Your Life Path So Far

For most of us, childhood is kind of like a river, and we’re kind of like tadpoles.

We didn’t choose the river. We just woke up out of nowhere and found
ourselves on some path set for us by our parents, by society, and by
circumstances. We’re told the rules of the river and the way we should swim
and what our goals should be. Our job isn’t to think about our path—it’s to
succeed on the path we’ve been placed on, based on the way success has
been defined for us.

For many of us—and I suspect for a large portion of Wait But Why readers—
our childhood river then feeds into a pond, called college. 1 We may
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have some say in which particular pond we landed in, but in the end, most And other higher education.

college ponds aren’t really that different from one another.

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In the pond, we have a bit more breathing room—some leeway to branch
out into more specific interests. We start to ponder, looking out at the
pond's shores—out there where the real world starts and where we'll be
spending the rest of our lives. This usually brings some mixed feelings.

And then, 22 years after waking up in a rushing river, we’re kicked out of the
pond and told by the world to go make something of our lives.

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There are a few problems here. One is that at that moment, you’re kind of
skill-less and knowledge-less and a lot of other things-less:

But before you can even address your general uselessness, there's an
even bigger issue—your pre-set path ended. Kids in school are kind of like
employees of a company where someone else is the CEO. But no one is the
CEO of your life in the real world, or of your career path—except you. And
you've spent your whole life becoming a pro student, leaving you with zero
experience as the CEO of anything. Up to now, you've only been in charge
of the micro decisions—"How do I succeed at my job as a student?"—and
now you're suddenly holding the keys to the macro cockpit as well, tasked
with answering stressful macro questions like "Who am I?" and "What are
the important things in life?" and "What are my options for paths and
which one should I choose and how do I even make a path?" When we leave
school for the last time, the macro guidance we've become so accustomed
to is suddenly whisked away from us, leaving us standing there holding our
respective dicks, with no idea how to do this.

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Then time happens. And we end up on a path. And that path becomes our
life’s story.

At the end of our life, when we look back at how things went, we can see
our life’s path in its entirety, from an aerial view.

When scientists study people on their deathbed and how they feel about
their lives, they usually find that many of them feel some serious regrets. I
think a lot of those regrets stem from the fact that most of us aren't really
taught about path-making in our childhoods, and most of us also don't get
much better at path-making as adults, which leaves many people looking
back on a life path that didn't really make sense, given who they are and
the world they lived in.

So this is a post about path-making. Let’s take a 30-minute pre-deathbed

pause to look down at the path we’re on, and ahead at where that path
seems to be going, and make sure it makes sense.

The Cook and the Chef—Revisited

In the past, I’ve written about the critical distinction between “reasoning
from first principles” and “reasoning by analogy”—or what I called being
a “chef” vs. being a “cook.” Since writing the post, I notice this distinction
everywhere, and I’ve thought about it roughly 2 million times in my own life.

The idea is that reasoning from first principles is reasoning like a scientist.
You take core facts and observations and use them to puzzle together a
conclusion, kind of like a chef playing around with raw ingredients to try to
make them into something good. By doing this puzzling, a chef eventually
writes a new recipe. The other kind of reasoning—reasoning by analogy—
happens when you look at the way things are already done and you
essentially copy it, with maybe a little personal tweak here and there—kind
of like a cook following an already written recipe.

A pure verbatim recipe-copying cook and a pure independently inventive

chef are the two extreme ends of what is, of course, a spectrum. But for any
particular part of your life that involves reasoning and decision making,
wherever you happen to be on the spectrum, your reasoning process can
usually be boiled down to fundamentally chef-like or fundamentally cook-
like. Creating vs. copying. Originality vs. conformity.

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Being a chef takes a tremendous amount of time and energy—which makes
sense, because you’re not trying to reinvent the wheel, you’re trying to
invent it for the first time. Puzzling your way to a conclusion feels like
navigating a mysterious forest while blindfolded and always involves a
whole lot of failure, in the form of trial and error. Being a cook is far easier
and more straightforward and less icky. In most situations, being a chef is a
terrible waste of time, and comes with a high opportunity cost, since time
on Earth is immensely scarce. Right now, I’m wearing J. Crew jeans and a
plain t-shirt and a hoodie and Allbirds shoes, because I’m trying to conform.
Throughout my life, I’ve looked around at people who seem kind of like me
and I’ve bought a bunch of clothes that look like what they wear. And this
makes sense—because clothes aren’t important to me, and they’re not how
I choose to express my individuality. So in my case, fashion is a perfect part

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of life to use a reasoning shortcut and be a cook.

But then there are those parts of life that are really really deeply Also hoodies are cozy and Allbirds

important—like where you choose to live, or the kinds of friends you choose are like wearing socks all the time
and jeans are magical pants you
to make, or whether you want to get married and to whom, or whether you
never have to actually wash
want to have kids and how you want to raise them, or how you set your unless you spill something colorful
lifestyle priorities. on them.

Career-path-carving is definitely one of those really really deeply important

things. Let’s spell out the obvious reasons why:

Time. For most of us, a career (including ancillary career time, like time
spent commuting and thinking about your work) will eat up somewhere
between 50,000 and 150,000 hours. At the moment, a long human life runs
at about 750,000 hours. When you subtract childhood (~175,000 hours) and
the portion of your adult life you’ll spend sleeping, eating, exercising, and
otherwise taking care of the human pet you live in, along with errands and
general life upkeep (~325,000 hours), you’re left with 250,000 “meaningful
adult hours.” 3 So a typical career will take up somewhere between 20%
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and 60% of your meaningful adult time—not something to be a cook about. Fun meals and exercise fall into
this category.

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Quality of Life. Your career has a major effect on all the non-career hours as
well. For those of us not already wealthy through past earnings, marriage,
or inheritance, a career doubles as our means of support. The particulars
of your career also often play a big role in determining where you live, how
flexible your life is, the kinds of things you’re able to do in your free time,
and sometimes even in who you end up marrying.

Impact. On top of your career being the way you spend much of your time
and the means of support for the rest of your time, your career triples as
your primary mode of impact-making. Every human life touches thousands
of other lives in thousands of different ways, and all of those lives you alter
then go on to touch thousands of lives of their own. We can’t test this, but
I’m pretty sure that you can select any 80-year-old alive today, go back in

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time 80 years, find them as an infant, throw the infant in the trash, and
then come back to the present day and find a countless number of things
changed. All lives make a large impact on the world and on the future—
but the kind of impact you end up making is largely within your control,
depending on the values you live by and the places you direct your energy.
Whatever shape your career path ends up taking, the world will be altered
by it.

Identity. In our childhoods, people ask us about our career plans by asking
us what we want to be when we grow up. When we grow up, we tell people
about our careers by telling them what we are. We don’t say, “I practice
law”—we say, “I am a lawyer.” This is probably an unhealthy way to think
about careers, but the way many societies are right now, a person’s career
quadruples as the person’s primary identity. Which is kind of a big thing.

So yeah—your career path isn’t like my shitty sweatshirt. It’s really really
deeply important, putting it squarely in “Definitely absolutely make sure to
be a chef about it” territory.

Your Career Map

Which brings us to you. I don’t know exactly what your deal is. But there’s a
good chance you’re somewhere in one of the blue regions—

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I personally hope my retirement is
just as rich and vibrant as a career
path, which means I’ll need to
continue to reflect on my path in
Retirement Orchard.

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—which means your career path is a work in progress.

Whether you’re yet to start your career or well into it, somewhere in the
back of your mind (or maybe in the very front of it) is a “Career Plans” map.

We can group map holders into three broad categories—each of which is

well-represented in the river, in the pond, standing on the shore, and at
every stage of adult life.

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One group of people will look at the map and see a big, stressful question mark.

These are people who feel indecisive about their career path. They’ve been
told to follow their passion, but they don’t feel especially passionate about
anything. They’ve been told to let their strengths guide them, but they’re
not sure what they’re best at. They may have felt they had answers in the
past, but they’ve changed and they’re no longer sure who they are or where
they’re going.

Other people will see a nice clear arrow representing a direction they
feel confident is right—but find their legs walking in a different direction.
They’re living with one of the most common sources of human misery, a
career path they know in their heart is wrong.

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The lucky ones feel they know where they want to go and believe they’re
marching in that direction.

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But even these people should pause and ask themselves, “Who actually
drew this arrow? Was it really me?” The answer can get confusing.

I’m pretty sure all of these people would benefit from a moment of career
path reflection.

The Okay But Why Do You Think You Can Help Me With My
Career Reflection You Draw Stick Figures for a Living Blue Box

Extremely fair question. One thing I always ask myself as I pick topics to
write about is, “Am I qualified to write about this?” Here are the reasons I
decided to take on this topic:

1) I have spent most of the last 20 years in a perpetual state of analyzing my

own career path.

