation: Open-ended problems whose solu-
tions require designers not only to determine what
needs to be designed, but also to answer an even
more important question: Why does something need
to be made?
An important additional category to note is
“Unsolvable Problems.” Students often find ways to
approach lose-lose situations with creativity and fresh
perspectives that provide new ways of influencing
major societal issues. We often throw one unsolv-
able problem into the mix as a final assignment for
the class, for all of us to understand exactly how far
a designer’s reach can truly extend in dealing with
wicked problems.
Tasking students with an insoluble problem may
seem a bit sadistic, but it’s one of the best ways for
designers to understand what it feels like to grapple
with—and identify in the future—whether a problem
is wicked (i.e. influenceable, but not solveable). For
more on this topic, see our rationale for Challenge #79
on page 69 of this e-book.
Using Exercises in Your Existing Classes
When David taught Creative Workshop classes, each
class period was four hours and consisted of solving
five challenges in a row. This was a great way to intro-
duce a range of brainstorming methods, focus on a
series of challenges that teach a specific skill, or break
a large-scale project into digestible chunks.
It’s also possible to string out challenges over a series
of weeks in a recurring fashion. At frog design’s Seattle
studio, David set up a biweekly lunchtime series to
explore different methods of physical prototyping,

using challenges from the book and timeboxing to
teach different ways of building and evaluating com-
plicated systems in a low-fidelity format.
Solution Structures
What is a solution structure? It’s a method of engineer-
ing social situations around specified challenges that
makes them much harder to solve—forcing student
designers to learn how to collaborate more effectively.
In teaching classes involving Creative Workshop, we
invented the following solution structures. See which
ones you can come up with as well!
STRUCTURE 1: 30 Days in 30 Minutes
Teams of three or four students are provided with
a challenge, which they must solve in 30 minutes.
Those 30 minutes are divided up into the following
timeboxes:
8 minutes: Each team reaches a goal that is set
by the teacher.
2 minutes: The teacher serves as the client, provid-
ing quick feedback to the teams and providing
the next milestone.
8 minutes: Each team scrambles to incorporate
the feedback and reach the next milestone.
2 minutes: The teacher/client gives another round
of feedback and sets the final milestone.
8 minutes: Each team incorporates the final feed-
back and completes the final solution(s) for the
challenge.
Last 2 minutes: Each team has 30 seconds to
present their solutions.
As an example that describes how this works in action:
We provided a class with the “Storybook Ending” chal-
lenge in Creative Workshop, in which they had 30 min-
utes to come up with the plot and character studies
for a children’s book.
Over the first 8 minutes of solving the challenge, they
had to ideate around the theme of their book. In the
second 8 minutes, they had to move from the theme
to a full-blown plot and characters. In the last 8 min-
utes, they had to create a character study and a
moral for their book.
We required the students to show an artifact for each
client review, usually in sketch form. Sharing a solution
verbally is not acceptable to the client. (When was the
last time you walked into a client review and told them
about your design idea without some tangible render-
ing of it?)
This is a solution structure we have used in every
Creative Workshop class period, continually varying
the challenges and the unique deliverables required
during each sprint; it forces students to work in parallel
and quickly divide large design problems into smaller
sub-tasks, which is a crucial skill for any work setting.
STRUCTURE 2: the Round-robin
It’s useful to teach at least one class period in a quar-
ter or semester where the output from one challenge
is directly inputted into the next challenge they’ll need
to solve, while rotating the students into an entirely
lateral design domain.
As an example: in collaboration with the designer
Scott Scheff, we created a five-challenge sequence
where one of my classes had to create a “record store
of the future.”
In the first challenge, the students came up with the
name of the store and its logo.
In the second challenge, they planned out the store
space in Manhattan based on a defined set of con-
straints provided by their real estate broker.
The third challenge required them to brainstorm user
flows for a mobile application necessary to buy and
download music while in the space.
In the fourth challenge, they created a 30-second
TV ad for their store that had to include handmade
puppets.
For the fifth and final challenge, they had to craft
a pitch for investment capital based on everything
they’d created in the first four challenges.
STRUCTURE 3: Variable Client Feedback
For certain challenges, we’ve stopped the students
midway through solving a challenge and provided
them “client feedback” as an additional constraint.
Another fun way to deliver “client feedback” is to
isolate a student from the overall class, take them

outside the classroom, and have them draw random
feedback out of a hat that they spout back to the
class in response to their work midstream. This not only
makes the class become more creative in response to
“out of nowhere” feedback, but also helps the student
play-acting the client see what such a situation feels
like from a client’s perspective.
Refer to page 10 of Creative Workshop for a starter set
of client feedback items that will keep your class on
their toes.
Throw Yourself Under the Bus
It’s helpful to read out a particularly difficult challenge,
execute the challenge at the same time as the class,
and then be a part of the critique process.
Class Lectures
As you plan the challenges that form the arc of each
class period, consider what mini-lectures may be
required that will help to solidify specific skills that
you’re teaching.
As an example, we’ve introduced new brainstorming
methods at the start of a class period, then had the
students utilize those methods across a set of chal-
lenges to provide them a chance to road test each
one individually.
In another case, a lecture that closed out a class
helped to set up ground rules for how the students
could best fulfill design research in the midst of their
busy schedules.
For sample lectures (in a raw format) that we
delivered during the classes, take a look at the
class archive here: http://changeorder.typepad.
com/80_works_for_designers/lectures/
Closing Portfolio Review
When teaching a class that solves 40 to 80 challenges,
the last class period should be reserved for a final
challenge and a review of all of the work created by
each student over the life of the class.
Students learn a great deal by placing 40 to 80 design
executions in sequence on a table for the entire
class to comment on. This process can take a num-
ber of hours, so we’ve encouraged students to bring
food and drink and make it a celebration for having
survived the entire quarter or semester.
Also, consider a special prize for those students who
complete all of the challenges. It’s unlikely that most
students will be able to turn in a solution for all the
projects. (So far, there has been only one.)
Time Constraints
Assume at least 40 minutes of class time for each
challenge the class attempts, including critique.
We’ve also allocated 40 minutes to discuss all take-
home assignments, which are shared out for in-class
critique and review.
As an example: We have taught classes over the quar-
ter system, meeting every week for four hours. In each
class, we fulfilled five challenges, and three challeng-
es were provided as take-home work.
A Creative Workshop class can be conducted over
the course of a semester, but the shorter the time
period for the entire class, the greater the benefit. For
a 7-week seminar, the class would need to complete
12 projects per week, while over a semester there may
not be as much time pressure. This may require the
teacher to intentionally manufacture such pressure.
Class Rules Regulations
Alongside the class syllabus, we’ve provided the fol-
lowing three guidelines to students:
1. You should fulfill every assignment and bring it to
class, no matter what. Work fast. Turn your editor off.
Take as many risks as possible. The greater the risk in
the work that you’re attempting, the more important
that you bring it to class. You shouldn’t have time to sit
around and think about whether what you’re doing is
good. You should feel uncomfortable every time you
show a solution to the class, no matter how much time
you have to prepare it.
2. Everything is shown to the group, no matter what.
Each assignment will be viewed and commented
upon by the group. Listen to how other people view
it, and what they think it can become from their vari-
ous perspectives. This is invaluable input. Don’t rush
to defend what you meant to accomplish in the time
frame. This class is about possibilities as much as
finality, and it’s possible that the input of your peers
may push your work in new directions you hadn’t
considered.

3. Failure on some of the projects will happen, and is
a desirable outcome. Keep notes on what works and
what doesn’t work. Be willing to throw away work in
progress to start over with what you’ve learned. Only
when we reach the end of our class should you focus
on what can be extracted from your best works over
the life of the class. Until then, keep a record of your
working process and progress, not what you’ll be
including in your portfolio.
How Do You Grade Creative
Workshop Classes?
In a class such as this, fair grading is based on two
factors: in-class participation and solving all of the
challenges posed by the teacher and class.
Participation
To receive credit, students will be required as part of
their in-class work to:
• Regularly critique challenge solutions in a group
• Work collaboratively to solve challenges as teams
• Keep a written record of what they’re observing
about their working progress each week, either
on a public blog or in a journal format that can
be shared when appropriate with the class
• At the end of the class, help classmates identify
which projects may become part of their portfolio
(with any additional polish)
Challenge Completion
Students receive credit for each challenge they pro-
vide a solution for and present to the class. This is for
both in-class and take-home challenges, including
ones that integrate work from previous solutions into
new solutions.
SAMPLE Grading Methodology
At the end of a course with 80 creative challenges, a
student could receive points as follows:
• 10 points for each of the 80 challenges that are
shown to the class. This adds up to 800 points
over the life of the class. If a student misses a
class, they still need to turn in the take-home and
missed in-class challenges, or fulfill appropriate
substitute challenges as assigned by the teacher.
• 200 points will be provided for direct class partici-
pation and involvement
The student’s grade could then be their earned points
divided by 10 on a standard 100-point scale.
What Skills Should Students Have Before
Taking a Creative Workshop Class?
Students without an initial foundation of craft-based
design skills—ideally with at least one to two years
of design education—may find a Creative Workshop
class with 40 to 80 challenges quite demanding.
When we have taught a class, a portfolio review was
required for student entry to ensure they would not
need to fully acquire design fundamentals while solv-
ing all 80 challenges.
Planning the Arc of a Creative
Workshop Class
On the next page are examples of how the above
ingredients fit together as part of an 80 Works class,
as well as a blank template you can use to plan your
own. (This is based on the quarter system, which is
used in Washington state).
The challenges can be arranged over the length
of the class in escalating difficulty and time invest-
ment. There should also be take-home assignments
that require small group collaboration alongside
individual exercises, much like what a designer experi-
ences when entering into an in-house or studio work
environment.
The final two to three weeks of the class can contain
the most complex, most open-ended challenges you
can muster.

Week 1 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
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Week 2 In Class ____________ _ _______________________
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Homework ____________ _ _______________________
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Week 3 In Class ____________ _ _______________________
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Homework ____________ _ _______________________
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Week 4 In Class ____________ _ _______________________
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Homework ____________ _ _______________________
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Week 5 In Class ____________ _ _______________________
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Homework ____________ _ _______________________
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Week 6 In Class ____________ _ _______________________
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Homework ____________ _ _______________________
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Week 7 In Class ____________ _ _______________________
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Homework ____________ _ _______________________
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Week 8 In Class ____________ _ _______________________
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Homework ____________ _ _______________________
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Week 9 In Class ____________ _ _______________________
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Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 10 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
Week 11 In Class ____________ _ _______________________
Category Challenge Name Category Challenge Name
Creative Workshop Planning Worksheet: Quarter System (Sample Class Structure)
Foundation Hello, My Name Is
Foundation
Foundation
Interpretation Group:
Execution
Foundation
Execution
Materiality
Foundation
Execution Group:
Execution
Execution
Materiality Group:
Foundation
Execution
Execution
Foundation
Execution Group:
Execution
Materiality Group:
Instruction
Observation Group:
Execution
Materiality
Interpretation
Execution Group:
Execution
Innovation Group:
Interpretation
Observation
Materiality
Innovation Group:
Execution
Fundamentals
Innovation Group:
Instruction
Observation
Instruction
Execution
Innovation Group:
Interpretation
Execution
Observation
Innovation
Innovation
Fundamentals
Innovation Group:
Interpretation
Instruction Group:
Innovation Group:
Instruction
Innovation
Interpretation
Execution
Fundamentals Group:
Execution Group:
Innovation Group:
Observation
Materiality
Execution
Innovation
Execution
Instruction Group:
Innovation Group:
Innovation
Interpretation
Execution
Innovation Group:
Innovation Group:
Interpretation Well, in My Book
Interpretation “Kobiyashi Maru”
Begin to reduce
time limits by here…
This is a “breather
class”before the
final stretch
From here out,
problems are too
hard for solo
designers to solve
Introduction to
timeboxing focus
on fundamentals
Beginning to explore
collaborative design
practices
Starting to bring
in design research
methods
Provide class
brainstorming
techniques
Overwhelmingly
hard problems in
brief time frames

Week 1 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 2 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 3 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 4 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 5 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 6 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 7 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 8 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 9 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Week 10 In Class ____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
____________ _ _______________________
Homework ____________ _ _______________________
____________ _ _______________________
Week 11 In Class ____________ _ _______________________
Category Challenge Name
Creative Workshop Planning Worksheet: Quarter System

21Teaching the Challenges: Foundation
Teaching the Challenges:
Foundation
Hello, My Name Is
The Goal
• Logo design
• Expansion into personal identity system
The True Goal
• Learn to organize disparate thematic elements
into a concise statement
• Separate the designer from the work, and
internalize the objectivity that comes with this
separation
• Design for change and growth: understanding
that a permanent mark does not necessarily
mean a unchangeable brand
When To Use It
• Younger designers, especially those right out
of school
• Designers transitioning into freelance after work-
ing in-house or spending time at an agency
• Career transition
Further Thoughts
Designers have difficulty with their own identities for a
number of reasons. In choosing a logo, participants
have to decide which skills to highlight and which
to let fall away. This can be traumatic, especially for
younger designers, who still want to Go and Be and
Do Everything.
This logo is for the artist one has become, and does
not limit the artist that one will be. Remind everyone
that designers grow and mature, and just like people,
some of our more enduring brands (from IBM to the
United States Postal Service) have also evolved their
colors, font selections, and iconography.
If your students are really stuck, limit the logo to a par-
ticular aspect of their work. While having four logos—
showing wizardry in After Effects, advertising, Maya,
and wedding invitations—isn’t practical in the real
world, this initial constraint can help to organize the
thoughts of a frantic Renaissance designer.
Easy as ABC
The Goal
• Create a typeface out of found objects
• Add additional symbols or create a poster using
the typeface
The True Goal
• Separate letters from each other and understand
them as stand-alone forms
• Document the creative process
When To Use It
• Designers who are overly attached to a comput-
er-driven process
• Designers who feel they are not “crafty” or “artsy”
• Anyone who loves to argue over which font is
worse, Papyrus or Comic Sans

22 Teaching the Challenges: Foundation
Further Thoughts
We learn words by first learning letters, and so abece-
darian exercises tend to rely on more rudimentary
approaches. Most of the work will likely fall into two
categories—the same material being used for all of
the letters (jeans, ribbons, pushpins), or the word for
the material starts with the letter being illustrated (B is
for Boy, C is for Cat). Be on the lookout for typefaces
that highlight the disconnect between the words for
the objects and the letters they illustrate, as the inspi-
ration for material choices may not be obvious to the
entire class. This can make for good group discussion.
Despite the description of a typeface of “twenty-six
characters,” don’t let that limit your participants. If
someone speaks Greek, encourage him to compose
from that alphabet. If he can present to the class a
chart for comparison, even better.
However, American Sign Language (ASL) and other
hand-language systems are easy to replicate for this
assignment, and they could be great temptations for
students. Depending upon the class, you might want
to clarify whether these are allowed or not.
Time Machine
The Goal
• Bring an old ad into the future after research
• Or take a modern ad and push it back in time
The True Goal
• Learn to identify what works and what doesn’t
while integrating historical motifs into a design
• Isolate individual elements in a design and adapt
them appropriately, while maintaining overall
cohesion
• Understand the transient nature of visual descrip-
tors and textual explanation despite the fact
that the driving forces for the products have not
changed (survival, acceptance, status, etc.)
When To Use It
• Designers who struggle when moving deliver-
ables between print to screen
• Around discussions of “timeless” or “iconic”
design
Further Thoughts
We think of research when it comes to designing
products: How will a consumer use this? What kinds
of features do they want? But the research for this
assignment serves another purpose: to understand
how design elements, motifs, and compositions have
evolved from decade to decade. Start conversations
about basic subjects such as font choice and white
space. The why? of these choices may be a tired and
common question, but getting designers to see the
pervasiveness of a particular visual trend can be pow-
erful. This will help them to see patterns in their own
work and in the work of others. And by watching the
progression of present-day work, it can also help them
plan for future projects.
Advertising has been around forever, and while the
pictures and the products have changed, our basic
needs haven’t. Though this is a research assignment
at heart, it is also a great idea to point out what’s hap-
pening beneath the visuals. What are we really selling
when we design an ad? What are we really saying?
“We become very attached
to our computers… we
encounter a lot of design
through our computer…
but any disciplined
designer will tell you,
it’s just not the same
as pencil and paper.”

