How to Pick a Career Path

(That Actually Fits You):

The Worksheets

Wait But Why

based on the WBW article by Tim Urban
(Read the article first.)

© 2018, Wait But Why Inc.

Some rules
● This probably won’t make sense if you haven’t read the original article, so
start there: “How to Pick a Career Path (That Actually Fits You)” – Wait But
Why
● These worksheets are a deeper-dive extension of the post to help reflect on
your career path from first principles. It might take a while. Grab a few blank
sheets of paper and set aside an hour or two, go one section at a time, or
skim through it for ideas.
● Be honest with your answers—write down whatever you actually think, even
if it feels a little weird. The whole point is to find something that’s a good fit
for you, so your answers have to be authentic and you have to get past the
most obvious answers.
● Don’t forget that this is a no-pressure situation! This is just a framework to
help you think through some possible options—never more than a rough
draft and always revisable.
Sketch your life path so far
Starting from birth, draw a path that sums up your major life / career / lifestyle moves
up until today.
Evaluate your career path so far
Think about the jobs you’ve had in the past. (If you haven’t had a job yet, think about roles you’ve
had in school or even at home.) Evaluate each one:

Why did you take on the role in the first place?

How did the job meet your expectations? How was it different than
expected?

What felt right about the job or company? What felt like a bad fit, or
made you frustrated and/or unmotivated? These factors can be anything about the
day-to-day, no matter how small, or can be bigger things like belief in or disagreement with the
company’s purpose.
Draw your Career Plans map
What are you currently pointed towards? Do you have a plan for where things are
going? How do you feel about it?
Part 1: Your Want Box
Your Yearning Octopus
Everyone has a Yearning Octopus in their head that determines what they
want in life. On the next page is an example of what might be a typical one.
Draw your octopus
On the next page, sketch what yours might look like (with tentacles and segments
that represent what really drives you). Really think through what your most
prominent drives or fears are, along with others that may lie underneath but not
have as much influence.
Dissect the octopus
Think about each yearning or fear, one by one, and interrogate it. Ask
yourself why you feel that way, and why you feel that way, and keep going
until you arrive at where you think the feeling originated.

At the end of each interrogation, ask yourself:

Who really wants this?

Is this a core you thing, or is it derived from the feelings of others? If you believe
it’s not really you underneath a particular motivation, evict the imposter and
replace it with either a question mark or something you think better represents
your authentic self.
Go down to Denial Prison
Part of who you really are may be buried pretty deep, suppressed or denied. Try to get in touch with
these feelings. Some questions that might help:

Who were your biggest influences growing up? How about today? What
did they want for you?

Do you ever act in direct conflict with what you say you want?

What are you curious about in passing that you’ve never really dug into?

How do you spend your money/time/attention when you aren’t working?

Rank your yearnings & fears
Once your octopus represents a draft of the things you feel you really
want, deep down, try to rank those things in order of what you care about
most. If it helps, you can use the shelf on the next page, which divides
things into five categories:

● Non-negotiable bowl — things you hope to guarantee yourself.

Use this only sparingly.

● Top shelf — things to strive hard for.

These things will drive most of your career choices, so be selective.

● Middle shelf — things to avoid total failure at.

This shelf is good for the less-important qualities you feel you can’t totally neglect.

● Bottom shelf — things to keep in mind.

Nice to have, but not at the expense of anything above it.

● Trash can — things to reject.

Things you’re actively choosing to deny.
YEARNING HIERARCHY
Fill in your Want Box
On the next page, with all of this in mind, jot down some potential career
options that seem to fit who you really are. Don’t worry about what’s
possible or not possible—the Want Box is simply about all the options that
feel right to you.
WANT BOX
Part 2: Your Reality Box
The Career Landscape
List at least 25 career fields that exist today or could exist in the near future:

1. 13.
2. 14.
3. 15.
4. 16.
5. 17.
6. 18.
7. 19.
8. 20.
9. 21.
10. 22.
11. 23.
12. 24.
25.
Look at specific game boards
Each career is its own unique game board. For careers in any fields that sound interesting to
you, think about what the game boards and rule books might look like today. Ask yourself:

How does conventional wisdom define the rules for this career?

Are there any less obvious factors that are critical to the game?
Example: Beyond acting skills, an acting career requires thick skin and a knack for networking.

How have people most recently found success in this area?

Are there any loopholes or shortcuts to be exploited?

Draw your career paths
For the careers that interest you, define a starting point and a success
point:

● Starting point — defined by where you are now: your current set of
relevant skills, knowledge, and connections in the field
● Success point — defined as the minimal level of success you’d need
to achieve to feel happy about having chosen the path
Plot these points out for different career options on the next page.
Evaluate your potential
For each career path, think about the distance between your starting point
and success point (the progress you’ll need to make), and the challenge at
hand in trying to make that progress. This depends on two key factors:

● Pace — how quickly you can progress at playing the game

● Persistence — the amount of time you’re willing to put in

Progress is a product of these two components:

Progress = Pace x Persistence

You’ll define these variables in the next step.