2) My path has taken a lot of turns—from wanting to be a movie star when I

was 7 to wanting to be the president when I was 17 to wanting to write film
scores when I was 22 to wanting to be an entrepreneur when I was 24 to
wanting to write musicals when I was 29 to most recently wanting to be a
writer-ish guy.

3) After being pretty all over the place about my career path for most of my
life, I actually love my job now. That’s always subject to change, but being
able to look at the decision-making processes that led me to confusing or
frustrating places, side by side with the decisions that led me to a more
fulfilling place, has offered me some wisdom on where people tend to go
wrong.

4) On top of having my own story to look at, I’ve had a front-row seat for the
stories of my dozen or so closest friends. My friends seem to share my career
path obsessiveness, so between observing their paths and talking with them
about those paths again and again along the way, I’ve broadened my views
on the topic, which helps me to distinguish between the lessons that are
my-life specific and those that are more universal.

5) Finally, this isn’t a post about which careers are better or worse than
others or which career values are more or less meaningful—there are lots
of social scientists and self-help authors out there with good data on that,
and I’m not one of them. It’s instead a framework that I think can help a
career-path reflector better see their own situation, and what really matters
to them, clearly and honestly. This framework has worked really well for me,
so I think it can probably be helpful for other people too.

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Now that you’ve taken a fresh look at your Career Plans map, along with
whatever arrow may or may not be on it, put it down and out of sight. We’ll
come back to it at the end of the post. It’s time now for a deep dive—let’s
think about this from scratch. From first principles.

Deep Analysis, Part 1: Your Want Box

In the cook-chef post, I designed a simple framework for how a chef makes
major career choices. At its core is a simple Venn diagram.

The first part of the diagram is the Want Box, which contains all the careers
you find desirable.

The second part of the diagram is the Reality Box. The Reality Box is for
the set of all careers that are realistic to potentially achieve—based on a
comparison, in each case, between your level of potential in an area and
the general difficulty of achieving success in that area.

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The overlapping area contains your optimal career path choices—the set of
arrows you should consider drawing on your Career Map. We can call it the
Option Pool.

This is straightforward enough. But actually filling in these boxes accurately

is way harder than it looks. For the diagram to work, it has to be as close to
the truth as possible, and to get there, we have to lift up the hood of our
subconscious and head down. Let’s start with the Want Box.

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The hard thing about the Want Box is that you want a bunch of different
things—or, rather, there are a bunch of different sides of you, and each of
them wants—and fears—its own stuff. And since some motivations have
conflicting interests with others, you cannot, by definition, have everything
you want. Going for one thing you want means, by definition, not going for
others, and sometimes, it’ll specifically mean going directly against others.
The Want Box is a game of compromise.

The Yearning Octopus

To do a proper Want Box audit, you need to think about what you yearn for
in a career and then unpack the shit out of it. Luckily, we have someone
here who can help us. The Yearning Octopus.

We each have our own personal Yearning Octopus 5 in our heads. The 5
particulars of each person’s Yearning Octopus will vary, but people also
You know he’s actually a Yearning
aren’t all that different from each other, and I bet many of us feel very
Pentapus, I know he’s actually a
similar yearnings and fears (especially given that I find that Wait But Why Yearning Pentapus, and he knows
readers tend to have a lot in common). he’s actually a Yearning Pentapus—
but let’s just leave it alone.

The first thing to think about is that there are totally distinct yearning
worlds—each living on one tentacle. These tentacles often do not get along
with each other.

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It gets worse. Each tentacle is made up of a bunch of different individual
yearnings and their accompanying fears—and these often massively conflict
with each other too.

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Let’s take a closer look at each tentacle to see what’s going on.

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The Personal Yearnings tentacle is probably the hardest one to generalize
here—it’s pretty particular to each of us. It’s a reflection of our specific
personality and our values, and it bears the burden of probably the most
complex and challenging human need: fulfillment. It’s also in the shit
dealing with not only our current selves, but a bunch of our past selves
too. The dreams of 7-year-old you and the idealized identity of 12-year-
old you and the secret hopes of 17-year-old you and the evolving passions
of your current self are all somewhere on the personal tentacle, each
throwing their own little fit about getting what they want, and each fully
ready to make you feel horrible about yourself with their disappointment
and disgust if you fail them. On top of that, your fear of death sometimes
emerges on the personal tentacle, all needy about you leaving your mark
and achieving greatness and all that. The personal tentacle is why you don’t
find very many billionaires content to spend the rest of their life sipping
cocktails on the beach—it’s a highly needy tentacle.

And yet, the personal tentacle is also one that often ends up somewhat
neglected. Because in many cases, it’s the ickiest set of yearnings to really
go for; because the fears of this tentacle aren’t scary in an immediate way—
they creep in out of the background over time; and because the personal
tentacle is always at risk of getting bowled over early in your career by the
powerful animal emotions of the other tentacles. This neglect can leave
a person with major regrets later on once the dust settles. An unfulfilled
Personal Yearnings tentacle is often the explanation, for example, behind a
very successful, very unhappy person—who may believe they got successful
in the wrong field.

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The Social Yearnings tentacle is probably our most primitive, animal side,
with its core drive stemming back to our tribal evolutionary past. On the
tentacle are a number of odd creatures.

As we’ve discussed before on this blog, we all have a Social Survival

Mammoth living in our heads who’s earth-shatteringly obsessed with what
other people think of us. This means he craves acceptance and inclusion
and being well-liked, while likewise being petrified of embarrassment,
negative judgment, and disapproval. He really really really wants to be in
the in-group and he really really really doesn’t want to be in the outgroup.
He’s quite cute though.

Then there’s your ego, who’s a similar character but even more needy. Your ego
doesn’t just want to be accepted; it wants to be admired, desired, and fawned
upon—ideally, on a mass scale. More upsetting to it than being disliked is being
ignored. It wants to be relevant and important and widely known.

There are other characters milling about as well. Somewhere else on the
social tentacle is a little judge with a little gavel who gets very butthurt
if it thinks people aren’t judging you fairly—if you’re not appropriately
appreciated. It’s very important to the judge that people are aware of
exactly how smart and talented you think you are. The judge is also big
on holding grudges—which is the reason a lot of people are driven more
than anything by a desire to show that person or those people who never
believed in them.

Finally, some of us may find a loving little dog on our social tentacle who
wants more than anything in the world to please its owner, and who just
cannot bear the thought of disappointing them. The one problem with this
adorable creature is that its owner isn’t you. It’s a person with so much
psychological power over you that, if you’re not careful, you may dedicate
your whole career to trying to please them and make them proud. (It’s
probably a parent.)

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The Lifestyle Yearnings tentacle mostly just wants Tuesday to be a good day.
But like, a really pleasant, enjoyable day—with plenty of free time and self-
care and relaxation and luxuries.

It’s also concerned with your life in the big picture being as great as
possible—as far as your lifestyle tentacle is concerned, you should be able
to do what you want to do in life, when and how you want to do it, with the
people you like most. Life should be full of fun times and rich experiences,
but it should also roll by smoothly, without too much hard work and as few
bumps in the road as possible.

The issue is, even if you place a high priority on your lifestyle yearnings, it’s
pretty difficult to keep the whole tentacle happy at the same time. The part
of the tentacle that just wants to sit around and relax will hold you back
from sweating to build the kind of career that offers long-term flexibility
and the kind of wealth that can make life luxurious and cushy and full of
toys. The part of the tentacle that only feels comfortable when the future
feels predictable will reject the exact kinds of paths that may generate the

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long-term freedom another part of the tentacle longs for. The side of you
that wants a stress-free life doesn’t get along very well with the side of you
that thirsts to be hang gliding off a cliff in Namibia like Richard Branson.

The Moral Yearnings tentacle thinks the rest of the tentacles of your
Yearning Octopus are a real pack of dicks—each one more self-involved and
self-indulgent than the next. The parts of you on the moral tentacle look
around and see a big world that needs so much fixing; they see billions of
people no less worthy than you of a good life who just happened to be born
into inferior circumstances; they see an uncertain future ahead that hangs
in the balance between utopia and dystopia for life on Earth—a future
we can actually push in the right direction if we could only get our other
tentacles out of our way. While the other tentacles fantasize about what you
would do with your life if you had a billion dollars in the bank, the moral
tentacle fantasizes about the kind of impact you could make if you had a
billion dollars to deploy.

Needless to say, the other tentacles of your Yearning Octopus find the
moral tentacle to be insufferable. They also can’t begin to understand
philanthropy for philanthropy’s sake—they think, “Other people aren’t me,
so why would I spend my time and energy working to help them?”—but they
can understand philanthropy for their own motive's sake. While the moral
and lifestyle tentacles tend to be in direct conflict, others may sometimes

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find common ground—the social tentacle can get very into philanthropy
if it’ll happen to win you respect and admiration from a highly regarded
social group, and some people’s personal tentacle may find the meaning or
self-worth it so craves in a philanthropic endeavor.