One Line Logo
The Goal
• Create a logo from a single unbroken line
• With one or more partners, create a logo from
individual unbroken lines
The True Goal
• Learn to incorporate mistakes into a design
• Use basic sketching skills to communicate a com-
plex identity rather than use the staid approach
of type, image, and color selection
When To Use It
• Designers who rely heavily on the computer to
drive process
• Alongside projects that are grounded by photo-
graphs, type, or materials
Further Thoughts
This exercise is one of several found throughout the
book that is meant to help designers get back to
basics—in this case, sketching.
We become very attached to our computers, espe-
cially when the early stages of discovery rely so heavily
on it. Whether it’s through emails or Internet research
about our client, we encounter a lot of design through
our computer. It’s only natural to simply switch pro-
grams when it comes to the physical work of design-
ing. There are even programs meant to mimic the act
of sketching.
But as any disciplined designer will tell you, it’s just not
the same. With paper and pencil, the mistakes are
more tangible than on screen. It’s easier to see where
the design has come from and where it is going to.
Should strident challenges arise, students can always
do the assignment twice (with a different client, of
course), once with a computer and once without.
Allow them to time their iterations, track their progress,
and explore the efficacies of each process.
I’m Drawing a Blank
The Goal
• Make a folder using white as the dominant color
• Create associated sell sheets
The True Goal
• Understand what people mean when they talk
about “white space” as a design element
• Learn to unravel overly complicated layouts and
brand systems, reducing them to their most pow-
erful elements
• Discover new uses for small but powerful
applications of other colors
When To Use It
• Designers transitioning from Internet to print
• Students having difficulty negotiating the bal-
ance of text to image
• As a reward for designers who rarely find an outlet
for their “minimalist” approach, or as a punish-
ment for those who feel the need to fill every inch
of a page
Further Thoughts
Color is one of the more powerful tools we employ as
designers. But often, we’re limited to the real world
interpretations of those colors—grass is green, skies
are blue. With color being constantly attached to
images illustrating reality, it’s easy for students to for-
get about red, green, and white as pure design ele-
ments. Especially when people start throwing around
the concept of white space.
As a color, white doesn’t get a lot of respect. It’s usu-
ally treated as the one that’s there when nothing else
bothers to show up. As a result, the power of white is
confined to being a simple buffer between other ele-
ments. This exercise requires the designer to fully focus
on white as its own unique entity.

But it’s not all about white. By using white as the domi-
nant element, students are forced to more closely
analyze their other color selections. In a sea of white,
a two-inch tall logo in red can become a beacon.
While that’s easy for a teacher to say to a student, it
doesn’t sink in until the decision is visible on the page.
Mr. Blue
The Goal
• Design a magazine using the color blue as the
driving design concept
• Expand this into spreads, masthead, and an over-
all grid scheme
The True Goal
• Identify and then break down beliefs around
color theory associations
• Understand that color is not restricted to a par-
ticular hue
• Train the eye to detect subtle shadings and
undertones
When To Use It
• Designers consistently working in the same color
palette
• In conjunction with discussions around readabil-
ity, culture, and psychology
Further Thoughts
Red means angry, blue means sad, green means
envious. As designers, we don’t need to know where
these associations come from, but we do need to
know that they exist. We also need to know that they
are changeable; the proper use of blue in a layout
can work with other elements to make the audience
laugh or cry.
Another color assignment, “Mr. Blue” plays with
our ideas about color association and meaning.
Realistically, you could use any color for this chal-
lenge, but as blue has the distinction of being the
most popular color, there are more potential concep-
tual associations to play with.
From a technical perspective, designers should be
able to visually recognize branded colors (Starbucks
green, Coca-Cola red). But beyond reading PMS col-
ors and RGB values, we also have to communicate
subtle differences in hue through verbal descriptions
in meetings with our teams and clients. Given its per-
ceptual subjectivity, color is difficult to speak about;
the ability to speak clearly and confidently about visu-
al components and their related effects cannot be
overemphasized. So as students present their solution
to this challenge, encourage them to be as precise as
possible in how they describe their work.
Gridlocked
The Goal
• Learn to place elements in a fixed grid
• Learn to adjust grids based on new content
requirements
The True Goal
• Understand that certain pieces of a design may
run counter to a preferred aesthetic
• Learn to view designs as a whole, and then learn
to break them into their constituent parts
• Learn to think about the grid as a powerful tool,
rather than an unfortunate necessity
When To Use It
• As a reward for designers who feel “discipline” is
a strong suit
• To break designers from the habit of leaning on
the same layouts
• For less experienced designers who may know
about grid systems, but may not understand how
to construct them
Further Thoughts
Ah, the grid. Bane of many a designers’ existence, a
throwback to the old ways of doing things, when the
grid was brandished as a weapon by anal-retentive
Swiss professors willing to do anything to crush the
creative spirit of an aspiring artist.

But while the grid is powerful, it is actually benevolent.
The grid allows us to not only view a layout as one
cohesive unit, but it also forces us to consider each
individual element in relation to the others. When the
grid we’ve initially set for a layout changes rapidly, we
have to re-identify the prioritization of elements in the
layout (because it may not be the same), and we are
forced to consider each element anew. The physical
position of elements is just as important as the ele-
ments themselves.
When we become more comfortable with the grid
and its ability to focus the eye on particular content
elements, we can easily adapt that content for mul-
tiple formats. Changing a two-page spread into a tri-
fold brochure is a lot less of a headache when we’ve
had this kind of practice.
Spray Paint Wars
The Goal
• Use graffiti hand-lettering to design a logo, story-
board, and storefront
• Develop an event for the store
The True Goal
• Learn to spot assumptions and stereotypes
• Identify when to use those assumptions and when
to ignore them
• Begin to craft a vocabulary around promoting
public events
When To Use It
• Students who need to hone their illustration skills
• Whenever a portfolio shows signs of being too
homogenous, especially when a student’s work
indicates that the prevalence of similar material
is being dictated purely by preference and not
ability
• Designers who want to incorporate live event pro-
motion into their repertoire
Further Thoughts
Graffiti conjures up some specific, and perhaps unfair,
associations. As designers, we have to be able to
recognize the difference between reality and our own
biases. At the same time, we also have to be aware
that those same biases may exist in other people. This
is pretty obvious—not everyone thinks like us—but with
graffiti, there’s a lot of controversy over its artistic value.
This is not just a struggle related to class and culture.
It’s also about creativity, control, spontaneity, and art
in the public domain. The reasons behind the stigma
and the reverence are complex.
So, this exercise is a great way to explore our opinions
about a complicated hot-button topic, so that we can
determine how to talk to our clients about such design
choices in the future. This challenge is also good for
honing illustration skills; street artists work very hard to
develop a personal voice in their work under extreme
conditions.
The opportunity to create a public “happening”
around something as polarizing as graffiti is some-
thing that designers don’t often get to grapple with.
And while we want to maintain our own individual
style, just like street artists do, we have to remember
that their work often incorporates elements from the
surrounding environment. Students can really push
this challenge by placing the store in different local
neighborhoods, anticipating community responses
and designing the logo and events accordingly.
“The rules of typography are not only the most helpful
for constructing a powerful layout—they are also
unfortunately the most common for a client to ignore.”

Tragic Sans
The Goal
• Create a brochure cover using five or more
distinct fonts
• Add two more fonts to a brochure display setup
The True Goal
• Learn typography and arrangement as distinct
design elements
• Deal with clients who make truly terrible
aesthetic decisions
• Cultivate simplicity in complex layouts
When To Use It
• Designers whose work is consistently austere
or simplistic
• To settle battles between typeface snobs
• In conjunction with discussions around
readability, clutter, and distraction
Further Thoughts
By now, everyone should have a basic understand-
ing of the rules of design. But our clients usually aren’t
designers, and their tastes might offend every single
principle we hold dear. So sometimes the rules we live
by have to be broken. And the rules of typography are
not only the most helpful for constructing a powerful
layout—they are also unfortunately the most common
for a client to ignore.
We think of fonts within certain frameworks, as being
appropriate for one particular use but never for anoth-
er. Fonts have “looks” and styles; some seem futuristic
and others are perfect for more classic approaches.
What happens when we separate each typeface from
those associations? Can we change emotional reac-
tions through word arrangement?
The easiest solution to this challenge is to use one
word per font. And while that addresses the issue of
simplicity, it might not help a designer deal with the
aesthetic crisis that multiple fonts can present. To
really challenge them, consider setting a word count
minimum. As an alternative, try requiring a minimum
number of additional design elements (i.e. five fonts
and a minimum of two photos), or require the use of
typefaces generated in “Easy as ABC.”
Grungevetica
The Goal
• Distress the Helvetica typeface in a manner
related to the original version
• Design a poster that incorporates the
updated font
The True Goal
• Learn what makes a particular construction work,
and what doesn’t
• Gain a working vocabulary for describing neces-
sary changes
• Understand how to dissect a type-based solution
into forms, principles, and execution
When To Use It
• To reward students who feel constrained in their
output (i.e. any designer that has worked too
long with an in-house style guide)
• With anyone dismissive of design history’s role in
its future
“Designers have to be able to teach
themselves about a particular
field or product and then design
appropriately for it. When we
present work to a client, we have
to demonstrate a mastery of those
concepts, even though we usually
are not experts in that field.”

Further Thoughts
It’s time to shake up the establishment, but the estab-
lishment doesn’t always want to be shaken up. How
do we describe the need for an update to our client
while still maintaining their original spirit? Coming up
with fresh ideas is difficult enough; how do we make
something classic fresh, when changing its form may
be considered verboten?
Be sure to emphasize each student’s description of
their solution when solving this challenge. It’s not
enough for a student to run over a sheet of typewrit-
ten paper with a car and call it done. There has to be
a solid conceptual bridge between the original font
and the distressed output. Making these connections
with photographs and logos is easy; typography is
another beast entirely.
Future Penmanship
The Goal
• Design a futuristic logo using a hand-drawn solution
• Extend this logo into Flash animation, stationery,
or a Web site
The True Goal
• Discover how to handle seemingly conflicting
aesthetics
• Understand how to research challenging ideas
When To Use It
• Designers who are showing a profound lack of
research skills, or who are showing a weakness in
being able to synthesize research information
• In any class where there is a marked lack of hand
illustration skills and/or understanding of the emo-
tional and rational impact of typeface choice
Further Thoughts
Designers have to be able to teach themselves about
a particular field or product and then design appropri-
ately for it. When we present work to a client, we have
to demonstrate a mastery of those concepts, even
though we usually are not experts in that field.
There may be students that already have an under-
standing of quantum computing. This doesn’t excuse
them from the research aspect of their project; in fact,
they are under an even heavier burden in that they
will have to scale their knowledge into a smaller out-
put, rather than build up their newfound knowledge
into a larger output.
With regard to execution: what we’re working with in
this exercise is similar to the typography-focused chal-
lenge “Tragic Sans”—only this time, we’re dealing with
more ambiguous concepts from the client. Typefaces
and logos conjure up certain feelings and resonanc-
es dependent upon the content surrounding them.
Certain images and their presentation make us feel
a company is conservative; others make them seem
more cutting-edge. Sometimes, our clients challenge
our interpretations, and a designer must know how to
address those concerns.
Strange Chemistry
The Goal
• A cover for an annual report using a handwritten
solution with refined photography
• Design an online experience that animates these
two different aesthetics
The True Goal
• Understand how creative juxtapositions generate
novel, potent relationships
• Avoid politics, sticking to the task at hand
When To Use It
• Surrounding discussions of the emotional
influence of particular design elements
• Designers see this challenge strictly as an
ideological exercise
Further Thoughts
Putting opposite things together is a reliable way of
generating new and exciting relationships within a
design. But with this challenge, it’s the content that
can derail the process.

Despite the type of client involved, this isn’t about
how we feel about chemicals or the green movement.
It’s about putting disparate concepts together and
studying how they interact. Public opinion toward the
environment and toward industry is frenzied right now,
but don’t let students get caught up in the politics.
Make sure that students do not become distracted
by the ideas represented here. While it is important to
be able to identify our ethics surrounding the clients
we feel comfortable representing, it is also important
to be able to recognize basic design problems even
within domains that may be ethically fraught. If we
can’t, then we lose the ability to migrate our execution
skills from client to client.
In short, this challenge is about nailing the basics.
There will be plenty of time in other challenges for
them to struggle with ethical issues.
Three in One
The Goal
• Use a single item and accompanying text to
convey three different meanings
• Storyboard your favorite execution for a
television spot
The True Goal
• Begin to understand the stories behind everyday
items and how copy can manipulate those stories
• Gain an appreciation for how people of other
backgrounds perceive common objects
When To Use It
• Groups of students from diverse backgrounds
• Groups that have exhibited polarized attitudes
(or single-minded executions)
Further Thoughts
There is a great power in universal symbols. Olive
branches mean peace, frowning faces mean sad-
ness, snow means Christmas. Unless you’re Jewish. Or
if you live in California. Or if…
Ah, symbols. We know how easy it is to miss the mark
when we assume everyone sees the same things that
we do. We attach meanings to pictures because of a
staggering variety of influences, most of them specific
to our families, our hometowns, or our social circles.
Everyone has a story to tell, and these stories have a
profound effect on how we perceive ordinary objects.
But we can’t realistically design for each individual
interpretation; eventually, we have to pick an image
and some text and make it work.
So for this challenge, encourage your students to
talk about their images and the text they choose to
accompany it. When we explore how text plays with
these perceptions and attitudes, we can watch how
our reaction to an object changes. More importantly,
we can learn how to use text and images to change
other people’s reactions. This is what effective adver-
tising is all about.
“Students can really struggle with iteration, mostly
because they don’t know how to incorporate failure
into their process… If you think something, and it’s
terrible, no one will ever know. But you can’t deny
what’s staring back at you on the page.”