List your strengths & weaknesses
Rather than worrying about your specific skill sets, think about the things that will affect your
pace and persistence. Here are some examples:

Pace Strengths Persistence Strengths

● Chefness (adaptability, humility, the ability ● Patience
to reason independently and trust it) ● Resilience
● Likability, social skills ● Determination
● Cleverness, savvy ● A willingness to appear unsuccessful for a
● Lifestyle flexibility (ability to prioritize work) good chunk of time
● Ability to deeply focus
● General talent and speed of learning

Pace Weaknesses Persistence Weaknesses

● Stubbornness ● Restlessness
● Intellectual laziness ● Need for instant gratification or
● Tendency to procrastinate acknowledgement
● Other priorities (family, debt, lifestyle ● Short runway to retirement
balance) ● A fear of failing at something for too many
years; an urgency for success

Try to think about what you really know to be true about yourself, based on feedback from
other people and examples of your actual behavior.
Fill in your Reality Box
Look at each career path and evaluate your potential:

How can you improve your pace- and persistence-related strengths?

With enough time, could you get good enough at the career’s game to
reach your definition of success?

If it seems like your Pace x Persistence in a career is enough to cover the

path’s total length, write that career in your Reality Box on the next page.
REALITY BOX
Part 3: Your Option Pool
& Picking a Path
Fill in your Option Pool
Right now, you have two lists:

● Want Box — careers that sound good to you

● Reality Box — careers that seem potentially possible to succeed at

These boxes overlap to make your Option Pool. Using your Want & Reality
Boxes, fill in the Option Pool on the next page with any careers that fall into
this overlap.
OPTION POOL
Connecting the Dots
into the Future
Pick a career path
With all of this in mind, redraw your Career Plans map. What’s your next move? How do you feel
about it?

Remember that choosing a path now is just like making a hypothesis. You can’t predict
where you’ll end up, and you can continue to adjust your plan as you gain experience.
Tell your plan to Future You
Draw your future self on your deathbed. Then draw your current self telling Deathbed
You about your new mission:

● What you want (the non-negotiable and top-shelf priorities in your Want Box)
● The career path you’re starting down (your hypothesis)
● Your reason for choosing this particular macro mission

Do one last gut check: Is Deathbed You cool with it?

(If this freaks you out too much, try the opposite. Imagine a 90-year-old you traveling back in time to tell you
how your life went. What is Current-Age You hoping to hear?)

Return to this “mission statement” whenever you feel restless or unsure

about your macro mission. If you think it’s time to make a change, move on
to the last section.
The Next Jump?
Find your place on the inertia spectrum
When it comes to change, think about whether you tend to have cement
shoes or winged shoes or something in between.

In times of fight-or-flight, which impulse tends to be stronger?

In retrospect, have you stayed in past jobs (and relationships) longer

than you should have? Or have you jumped ship too early?

Do you give second chances easily?

Are you more likely to be bored or content?

Understanding what drives you—inertia or restlessness—will help you get

better at the game of jumping from dot to dot in your career.
Test your restlessness (wing-footed)
If you’re restless by nature, answer these questions when you feel like it’s time for a change.

Is someone you admire, fear, or want to impress pushing you towards jumping?

What can you do to make things better if you stay? What have you done so far?

What do you expect to change if you leave? How?

Have you learned something new about the job, the career landscape, or
yourself since you started? Do you need to enhance your mission, or get a new one entirely?

How does Deathbed You feel about jumping? Will you be proud of your boldness, or
disappointed in your impulsiveness?
Test your restlessness (cement-footed)
If you’re usually beholden to inertia, answer these questions when you’re feeling unsure about
things.

Is someone you admire, fear, or want to impress holding you back?

Imagine one year has passed. Where do you instinctively picture yourself? How will your life
look next year if you stay on your current path? What might it look like if you make the change?

What’s the worst that could happen if you stay? What’s the best case if you jump?

How can you minimize “risk” if you jump? What qualities do you already have that prepare
you for the change? Can you make a mission-enhancing jump rather than reevaluating your mission
entirely?

How does Deathbed You feel about staying? Will you regret dragging your feet, or be
grateful that you chose the sounder path?
Moving forward
Self-reflection is a hard thing to do, so well done!

It’s even harder to act on our conclusions. If this exercise has brought on any
epiphanies about your path, do whatever you can to act on them moving forward.
What you want and what’s possible are both works in progress and always in flux,
so don’t forget to come back here and reevaluate things from time to time.

Good luck!