That’s why, when you do something philanthropic—or anything altruistic,

really—there are a few separate things going on in your head. The part of
you determined to get proper public credit for the deed lives on your social
tentacle; the part of you that thinks “God I’m a good person” lives on your
personal tentacle; and the part of you that really loves seeing the person
or group you helped be better off lives on your moral tentacle. Likewise,
not doing anything for others can hurt you on multiple tentacles—the
moral tentacle because it feels guilty and sad, the social tentacle because
this may cause others to judge you as a selfish or greedy person, and the
personal tentacle because it may lower your self-esteem.

Your Practical Yearnings tentacle thinks all of this is fine and great—but
it would also like to point out that it’s March 31st and your rent is due
tomorrow, and the funny thing about that is that it logged into your bank
account and saw that the number of dollars in it is actually less than the
number of dollars that your landlord will need from you sometime in the
next 34 hours. And yeah it knows that you deposited that check on Thursday

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and that it’s supposed to clear tomorrow morning, but your practical
tentacle also could have sworn that just last month, all the tentacles
promised that they’d make some sacrifices in order to build up at least a
little bank account cushion so that simply paying the rent wouldn’t have to
be really fucking stressful every month. Your practical tentacle also can’t
help but notice that your social tentacle offered to buy a round of drinks
for all nine people you went to the bar with last Saturday so those people
would think of you as a classy, generous person, and that your lifestyle
tentacle chose to rent what sure seems like a pretty nice-ass apartment
for someone now living check to check, and that the updates have gotten
real quiet from your friend about that bagel delivery service he started six
months ago that your moral tentacle happily invested $2,500 in to help it
get off the ground, and oh also that meanwhile your personal tentacle has
everyone sweating their dick off working at two comedy-writing internships
simultaneously that somehow manage to bring in less money combined
than you made dressing up as an Egyptian enchantress to wait tables at
Jekyll & Hyde sophomore year of college.

At its basic level, your practical tentacle wants to make sure you can
eat food and wear clothes and buy the medicine you need and not live
outside. It doesn’t really care how these things happen—it just wants them
to happen. But then everyone else on the octopus makes your practical
tentacle’s life super hard by being fucky about things. Every time your
income goes up, your lifestyle tentacle decides to raise the bar on what it
wants and expects, leaving your practical tentacle continually in the shit
trying to cover it all so you don’t have to run up your credit card debt. Your
personal tentacle has all of these weird needs that take up a lot of time
and more often than not aren’t exactly big money-makers. And while your
practical tentacle would be totally down to just ask your rich uncle for
money to help out, your social tentacle outlawed asking others for money
because “it’s not a good look,” with your personal tentacle chiming in that
“yeah, we’re better than that.”

So that’s the situation. You’ve got this Yearning Octopus in your head with
five tentacles (or however many yours has), each with their own agenda,
that often conflict with each other. Then there are the distinct individual
yearnings on each tentacle, often in conflict amongst themselves. And if
that weren’t enough, you sometimes have furious internal conflict inside a
single yearning. Like when your desire to pursue your passion can’t figure
out what it’s most passionate about.

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Or when you want so badly to be respected, but then you remember that a
career that wins the undying respect of one segment of society will always
receive shrugs from other segments and even contemptuous eye rolls from
other segments still.

Or when you decide to satisfy your urge to help others, before realizing
that the part of you that wants to dedicate your life to helping to mitigate
humanity’s greatest existential risks has palpable disdain for the part
of you that would rather make a tangible positive impact on your local
community—while the part of you that can’t stand the thought of the
millions of today’s humans without access to clean water finds both of
those other yearnings to be pretty cold and heartless.

So yeah, your Yearning Octopus is complicated. And no human in history

has ever satisfied their entire octopus—that’s why you’ll never find it
fully smiling. Human yearning is a game of choices and sacrifices and
compromise.

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Dissecting the Octopus

With that in mind, let’s return to your Want Box. When we think about our
career goals and fears and hopes and dreams, our consciousness is just
accessing the net output of the Yearning Octopus—which is usually made
up of its loudest voices. Only by digging into our mind’s subconscious can
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we see what’s really going on. 6 There are printouts at the bottom of
the post if you'd like to work through
your analysis on paper.
The cool thing is that we all have the ability to do that. The stuff in your
subconscious is like stuff in the basement of a house. It’s not off-limits
to us—it’s just in the basement. We can go look at it anytime—we just
have to A) remember that the house has a basement, and B) actually
spend the time and energy to go down there, even though going down
there might suck.

So let’s head to the basement of your mind to look for the octopus.
Unless you’re one of those people who’s really practiced at analyzing your
subconscious, it might be dark in the basement, making it hard to see your
octopus. The way to start turning the lights on is by identifying what your
conscious mind currently knows about your yearnings and fears, and then
unpacking it.

Like if there’s a certain career path that sounds fantastic to you, unpack
that. Which tentacles in particular are yearning for that career—and which
specific parts of those tentacles?

If you’re not currently working towards that career you supposedly yearn
for, try to figure out why not. If you think it’s because you’re afraid of failing,
unpack that. Fear of failure can emerge from any of the tentacles, so that’s
not a specific enough analysis. You want to find the specific source of the
fear. Is it a social tentacle fear of embarrassment, or of being judged by
others as not that smart, or of appearing to be not that successful to your
romantic interests? Is it a personal tentacle fear of damaging your own
self-image—of confirming a suspicion about yourself that haunts you? Is it
a lifestyle tentacle fear of having to downgrade your living situation, or of
bringing stress and instability into a currently predictable life? Or maybe
that fear of a living situation downgrade isn’t actually emerging from your
lifestyle tentacle, but more so from your social tentacle—in other words, is
it possible you're indifferent about the apartment change itself but super
concerned about the message a lifestyle downgrade sends to your friends
and family? Or are there financial commitments you simply cannot back
out of at the moment, and your practical tentacle is in a genuine panic
about how you’ll make ends meet should this career switch take longer

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than expected to work out, or not work out at all? Or are a few of these
combining together to generate your fear of making the leap?

Perhaps you don’t really think it’s fear of failure that’s stopping you,
but something else. Maybe it’s a dread of the change in identity—both
internally and externally—that inevitably accompanies a career move
like this. Maybe it’s the heavy weight of inertia—an intense resistance to
change—that seems to exist in and of itself and overpowers all of your
other yearnings. In either case, you’d want to unpack the feeling and ask
yourself exactly which tentacles are so opposed to an identity shift, or so
driven by inertia.

Maybe you pine to be rich. You fantasize about a life where you make $1.2
million a year, and you feel a tremendous drive to make it happen. All five
tentacles can feel a desire for wealth under certain circumstances, each for
their own reasons. Unpack it.

As you unpack an inner drive to make money, maybe you discover that at
its core, the drive is more for a sense of security than for vast wealth. That
can be unpacked too. A yearning for security at its simplest is just your
practical tentacle doing what your practical tentacle does. But maybe it’s
not actually basic security you want as much as a guarantee of a certain
level of fanciness demanded by your lifestyle or social tentacle. Or perhaps
what you really want is a level of security so over-the-top secure it can
no longer be called a security yearning—instead, it may be an impulse
by the emotional well-being section of your lifestyle tentacle to alleviate
a compulsive financial stress you were raised to forever feel, almost
regardless of your actual financial situation.

The answers to all of these questions lie somewhere on the tentacles of

your Yearning Octopus. And by asking questions like these and digging deep
enough to identify the true roots of your various yearnings, you start to turn
on the basement light and acquaint yourself with your octopus in all its
complexity.

You’ll also come to understand which of your inner yearnings seem to speak
the loudest in your mind and carry the most pull in your decision-making
processes. Pretty quickly, a yearning hierarchy will begin to reveal itself.
You’ll identify yearnings that speak loudly and get their way; yearnings that
cry at the top of their lungs but get continually elbowed out of the way by
higher-prioritized parts of the octopus; yearnings that seem resigned to
their low-status positions in the hierarchy.

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Searching for Imposters

We’re making good progress—but we’re just getting started. Once you have
a reasonably clear picture of your Yearning Octopus, you can start doing the
real work—work that takes place another level down in your subconscious,
in the basement of the basement. Here, you can set up a little interrogation
room and one by one, bring each yearning down into it for a cross-
examination.

You’ll start by asking each yearning: how did you end up here, and why are
you the way you are? Desires, beliefs, values, and fears don’t materialize
out of nowhere. They’re either developed over time by our internal
consciousness as observations and life experience pour in, or they’re
implanted in us from the outside, by someone else. In other words, they’re
the product of either you the chef or you the cook.

So the goal here in your creepy interrogation room is to tug on the faces of
each of your yearnings to find out if it’s authentically you, or if it’s someone
else disguised as you.