10 x 10
The Goal
• Design a container by drawing 100 sketches
• Design a Web site for the container using the
same process
The True Goal
• Understand that there really is no limit to the ideas
in our minds—we just need to get them out of our
thoughts and onto paper
• Confront truly terrible ideas and learn that they
are a powerful part of the design process
When To Use It
• Designers who don’t like making mistakes and
want to “get it right” quick
• Around discussions concerning hand sketching
vs. computer work
Further Thoughts
It’s trendy right now to talk about mind-body relation-
ships, about intuitiveness and flow. There are many
nebulous and sometimes bizarre ways that people
talk about the creative process. You can put all of that
stuff aside. Because like a lot of things, the truth is that
design is something you often have to physically do.
Sometimes, you can’t think through a problem in your
head, you have to put pencil to paper and work on it
in the real world. With a deadline breathing down your
neck, you don’t have time to figure out why such a
physical process works, you’re just glad that it does.
Students can really struggle with iteration, mostly
because they don’t know how to incorporate failure
into their process. Most don’t know how to frame the
concept of failure, and this is true even of more expe-
rienced designers. Every one of the sketches gener-
ated for this challenge isn’t going to be The One, and
facing the fact that we aren’t geniuses all the time is
a little humbling for some. If you think something, and
it’s terrible, no one will ever know. But you can’t deny
what’s staring back at you on the page.

30 Teaching the Challenges: Execution
Execution
Sixty Second Deadline
The Goal
• Create billboard copy in sixty seconds
• Develop a series of billboards based on the most
effective execution
The True Goal
• Learn to think efficiently under extreme time
pressure
• Understand how design permeates our experi-
ence, and that everything and anything is fair
game when it comes to generating concepts
When To Use It
• Students who idolize design as a pure, completely
artistic discipline
• Whenever the class seems to be progressing at a
nice, safe pace
Further Thoughts
We can segregate parts of our life from design,
because we don’t see how they contribute to our pro-
cess as designers. What does a toothbrush or a blue
sock say about my process? your students may ask. It
can say plenty if you let it, and once you’ve guided
them through this challenge, they’ll see why.
It’s easy to apply design principles to things that are
“designery”. But when we can see those principles
at work around things like hammers, popcorn, and
headphones…that’s when we know we understand
those principles. It’s not about being a slick salesman
and coming up with a brilliant headline that makes
everyone want to buy dust bunnies. It’s about seeing
the connections between the lofty and the mundane,
and realizing that any sort of material can contribute
to the effectiveness of our work.
The sixty-second deadline is an added bonus for dis-
cipline. Even the best marathon runner knows how to
sprint to the finish.
Hey, You Made That Up!
The Goal
• Invent a product based on a random combina-
tion of syllables and develop a storyboard for a
related motion-graphics piece
• Add voiceover and music to the movie
The True Goal
• Learn how to set goals in open-ended scenarios
• Think about how to describe products or ideas
through motion
When To Use It
• Designers who have little to no experience with
motion design
• Students who thrive on constraint-based
scenarios
Further Thoughts
There’s a strange relationship between the sound of a
product name and the product itself. Certain letters

31Teaching the Challenges: Execution
evoke specific emotions, and there have been
a number of articles written about the effects of
sound on our purchasing decisions. In this challenge,
students will have to grapple with how the name of
a product operates on a sensorial level with a poten-
tial consumer.
All of those thoughts in the last paragraph about
sound and feel in the naming of a product? A red
herring for your students.
The real reason why this one is such a challenge—
and that it has defeated scores of designers to date—
is because the name of the product has nothing to
do with it.
What students are actually doing here is designing
with absolute freedom around the content. We’re
used to having tightly defined constraints driving
our design process, and it’s difficult to do whatever
we want without any guidance. When solving this
challenge, the name doesn’t have to relate to the
product in any way whatsoever. A savvy designer
could plot a solution for anything and just tack
the name on at the end.
But don’t tell your students!
Free Association
The Goal
• Create the cover of an annual report using three
unrelated elements
• Develop an interactive experience from the
concept
The True Goal
• Break down expectations around logic, order,
and sensibility
• Learn to craft a visual narrative with wildly differ-
ent components
When To Use It
• Students who have difficulty perceiving trends or
common features across multiple elements
• Anytime the class needs to stretch their concep-
tual thinking skills
Further Thoughts
Annual reports have to convey a vast amount of infor-
mation to a diverse audience of shareholders. At the
very minimum, a design team working on an annual
report has to blend hard data, corporate political spin,
and idealized artwork. They have to make it work with
a foundation built largely of subjective interpretations.
And as an added challenge, all of those elements
have to work together so well that the entire effect is
subtle, not melodramatic or obvious.
Sometimes, the elements provided just don’t form a
cohesive whole. But we can’t change a company’s
logo or their office mascot. We can’t change where
their headquarters is located or how attractive the
development team is. We have to build the best story
that we can.
When kicking off this challenge, be sure to have stu-
dents select the elements one at a time. Additionally,
it’s best to do this challenge in class, if only to protect
the separate random generation of the three ele-
ments. Students can easily reverse-engineer the pro-
cess if given the opportunity. If there seems to be too
easy of an agreement between the three elements,
you may try having students pick one element for the
person on their left and then another for the person
on their right. Do whatever it takes to prevent relation-
ships from being drawn too quickly.
“We’re used to
having tightly defined
constraints driving
our design process.
It’s difficult to do
whatever we want
without any guidance.”

I’m Feeling Really,
Really Lucky
The Goal
• Redesign the user interface of a randomly
selected webpage
• Expand that redesign to the entire site
The True Goal
• Work with strong, established Web sites or
within deeply embedded systems to find small
but significant ways to better them
• On a practical level, build a vocabulary for
assessing the effectiveness and purpose of a
Web site’s information architecture and user
interface design
• Understand how interfaces can be broken down
into constituent parts and how their qualities
change when they are attached to or detached
from other elements in the design
When To Use It
• Designers who seem too comfortable with
a design being “done”—i.e. the ones that display
anger or anxiety when you suggest moving a
headline a few pixels
• With younger students, as it is easy to divide
a class into those that grew up with computers
and those that didn’t
• In conjunction with conversations about working
with established brands
Further Thoughts
There are two main approaches to explore for this
challenge, one for the client and one for the designer.
Of course, in the real world, we balance these two
approaches, but it can be helpful for young designers
to study each approach separately.
Depending upon the needs of your class, you can
look to the client for direction when he brings strongly
established work to an agency for improvement. In
these situations, designers have to identify what com-
ponents contribute to the direction and image of the
company and eliminate those that detract from it—
even if those components are highly functional within
the Web site.
On the other side of the challenge is the approach
that identifies pieces within a web environment strictly
by effectiveness and usability. Here, the designer’s
approach drives the project rather than the brand.
While it may seem strange to analyze a Web site from
a purely functional perspective, it’s helpful to remind
your students that well-organized Web sites tell their
own particular story about a company and its direc-
tives. It’s less a straightforward narrative and more like
how a stage is set for the story in advance.
All in all, this is a very basic challenge. Though the
class could spend a lot of time in discussions about
user-centered design vs. brand-centered design,
don’t let those topics distract from the task at hand.
In this challenge, students are deciding in the initial
stages of design exactly who’s calling the shots. Are
we respecting the brand or our own experience? Are
we able to tell the difference?
“Informed choices about our tools help us make
informed choices about our processes. That
helps us develop effective work for our clients.”

It Sounds Better on Vinyl
The Goal
• Make an LP album cover that uses a photograph
and transitions into illustration, or vice versa
• Design the back cover, sleeve, and label for the
record
The True Goal
• Combining skill sets and determining the
common processes behind each
• Using imagery to convey similar themes in a
different art form: music
When To Use It
• Whenever class is feeling a little too much like
work
• Students who struggle with transferring and
applying similar systems and vocabularies
across multiple media
Further Thoughts
The more things change, the more they stay the same.
The layman’s definition of innovation requires that a
designer truly believe that something new can be
brought into the world. And while it’s powerful to imag-
ine the new and exciting things that certain technolo-
gies can bring to us, it’s helpful to remember that the
lessons we learned about the previous technology still
might apply. The systems can be transferred.
The ways that we thought about vinyl records didn’t
simply vanish when the compact disc came to market.
The same can be said about illustration, photography,
and the Internet. Humans have developed very specif-
ic ways to talk about the representation of an image,
regardless of how that representation occurs. There
may be things that can be done in film that can’t be
done on stage, but the ideas represented by both art
forms remain the same.
By deeply exploring the similarities in representative
systems, we can more clearly understand and exploit
those differences. The true power of a particular
technology or media comes from being able to
extract from it exactly what makes it special and
vital to the task at hand. Why do we choose Adobe
Illustrator over a pencil and paper? When is a white-
board better than a handful of sticky notes?
Informed choices about our tools help us make
informed choices about our processes, and that helps
us develop effective work for our clients.
Storybook Ending
The Goal
• Develop a storybook for children
• Ask a toddler to help finish the book
The True Goal
• Learn to tell stories in their simplest form: as the
progression of a single idea over time
• Learn how to establish closure as part of a long-
form narrative
When To Use It
• Students overly comfortable with generating
static ideas in single outputs, or the opposite,
ideas that open up to lots of potential but that
have no final destination attached to them
• Designers worried about creating
meaningful work
Further Thoughts
Telling stories is integral to what we do as designers,
but all too often, we come up with a driving image
and leave it at that. Developing a campaign for a car
that says “freedom” or a perfume that says “beauti-
ful” is relatively easy. But moving that idea across time
can be difficult, even though it’s what makes really
fantastic work. What happens when the customer
buys “freedom,” and where does it take them? How
do we communicate the possible journeys contained
in a technology or service?
Students will be building a foundation for things like
developing personas, targeting demographics, and
creating integrated campaigns—storytelling as a

professional discipline. But you don’t have to tell them
that. The first thing for them to master is how to actu-
ally write a story, and that means that the work needs
a beginning, a middle, and an end. On the surface,
this seems counter to everything that we do; we’re
supposed to be letting the customer decide the story.
We give them choices and freedom and all of that.
But people don’t really work that way. They don’t exist
in a vacuum. They communicate in stories. They need
inspiration. They compare. They can’t forge their own
path if they don’t feel like they know what the other
options are.
Storytelling in design is a good way to communicate
to your team and your client what you’re doing. It’s
a good way to focus your research and narrow your
approach. But when you really push the concept,
storytelling is about giving your audience tools they
can apply. The children’s book in Creative Workshop is
about patience. Children take the story and apply it to
their lives. If it’s not applicable, it won’t resonate. And if
it doesn’t resonate, it won’t create the most rewarding
thing in our careers: meaning.
Dead Philosophers Rock
The Goal
• Create a set of philosophy books that are
visually linked
• Use those concepts in an interactive timeline
for a Web site
The True Goal
• Learn to research and prioritize information
• Develop boundaries to narrow focus within over-
whelming topics or fields
When To Use It
• Designers that have only had to create single
items—an ad here, a poster there
• Students that have developed style sheets and
visual systems, but may need help in applying
that knowledge to more complicated approach-
es beyond just typefaces, colors, and margins
Further Thoughts
This is a practical challenge, because it deals with the
repercussions of research. In order to create a good
series, students are going to have to decide what
would be covered in each book. Philosophy is com-
plicated. There are hundreds of schools, philosophers,
movements, and concepts to sort through. Beyond
the obvious task of making books that look good
together, are the challenges of setting boundaries,
determining categories, and deciding what moves to
the final product and what gets left behind.
Invariably, a student will ask “Should I include
Philosopher X?” Here’s our answer:
We screen out information all day long, usually
because of efficiency. We don’t need to look at the
sky to know if it’s raining. We decide that the question
of “Is it raining?” can be better answered by listening
for the rain, or by looking for puddles, or other informa-
tion. We prioritize the available options. The activity of
“looking at the sky” doesn’t make it to the final product.
Does Philosopher X give you any information that
couldn’t be obtained elsewhere? Or is Philosopher X
the preferred way of acquiring that knowledge?
If students need more work in this area, you can
dramatically increase the amount of time for the chal-
lenge in order to ask for more detail in the execution
and the overall editorial approach for the books. They
can produce a table of contents or a timeline for
each book. Have students compare their organiza-
tional systems, so everyone receives broad exposure
to the different ways that complex information can
be prioritized by different people. They should be pre-
pared to explain and defend their decisions in front
of the class regarding what might be included in the
individual books.
Opposites Attract
The Goal
• Design a book cover
• Repeat the process using a specific pre-deter-
mined constraint on the output (collage, type-
only, etc)

The True Goal
• Explore objectivity and control in representing
these concepts
• Determine individual opinions around cultural
norms or restrictions
When To Use It
• Designers looking for ways to make their work
more politically viable
• Around discussions regarding gender, discrimina-
tion, idealism, and social agreement
Further Thoughts
We carry a lot of cultural baggage. Our culture’s
opinions about abstract ideas such as peace, beauty,
good, and bad can be seen in nearly everything,
from the colors we use to identify gender to the prod-
ucts that television characters have in their homes.
We’re faced with all sorts of subtle (and sometimes not
so subtle) messages on a regular basis about how we
should or shouldn’t interact with the world around us.
This challenge is about learning to identify those influ-
ences. It’s about understanding what words really
mean, to ourselves and to each other. It is not about
being different or about rejecting the opinions of oth-
ers. If two people disagree on what it means to be
beautiful, one of them is not “normal” while the other
is “subversive.” They simply view those concepts from
different perspectives, both of which are vital to a
flourishing culture.
On the other hand, this challenge isn’t carte blanche
to put any old image on the cover because someone,
somewhere, will find that it speaks to them. This project
can help people establish and explain “normal”
(or demographically applicable) for a particular
project so they can build conceptual systems from
that viewpoint.
Book Report
The Goal
• Turn a book synopsis into a book cover
• Either continue the design into front matter and
chapter headings, or read the book and make
appropriate revisions
The True Goal
• Efficient storytelling
• Identifying single images to convey story themes
When To Use It
• Students who come from disparate educational
and cultural backgrounds
• Designers who have worked alone for long
periods of time
Further Thoughts
Book covers tell the story of a story. They have to bal-
ance representing another person’s view while also
justifying their presence as an essential contributor.
Just like a designer…
Depending upon how advanced your students are,
you can easily restrict this challenge to revolve around
its most basic lesson: listening to others. How much
information can we glean about a topic from only a
few minutes of explanation? How quickly can we iden-
tify and communicate the main topics and images
from a particular experience? How much does our
relationship with a person influence the information
that we extract?
Once your students are ready to move this assignment
beyond listening, you can start a discussion about
“How much does our relationship with a person
influence the information that we extract?”

