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
Teaching the Challenges:
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?”

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