You can pull on a yearning’s face by playing the Why Game. You’ll ask
your initial Why—Why is this something I want?—and get to some kind of
Because. Then you’ll keep going. Why did that particular Because lead you
to want what you now want? And when did that particular Because gain so
much gravity with you? You’ll get to a deeper Because behind the Because.
And if you continue with this, you’ll usually discover one of three things:

1) You’ll trace the Why back to its origin and reveal a long chain of authentic
evolution that developed through deep independent thought. You’ll pull on
their face and confirm that the skin is real.

2) You’ll trace the Why back to an original Because that someone else
installed in you—I guess the only reason I actually have this value is
because my mom kind of forced it on me—and you realize that you never
really thought to consider whether you actually independently agree with it.
You never stopped to ask yourself whether your own accumulated wisdom
actually justifies the level of conviction you feel about that core belief. In
a case like this, the yearning is revealed to be an imposter pretending to
be an authentic yearning of yours. You pull on its face and it’s a mask that
comes off, exposing the yearning’s original installer underneath.

3) You’ll trace the Why back and back and get kind of lost in a haze of “I
guess I just know this because it’s true!” This could be an authentic you

25
thing, or just another version of #2, in an instance where you can’t recall
the moment this feeling was installed in you. Somewhere deep in you, you’ll
have a hunch about which it is.

In a #1 scenario, you can be proud that you developed that part of you like
a chef. It’s an authentic and hard-earned feeling or value.

In a #2 or maybe #3 scenario, you’ve discovered that you’ve been duped.

You’ve let someone else sneak onto your Yearning Octopus while you
weren’t looking. When it comes to that particular belief of yours, you’re a
cook following someone else’s recipe—an obedient robot reciting desires
and fears out of someone else’s brain.

There’s a chance you’re an unusually wise person whose examination

reveals an octopus developed mostly by you and kept readily up to date.
More likely, you’re like me and most of my friends—your interrogation
room reveals some definite imposters, or at least a lot of ambiguity. Like,
underneath one mask, you’ll find your mom.

26
27
28
You’ll pull off others to reveal the values and judgments of broader
conventional wisdom, or the viewpoints of your more immediate
community, or what’s considered cool by the dominant culture of your
generation or the immediate culture within your closest group of friends.

Sometimes you’ll get to the end of a Why-Because pathway only to find

the philosophy in a famous novel, or something a celebrity hero of yours
once said in an interview, or a strong opinion one of your professors always
repeated.

You might even find that some of your yearnings and fears were written
by you…when you were seven years old. Like a childhood dream that was

29
etched into the back of your consciousness as the thing you believe you
really want, when you’re being truly honest.

30
The interrogation room probably won’t be that fun a time. But it’s time well
spent—because you’re not your 7-year-old self, just like you’re not your
parents or your friends or your generation or your society or your heroes or
your past decisions or your recent circumstances. You’re Current-Age You—
the only person, and the only version of yourself, who is actually qualified
to want and not want the things you want and don’t want.

To be clear, this isn’t to say that it’s wrong to live by the words of a wise
parent or a famous philosopher or friends you respect or the convictions of
a younger you. Humble people are by definition influence-able—influences
are an important and inevitable part of who each of us is. The key
distinction is this:

Do you treat the words of your external influences as information, held

and considered by an authentic inner you, that you’ve carefully decided
to embrace? Or are your influences themselves actually in your brain,
masquerading as inner you?

Do you want the same thing someone else you know wants because
you heard them talk about it, you thought about it alongside your own
life experience, and you eventually decided that, for now, you agree? Or

31
because you heard someone talk about what they want or fear, and you
thought, “I don’t know shit and that person does, so if they say X is true, I’m
sure they’re right”—and then you etched those ideas into your mind, never
again feeling the need to question them?

The former is what chefs do. The latter is what you do when you’re being an
obedient robot. And a robot is what you become when at some point you
get the idea in your head that someone else is more qualified to be you
than you are.

The good news is that all humans make this mistake—and you can fix it. Just
like your subconscious is right there for viewing if you want to view it—it’s
also there for changing and updating and rewriting. It’s your head—you’re
allowed to do with it what you want.

So it’s time for some evictions. Masked imposters have to go. Even mom
and dad.

At the end of this, your octopus may look a little barren, leaving you feeling
a little like you don’t know who you even are anymore. We usually think
of this as a bad feeling, or even an existential crisis, but it actually means
you’re doing better than most people.

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The drop from naive over-confidence to wise, realistic humility never feels
good, but pausing the roller coaster while it’s still on that first cliff and
avoiding the pain—which turns out to be a lot of people’s move—isn’t a
great strategy. Wisdom isn’t correlated with knowledge, it’s correlated
with being in touch with reality—it’s not how far to the right you are on
the graph, it’s how close you are to the orange line. Wisdom hurts at
first, but it’s the only place where actual growth happens. The irony is
that the cliff-pausers of the world like to make the wiser, braver valley-
dwellers or continual-climbers feel bad about themselves—because they
fundamentally don’t get how knowing yourself works. They haven’t reached
that stage yet.

Getting to know your real self is super hard and never complete. But if
you’ve tumbled off the cliff, you’ve gone through a key rite of passage and
progress is now possible. As you climb up the orange line, you’ll slowly but
surely begin to repopulate your Yearning Octopus with your real self.

At the moment, it probably won’t be obvious what those missing yearnings

of yours are exactly—because they’re on an even deeper floor of your
subconscious. They’re in the basement of the basement of the basement—
in a place called Denial Prison.

Denial Prison

Our brain’s Denial Prison is a place most of us don’t even know is there—it’s
where we put the parts of us we repress and deny.

The authentic yearnings of ours that we’re in touch with—i.e. those that
proved to be authentic during interrogation—were easy parts of our
true selves to find in our subconscious, lying in plain sight, right below
the surface of our consciousness. Even our conscious mind knows these
yearnings well, because they frequently make their way upstairs into our
thoughts. These are the parts of us we have a healthy relationship with.

But then there are the parts of you that weren’t living on your octopus
where they’re supposed to be—instead, you found an imposter in their
place. These lost parts of you are often incredibly hard to access, because
they’ve been living deep in your subconscious, on a floor so low it’s almost
not there at all. Almost.

Some parts of us are banished down on basement #3 because they’re

extraordinarily painful for us to acknowledge or think about. Sometimes
new parts of us are born only to be immediately locked up in prison as

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part of a denial of our own evolution—i.e. out of stubbornness. But there
are other times when a part of us is in Denial Prison because someone
else locked it up down there. In the case of your yearnings, some of them
will have been put there by whatever masked intruder had been taking its
place. If dad has successfully convinced you that you care deeply about
having a prestigious career, he probably has also convinced you that the
part of you that, deep down, really wants to be a carpenter isn’t really you
and isn’t what you really want. At some point during your childhood, he
threw your passion for carpentry into a dark, dank Denial Prison cell.

So let’s gather your courage and head down to the basement of the
basement of the basement of your mind and see what we find.

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You may pass some unpleasant characters.

Leave them for another time—right now, search for locked-away career-
related yearnings. Maybe you’ll find a repressed passion to teach. Or a
desire to be famous that your particular tribe has shamed you out of. Or
a deep love of long blocks of free, open leisure time that your hornier,
greedier teenage self kicked downstairs in favor of a raging ambition.

There will be certain parts of your authentic self you won’t be able to
uncover in Denial Prison—it’s pretty dark down there. But be patient—now
that you’ve done your audit and cleared space for them on your octopus,
they may begin to emerge.

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Priority Rankings

The other part of our Yearning Octopus audit will address the hierarchy
of your yearnings. Almost as important as the yearnings themselves is the
priority they’re given. The hierarchy is easy to see because it’s revealed in
your actions. You may like to think a desire to do something bold is high up
on your hierarchy, but if you’re not currently working on something bold, it
reveals that however important boldness is to you, something else—some
source of fear or inertia in you—is currently being prioritized above it.

It’s important to remember that a ranking of yearnings is also a ranking

of fears. The octopus contains anything that could make you want or not
want to pursue a certain career, and the reverse side of each yearning is
its accompanying fear of the opposite. The reverse side of your yearning
to be admired is a fear of embarrassment. If you flip over your desire for
self-actualization, you’ll see a fear of underachieving. The other half of
your craving of self-esteem is a fear of feeling shame. If your actions don’t
seem to match what you believe is the internal hierarchy of your yearnings,
usually it's because you’re forgetting to think about the role your fears are
playing. What looks like a determined drive for success, for example, might
actually be someone running away from a negative self-image or trying
to escape feelings like envy or under-appreciation. If your actions seem
beholden to yearnings that you don’t believe you actually care that much
about, you’re probably not looking closely enough at your fears.

With both yearnings and fears in mind, think about what your internal
hierarchy might look like, and return that same important question: “Who
made this order? Was it really me?”

For example, we’re often told to “follow our passion”—this is society saying
“put your passion yearnings at the top of your hierarchy.” That’s a very
specific instruction. Maybe that’s the right thing for you, but it also very well
might not be. It’s something you need to independently evaluate.