balance in creative work. It’s frustrating to watch a
movie trailer that gives away the whole film. It’s irritat-
ing when a commercial is too obvious. Designs can
careen out of control sooner than we think; suddenly
a layout that casually informed now tells us far too
much. The push and pull of visual storytelling requires
delicate balance.
As designers, we want to be true to the vision and
voice of our clients, but we don’t want to be parrots.
After all, we have our own unique talents to wield. How
do we turn someone else’s experience into something
universally appealing without it becoming exploitative,
or worse, dishonest? And how do we do all of that in a
way that makes us look good?
He Shaves, She Shaves
The Goal
• Design gender-specific and gender-neutral
packaging
• Place these products in a display and incorpo-
rate them into a point-of-purchase environment
The True Goal
• Learn to transition work from the page to the
physical world
• Uncover how we interact with design elements
within 3D space
When To Use It
• Designers without product design experience
• Around introductions to form and how the shap-
ing of a substrate can dictate a design direction
Further Thoughts
We’re trained to think of the page (or the screen) as a
launch pad, a space that allows us to realize our wild-
est designs. But the page is a flat surface, and design-
ers need to be in a different headspace altogether
when they use the page to design 3D products.
This is not about shading or drawing techniques; it’s
about the mental complexities involved in moving a
3D shape from your head to the 2D space of the page,
then into the world as a 3D object again. This is the
first challenge in the book that exploits these com-
plexities, because unlike the “10 x 10” challenge, this
requires three unified outcomes to the problem.
On a side note, though the design examples in the
book involve the same product shape with slightly
different label options, remind your students that the
form need not be the same for each version of the
product. Can they develop a consistent visual system
for a series of products where the container itself
defines its use rather than the label?
Totally Cereal
The Goal
• Design a cereal package based on a brief mar-
keting statement
• Sketch a flattened view of the package that
shows all of the panels
The True Goal
• Work on that old chestnut: showing, not telling—
and when to let this imperative drive the design
process
• Understand why certain products need to be
seen rather than described
When To Use It
• Designers who need more experience with
designing a story around a parity product
• Students who have trouble visualizing dimension-
al packaging concepts
Further Thoughts
Further on the product design front, this challenge lets
designers work with packaging’s role in visualization
rather than its role as “logo holder.”
What does that mean? In the previous challenge, we
looked at shaving cream, a product that doesn’t
need to be seen in order to be sold. The labeling
merely has to describe the product from a functional
perspective. We need to know who makes it and
when to use it. No one’s going to eat it.

Cereal packaging, like most food packaging, is a
challenge specifically because people do eat the
contents. There are very few boxes of the stuff out
there that don’t have a picture of at least one or
two flakes on the front (enlarged to show detail).
Consumers want to see what they eat, and a picture
can easily tell them about the crisped rice, raisins, or
choco-biscuits. Plus, pictures leave room on the box
for the nutritional information, which isn’t so easy to
convey in a photograph.
Encourage your students to play with the idea of
showing as a way of telling about a product. Note that
the examples in the book play with how the cereal
is shown; some have illustrations, while others have
clear panels to display the actual product. What
determines a designer’s decision to show the actual
product as opposed to a representation of it? There
are many examples of this on the market with different
products. Why do we need to see the actual pencils
we buy but not fish sticks?
Imaginary Film
The Goal
• Design a DVD cover for an imaginary film
• Design a movie poster for that film
The True Goal
• Learn how to make single images convey com-
plex stories, successfully
• Understand the vocabulary of images and text
within a cinematic context
When To Use It
• Designers who are coming from or moving into
the realm of video
• Around conversations of visual complexity —
specifically when a design should be simplified
and how to do it
Further Thoughts
This challenge works very well with “Book Report.”
It’s the same concept in reverse. Though the “have
the audience guess” part of the challenge sounds
fun, it’s actually the most important part. Like a book
cover, DVD packaging has to sell the product inside.
But a DVD is selling visual images rather than the
audience’s imagining of those images. As a result, a
designer working with video or film has to communi-
cate a story with a greater degree of precision.
There’s an entire cinematic philosophy around how
certain angles, motifs, and even wardrobes commu-
nicate critical details to an audience. But a designer
doesn’t necessarily need to understand all of that to
create an effective package. Students will need to
come up with a good story and then design for that
story; generating their own ideas will be enough of a
challenge without having to worry if the design really
says, “The butler did it!”
The Take It Further for this challenge will help students
work with a larger form, which of course means that
they have to further refine their original output. Use this
poster constraint with students are struggling to sim-
plify their designs.
Creature Feature
The Goal
• Design a Web site about the history of monster
movies
• Design an interactive experience around a par-
ticular monster movie
“Designs can careen out of
control sooner than we think;
suddenly a layout that casually
informed now tells us far
too much. The push and pull
of visual storytelling requires
delicate balance.”

The True Goal
• Learn how to construct taxonomies for Web site
information architecture
• Explore how to art direct Web sites to include
more immersive video content
When To Use It
• Designers ready to tackle larger Web sites with
more intricate information architecture
• Students looking to incorporate video into their
Web site designs
Further Thoughts
This is another challenge that builds on the lessons
learned in a previous challenge; this time, it’s “Dead
Philosophers Rock.” The key difference here is that,
even at its most comprehensive, the history of monster
movies is relatively short and sweet when compared
to the history of philosophy.
It’s easy to put a lot of information on a Web site, but
it’s difficult to make the content useable, let alone
entertaining. Designers have to plan the journey of a
user through a system. Each question in the construc-
tion of the monster movie site points to a particular
skill required for effective Web design.
Deciding on an effective way to let a user search for a
particular movie, for example, can lead a student in
any number of directions. Are movies identified by title
and year? What about theme or actor? Is there a way
to find movies that are based on classic horror novels?
Designers can apply any organizational system they’d
like to the site; they just have to defend their decisions.
Ten-Second Film Festival
The Goal
• Create the user interface for a short movie festival
• Consider the ramifications of shorter movies—
five seconds or even two
The True Goal
• Think about sequential content and how to orga-
nize it
• Minimize the amount of effort it takes for a user to
move through a large volume of data to access
content they want
When To Use It
• Whenever your students have become compla-
cent or over-confident in their Web site design
skills
• In discussions about effort and ease within inter-
face design
Further Thoughts
We don’t mean to bait-and-switch on you, but some-
times it’s best to sneak up on a lesson in order to
capture it. This challenge has nothing to do with the
actual output. The Web site is secondary. This chal-
lenge is about determining how to deal with so many
tiny pieces of film.
“Social media has transformed the way we think
about the effective length of a communicated idea.
And while social networking tools are a nice place
to start for students that are stuck, they don’t
address the root of the problem.”

Ten seconds isn’t very long. If your students think this
one is too easy, just ask them to quantify one key com-
ponent of the user experience—exactly how many
clicks is it going to take to watch all of the movies in
the festival? What if there are 50 films? Over a hun-
dred? If they’re paying attention, your students will be
cowed by the cacophany of clicks filling their heads.
The ideal user experience is going to take work.
Social media has transformed the way that we think
about the effective length of a communicated idea.
And while social networking tools are a nice place to
start for students that are stuck, they don’t address the
root of the problem. These short films have to be dis-
played, rated, selected, and sorted with relative ease,
and that has its own inherent complexity.
I’ve Got a Golden Ticket
The Goal
• Design a store experience with only three
products
• Make a physical prototype of those products
The True Goal
• Begin to design for an experience rather than for
individual content items
• Think about overall brand decisions rather than
specific pieces of merchandise
When To Use It
• As an introduction to environmental and interior
design
• Students who are less experienced in brand or
theme-driven designs
Further Thoughts
The viability of a space is driven by market forces. If
you aren’t buying something there, it’s a bad store.
And the more product that you have in a store, the
more money you can make. Stores have stuff. The
more stuff, the more profit. It’s all pretty simple. And
insidious.
Because the “more stuff” ideal can backfire, causing
brand confusion or even indifference among consum-
ers. The question here is whether you can design an
effective selling environment with a limited number
of products. Can your students conjure a space
that entices people to buy, simply by being a well-
designed space? Can a company’s product (and
their store) become successful, not because it has
blanketed every corner of the market with dozens of
unique products, but because it does one thing and
does it well?
If there are students struggling with environmental
design, send them back to “He Shaves, She Shaves.”
Environmental design is a large can of shaving cream;
well-thought out and elegant packaging design fits
within it. We are already conditioned to think of a store
as a place where you buy things, so thinking of the
store itself as a large package shouldn’t be too much
of a stretch.
Flapping in the Wind
The Goal
• Develop a guerrilla marketing campaign
• Write an experience of this event from an “as-it-
happens” perspective to refine the overall idea
The True Goal
• Build methods to communicate highly personal
experiences in objective terms
• Learn to communicate anticipated outcomes
that are not directly sales-related to clients
When To Use It
• Designers needing to work on personal communi-
cation skills
• Students who have not done design work around
real-world experiences
Further Thoughts
Guerrilla marketing events are just that: events.
And like most events, we relate them to others in

photographs or status updates, because we under-
stand that every person’s experience of that event is
unique. From a marketing perspective, however, we
have to be focused. It has to raise brand awareness.
People can’t just have their own grand time while our
client gets nothing.
The Take it Further will help students work with their
own vocabulary around subjective events. Students
probably won’t have a lot of experience in objectify-
ing personal experience. It’s not a skill many of us
have to begin with. When we communicate with
clients, however, we have to turn uniquely personal
experiences with singular events into relatable stories
for our clients to invest in. Our target audiences have
to be unique, but not so unique that they won’t fit into
a particular archetype or demographic. If we give
a client too many individuals to design for, the event
looks less like marketing genius and more like an
entertaining distraction.
Going to Seed
The Goal
• Make an online magazine with a unique grid
• Transition this online experience into a print
solution
The True Goal
• Learn the difference between use of grid systems
for the Internet and grid systems for the printed
page—they each have their own quirks
• Find out how to make a grid feel invisible
When To Use It
• Designers transitioning to the Internet from print
• Students whose designs are overly strict or rigid
in appearance
Further Thoughts
It’s two dozen exercises later, and the grid is still
important.
Organizationally speaking, the grid systems used
on the Internet are solid. They are consistent and
inflexible. We sculpt our content to fit the grid, trim-
ming video windows and scooting menu bars around
like Tetris blocks. Designers are proud when their
Herculean efforts to “make it fit” yield a dizzying for-
tress of perfectly arranged rectangles and squares.
None of those strategies will work for this particular
client, whose entire brand goes against that aesthetic.
Designers have to maintain the grid on Web sites
for obvious reasons, but it is possible to fold a sense
of openness into the interface. Challenge your stu-
dents to find other ways to keep their content straight.
If your students have ever studied the Fibonacci
sequence, they can tell you that it’s easy to see it
clearly in the nautilus shell. But do they know it’s also
in the center of a sunflower, a structure few think of
as being orderly?
Sell Me a Bridge
The Goal
• Make a compelling online banner for a low-
excitement place
• Develop a rich media ad to romance the actual
location
The True Goal
• Learn how to finish assignments that you really
don’t want to do
• See above, this is a very difficult thing!
When To Use It
• Students who have not worked in the “real world”
• Designers overly attached to their politics, their
typefaces, or their hipster license
Further Thoughts
It would great if our careers contained an endless
stream of cool projects. We could be art directing
photo shoots on exotic tropical islands, designing
posters for blockbuster movies, or spending long
dreamy days putting the finishing touches on our
3,977th album cover design for artists like U2. But a
career in design doesn’t always work that way.

We sometimes have to take on projects we don’t
want, working for clients we don’t like. We might not
even realize how terrible a project is until we’re several
weeks into it.
Figuring out how to stay motivated during these dark-
est of hours is the number-one challenge for any
creative professional. And the fickle nature of creative
motivation means that we’re continually reassess-
ing what helps to motivate our best work. Barrelling
through one project might require Pink Floyd’s “The
Wall” on continuous loop, while the next late night
might demand pounds of dark chocolate.
Students develop a sense of their strengths and weak-
nesses with particular skills and programs pretty fast.
But beyond those tools and skills, we always have a
client who needs us to deliver a convincing final prod-
uct—no matter whether we’re disconnected from the
subject matter at hand or just plain hung over.
Sometimes our most powerful—and overlooked—tool
is willpower.
Let’s Take a Nap
The Goal
• Create a poster using techniques that are in
opposition to your usual style
• Print the poster and observe people’s reactions
to it
The True Goal
• Work to define your personal style and find ways
to expand your repertoire
• In Take it Further, begin to work with observing
reactions to design in the general public
When To Use It
• Students who have yet to develop a style, or those
in denial about the obviousness of their style
• On the subject of the challenge: conversations
about work-life balance
Further Thoughts
We’ve all got talent. And we all know where to find tal-
ent if we don’t have it: the people we know. But after
a while, we can sink into familiar relationships with our
talents and our friends. We become known for that
one cell phone ad we did a few years back. We have
the dog portrait lady on speed-dial. At first, it’s style.
Then, we move on to stuck.
Style is really about preferences and the decisions
we make that appeal to us. As designers, we tend to
have a greater technical mastery within the media
we prefer. From the wonders of ravioli to the effort-
lessness of Helvetica, we simply have a more robust
vocabulary for what we like. In this challenge, stu-
dents will first have to identify their preferences, then
decide on what would comprise its opposite. Are
hand-drawn scribbles really the opposite of sans-serif
typefaces? Have them explain their choices, as subtle
design preferences can permeate work when no
one’s looking.
Sleeping is a good metaphor for discussions around
style. When we step away from the daily grind to sleep,
we encounter the weird and wonderful inside of us.
“Figuring out how
to stay motivated
during these darkest
of hours is the number-
one challenge for any
creative professional…
Sometimes our
most powerful—
and overlooked—
tool is willpower.”

