The Career Talk I Wish I Had

Sean Walberg <sean@ertw.com>
The Career Talk I Wish I Had
Why don’t they teach this stuff in school?

Before We Start…

What I Want (in no particular order)
● Do interesting things
● Get paid well
● Have time for friends, family,
and other interests

You, and only you,
are in charge of
managing your
career.

Your Career Is A Story

A story has:
A plot
A beginning, middle, and
end
A conﬂict.
A hero

Unlike a movie…
You can change the story
as you go

Getting what
you want takes
time
Break it up into phases
1. Optimize for experience
2. Optimize for money
3. Optimize for time
* Within reason/where practical

Experience
Experience is cumulative
Experience builds on
previous experience
Even knowing that
technology-we-dont-use-an
ymore is valuable
Our knowledge and
experience is what we sell
to get us what we want.

Strive to be a
T-shaped
person
In depth knowledge of “your
thing”, working knowledge of
adjacent topics.
T
< General Knowledge >
<
Specialized
Knowledge
>

Your goal is to be the
expert in your “thing”
and to be able to have
intelligent conversation
with anyone else in the
room about their thing.

How do I become
T-shaped?
● Read
● Watch videos
● Ask questions
● Try things out
● Hobbies
● Etc
Learning, itself, is a skill
you need to practice.

Hobbies
Of course hobbies count.
You’re not selling “years of
experience”, you’re selling
“depth of experience”.
Hobbies indicate interest and
curiosity.
It doesn’t mean your whole life
is dedicated to IT, it just means
this is a topic you’re interested
and curious about.

Where do you
operate?
Commando, infantry, police?
Horizon 1, 2, or 3?
Pioneer, settler, town planner?

These categories are not about skill
Commandos deal with uncertainty and ﬁgure out the kernel of the product
Infantry reﬁnes the product, scales it, and makes it broadly usable
Police build process, repeatability, and economies of scale

You are a product. A package.

You trade your time for money.

Don’t fall into the
thinking that your
product is time.

Or that your
employer wants
time.

Sorry
I can’t tell you what your product is, or what you are trading your time for.
But I can tell you, your product is not “software developer III” or “junior assistant
webmaster”. It’s almost certainly not your job title.

Your product
solves a problem
employers
desperately need
solved.

Working A Job

Do your best

To raise the
ceiling, we must
also raise the
ﬂoor.

Team of 10 adds a “10x engineer” = “20 engineers”
Team of 10 collectively makes themselves twice as good = 20 engineers
Work at making your team better.
Improving daily work is more important than doing
daily work.

There is something you’re 10x better at
Think back to our T-Shaped discussion. Or maybe it’s your knowledge of keyboard
shortcuts. Anything that makes the team move
faster.

Mentorship
Seek mentorship
Don’t think “will you mentor me?”
Think “who do I admire and what can I learn
from them?”
Ask questions. Observe.
Give mentorship
How can you share your skills?
Ask questions, give opportunities.
You don’t need all the answers, just be willing to
help ﬁgure things out.
Model ideal behavior.

Manage your manager
Don’t be passive - tell them things
What are their goals?
How can you help them be successful?
Push for what you want, in terms of what they
want.
Make decisions easy for them.
Revenue? Expense? Velocity? Satisfaction?
Your contribution to their metrics
Doing X will contribute to metric Y

Negotiation isn’t evil,
and it starts with
understanding how
value is measured.

What is your (ﬁnancial) contribution to the
company?
Are you an expense or revenue department?
What are the ways that your position directly or
indirectly contributes to that number?
Budget - income or expense?
Features that drive revenue?
Sales that bring in revenue?
Work that reduces expense?
Skills that avoid hiring outside?
Design that protects revenue/expense?

It’s diﬃcult to
negotiate if both
sides can’t agree
on value.

This is important when convincing people
Frame your negotiations with their goals
in mind
Speak to their goals and budget needs
Helping others be successful is a much
better relationship

Finally, say “yes”
more. 90% of
success is just
showing up.

Finding The Next Job

When is it time to go?

That said…
You’re always in job hunting
mode.
Keep close to old
colleagues
Understand the market
Help people

A good network means a soft landing
1. Find postings
2. Apply for posting with resume
3. Wait for interview
4. Impress panel
5. Wait
6. More process
7. Get hired
1. Hear of colleague who is hiring
2. Talk to them
3. Have them ﬁght for you
Sounds good, but…

How does this work for my ﬁrst job?
The same way.

If you want a job
ask for advice. If
you want advice,
ask for a job.

Just apply for the
job.
You’re probably
qualiﬁed.

Let’s wrap this up.
● You’re in charge of your career
● Set goals and work toward them over time
● Become T-shaped
● Understand value and your contribution
● Ask for help, and help others
● Your network is your most valuable asset

Thanks!
sean@ertw.com
seanwalberg.com

The Career Talk I Wish I Had

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