To get this right, let’s try to do a fresh ranking, from first principles, based
on who we really are, how we’ve evolved over time, and what really matters
to us most, right now.

This isn’t about which yearnings or fears have the loudest voices or which
fears are most palpable—if it were, you’d be letting your impulses take the
wheel of your life. The person doing the ranking is you—the little center
of consciousness reading this post who can observe your octopus and
look at it objectively. This involves another kind of compromise. On one

36
side, you’ll try to tap into all the wisdom you’ve accumulated throughout
your life and make active decisions about values—about what you really
believe is important. On the other side, it’s about self-acceptance and
self-compassion. Sometimes you’ll have strong undeniable yearnings that
you’re not super proud of—whether you like it or not, those are part of you,
and when you neglect them, they may cause a continual stink and make
you miserable. Creating your yearning hierarchy is a give and take between
what’s important and what’s you. It’s probably a good goal to give higher
priority to your more noble qualities, but it’s okay to throw a bone to some
of your not-so-noble sides as well—depending on where you decide to draw
the line. There’s a wisdom to knowing when to accept your not-so-noble
side and when to reject it entirely.

To get all of this in order, we want a good system. You can play around with
what works for you—I like the idea of a shelf:

This divides things into five categories. The absolutely highest priority inner
drives get to go in the extra special non-negotiable bowl. The NN bowl is for
yearnings so important to you that you want to essentially guarantee that
they’ll happen—at the expense of all other yearnings, if necessary. This is
why so many of history’s legends were famously single-minded—they had a
very intense NN bowl yearning and it led them to world fame, often at the
expense of relationships, balance, and health. The bowl is small because
it should be used very sparingly—if at all. Like maybe only one thing gets
it. Or maybe two or three. Too many things in the NN bowl cancels out its
power, making that the same as having nothing in the bowl at all.

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Your group of top shelf yearnings is mostly what will drive your career
choices—but top shelf placement should also be doled out sparingly (that’s
why it’s not a very large shelf). Shelf placement is as much about de-
prioritizing as it is about prioritizing. You’re not just choosing which parts of
you are the most important to make you happy, you’re choosing which parts
of you to intentionally leave wanting or even directly opposed. No matter
what your hierarchy looks like, some yearnings will be left feeling very
unhappy and some fears will feel like they’re being continually assaulted.
This is inevitable.

That’s why most yearnings should be on the middle shelf, the bottom
shelf, or the trash can. The middle shelf is good for those not-so-noble
qualities in you that you decide to accept. They deserve some of your
attention. And they'll often demand it—core parts of you won’t go quietly
into non-prioritization, and they sometimes can really ruin your life if
they’re neglected.

Most of the rest will end up on the bottom shelf. Putting a part of you on
the bottom shelf is telling it, “I know you want these things, but for now,
I’ve decided other things are more important. I promise to revisit you a
little later, after I’ve gotten some more information, and if I change my
mind, you’ll get a shelf upgrade then.” The best way to think of the bottom
shelf is this: the more yearnings you can convince to accept a bottom shelf
rating, the better the chances your top shelf and NN bowl yearnings have
of getting what they want. Likewise, the fewer yearnings you put on the top
shelf, the more likely those on the top shelf will be to thrive. Your time and
energy are severely limited, so this is a zero-sum compromise. The amateur
mistake is to be too liberal with the NN bowl and top shelf and too sparing
with the large bottom shelf.

Then there’s the trash can, for the drives and fears you flat-out reject—
those parts of you that fundamentally violate the person your wisest self
wants to be. A good amount of inner conflict emerges from people’s trash
cans, and trash can control is a major component of integrity and inner
strength. But like the rest of your hierarchy decisions, your criteria for what
qualifies as trash should be derived from your own deep thought, not from
what others tell you is and is not trash.

As you go through this difficult prioritizing process—inevitably, at times,

against the screaming protests of unhappily deprioritized yearnings—
remember that you’re the only wise one in the room. Yearnings and fears
are impatient and bad at seeing the big picture. Even a seemingly high-
minded yearning, like those on the moral tentacle, can’t understand the

38
complete picture in the way you can. Many of the people who have done
wonders to make the world better got there on a path that started with
selfish motives like wealth or personal fulfillment—motives their moral
tentacle probably hated at first. The octopus won’t be the wise adult in the
room—that’s your job.

Finally, as we’ll discuss more later, this is not a permanent decision. It’s
the opposite—it’s a rough draft written in light pencil. It’s a hypothesis
that you’ll be able to test and then revise based on how actually living this
hierarchy feels in practice.

Your Want Box is ready to go. Now let’s turn to your Reality Box.

Deep Analysis, Part 2: Your Reality Box

The Want Box deals with what you find desirable. The Reality Box deals with
what’s possible.

But when we examined the Want Box, it became clear that it’s not
necessarily based on what you actually want—it’s based on what you think
you want—what you’re in the habit of wanting.

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The Reality Box is the same deal. It doesn’t show you reality, it shows your
best crack at what reality might be—your perception of reality.

The goal of self-reflection is to bring both of these boxes as close to

accuracy as possible. We want our perceived yearnings to be a true
reflection of our authentic inner selves, and we want our beliefs about
what’s possible to come close to mirroring what’s actually possible. For our
Want Box audit, we looked under the hood of the Want Box and found its
settings—your yearnings and fears. When we open the hood of your Reality
Box, we see a group of beliefs.

When it comes to your career possibilities, you’re dealing with two sets of
beliefs: beliefs about the world and beliefs about your own potential. For a
career option to qualify for your Reality Box, your potential in that career
area has to measure up to the objective difficulty of achieving success in
that area.

Us being us, we’re probably pretty bad at assessing either side of this
comparison accurately.

I don’t know how you think about career path difficulty, but in my
experience, people often see it like this:

There are traditional careers—stuff like medicine or law or teaching or

a corporate ladder, etc.—and these careers have predictable, set paths.
If you’re decently smart and work hard, you’ll end up in a successful,
stable situation.

Then there are less traditional careers—the arts, entrepreneurship, non-

profit work, politics, etc.—and these are wildcards. Success and stability are
no guarantee, and to reach great heights, it’s either a lottery ticket game of
luck, a genetic lottery game of innate talent, or some combination of the
two.

These are perfectly reasonable assumptions—if you live in 1952. Your beliefs
about the world of careers and about what it takes to succeed need just as
thorough an unmasking as your yearnings did—and I suspect that behind
most of them, you’ll find big, fat conventional wisdom. You might first pull
off the mask of one of your beliefs and find your parents or your friends

7
or your college career coach—but if you keep going and pull on their face,
you’ll usually see that it’s also a mask, and conventional wisdom is there
hiding behind it. A general conception, a common opinion, an oft-cited Did you know that 9 out of 10
statistic 7 —none of which have actually been verified by you, but all of restaurants fail?!

which are treated as gospel by society.

40
Today's world goes through dramatic changes each decade, which usually
leaves conventional wisdom wildly outdated. But we're wired for a more
ancient world where almost nothing ever changed, so we all reason like
cooks and treat conventional wisdom as equivalent to truth.

These problems then extend to how we view our own potential. When you
overrate the impact of innate talent on how people fare in their careers—
and you also conflate talent and skill level—it won’t leave you feeling great
about your chances at many paths. Because we better understand the
trajectory of traditional careers, we’re less prone to do this with them. A
first-year medical student sees an experienced surgeon at work and thinks,
“I can get there one day—just need to do about 20 years of hard work."
But when a young artist or entrepreneur or software engineer looks at the
equivalent of the experienced surgeon in their field, they’re more likely to
think, “Wow look how talented they are—I’m nowhere near that good,” and
get all hopeless. There’s also the other common notion, that people who
thrive in non-traditional careers had some “big break” at some point, like
hitting a lucky scratch card jackpot—and I don’t know many people who
want to risk their careers on scratch cards.

These are only a few examples of the slew of delusions and misconceptions
we tend to have about how great careers happen. So let’s brainstorm how it
might actually work:

The Career Landscape

I have no idea, mostly. And I think most people have no idea. Things are just
changing too quickly.

But that’s kind of the key point. If you can figure out how to get a
reasonably accurate picture of the real career landscape out there, you
have a massive edge over everyone else, most of whom will be using
conventional wisdom as their instruction booklet.

First, there’s the broad landscape—the set of all the jobs someone could
possibly have in today’s society. My current job description is: “Writer
of 8,000-to-40,000-word articles about a bunch of different topics, with
cursing and stick figures, on a remarkably sporadic schedule.” Think
conventional wisdom has any job openings for me with that description?
The landscape today is made up of thousands of options—some 40 years
old, some made possible only three months ago because of the advent
of some new technology—and the way things work today, if there’s an
option you want that’s not already out there, you can probably create it for
yourself. Pretty stressful, but also incredibly exciting.