42 Teaching the Challenges: Materiality
Materiality
Type Face
The Goal
• Construct a typographic portrait out of
quotations
• Construct a portrait of multiple people
The True Goal
• Think of type as an illustrative facet of design
• Understand how legibility truly functions within a
design
When To Use It
• Designers who are weak illustrators—they prob-
ably know who they are
• Students needing extra help in pairing images
with copy elements
Further Thoughts
This challenge revisits the work begun in “Easy as
ABC” from earlier in the book. Students learned in
that challenge to view and construct letterforms
from materials drawn from the outside world. Here,
they are being asked to mould those letters into
illustrative components, which seems easy. However,
we’re frequently taught that the most important thing
about a typeface is its legibility and transparency for
content. “If you can’t read it, you should change it…
make it simpler!”
For this challenge, that dictum is turned on its head.
Depending upon the chosen illustrative style and
typeface selection (or creation) made by the student,
the readability of the quotation could easily devolve in
order for the portrait itself to become more apparent.
Controlling this balance between typographic leg-
ibility and illustration fidelity is completely up to you.
If you want the portrait to be perfectly clear, or vice
versa, be sure to specify. Of course, the ultimate chal-
lenge would be to ask your students to deliver both on
equal terms.
Lick it Good
The Goal
• Make a set of six stamps
• Design a commemorative booklet for the stamps
The True Goal
• Develop a series within a limited style
• Understand how size influences fidelity
When To Use It
• Around conversations about size and visibility
• Students needing to learn how to be flexible
about when it’s appropriate to detail their work
Further Thoughts
Designers face a steep learning curve when extreme
size enters their world. Working on the fringes, large
and small, demands a more iconic style. Billboard
ads don’t have the capacity to convey the volume
of content that a magazine ad can. This may seem
odd, at first, considering that one is substantially larger

43Teaching the Challenges: Materiality
than the other. The fact is, once we reduce or explode
something past a certain size, we lose fidelity.
The intricacy of the illustration styles can be tricky
for students. They’ll watch as their seventeen-layer
collage stamp loses all detail and dimension when
reduced to something less than an inch wide. This
lesson easily transfers to treatments involving things
like company logos and photographs. There are
times when every pixel has to be perfect, and there
are times when no one’s going to be able to see the
brown gecko perched on the second leaf from the
top of the first palm tree in that commemorative post-
age stamp from Bali.
But realistically, the distances involved when viewing a
billboard have the same effect. Whether big or small,
this design problem will show up eventually.
So if they teach the same lesson, why did we pick
postage stamps over billboards?
Postage stamps are a lot easier to fit in a classroom.
Never Tear Us Apart
The Goal
• Make a poster out of torn objects
• Decide how the designs elements from the poster
could be used in a live setting
The True Goal
• Work in three dimensions, without a computer
• Gain a vocabulary for discussing representations
of real objects—especially via the medium of
photography
When To Use It
• Designers lacking photography skills or the abil-
ity to talk about photography (especially texture,
lighting, and dimensionality)
• Students who are too attached to their computers
Further Thoughts
It’s another anti-computer challenge! By now, your
students should have discovered that the computer,
while powerful, is only as strong as the designer at
the keyboard. And while interacting with the real
world is an important part of being a designer, it
can be a tough sell for those born and bred using
computer tools. Some people don’t want to deal
with clients or be outside taking pictures of bridges.
They’ll never have to ask a photographer to adjust
the depth of field to make the copy more legible or
to tone down the contrast so the logo really pops.
These masters of post-production can do it all with
Adobe Creative Suite.
There is something to be said for staying inside and
working away. However, there comes a point in every
designer’s career where she has to render a realistic
object. And good rendering requires a complete
understanding of the form in order to represent it
realistically on screen. It could be an apple or a car;
it really doesn’t matter. If she hasn’t manipulated and
observed three-dimensional objects in the real world,
her attempts at reproducing them on a computer
don’t stand a chance. She’s a mouse-click away
from the drop shadow of death.
Trompe L’Oh Wow
The Goal
• Make a logo that incorporates an optical illusion
• Create a corresponding branding kit that
includes a magic trick
The True Goal
• Fail as a group (probably)
• Celebrate individual genius (hopefully)
When To Use It
• Around discussions of easy projects
• Whenever your class needs to fail, or whenever
they need a class hero
Further Thoughts
This challenge can be deceiving. We know a lot of
individual optical illusions, but it’s difficult to finesse
those into workable designs.

So as the instructor, your job is a simple one: let your
students fail. This will probably be the first challenge
that few can complete in the time limit to a level of
satisfaction. Plus, depending on the experience of
your students, this may be the first project that any of
them have ever failed. Most designers don’t get the
opportunity to think about how to process failure and
talk to clients under those circumstances.
Then again, you might have a student who really
delivers. In that case, it’s a great opportunity for
your class to learn how to celebrate inspired design.
Recognizing the efforts of others, especially when
they’re doing better work than you are, is an essential
skill for any designer. We learn a lot when we
make mistakes, but we can learn just as much
when others don’t.
I Heart Plaid Candles
The Goal
• Design a high-end candle whose package incor-
porates a plaid pattern
• Expand to paisley, or design an advertisement for
release of the candles
The True Goal
• Challenge notions of attractiveness
• Begin to explore ethics and responsibility in
design
When To Use It
• Students who frequently borrow motifs from other
sources as “inspiration”
• Designers who need to explore more linear
designs or that need more work with color theory
Further Thoughts
There are two main paths for this challenge; feel free
to choose according to the needs of your class.
The first path is more obvious. Plaid can be garish and
hard to coordinate with. Of course, a lot of people
find plaid brands, such as Burberry, not only attractive
but also collectible. Can your students toe this line
between eye-catching and plain old ugly?
The second path is a little more time-consuming,
but it can be a great way to introduce people to the
concept of responsibility in design without requiring
a sermon.
We design things with sustainability in mind, use
soy-based inks, and try to keep unethical companies
out of our portfolios. Many a designer has vowed to
never work for an oil company. Appropriation can be
a dirty word.
What about plaid, though? Historically, the tartan is
representative of a particular culture, and the color
combinations are unique to each clan. Will your stu-
dents research this to find an arrangement that hasn’t
been used? Are alcohol companies off-limits while
their selected plaid is fine? This is a great opportunity
for students to understand what cultural meanings
may be hidden within the patterns they select, and
their limits around what they include in their work.
Outdoor Wedding
The Goal
• Make a set of wedding invitations out of natural
materials
• Make decisions regarding mass production of the
cards
The True Goal
• Work within a tight series, without taking copy ele-
ments for granted in terms of consistency
• Begin to plan assembly timetables and learn how
to adjust them
• Understand the complexities around how we
describe and label art
When To Use It
• Students lacking significant prototyping or assem-
bly experience
• Students requiring work in designing a tightly con-
trolled series

Further Thoughts
There are many different things happening in this
challenge. We’ll briefly touch on just three.
First, some students may have had experience design-
ing a series, but this challenge is a little tighter in
scope. Each invitation they create has to convey the
same information, and it’s only the decorative details
that differ. Because of this, your students may take
consistency for granted.
Next, from a timetable perspective—this may be one
of the first projects where a student is having to com-
plete multiple pieces for a project with a production
mindset. As you finesse the assignment, they’ll have
to decide how to best develop a flow for assembling
each finished piece. Help them make any adjust-
ments necessary for them to focus on shoring up
weaknesses in their production skills.
And finally, while we make a lot of unique works as
designers, very little could ever be considered art. This
challenge, including the Take it Further, can open
significant discussions around how we label art. Each
invitation is unique, but it’s being mass-produced for
commercial purposes. Is it design? Is it art? What if
one person assembles them all? What about three?
How are their answers influenced by the classic studio
art system, in which a single artist employs multiple
workers to execute proprietary designs?
Crane Promotion
The Goal
• Design a brochure that incorporates origami
• Design brochures that interlock
The True Goal
• Think of paper-crafting and prototyping in a new,
different light
• Uncover multiple uses for a single design, incor-
porating layered thinking
When To Use It
• Students who have had little experience in work-
ing with the medium of paper
• Students who think they know print design
inside out, and need to learn what they don’t
know about the complexities of dimensional
paper design
Further Thoughts
We’re halfway through the book; it’s time for some-
thing really cool!
Origami has a rich history, and it has recently expe-
rienced a renaissance of sorts. Paper-manipulation
and folding isn’t just for kids anymore; scientists use it
for atomic modeling. It’s a unique way to talk about
multiplicity in design. Can a piece work on multiple
levels, not only from a functionality perspective but
also on a representation level?
Students may struggle with the origami mechanism
itself, and that’s okay. We don’t have to master every
challenge thrown at us. The important thing for the
students who fumble their folds is that they internalize
how form can provide another level of meaning to our
work. A brochure that doubles as origami can imply
complexity and precision in the same way as the
architecture of an elegant building, or the unfolding
of a delightful user interface design.
“A brochure that doubles
as origami can imply
complexity and precision
in the same way as
the architecture of
an elegant building.”

Just My Prototype
The Goal
• Generate a web site redesign through paper
prototyping
• Move a user interface design in a more functional
direction by incorporating tool tips, menus, or
other navigation
The True Goal
• Begin thinking about usability and functionality,
and how those ideas might be compromised
without exploring physical representations of a
system
• Discuss the differences between screen testing
and physical testing methods
When To Use It
• Around instruction about prototyping
• When discussing the importance of usability
Further Thoughts
Much like “I’m Feeling Really, Really Lucky,” this chal-
lenge will force designers to play with the information
architecture and overall organization of content for a
user interface. The use of physical prototyping allows
the students to go through an easy-to-understand
process before they jump onto the computer to apply
spit and polish.
This also provides a venue for students to begin think-
ing about how to test their organizational ideas before
they fully execute any interface design. Encourage
your students to take their raw, interim paper pro-
totypes and put them in front of people. Does the
arrangement of content make sense? What would
those people expect if they were to click on one of the
items on the page? Do the words on each sticky note
make sense to them?
The lower the fidelity in a user interface design, the
more a designer can focus on meeting your user’s
expectations regarding content arrangement. This
is information students may not be able to glean as
quickly if they expended the time and energy to fully
execute every interface concept that came to mind.
Reduce, Reuse,
Redecorate
The Goal
• Design a piece of furniture out of bulk recyclable
materials
• Show how the piece would be sold online
The True Goal
• Start discussions about waste and sustainability in
design with clients
• Educate ourselves about reusability strategies, as
most of us are already familiar with strategies for
reducing resource impact at the start of a project
When To Use It
• Students with little practical experience in
sustainability
• Designers accustomed to producing interfaces,
where concerns about disposability and reuse
may be minimized
Further Thoughts
The actual output of this challenge is less important
than your students understanding that there is a real
physical cost to producing material for clients. A sim-
ple red-and-white swirling holiday design on a paper
cup for a powerful client can introduce thousands of
pounds of waste in a very short time, depending upon
the scope of the project. How do you measure the
impact of the cup’s manufacture, usage, and dispos-
al, and more importantly, can you take some measure
of responsibility for it?
While we may not be able to convince our clients to
hold off on sending a million pieces of direct market-
ing through the mail, as opposed to only announc-
ing their big annual sale on their Web site, we can
encourage them to use recycled or reclaimed materi-
als in production. We can educate them about reus-
ability strategies for their particular product. We can

start the conversation and be informed about the
available options. Some clients will never consider (or
even be aware of) alternatives until we suggest them.
Sustainability efforts are most effective when they are
part of the overall design strategy, rather than treated
as an afterthought.
Printed and Sewn
The Goal
• Craft an identity system that incorporates sewn
elements
• Extend that motif into a Web-based system
The True Goal
• Determine how to incorporate individual flourishes
into an identity system
• Think about the small ways that our style perme-
ates our work
When To Use It
• Students who would like “craftier” projects
• Designers feeling as though most of their projects
can’t be influenced by their personal style
Further Thoughts
There are standard tools we reach for that are part of
our artist’s arsenal: pencil, eraser, pen, whiteboard,
paintbrush, and so forth. Then, there are what we
might call craft-only tools, which do not lend them-
selves to the individual artist looking to quickly mass-
produce a design idea in a cost-effective manner.
Can you imagine making 10,000 business cards out of
needle, thread, and cloth?
This challenge will help designers understand the time
cost that comes from wanting to place individual flour-
ishes onto items that are mass produced—either for
efficiency of production, to minimize overall cost, or to
achieve effects that can’t be made easily in the home,
like embossing and debossing.
Such treatments often help a design idea transcend
the ordinary and truly stand out for a client, but every
designer must be aware of the cost of each flourish,
both in person-hours, hard costs, and corners that
can’t be cut without degrading the original idea
into a ghost of its former glory. After all, who wants
a sublime design idea to unravel before their very
eyes because of a detail that the client didn’t want
to pay for?
Record Store
Puppet Theatre
The Goal
• Develop a 30-second commercial shot in one
take with no effects—with puppets!
• Design an in-store event with the puppets
“Some clients will never consider (or even be
aware of) alternatives until we suggest them.
Sustainability efforts are most effective when
they are part of the overall design strategy,
rather than treated as an afterthought.”

The True Goal
• Start building a framework for video prototyping
• Work within the frame, and learn about how to
actualize what you are pre-visualizing in your
mind
When To Use It
• Students without extensive film production
experience
• Designers lacking the eye to develop high quality
executions the first time out
Further Thoughts
Many a photography instructor laments the digital
age. Computer programs give us the ability to do
nearly anything with our images, but we lose a lot
of discipline in the initial stages of creation when we
can “fix it in post.” We sacrifice quality for the bells and
whistles of the finishing touches.
We can also lose the ability to see what’s in front of us,
because we’re always looking to the future. Imagine
how powerful our photographs, layouts, and logos
would be if we stopped thinking about fixing our mis-
takes after the fact. How much more effective would
our ideas be if they were already there in what we
captured, if they were—using trendy slang—“real”
and authentic?
In raw video, especially how it’s handled in this
challenge, students can’t hide a flawed concept.
Impromptu video exchanges like this reveal the holes
in any raw ideas, because without the shine of post-
production, students are forced to process exactly
what they see during filming. They may think they’re
making the puppets talk while on camera, but the
truth is the opposite once they start to watch what’s
been recorded.