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Then, there’s each specific career path. A career path is like a game board.
The conventional wisdom bookshelf contains instruction booklets for only
a small fraction of today’s available game boards—and those that it does
have usually tell you how that game was played in the past, even though
the current game board has evolved significantly into something with
new kinds of opportunities and different rules and loopholes. When you
consider a career path today, to make an accurate assessment of what
the path looks like and what kinds of strength-weakness profiles it favors,
you have to understand what that career’s current game board looks like.
Otherwise, it’s like trying to evaluate your chances of being a professional
basketball player based on your height and strength without realizing
that, say, basketball has evolved and is now played on oversize courts that
contain 10 different 7-foot hoops, and the current game favors speed over
height and strength.

This is promising news. There are likely dozens of awesome career paths
that beautifully match your natural strengths, and it’s likely that most
other people trying to succeed on those paths are playing with an outdated
rulebook and strategy guide. If you simply understand what the game board
really looks like and play by modern rules, you have a huge advantage.

Your Potential

And this brings us to you and your particular strengths. Not only do
we assess our strengths based on the wrong game boards (like in our
basketball example)—even when we have the right game board in mind,
we're often bad at identifying the real strengths that that game calls for.

When assessing your chances on a certain career path, the key question is:

With enough time, could you get good enough at this game to potentially
reach whatever your definition of success is in that career?

I like to view this journey to “good enough at the game to succeed” as a

distance. The distance starts with where you are now—point A—and ends
with you reaching your definition of success, which we can draw with a star.

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The length of the distance depends on where point A is (how far along you
are at the current moment) and where the star is (how lofty your definition
of success is).

So if you’re a college graduate who majored in computer science and

your career goal is to be a middle-of-the-ladder engineer at Google, your
distance might look like this:

But if you’ve never done any kind of computer science before, and your
career goal is to be the top engineer at Google, you’ve got a much longer
road ahead:

If your goal is to create the new Google, the road gets much, much longer.

At this point, conventional wisdom might emerge as a voice in your head

and point out that simply getting good enough at a certain skill doesn’t
actually guarantee success—you might reach the star on a career path and
still find that you haven’t “made it” yet.

That’s mostly wrong, because it's misunderstanding the star. The star isn’t
about a particular skill level—e.g. coding ability or acting skills or business
savvy—it’s about the entire game. In traditional careers, the games tend
to be more straightforward—if you want to be a top surgeon, and you get
incredibly good at surgery, you’ve probably hit your star and you’ll have
your career. But the game boards in less traditional careers often involve
many more factors. Reaching the “I want to be a famous actor” star doesn’t

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simply mean getting as good at acting as Morgan Freeman, it means getting
as good at the entire actor game as most movie stars get by the time they
break through. Acting ability is only one piece of that puzzle—you also need
a knack for getting yourself in front of people with power, a shrewdness for
personal branding, an insane amount of optimism, a ridiculous amount of
hustle and persistence, etc. If you get good enough at that whole game—
every component of it—your chances of becoming an A-list movie star are
actually pretty high. That’s what hitting the star means.

But conventional wisdom doesn’t get how non-traditional careers

work—it only thinks in terms of a narrow aspect of success: talent and
hard work. When career paths have game boards with much more going
on, conventional wisdom just throws its hands up and calls it “luck.” To
conventional wisdom, becoming a movie star requires some talent, but
mostly, hitting a rare scratch ticket jackpot.

So how do you figure out your chances of getting to any particular star? It’s
all about a simple formula:

Distance = Speed x Time.

In our case, the more apt wording might be:

Progress = Pace x Persistence.

Your outlook on any career quest depends on A) the pace at which you’ll be
able to improve at playing that career's “game” and B) the amount of time
you’re willing to persist in chasing that star. Let’s talk about both of these:

Pace

What makes someone slower or faster at improving at a career game? I’d

say it comes down to three factors:

Your level of chefness. As we discussed earlier, chefs look at the world with
fresh eyes and build conclusions based on what they observe and what
they’ve experienced. Cooks arrive at conclusions by following someone
else’s recipe—in the case of careers, the recipe is usually conventional
wisdom. Careers are complex games that almost everyone starts off bad
at—then the chefs improve rapidly through a continual loop…

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…while cooks improve at a snail’s pace, because their strategy is just
following a recipe which itself barely changes. What’s more, in a world
where career games are constantly evolving and morphing, the chef’s
tactics can evolve in real time and keep up. Meanwhile, the cook’s recipe
just grows more and more outdated—a problem they remain oblivious to.
This is why I’m pretty convinced that at least for less traditional careers,
your level of chefness is the single most important factor in determining
your pace of improvement.

Your work ethic. This one is obvious. Someone who works on their career
60 hours a week, 50 weeks a year, is going to move down the path almost
four times faster than someone who works 20 hours a week, 40 weeks a
year. Someone who chooses a balanced lifestyle will move slower than a
single-minded workaholic. Someone with a propensity towards laziness or
procrastination is going to lose a lot of ground to someone who’s good at
putting in consistent work days. Someone who frequently breaks from work
to daydream or pick up their phone is going to get less done in each work
hour than someone who practices deep focus.

Your natural abilities. Talent does matter. Smarter, more talented people
will improve at a game at a faster rate than less naturally gifted people.
But intelligence and talent are only two types of natural ability that come

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into play here. Cleverness and savvy matter too, and those qualities don’t
always correlate with raw intelligence. Depending on the type of career,
social skills can be critically important as well. In many careers, likable (or
subtly manipulative) people have a big advantage over less likable people—
and those who enjoy socializing will put in more people hours over time,
and build deeper relationships, than antisocial types.

Other things, like existing connections, existing resources, and existing

skills matter, of course, but they’re not components of pace—they’re part of
the location of point A.

Persistence

When I say persistence, I'm referring to long-term persistence (as opposed

to day-to-day work ethic). Persistence is simpler than pace. The more
years you’re willing to commit to chasing a star, the farther along the road
towards the star you’ll get. A car going 30 mph that quits driving after 15
minutes gets a lot less far than a car that drives 10 mph for two hours.

And this is why persistence is so important. Someone who has decided

they’re only willing to give a dream career a shot for three years before
they’ll go for their fallback plan has essentially disqualified themselves
from a chance at their dreams. It doesn’t matter how awesome you are—
if you'll give up after two or three years of not breaking through, you’re
unlikely to succeed. A few years is just not enough time to traverse the
typically long distances it takes to get to the raddest success stars, no
matter how impressive your pace.

Your Real Strengths and Weaknesses

With our pace-times-persistence equation in mind, let’s revisit the concept

of strengths and weaknesses. It’s not that "strengths and weaknesses"
is a bad concept—it’s that we think about it all wrong. When we list our
strengths, we tend to list our areas of existing skill more than anything
else. Instead, strengths should be all about pace and persistence qualities.
Originality or lack thereof should be a critical component of the discussion,
making qualities like agility and humility (trademark chef traits) notable
8
strengths, and qualities like stubbornness 8 or intellectual laziness Stubbornness is a cook quality

(classic cook traits) important weaknesses. The subtleties of work ethic, because it means being a cook
to your previous self—i.e. treating
like a knack for deep focus or a propensity to procrastinate, should also be
your previous self’s opinions
a major part of the discussion, as should natural abilities beyond talent, and methods and habits as your
like savvy and likability. Qualities related to persistence, like resilience and permanent recipe.

determination and patience, should be thought of as promising strengths,

46
while a social tentacle clamoring to appear successful as quickly as
possible should be viewed as a bright red flag.

Most importantly, these items shouldn’t be discussed as a snapshot of

where they are now, but rather in terms of your potential for improvement
in each of them. If you handed 25-year-old Michael Jordan a basketball for
the first time, he’d suck. But calling basketball a “weakness” of his would
be getting it very wrong. Instead, you’d want to watch him practice over
the next six weeks and evaluate the slope of his improvement. This lesson
applies to specific skills—but most general pace and persistence qualities
can also be worked on and improved if you focus on them.

Filling in the Reality Box

Your true Reality Box would literally include all career paths for which you
think a highly improved version of yourself could, with an entire lifetime of
effort, reach the minimum star you’d be comfortable defining as success.
This would be an impossibly big list, only ruling out paths that are clearly
far too long for you to traverse at your maximum possible pace on the path
(like me chasing a career as an Olympic figure skater). But it’s still useful to
pause for a minute and reflect on the vast extent of your full Reality Box—
just acknowledging how many options are truly open to you can put you in 9
the right mindset. 9 Or totally paralyze you and ruin
your happiness!
So to be a bit more efficient, let’s worry about the parts of the Reality Box
that might actually end up in your Option Pool (the middle of the Venn
diagram where the Want and Reality Boxes overlap). To complete our Reality
Box audit with that caveat, we need to evaluate:

1) The general landscape. Take our best crack at evaluating the world’s
current career landscape—the full range of options available (or create-able).

2) Specific game boards. For any careers that sound remotely interesting,
ponder what the deal might be with that career's current game board—
the parties involved, the way success seems to be happening for others
recently, the most up-to-date rules of the game, the latest new loopholes
that are being exploited, etc.

3) Starting point. For those paths, evaluate your starting point, based on
your current skills, resources, and connections relevant to that field.

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4) Success point. Think about end points and where on each line your
star should be placed. Ask yourself what’s the minimum level of success
you’d need to achieve in order to feel happy about having chosen that
career path.

5) Your pace. Make an initial estimate for what your pace of improvement
might be on these various game boards, based on your current pace-
related strengths and how much you think you can improve at each of them
(in other words, how much your speed might be able to accelerate).

6) Your level of persistence. Evaluate the amount of time you think you’ll be
willing to put into each of these respective paths.

Now it's just math. You take your game board and make it a line, you
plot starting points and success stars that together generate the various
distances in front of you, and for each, you multiply your pace by your level
of persistence. If it seems like the product of your pace and persistence for
a given career path might be able to measure up to the path’s total length,
that career lands in your Reality Box. Of course, it's impossible to get
exact values for any of the above factors, but it's good to at least know the
equation you're working with.

A from-first-principles Reality Box audit may bring some overly optimistic

people down to Earth, but I suspect that for most, an audit will leave them
feeling like they have a lot more options than they realized, empowering
them to set their sights on a bolder direction.
10
John Venn really pulled something

A good Reality Box reflection warrants yet another Want Box reflection. off here. A Venn diagram is the most
obvious possible kind of diagram,
Reframing a bunch of career paths in your mind will affect your level of
and somehow, John Venn convinced
yearning for some of them. One career may seem less appealing after everyone he invented it. And this
reminding yourself that it will entail thousands of hours of networking or is despite openly saying he didn’t

multiple decades of pre-success struggle. Another may seem less daunting invent it. Venn explains: “I began at
once somewhat more steady work
after changing your mind about how much luck is actually involved. There
on the subjects and books which
will be other career paths you hadn’t considered wanting because you I should have to lecture on. I now
hadn’t considered them as real options, but some deep reflection has first hit upon the diagrammatical

opened your mind to them. device of representing propositions

by inclusive and exclusive circles.
Of course the device was not
This brings us to the end of our long, two-part deep dive. After a fairly new then, but it was so obviously
exhausting box-auditing process, we can return to our Venn 10 diagram. representative of the way in which
any one, who approached the
subject from the mathematical
side, would attempt to visualize
propositions, that it was forced
upon me almost at once.”

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Assuming some things have changed, you have a new Option Pool to look
at—a new list of options on the table that seem both desirable to your
high-priority rankings and possible to achieve. We’re ready now to return to
where we were before we started our analysis: the present moment. With
these options in front of us, we're ready to lift our heads up out of analysis
and look forward into the future.

Connecting the Dots into the Future

It’s time to bring back your Career Plans map that I made you put down at
the beginning of the post—the one with the arrow or the question mark.
If there had been a clear arrow on your map before your audit, check out
your new Option Pool. Given everything you’ve reflected upon, does your
current career plan still qualify to be there? If so, congrats—you’re ahead
of most of us.

If not, well that’s shitty news, but it’s also good news. Remember, going
from a false arrow to a question mark is always major progress in life.

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And actually, a new question mark implies having made the key cliff jump
on two roller coasters: getting to know yourself and getting to know the
world. Major step in the right direction. Cross out the arrow and join the
question mark crowd.

Now the question mark crowd has a tough choice. You gotta pick one of the
arrows in the Option Pool.

It’s a tough choice—but it should be way less tough than it is. Here’s why:

Careers used to be kind of like a 40-year tunnel. You picked your tunnel, and
once you were in, that was that. You worked in that profession for 40 years or
so before the tunnel spit you out on the other side into your retirement.

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The truth is, careers have probably never really functioned like 40-year-
tunnels, they just seemed that way. At best, traditional careers of the past
played out kind of like tunnels.

Today’s careers—especially the less traditional ones—are really really not

like tunnels. But crusty old conventional wisdom has a lot of us still viewing
things that way, which makes the already hard job of making big career
path choices much harder.

When you think of your career as a tunnel, it causes an identity crisis in

anyone who doesn’t feel sure of who exactly they are and who they’ll want
to be decades from now—which is most sane people. It enhances the
delusion that what we do for work is a synonym for who we are, making a
question mark on your map seem like an existential disaster.

When you think of your career as a tunnel, the stakes to make the right
choice seem so high that it explodes the feeling of tyranny of choice. For
perfectionist types especially, this can be utterly paralyzing.

When you think of your career as a tunnel, you lose the courage to make
a career switch, even when your soul is begging for it. It makes switching
careers feel incredibly risky and embarrassing, and it suggests that
someone who does so is a failure. It also makes all kinds of multi-faceted,
vibrant, mid-career people feel like they’re too old to make a bold switch or
start a whole new path afresh.

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But conventional wisdom still tells many of us that careers are tunnels. As
the icing on its shit cake—on top of helping us yearn for things we don’t
actually want, deny yearnings that we feel deep down, fear things that
aren’t dangerous, and believe things about the world and our potential that
aren’t accurate—conventional wisdom tells us that careers are a tunnel to
help us daunt the shit out of ourselves unnecessarily.

Today’s career landscape isn't a lineup of tunnels, it’s a massive, impossibly

complex, rapidly changing science laboratory. Today’s people aren’t
synonymous with what they do—they’re impossibly complex, rapidly
changing scientists. And today’s career isn’t a tunnel, or a box, or an
identity label—it’s a long series of science experiments.

Steve Jobs compared life to connecting the dots, pointing out that while it’s
easy to look at your past and see how the dots connected to lead you to
where you are, it’s basically impossible in life to connect the dots forwards.

If you look at the biographies of your heroes, you’ll see that their paths
look a lot more like a long series of connected dots than a straight and
predictable tunnel. If you look at yourself and your friends, you’ll probably
see the same trend—according to data, the median time a young person
stays in a given job is only 3 years (older people spend a longer time on
each dot, but not that much longer—10.4 years on average).

So seeing your career as a series of dots isn’t a mental trick to help you
make decisions—it’s an accurate depiction of what’s actually happening.
And seeing your career as a tunnel isn’t just unproductive—it’s delusional.

Likewise, you're limited to focusing mainly on the next dot on your path—
because it’s the only dot you can figure out. You don’t have to worry about
dot #4 because you can’t anyway—you’re literally not qualified to do so.

By the time dot #4 rolls around, you will have learned stuff about yourself
you don’t know now. You’ll also have changed from who you are now, and
your Yearning Octopus will reflect those changes. You’ll know a lot more
than you currently do about the career landscape and the specific game
boards you’re interested in, and you’ll have become a much better game
player. And of course, that landscape—and those game boards—will have
themselves evolved.

The fantastic website 80,000 Hours (which exists to help young, talented
people work through their career choices) has compiled a lot of data to

52
back this up: data on the fact that you’ll change, that the world will change,
and that you’ll only learn with time what you’re actually good at. Popular
psychologist Dan Gilbert also eloquently describes just how bad we are at
predicting what will make us happy in the future.

Pretending you can figure out what dot #2 or #4 or #8 should be now is

laughable. Future dots are the worry of a future, wiser you living in a future
world. So let’s focus on dot #1.

If we’re thinking of ourselves as scientists and of society as a science lab,

we should think of your current freshly revised Want-Reality Venn Diagram
as nothing more than an early, rough hypothesis. Dot #1 is your chance to
test it out.

Hypothesis testing is intuitive in the dating world. If a friend were toiling

over what kind of person she wants to marry but never went out with
anyone, you’d tell her, “You can’t figure this out on your couch—you’ve gotta
start going on dates, and that’ll teach you what you want in a partner.” If
that friend then went on a solid first date and returned home to toil for
hours about whether or not this new person was The One, you’d again have
to correct her. You’d say, “There’s no way you can know that from just one
date! You have to get some experience dating this person to learn what you
need to learn to make that decision.”

We can all agree that this hypothetical friend is pretty nuts and is lacking
a fundamental understanding of how you find a happy relationship. So
let’s not be like her when it comes to picking our career. Dot #1 is a chill
situation—it’s just a first date.

This is awesome news—because it makes it a lot less scary to draw an arrow

on your map if it’s only an arrow to dot #1 of your future. The real cause
of tyranny of choice is accurately seeing the sheer number of options you
have in today’s world while delusionally seeing those careers as the 40-year
tunnels of yesterday’s world. That’s a lethal combo. Reframing your next
major career decision as a far lower-stakes choice makes the number of
options exciting, not stressful.

And that's all great in theory. But now comes the hard part.

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Making Your Move

You’ve reflected and reflected and reflected and weighed and measured
and predicted and considered. You’ve chosen a dot and drawn an arrow.
And now you have to actually make the move.