49Teaching the Challenges: Instruction
Instruction
Robot Army
Mail-Order Kit
The Goal
• Design a robot that can be assembled in
10 minutes with instructions
• Extend that design into a robot that can be
personalized
The True Goal
• Work within time constraints and learn to appre-
ciate skilled and unskilled approaches to those
constraints
• Determine instructions for what you create for
others to follow—and how to write them
When To Use It
• Designers who have just left school or are new to
an agency setting
• Older and more experienced students ready to
improve mentoring skills
Further Thoughts
Designers don’t often get to order people around,
at least not at the beginning of their careers. We’re
always someone’s lackey.
On the one hand, this is a good thing. In those first
few years, we’re unlearning a lot of bad habits from
school. Almost every situation is a process or fea-
ture of an application that is new to us. We’re being
instructed all the time.
On the other hand, when anyone and everyone is
telling us what to do, we can lose sight of exactly what
goes into effective teaching and instruction. We also
might not have time to explain our work in the same
way that we did at college.
In this challenge, students have to figure out exactly
how to tell someone what to do within a very short
time period. Instructions must be precise and effec-
tive; don’t allow them to provide any extra screws in
this project. There should be no waste in the process
that each student defines.
Poster by Numbers
The Goal
• Design a set of instructions to make a poster
• Provide feedback to your designer based on the
product
The True Goal
• Learn to balance control and direction in design
when dealing with other people
• Teaching students how to consider the creation
of a creative brief
When To Use It
• Students who have never supervised another
designer
• Students who have supervised other designers,
but that are uncomfortable with the process

50 Teaching the Challenges: Instruction
Further Thoughts
This challenge is less about creating more robots (a lá
the previous challenge) and more about control and
art direction. In effect, this challenge is about con-
structing a creative brief.
Within a short period of time, students will need to
determine not only the instructions for assembling a
poster, but also how to negotiate the aspects of those
instructions that they can’t (or don’t want to) control.
Are they really going to specify where each line of
copy will go by using measurements in millimeters? Or
is their approach more freeform, which can also be
a minefield if their instructions involve too many ele-
ments and not enough direction?
If you have a little more time, you can have each
student create their poster and then write the instruc-
tions from it. Have them withhold their own poster until
another student has finished following their directions.
Then, have them analyze the differences to see where
they are comfortable in giving up control, and where
their instructions may need to be finessed.
Seeing What Sticks
The Goal
• Execute a one-page visual that explains how you
make pasta
• Use that visual to improve one or more steps in
your process
The True Goal
• Learning to observe before adjusting behavior
• Understanding process before attempting to
improve it
When To Use It
• Students who are quick to critique work
• Designers who need more observation-based
experience
Further Thoughts
Whatever you do, don’t make this more complicated
than making pasta. As soon as you give in to students
complaining about how pasta is too simple, you’ll
invite all sorts of trouble into this challenge. A student
who can’t manage to construct a visual narrative
around a simple task has no business asking for
something more difficult. This is about observation, not
execution, and we don’t know how anyone can be
“too good” at observing behavior.
As designers, we can’t try to change a process unless
we understand it. We need to know it inside and out,
and there are relatively few that we can simply imag-
ine in our heads. We have to see it and watch how
things play out. Simple tasks like pasta preparation
are straightforward, but they still incorporate the indi-
vidual style and flair of the user. If we miss these details,
assuming that it’s just a simple task, we miss most of
the opportunities for improving an experience.
Further on that last point…this is also a good experi-
ence for students to talk about cultural fixations on
improvement. If we’re constantly looking to improve
something, how will we ever appreciate what we have
when it really is perfect? This isn’t about allowing mis-
takes; it’s about understanding the essential nature
of certain ways that we work as humans. There are
things about who we are and how we function that
don’t need to be fixed.
Check Me Out
The Goal
• Improve the checkout experience at a local gro-
cery store by developing a user flow
• Ask test subjects to interact with your ideas
through prototyping
The True Goal
• Learn to incorporate and explain significant vari-
ables within a user flow
• Wield observational methods in a bustling live
setting
When To Use It
• Students beginning work in user experience and
ready to move into the field of design research

51Teaching the Challenges: Instruction
• Around discussions about outliers and unpredict-
ability in design—how many people do we have
to compensate for in what we create?
Further Thoughts
This challenge is a direct application of the lessons
learned from “Seeing What Sticks,” the previous chal-
lenge. This is a complex interactive system, and it will
have to be observed in the wild. While the student
is still the subject, she’ll have a lot more exposure to
random elements, including other customers, varied
goods, and multiple technologies.
This is a great opportunity for students to compare
user flows to begin to grasp just how different people
are when it comes to how they fulfill complicated
tasks. Everyone’s user flow will have some similarities
though, and that’s how students should approach the
problem. By casting a wide net over the system, they
will have to let some eccentric users escape, but their
improvements will have a greater impact. Talk to stu-
dents about how they can take all of their user flows
and synthesize them into a single flow that accommo-
dates all of the major observed behaviors.
And don’t let your students move on to this challenge
unless they’ve made significant progress with their
pasta. It’s never smart to go shopping on an empty
stomach.
The Sustainability Game
The Goal
• Create a simple game for children about
sustainability
• Think about distribution strategies that are also
sustainable
The True Goal
• Think about game design as system design
• Understanding the exponential relationship of
adding variables to a complex system
When To Use It
• Designers with a propensity for overdeveloped
systems or designs
• In discussions around simplicity and efficacy
Further Thoughts
You could easily make this challenge all about the
content. How do you explain sustainability to a child?
How do you get an audience excited about a topic
over which they have little to no control? How do you
make something simple yet effective?
It’s this last question that’s really the focus of this
challenge. Designing a game is very systematic.
There are a number of paths a player can take and
a certain number of obstacles that they will encounter
along the way. What we often forget is that each
additional variable or feature that we include has
major repercussions.
For each element we add to our game, we add
another layer of exponential complexity to the system.
Each token or card needs an explanation and each
one can move the game in a different direction, even
when the end goal doesn’t change. The challenge
for students will be to design a system that represents
a multi-faceted idea. The system will have to balance
between glossing over content when appropriate and
not confusing the user with too much detail.
“Designing a game is
systematic. There are
a number of paths a player
can take and a certain number
of obstacles that they will
encounter along the way.
What we often forget is that
each additional variable or
feature that we include has
major repercussions.”

52 Teaching the Challenges: Observation
Observation
Patience, Grasshopper
The Goal
• Design a greeting card
• Create a series of cards or other printed
sentiments
The True Goal
• Teach in-depth observation skills
• Focus on how observed moments can become
insights
When To Use It
• If students aren’t paying close attention to impor-
tant details
• As an introduction to design research techniques
Further Thoughts
Designers like to make things. They walk around with
sketchbooks, mechanical pencils, mobile phones,
and other tools that help them capture the details that
surround them. These tools become extensions of how
we make sense of the world: through words, sketches,
photos, and other artifacts.
By tearing these tools out of the designer’s hands,
and forcing them to make sense of the world without
recording their thoughts in a tangible form, they must
become aware of what they are thinking and feel-
ing. We hope that this challenge will help them find
a greater capacity to consider potentially conflicting
and divergent observations.
So, in a sense, this challenge will help make your
students more sensitive and empathetic. They’ll be
primed to suspend judgment and make associative
leaps from data wherever they are, even when they
aren’t “designing.”
Tour de Home
The Goal
• Create signage for your neighborhood
• Design walking tour materials
The True Goal
• Improve in-depth observation skills
• Construct effective wayfinding systems that repre-
sent more subtle landscapes
When To Use It
• Students interested in map design and
informatics
• In a class where important details are consistently
overlooked by the students
Further Thoughts
How many trees are across the street from your front
door?
You see them every day, so you should know, right?
You probably don’t because you might be on autopi-
lot, desensitized to the surroundings that you see most
frequently. Yes, you are paying attention; it’s more
likely that you’ve got more important things on your

53Teaching the Challenges: Observation
mind. If you’re focusing on tuning in a Pandora sta-
tion or chatting with your friend about tonight’s dinner
plans, you don’t really need to count the trees. They
just aren’t a priority.
This challenge forces students to observe things
they’re already familiar with in their neighborhood,
with a fresh perspective. It makes them learn how
to “other” themselves, seeing how the people in their
community value the things around them. That coffee
shop may have better coffee, but that other shop is
closer to the dog park. Students will have to observe
not only the surroundings they see every day, but also
how their neighbors prioritize those spaces.
Encourage students to flex their poetic muscles
with their signage. Every neighborhood has a great
restaurant and a quirky jeweler. But not every street
hides a beautiful bench overwhelmed with ivy—the
best place in the city to watch fire-engine red leaves
wavering in the autumn wind. It’s these hidden gems
that make a place worth visiting.
Wacky Vendo
The Goal
• Make a vending machine
• Show it in the context of a photograph
The True Goal
• Learn to design for interaction and how self-con-
tained products may influence flow in a public
space
• Explore basic principles of industrial design in
action
When To Use It
• Students wanting to explore the interplay
between industrial and interaction design
• As a lighter moment between more difficult
challenges
Further Thoughts
This challenge can be as deep or as shallow as you
need it to be.
In a few short minutes, your students could produce
absurd sketches of all sorts of off-the-wall vending
machine ideas.
Or, with some initial research and planning, they
could generate truly innovative concepts that facili-
tate anything from providing food to homeless people
to offering them customized automatic MP3 down-
loads to their iPads. You could even have students
tackle the mechanical and industrial engineering
necessary to build their ideas out.
Either way, the overall premise is wacky enough that
students won’t take it too seriously—which makes it a
great way to introduce the core skills necessary for the
larger interaction and industrial design challenges
they’ll be working on later in the book.
Excuse Me, I’m Lost
The Goal
• Redesign local hospital signage
• Create a complete wayfinding system
The True Goal
• Begin to empathize with a target audience
• Translate observed customer problems into
design improvements
When To Use It
• Any time there is a question about whether
design problems can be solved in the mind
without direct observation; by now, your students
should know this is a trick question
• Designers interested in wayfinding and informa-
tion design
Further Thoughts
An improvement in finding the emergency room can
save lives. For students concerned about “making a
difference” with their work, this challenge is a great
start. But alongside manipulating motivation, make
sure that your students stay grounded in the prac-
ticalities of this assignment. Efficient flow through a
public space is the result of many factors; signage

54 Teaching the Challenges: Observation
immediately springs to mind, but what about the
language of those signs, or things like lighting, arrows,
furniture, and paint?
If you have extra time, consider splitting your class into
two teams. Give half of your class photos of specific
problem areas at a local hospital and ask them to
redesign it with no other information. Send the other
team directly to the hospital to observe the same area
for an hour or two before attempting a redesign. Then,
have each half of the class present. Let them discuss if
there are any perceived differences in the output.
Thinking Outside
the Wrist
The Goal
• Design a wristwatch
• Make a prototype and see how it changes
behavior
The True Goal
• Find unique design opportunities within a well-
served market
• Reinforce the concept of effective time
management
When To Use It
• Designers who are beginning to work with diary
studies or more personal research methods
• Students transitioning from school or from free-
lance to agency commitments
Further Thoughts
This challenge can work on two different levels. If
you’ve got a group of designers fresh out of school
or moving into an agency from the freelance world,
have them work on this as a time management lesson.
When we’re in school or working for ourselves, we can
stay up until 3:00 am to finish a project. We can gener-
ate sketches on weekends and walk the dog during
client meetings. In these situations, our work time
spreads throughout the days and we lose the ability
to track when we’re actually working. It takes a lot of
discipline to prevent this freedom from turning into
anarchy. Worst-case scenario? We don’t bill properly,
we lose money, and we lose sleep. This challenge will
help designers understand how they’re whittling away
the hours.
If your students have been out of the classroom for a
while, the time management portion of this assign-
ment may not be as applicable. If this is the case,
have them focus more on the personal research por-
tion of the challenge.
We often think about design research as the observa-
tion and analysis of other people’s behavior, revealing
how those behaviors are influenced by their attitudes,
beliefs, needs, and desires. When we have to observe
our own behaviors, we tend to lose the ability to pin-
point those same factors. A week-long diary study will
help designers gain empathy for their future subjects.
“When we’re in school or
working for ourselves, we can
stay up until 3:00 am to finish
a project… It takes a lot of
discipline to prevent this
freedom from turning
into anarchy.”

55Teaching the Challenges: Innovation
Innovation
CD, LP, EP, DP
The Goal
• Create a new product for the music industry
• Make a business plan for it
The True Goal
• Introduce the themes of systems thinking
• Learn to identify and explain design opportunities
to clients
When To Use It
• Students who require too much instruction to get
them moving
• As an excuse to lecture about “design thinking”
rather than just “design doing”
Further Thoughts
This is a tiny big problem.
It’s tiny because if you just take the problem state-
ment at face value, you could design any number of
beautiful, functional executions that consumers would
probably buy.
It’s big because there’s a complex set of interrelation-
ships between the actual actors in the system you’re
working within: the music companies, music publish-
ers, distributors and wholesalers, artists, existing music
ecosystems, and on and on.
Any student wishing to provide a tiny solution must
have a big rationale to explain its viability. If the class
gravitates toward bigger solution, each student must
have a set of artifacts that explain what their solution
would tangibly look like to a music buyer.
You can leave it open-ended, and see where your
students take it, or you can force them down one of
the above paths.
Either way, don’t let them just press it on 40-gram fus-
chia vinyl and call it a day. It’s not really a solution if it
just sits there looking cool.
iPhone Americana
The Goal
• Create an iPhone app
• Extend it to another platform
The True Goal
• Learn information architecture methods for appli-
cation design
• Provide an emotional heft to an otherwise func-
tional experience within a strong cultural motif
When To Use It
• Designers who haven’t learned to objectively rep-
resent aspects of different cultures or with groups
that are from wildly different backgrounds
• Students transitioning into mobile design from
other platforms
Further Thoughts
Interactive products can have a personality. They can
dance, breathe, laugh, stretch their arms, and yawn.

56 Teaching the Challenges: Innovation
They can have a tone of voice, a way of holding your
hand as you cross the street, and sometimes even
giggle when you tickle them.
When designing products that have both a body
and a soul, we can dive so deeply into the functional
details that we lose sight of what people want to
accomplish with our application—make it easier to
read a novel, or play their favorite songs like a jukebox
in an old honky-tonk. We have to balance functional-
ity with delight.
Prod your students to describe, when explaining their
application ideas, not only what it can do for its user,
but also how it will establish an emotional connec-
tion. Those explanations should also include a strong
analysis of the cultural component of this challenge.
We are all products of our upbringing, and mobile
applications are moving quickly to become exten-
sions of those relationships. If we can’t define cultural
quirks and eccentricities, we certainly can’t capture
them…or eliminate them.
Biodegradable Backyard
The Goal
• Make backyard products intended to biodegrade
• Build a prototype or design a marketing strategy
for the product
The True Goal
• Analyze the environmental impacts of substrate
selection
• Reimagine how a product serves a specific set of
use cases over time
When To Use It
• Students who believe sustainability is easy, or
those that need more experience understanding
the environmental impact of product construc-
tion and use
• Designers who have worked with a limited palette
of materials
Further Thoughts
Which came first: the compost or the composter?
While this challenge may seem like a 100% net posi-
tive for any designer solving it—making things that
unmake themselves, contributing to a healthier planet,
and all that falderal—a better approach to solving this
challenge may emerge from a more holistic analysis.
Have your students look at the entire lifecycle of a
product. They should examine its manufacture, pur-
chase, utilization, obsolecence, and potential reuse
before it is composted or degrades. What are the
tradeoffs for a selected approach? Pros or cons? Is the
product using more energy before it hits the shelf than
it gains by biodegrading after its use?
If your students can’t answer these questions, then
send them back for deeper digging on these issues.
Otherwise, their designs may be feasible, but poten-
tially have a net-negative impact.
More Is Less
The Goal
• Redesign the packaging for a durable consum-
able product
• Develop a prototype and observe others using it
The True Goal
• Change people’s behavior through product
presentation
“Interactive products can
have a personality… They can
have a tone of voice, a way of
holding your hand as you cross
the street, and sometimes even
giggle when you tickle them.”

• Analyze the environmental impacts of design
choices
When To Use It
• Students having trouble believing they can per-
sonally contribute significant change to the world
through their work
• Designers exploring different methods of behav-
ioral change, especially if they are transitioning
from a background in sales or marketing
Further Thoughts
This isn’t a challenge about designing snack packs.
Building off the lessons from “Biodegradable
Backyard,” students should be able to analyze the
supply chain for their product. Now they’ll have to
apply those same analytic skills to understand how
and why people consume their product. This chal-
lenge starts with the supply chain and throws in
consumer motivation. The students can control the
components in a product, but can they influence how
people use that product?
If the class isn’t taking a systems-thinking approach to
their solutions, their ideas will still have an impact—but
it won’t be the right kind of impact. People will just buy
more of less, rather than consume less of less.
This is harder than it sounds. But if students do a great
job, it’s likely they will have strong concepts that they
could potentially produce.
Veni, Vidi, Vino
The Goal
• Create a wine package
• Show what it would look like when sold in bulk
The True Goal
• Learn how aesthetic and material choices convey
affordability and luxury
• Understand when to apply wit as part of a design
solution
When To Use It
• As a fun in-class break between more difficult
challenges
• Students struggling with price/aesthetic desirabil-
ity dynamics within product design
Further Thoughts
Really, you can look too good.
When designing an annual report for a nonprofit, you
don’t want it to look like they have no need for money.
And while a celebrity can wear a thousand dollar skirt
with a no-name tank top, if you’re selling a $200 bottle
of wine to the masses, it had better not look like you
dragged it from the back aisle of a convenience store.
Students solving this challenge will need to determine
how the nuances of their design, from typeface to
illustration style to materials used, speak to its value.
Describing these key decision points will help them
to make a case for why their concept will work on
the shelf.
E.V.O.O. to Go
The Goal
• Make a container for olive oil
• Design an ad for selling the product
The True Goal
• Grapple with unusual materials-based constraints
• Place function squarely before form
When To Use It
• Designers without experience in industrial or
packaging design, especially if they are uncom-
fortable with incorporating science into their work
• Those more used to focusing on aesthetics than
utility
Further Thoughts
Olive oil is a viscous substance prone to spoil more
quickly than many other oils on the market. It can
go rancid quickly, especially if left out at high

temperature. It can’t be heated over medium-high
heat without beginning to smoke. Its flavor profiles can
vary wildly, based on how and where it is produced.
Unlike salt, which is stable at a range of temperatures
away from water, oil is a nightmare to contain.
Don’t let your students know that. Even if they read
the words above, they’ll need to do the appropriate
background research to make sure that any proposed
solution will reduce post-pour oozing and not taint
the flavor of the oil over time. This is the true bar they’ll
need to hit for their product to be successful in market.
If you’re feeling feisty, ask your students to make a
presentation about the science behind the challenge
before the class starts sketching. The best framing
of the challenge can then be used to evaluate
each solution.
TechnoYoga
The Goal
• Create an interactive application that tracks
yoga
• Design the mat
The True Goal
• Begin to grapple with gestural and touch
affordances
• As a way to think about the future of connectivity
• Provide practical experience in physically proto-
typing interactions
When To Use It
• When introducing the notion of interaction mod-
els or frameworks
• Students or designers who are accustomed to or
are more comfortable with solitary work
Further Thoughts
This challenge embodies the complexity inherent in
creating an application that tracks gestural input—
which is one of the primary futures for any designer
interested in pursuing a career in user experience.
As a further complication, it requires the designer to
have a functioning knowledge about the practice
of yoga: the taxonomy of yoga poses that any such
application would draw from; the different types of
yoga, and the teaching styles that accompany them;
as well as the physical props and rituals that accom-
pany each practitioner’s efforts. Otherwise, a design
solution would be completely off the mark. Figuring
out how to pool collective knowledge is useful for
any designer.
We also recommend limiting your student teams to
30 to 45 minutes to create a rough physical prototype,
then have them demonstrate it to the class by acting
out how the application would interact with a practi-
tioner over a series of poses. The students would have
to draw out the necessary screens or interfaces that
would describe each interaction.
The real power in this challenge comes from having
designers physically move through the space to real-
ize the success (or failure) of their solution. From this
point forward in the book, a large portion of the chal-
lenges will require this type of active visualization. If
students start here, they’ll definitely be limber enough
for the later work.
I Think, Therefore I Shop
The Goal
• Create a store that doesn’t sell products
• Build a prototype of the store experience
The True Goal
• Wrestle with the concept of what a “store” really is
• Consider how people consume ideas as part of a
real world experience
When To Use It
• As a back-door introduction to social innovation
• When explaining the notion of “customer
touchpoints” in the context of retail or environ-
mental design

• Students and designers transitioning from
sales-based disciplines, such as advertising
or marketing
• To directly address any lingering personality
issues
Further Thoughts
This challenge is philosophical in nature, but practical
in the desired output from students. It should be con-
ducted in groups, as opposed to individual output—
the final product will be richer as a result.
As one approach: Simply arrange your students into
groups, feed them this challenge, then stand back
and let them reach an endpoint before providing any
critique. This is a good opportunity for you to assign
specific people to teams, especially if there are any
continuing issues among students. When designers
on a team have to focus on ideas instead of being
distracted by a shiny prototype, they’ll need to deal
with each other as people rather than as a means to
produce an end. They’re exploring how people think,
and that includes their teammates.
Or, alternatively, if everyone is playing well with others,
you can push the work to explore the same themes
of cooperation. As the students are moving from their
big ideas to executing their tangible store designs,
help guide them towards exploring what technolo-
gies or unique moments are constructed within the
infrastructure of the store experience, rather than just
adapting existing technologies that people will bring
into the store (i.e. mobile devices or computers).
Your students should also be able to justify the cost of
investment in the store, and how it will afford staying
open. That will probably the hardest data point for
them to generate. But if they can’t provide such data
to potential investors, than why would they consider
any such idea viable?
Ready When You Are
The Goal
• Create an application for your coffee needs
• Decide how you’d promote the new functionality
in product marketing
The True Goal
• Convey the fundamentals of mobile application
design
• Learn about systems thinking—with a drug most
designers are already invested in
When To Use It
• Students deeply rooted in visual design that
have little experience in defining a controlled
set of use cases
• Designers needing work with building user flows
for application design
Further Thoughts
When starting to teach application design, it can
be tempting to throw the kitchen sink at design-
ers. User flows! Use cases! Functional requirements!
“When designing an annual report for a nonprofit,
you don’t want it to look like they have no need for
money… if you’re selling a $200 bottle of wine to
the masses, it had better not look like you dragged it
from the back aisle of a convenience store.”

Specifications! Wireframes! The list could go on
and on.
This challenge was intended as a way for students to
approach the discipline from an alternative direction:
via considering the fulfillment of a critical everyday
task that usually has little connection to a mobile
device. By starting with a contained set of use cases
and limited functionality, it’s easier for students to
understand the basic components necessary to also
generate much larger systems.
When David has taught this challenge in class, he’s
asked the students to role-play utilizing the applica-
tion, with one person being the “voice of the app,”
while another person pretends to interact with the
actual phone, speaking out loud what they’re doing.
The rest of the class takes notes, capturing what the
screens may look like as they move step-by-step
towards their perfect cappucino.
Let’s Dish
The Goal
• Design a dish
• Determine how to brand the dish for release to
market
The True Goal
• Experience how to sketch and prototype atypi-
cal shape languages—i.e. families of physical
objects that work together and feel like a family
• Learn how to summarize the most important
effects of an interactive, service-oriented
experience
When To Use It
• Students with little to no experience with industrial
design
• Designers with a solid background in fine art who
are feeling neglected
• When introducing the conceptual notion of archi-
tectural form
• With a class needing a fresh perspective on what
constitutes usability and function
Further Thoughts
We design things for a reason. We make a car to drive
in. We make forks to eat with. On very rare occasions,
we design products for a reason that runs counter to
their usual purpose. We might craft a chair that no
one can sit in, perhaps to make a political statement
or as a memorial. But the marketability of a chair that
no one can sit in is questionable.
This challenge is about particularity. Students are
designing a single object for a very specific task, and
it’s an object that is expected to have multiple uses.
Realistically, we don’t really think about usability with
dishes. It’s a dish. That’s just what it does. Getting
the class to explore how function informs design in
this context will require them to look at how they feel
about individuality, ritual, even sustainability.
If students can grasp how to think purposefully about
the specific uses of a product, there’s nothing stop-
ping them from applying those principles to the larger
world. Single purpose inventions like the Hippo Water
Roller and the Embrace Infant Warmer are only a few
steps away from Tithi Kutchamuch’s cups in the book.
Listen Up, Write It Off
The Goal
• Design a bus shelter ad
• Create a radio spot
“On very rare occasions,
we design products for a reason
that runs counter to their usual
purpose. We might craft a chair
that no one can sit in… But the
marketability of a chair that
no one can sit in is questionable.”

The True Goal
• Think through the requirements for an interactive
product
• Learn how to summarize the most important
effects of an interactive, service-oriented
experience
When To Use It
• To push students focused on communica-
tion design into thinking about what elements
truly comprise the products and services they
describe in marketing vehicles
• Designers still struggling with the “making a differ-
ence” part of their jobs
Further Thoughts
Students may consider it critical to fully explore how
their “volunteer bank” would work before they can
design the bus shelter. Others may immediately
brainstorm concepts for the bank via the medium of
advertising.
While both are valid approaches, we advocate that
students work through the logistics and user experi-
ence of the actual online experience before crafting
their ad—spending 60 minutes of the 90-minute time
period on that task alone. This will provide them with
a greater depth of understanding for not only the ad,
but also the holistic reason why people would want to
take part in utilizing such a service.
And isn’t that what a designer would want to under-
stand before crafting a solution?

62 Teaching the Challenges: Interpretation
Interpretation
I’d Buy That for a Dollar
The Goal
• Create a new dollar store chain
• Design packaging for what it sells
The True Goal
• Understand the implications for having holistic
control over a whole retail experience
• Consider sustainability impacts for an entire
business
When To Use It
• As a major class project, bridging product and
service design disciplines
• With more cause-oriented students, to help them
explode notions of how design impacts capital-
ism and consumption
Further Thoughts
This challenge has plenty of space for interpretation,
both on the part of the student and the teacher.
Depending on how the students approach the chal-
lenge, they could design the outside of the store, the
interior floor plan, the suite of products they’d want to
offer, the online experience for the store—practically
any combination of details to comprise a final output.
Be sure to ask students to define at the end of their
ideation phase what materials would be required to
create a well-rounded solution. Students should be
very clear about what depth of sustainability thinking
they’ve undergone alongside the development of
their design ideas. Of course, they have to make those
principles work with their strategy for how the business
will make money, even if students desire to twist or
subvert notions of consumption. When presenting to
the class, these rationales can be explicitly called out
and debated.
What’s in Store?
The Goal
• Create a window display for a store
• Plan the space for the whole store, including your
display
The True Goal
• Understand what gives great store displays their
stopping power
• Provide designers a taste of the visual mer-
chandising, interior design, and architecture
disciplines
When To Use It
• To convey the elements of planning a store space
in a fun manner
• With designers who have not had a lot of experi-
ence with product or window displays, or that are
looking to move from point-of-purchase displays
to something larger
• As a breather between harder challenges

63Teaching the Challenges: Interpretation
Further Thoughts
Like some design work in the domain of fashion, this
challenge is intentionally shallow and fleeting.
But if anyone challenges you on whether or not win-
dow displays qualify as design, we highly recommend
Simon Doonan’s Confessions of a Window Dresser to
tip the scales in your favor.
Urban Diapers
The Goal
• Create diaper packaging
• Think about how to tie marketability to the
packaging
The True Goal
• Understand what it means to craft a brand that
“zags” against an established product category
• Learn the essential components of product and
packaging design
When To Use It
• To help students learn how to approach the pro-
cess of crafting an identity system
• Designers who need more work in developing
archetypes or understanding demographics
Further Thoughts
Whenever a client says, “I want an idea that rises
above all that other crap in the market,” they may not
be asking for the output of this challenge.
However, the whole premise of “Urban Diapers” is that
if you’re going to be cleaning up after all sorts of crap,
you might as well do it with a punk-rock smile on your
face. Capturing the lifestyle and attitude of a defined
audience is the major focus for any designer tackling
this challenge.
Don’t be afraid to task your students with additional
deliverables, such as mood boards, documented
conversations with new parents, an audit of existing
packaging and advertising from competitors, and
any other data that may help to steer the approach
of a final solution. Otherwise, the student work may be
well-designed, but not catering to (or creating) desire
on the part of their audience.
As a shout-out: the design professor Jill Vartenigian
suggested the basis of this challenge when she co-
taught a Creative Workshop class with us.
Out of Gamut
The Goal
• Design an identity for a nonprofit association
• Create a color study
The True Goal
• Consider color interaction beyond just making
things look nice
• Learn about colors that may provide trouble for
the colorblind
• Incorporate accessibility into “common” design
work
When To Use It
• To help students learn how to approach the pro-
cess of crafting an identity system
• Designers who are lacking experience in acces-
sibility design
• As an introduction to researching color interac-
tion as a part of accessibility considerations
Further Thoughts
While this may seem on the surface like an improb-
able design scenario, the reality is that a percentage
of the people who look at or use every one of your
designs will be colorblind. This audience is every-
where and nowhere, rarely vocal unless they observe
a major faux pas that could cause great harm. (We
can’t imagine what would happen if we did a switch-
eroo on color position inside traffic lights.) In short,
accessibility considerations in design are as pressing
as they are prevalent, even when they aren’t immedi-
ately apparent.

Your students will need to do two types of research.
They will need to understand the various types of col-
orblindness, and they will need to validate their work
via third-party online tools, gauging its effectiveness.
Push your students to justify their decisions when
they present in class. Make them render versions
of their work as those who are colorblind would see
them. Group the whole classes’ work on the board
by colorblindness type before judging which solutions
work best. Or, if you have the ability, bring in a
special guest—a colorblind person—to have him
or her comment on the class’s work. Such input
would be invaluable.
Future-Casting
The Goal
• Create an art exhibit
• Determine what it would cost to produce
the exhibit
The True Goal
• Discern the fine line between art and design
in client assignments
• Take a trend and project its future effects via
design artifacts
• When done in teams, brush up on and solidify
brainstorming techniques
When To Use It
• When students are struggling to dream big
• Around conversations about durability in design
Further Thoughts
Every designer spends time thinking about the future.
For some students, the future is big, bright, shiny, retro:
kind of like the Jetsons. For others, it’s steampunk.
And let’s not forget the coming apocalypse of 2012,
followed by a new Ice Age. Somewhere along the
way, we might encounter Tron.
Every project we fulfill is about the future—the time
horizon is the only variable that consistently changes.
As you ease your students into the beginning of a new
decade, be prepared for them to explode with ideas.
What will need to ground their ideas, however, is a
clear rationale around their execution that explains
why their exhibit relates to a five-year vision of the
future—not two or three or seven or more. There must
be some unique attribute in the exhibit, whether
technological or social in nature, that clearly maps to
where our society will be in that possible future.
The specificity of the timeframe is precisely the kind of
detail that makes a beautiful solution to this challenge
easy enough to produce, but hard to conceptually
defend in a rigorous critique.
This Is For Your Health
The Goal
• Draw three illustrations in a specific style
• Develop spreads to connect layout to the illustra-
tion style
The True Goal
• Create hand-crafted illustrations within a speci-
fied art direction
• Think editorially about how illustration connects to
written content
When To Use It
• Designers who are fresh out of school or who
have been freelancing for a long period of time,
as this challenge will help them learn how to
Don Norman says, “Designers
fall prey to the two ailments of
not knowing what they don’t know
and, worse, thinking they know
things they don’t.”

interface with creative directors, art directors, edi-
tors, and writers
• Students with a very narrow illustrative style
Further Thoughts
Learning to work under editorial direction takes
practice. It’s not something you’re born with—it takes
assignment after assignment to learn to read the mind
of your editor, as it’s unlikely they’ll give you more input
than what is included in this challenge description.
Though this isn’t a real assignment for a publication,
pretend you’re an editor when you deliver it to your
students. When they start asking you for input and
direction, let them know you’re too busy to respond,
and that you’re looking forward to their work.
If you’re teaching this as an in-class assignment, con-
sider providing them new inputs or constraints halfway
through the time period.
Paper, Plastic,
Glass, Vapor
The Goal
• Create a brand position for bottled water
• Craft a vision document for venture funding
The True Goal
• Learn to force consideration of sustainabil-
ity issues in advance of agreeing to a design
problem
• Develop an opinion and take a stand when a
project opens itself to personal vision
When To Use It
• With a group that is ecologically minded
• When students are struggling to deliver articulate
rationales around their design concepts
Further Thoughts
Outside of March of the Penguins, few people expend
much energy thinking about life on Antarctica. This
continent is a protected eco-zone, with little precipita-
tion year over year.
For your students to understand the trade-offs inherent
in bottling water from this continent, they will need to
dig into a wide range of research sources. As a result,
they will become more educated about both the
protected resources and the systems that have been
created worldwide to try and deliver potable water
to an ever-increasing population. You may need to
clarify that they will need to research both subjects to
provide a well-reasoned solution to this challenge.
While few students have argued in my classes for bot-
tling water from Antarctica, some companies do exist
that are working to extract water near Antarctica. This
is an ethical grey area that may make for heated
class discussion (no pun intended).
Free Tibet Blog
The Goal
• Create an official blog for a celebrity
• Adjust your design for localization worldwide
The True Goal
• Create hand-crafted illustrations within a speci-
fied art direction
• Understand how deeply an interactive experience
can reflect the spirit of a person through history
When To Use It
• Demonstrating that designing seemingly small
things can require great attention to detail and a
sophisticated underlying rationale
• As a good introduction to localization concerns
Further Thoughts
This challenge can seem like a lark. Students may be
tempted to treat it as merely a fun aesthetic problem
to solve. But what would those same students do if
they were seated before the Dalai Lama, and such
a personage of renown were outlining for them the
overall ethos and import of the venture they were
about to undertake?

For students to generate deep and meaningful solu-
tions, they will have to take this challenge seriously.
Consider having another teacher play a representa-
tive of the Dalai Lama when the class presents
their solutions, to ensure that they will not describe
what they designed, but why they designed it in
that fashion and how it relates to the heritage
of Tibetan Buddhism.
Blinded by the Light
The Goal
• Help visually impaired people track sun exposure
• See if your solution would work for people with
other disabilities
The True Goal
• Learn what types of research are appropriate to
frame an approach for a design solution
• Discern how to design for populations with radi-
cally different limitations on how they might use a
particular product or service
When To Use It
• As an entry point into designing for those with
disabilities
• If a class has trouble grappling with abstract
problems
Further Thoughts
Don Norman says, “Designers fall prey to the two
ailments of not knowing what they don’t know and,
worse, thinking they know things they don’t.” Students
struggle with this challenge for this very reason.
If you don’t let them talk with visually impaired people
as part of their research, they have trouble justifying
their solutions.
If you do let them talk with visually impaired people,
they have very little time to formulate the right kinds of
questions to ask them or to observe what their needs
might be. This may not help them deliver the most
effective solution.
Essentially, no matter which path your students
choose, within two hours it’s unlikely they’ll feel good
about what they create.
This is one of the hardest lessons that any product
designer can learn: without the appropriate research
and validation, any well-intended solution can
be a poor fit for the needs of a poorly understood
audience.
Touch Screen of
Deaf Rock
The Goal
• Create an exhibit for deaf children
• Create a physical prototype of the exhibit at size
The True Goal
• Learn how to envision an interactive experience
without the use of all five senses
• Explore a range of approaches for creating arti-
facts that describe touch and gestural interaction
When To Use It
• When teaching students about touch and ges-
tural interfaces
• To teach the use of role-playing in quickly proto-
typing interactive experiences
Further Thoughts
This is one of our favorite challenges in the book. It’s a
ton of fun for designers to attempt in close collabora-
tion—and a fast way for students to learn the follies of
designing touch and gestural user interfaces.
An interesting spin on this challenge is to design the
exhibit for a deaf child and a potentially hearing
parent (or friends). The walkthrough would require
two or more people interacting with the exhibit
simultaneously.
We recommend that, as the teacher, you create time-
boxes for the students to brainstorm big-picture con-
cepts, a set time period for creating a solution at size,
and then serve as a third-party who walks through a

draft of the space and asks simple, open-ended ques-
tions about what details may not make sense. This will
help students bounce quickly between making the
design and reflecting on what elements of the design
may not be effective for a deaf child.
As a side note, keep a close eye on how the walk-
throughs are enacted by the teams. If you don’t serve
as the third-party reviewer, encourage students to act
normally when they go through the exhibit, speaking
out loud. Deaf people aren’t stupid; they can read,
intuit interactions, and learn from exhibits just like
everyone else. When you design with empathy, you
must also design with respect.
Sniff Test
The Goal
• Create an exhibit that contains scents
• Design the materials required to market the
exhibit
The True Goal
• Design for the sense of smell—which is rarely con-
sidered by designers
• Learn to work within unusual physical constraints
When To Use It
• Around lessons that demonstrate various meth-
ods of designing for environments
• Students needing additional work with collabora-
tive design practices
Further Thoughts
Trying to manage perfume within a public space, with
potentially thousands of visitors seeking to sample
those scents, could be a nightmare scenario. From
managing olfactory fatigue on the part of exhibit
visitors to constructing airtight spaces (or other novel
solutions that we’ve seen to this challenge), your stu-
dents will have lots of thinking to do.
But before you provide the challenge to them, you’ll
need to decide: Can a solution be “magic,” not con-
strained by the laws of chemistry and physics? Or must
your students do the appropriate research to back up
their solutions with a rationale around the feasibility
and costs of implementation?
Depending on which path you choose, the type of
effort your students will put into the challenge may
vary. We recommend having them do some big-
picture brainstorming, then researching which of their
range of ideas may be most feasible, then moving
from there.
It’s always easier to fit a really big idea into a smaller
box than to take a tiny idea and try to inflate it. In the
case of the latter, it’ll usually go pop!
Can You Hear Me Now?
The Goal
• Storyboard a TV spot
• Translate your idea into other media
The True Goal
• Explore in TV and video how sound is closely inter-
twined with image
• Gain empathy regarding communication design
for the disabled
When To Use It
• Students with a firm grasp of advertising design
that need to be pushed outside of their comfort
zone
“It’s always easier to fit a
really big idea into a smaller box
than to take a tiny idea and
try to inflate it. In the case of
the latter, it’ll usually go pop!”

• When teaching how to design for the disabled
Further Thoughts
We take sound for granted. We don’t realize how inte-
gral it is to most experiences of the world. That is, until
it isn’t there.
An effective execution for this challenge will essentially
be a moving print ad. You might want to consider
having your students act out their ads, sans voiceover.
Otherwise, they’re just going to describe out loud
what happens in each panel of their storyboard,
and that might get in the way of fully expressing
what they’re trying to communicate conceptually
with their spot.
Consider filming each performance, so the students
can compare their ideas after class. Then, show the
films to people who are not aware of the challenge or
the constraints. Do the ads communicate the ideas
that the students intended?
Bending Geography
The Goal
• Create a simplified map
• Abstract your map until it becomes decorative art
The True Goal
• Understand how good information design can
require finessing factual detail
• Manage a high volume of detail in an illustration
When To Use It
• When teaching best practices for wayfinding and
map-making
• Students who a bit too obsessed with Edward
Tufte
Further Thoughts
Mapmaker, mapmaker, make me a map. Not just any
Google Map with the appropriate pins and turn-by-
turn directions. Moving from Point A to Point B is just
one use of the map, and we’ve become addicted to
our phones, GPS devices, and other tools that we use
for traveling to all sorts of places. But there are situa-
tions where using those mapping systems become a
bit ineffective: inside buildings, within out-of-the-way
districts, and when attempting to understand the vari-
ous neighborhoods and suburbs of a downtown core.
Students may feel like they’re beholden to cram as
much as they can into their maps—and they should
resist this impulse. Less detail allows more finesse in
how a viewer of such a map understands the high-lev-
el relationships between roads, rivers, bodies of water,
and critical landmarks.
If you’re feeling spry, cover the city and task each of
your students with a neighborhood to render. Then,
piece all of the maps together like a patchwork quilt,
demonstrating to your students how many different
approaches there may be to rendering a simplified
view of a complex world.
“‘You want me to create something for myself,
that I’ll benefit from?’ Yes, that’s right:
design can be a self-affirming, rewarding act
that’s solely for your benefit.”

What Do I Know?
The Goal
• Make Twitter and Wikipedia have a baby
• Create the user interface for what experience you
think should be made
The True Goal
• Work collaboratively to frame a highly complex
problem in a group
• Learn to identify when a provided problem is wick-
edly complex
When To Use It
• As a final in-class “unsolvable problem”
• For students who consistently overestimate
their skills
Further Thoughts
In Star Trek lore, there is a definitive test that Starfleet
Academy students need to take in order to graduate.
In this test, each person is role-playing as the captain
of a Starfleet vessel, attempting to rescue a stalled-out
ship called the Kobiyashi Maru.
While each student initially thinks they can carry out
a rescue mission to save the people on the stranded
vessel, they quickly discover that it’s a no-win scenario,
as the vessel is in the Klingon Neutral Zone. No matter
what they do during the scenario, either their vessel or
the Kobiyashi Maru is destroyed.
The test, as Captain Kirk so impishly avoided by hack-
ing the test computer’s code, is not about winning.
It’s about how students think about the problem and
about grace in the face of powerlessness. It’s about
what it really means to be a leader. What Kirk did was
engineer the problem in such a way as to allow suc-
cess, which served as a testament to his understand-
ing of leadership. That’s what your students should
apply to this challenge.
Place your students in groups and have them attempt
this challenge. On its surface, the problem statement
for this challenge is too broad to solve within the
time limit. This is intentional. Your students will need
to agree upon what problem they need to solve
before they can provide a solution at the end of
their time limit.
If they don’t, there is no way to win.
Well, In My Book…
The Goal
• Design a book of personal wisdom
• Reconsider what form the book should take
The True Goal
• Learn how to be your own client
• Understand how to create space for reflection
When To Use It
• As a final take-home exercise for a Creative
Workshop class
• For students who need a break from “client work”
Further Thoughts
This challenge is a reward for every student’s hard
effort. It will force them to allocate time and space
for reflecting upon who they are and what they’ve
accomplished—with a tangible output that they can
return to again and again.
This challenge should feel like an antidote to the
self-sacrifice and service orientation that is imprinted
strongly upon designers of every skill level. “You want
me to create something for myself, that I’ll benefit
from?” Yes, that’s right: design can be a self-affirming,
rewarding act that’s solely for your benefit.
If you fear that the subject matter may be too broad
for your class, consider this variant: have your class
generate books that highlight what they’d learned
over the course of the class. They can be illustrated
with a select number of the challenge executions.
Regardless of your approach, this should feel less like
a portfolio, and more like a manifesto.

71About the Authors
About the authors
David Sherwin is an interaction designer and
art director with a depth of expertise in developing
compelling creative solutions for challenging business
problems. He is currently a Senior Interaction Designer
at frog design, a global innovation firm, where he
helps to guide the research, strategy, and design
of novel products and services for some of today’s
leading companies.
David is author of the books Creative Workshop:
80 Challenges to Sharpen Your Design Skills and
the forthcoming Design Business from A to Z (2012).
Both are published by HOW Design Press.
David is an active speaker and teacher, and his
writing has appeared in A List Apart, Design Mind,
PSFK.com, Imprint, and other periodicals. In his free
time, he maintains the blog ChangeOrder: Business +
Process of Design at http://changeorderblog.com.
Mary Paynter Sherwin is a poet, writer, editor, and
teacher of public speaking. Her poetry has been
published by Richard Hugo House, Midway Journal,
and Drash: Northwest Mosaic. She was recently includ-
ed in an online anthology on Rattapallax.org, where
she was named one of the Pacific Northwest’s Most
Innovative Poets.
Mary holds a degree in Commercial Photography
from Art Institute of Seattle, a certificate in Editing
from University of Washington, and is about to
complete a Liberal Arts degree in writing at
Evergreen State College.

72 Exercise #
For University Bookstore sales, contact FW Media at 1-800-289-0963.
My Design Shop: http://www.mydesignshop.com/product/creative-workshop/
Amazon: http://bit.ly/CWTheBook
The first 24 pages are available free on Scribd:
http://www.scribd.com/doc/42672850/Creative-Workshop

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