We’re super bad at this. We’re frightened people. We don’t like icky
things and making a bold, real-life step is icky. If there’s any ounce of
procrastination susceptibility in us, here’s where it’ll show itself.

The Yearning Octopus can help. As we discussed earlier, your behavior at

any given point simply displays the configuration of your octopus. If you’ve
decided on a life step and you can’t quite take it, it’s because the parts of
you that don’t want to make a move are ranked higher in your subconscious
than the parts of you that do. Your conscious mind may have tried to assign
lower shelf ratings to the parts of your octopus that lean towards inertia,
but your yearnings have rebelled. You’re a CEO not in control of their staff.

To fix this problem, think like a kindergarten teacher. In your class, a faction
of the 5-year-olds is rebelling against your wishes. What do you do?

Go talk to the 5-year-olds that are causing the trouble. They’re unpleasant,
defiant simpletons, but they can still be reasoned with. Talk to them
about why you’ve ranked them lower than others in the octopus hierarchy.
Describe to them the insights you gained from your Reality Box reflection.
Remind them about how connecting the dots works and about the chillness
of dot #1. You’re the teacher—figure it out.

The older I get, the clearer it becomes that our internal battle as the
kindergarten teachers of our mind is like 97% of life’s struggle. The world
is easy—you’re difficult. If you find yourself continually not executing your
plans in life and your promises to yourself, you’ve uncovered your new #1
priority—becoming a better kindergarten teacher. Until you do, your life will
be run by a bunch of primitive, short-sighted 5-year-olds, and your whole
shit will suck. Trust me, I know.

If your inner analysis does call for a career leap to a new dot, I hope that at
some point, you’re able to make the jump.

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After the Move

Jumping to a new dot is a liberating feeling, usually side by side with some
substantial internal havoc.

First of all, for a while at least, you’ll probably suck at what you’re doing on
your new dot. While your wise self will know that’s exactly how it should
be, your less wise selves will go into full existential meltdown mode. All
of the fears you so thoughtfully deprioritized in your octopus ranking will
think someone is murdering them and they’ll start trying to call 911. The
yearnings you did prioritize won’t be feeling much gratification yet, and
they’ll wonder if they were wrong all along about what they thought they
wanted. The yearnings you didn’t prioritize will get out the guitar and start
singing love songs for the greener-seeming grass you deprived them of. It
won’t be much fun.

Even if things do go well, you’ll be quickly reminded of the fact that the
Yearning Octopus is a generally unhappy creature. Core pieces of the
octopus will feel neglected or even assaulted, and every day that goes by,
you’ll be bearing the opportunity cost of the paths you were considering
but chose not to walk down—the versions of you in parallel universes where
you made other choices. You’ll think about their hypothetical advancement
in the world and worry about what you may have passed up.

55
As you get wiser, you’ll learn to view a largely unhappy octopus with
acceptance. You’ll let it whine and get good at tuning it out, knowing that
it’s whining in the exact way you planned for it to be.

The whining octopus is a reminder of why pure, elated happiness is never

a reasonable goal. The times you feel pure happiness are temporary, drug-
induced delusions—like the honeymoon phase of a new relationship or new
job or the high following a long-awaited success. Those moments are the
perfect golf shots of a mediocre golfer’s outing—they’re awesome, and you
should enjoy the shit out of them—but they’re not the new normal, and they
never will be.

A better goal is contentment: the satisfying feeling that you’re currently

taking the best crack you can at a good life path; that what you’re working
on might prove to be a piece of an eventual puzzle you can feel really proud
of. Chasing happiness is an amateur move. Feeling contentment in those
times when your choices and your circumstances have combined to pull it
off, and knowing you have all that you could ever ask for, is for the wise.

People talk about being present in the moment, but there’s also the
broader concept of macro-presence: feeling broadly present in your own
life. If you’re on a career dot that, when you’re being really honest with
yourself, feels right, you get to stop thinking and stop planning for a while
and just dig in. You’ll come back to the big picture later—for now, you can
put the macro picture aside, put your head down, and dedicate all of your
energy to the present. For a while, you can just live.

These moments don’t always last that long, so sink your teeth in. Put
everything you’ve got into the dot you’ve chosen. As far as you know, you
might be Michael Jordan holding his first basketball, so start playing.

The Next Dot?

At some point, your good feelings about the macro picture may sour. And
when they do, you’ll have to get back into analysis mode and figure out
what, in particular, is causing the restlessness.

Sometimes, the macro mission won’t be the problem. It’ll be that the chef
in you has decided that the mission itself calls for a strategic dot jump.
In these cases, jumping dots isn’t a release of persistence but the stuff of
persistence. This is the mission-enhancing type of dot jump.

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Other times, you’ll feel a darker kind of restlessness—the suspicion that you
may need to change up the macro mission. When this happens, you’ll have
to figure out if that feeling is emerging from the wise parts of you or simply
from your restless, deprioritized yearnings. A mission-changing dot jump
may be in order, but depending on which parts of you are asking for it, it
may also be the wrong move.

In these moments, it’s important to consider where you tend to be on

this spectrum:

The people on the left side of this spectrum are jump-shy. The cement-
footed. Their pitfall is staying way too long in the wrong things. The people
on the right are jump-happy—the wing-footed—and they have the opposite
pitfall: they’re quick quitters. 11 (You should be especially wary of cement
feet—psychologists believe that people at the end of their lives are most
11
likely to regret living by inertia: a commonly voiced regret is “I wish I had This spectrum, of course, is also

quit earlier,” and the most common advice of the elderly is, “Don’t stay in a highly relevant in relationships.

job you dislike.")

This is why these internal frameworks are important. They give you the
ability to analyze the source of your impulses. In our example, the question
is whether your impulse to jump missions is the result of genuine evolution
or quick-quitter bias. So think about your diagram. Is your restlessness just
the expected incessant whining of an octopus still correctly configured? The
weariness from a long trudge on what’s still the right path for you? Or have
you learned new information about yourself or the world during the trudge
that has corrected some off-base initial assumptions? Or maybe something
is fundamentally evolving—some blue or yellow loop activity:

57
If you feel that things have genuinely changed, you may decide to zoom
out even further and think about the big red loop, which deals with
fundamentally changing your mission:

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If a career is like connecting the dots, we should probably rank “getting
wise about dot-jumping” pretty high on our to-do list. The best place to
start is by looking at your own past. Studying your own past decisions,
with the flashlight of hindsight and accumulated wisdom, is like an athlete
studying game tape.

Looking at my own past, I can see a lot of dot jumps (or, while I was still in
school, career plan adjustments), and some of them look pretty unwise in
retrospect. But the clearer a picture I can see of my past bad decisions and
the thought patterns and behavioral habits that built them, the less likely
I’ll be to repeat them in the future.

Remembering that you’re kind of dumb is also a critical humbling exercise.

The insecurity of humility doesn’t feel very good, and the burden of having
to continually invent your own life map is never easy—but insecurity
and difficulty are the feelings of driving your own ship. It’s when we feel
too good that we run the risk of becoming overconfident, intellectually
complacent, and set in our ways. It’s exactly when we think we have life all
figured out that we end up losing our way.

Over the course of your life, your good and bad decisions will collaborate
to forge your unique life path. Often on this blog, I’ve written about how
irrational our fears can be and how badly they can hold us back. But we
should probably embrace the fear of end-of-life regret.

I’ve thankfully never been on anything that felt like a deathbed, but it
seems like there’s something about the end of life that lets people see
things with clear eyes. It seems like facing death makes all of those voices
in your head who aren’t actually you melt away, leaving your little authentic
self standing there all alone, in reflection. I think end-of-life regrets may
simply be your authentic self thinking about the parts of your life you
never got to live—the parts of you that someone else kicked down into your
subconscious.

My own psyche seems to back this up—looking back on my path so far,

the mistakes that bother me most are the ones that happened because
someone else took the wheel of my head and overruled the quiet, insecure
voice of my authentic self—the mistakes that I knew at the time, deep
down, were wrong. My goal for the future isn't to avoid mistakes, it's for the
mistakes I do make to be my own.

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That’s why I went through such an excruciatingly rigorous analysis in this
post. I think this is one of those few topics in life that’s worth it. Other
voices will never stop fiercely trying to live your life for you—you owe it to
that little insecure character in the very center of your consciousness to get
this right.

If you're into Wait But Why, sign up for the Wait But Why email list and we’ll
send you the new posts right when they come out. That’s the only thing we
use the list for—and since my posting schedule isn’t exactly…regular…this is
the best way to stay up-to-date with WBW posts.

For help analyzing your situation:

Some paper to write on: Your octopus. Your priority shelf. Some path
distances. Your career dot map.

For those who want to dig in even further: Alicia (WBW Manager of Lots of
Things) has put together a more involved group of worksheets.

For further exploration:

The site 80,000 hours—dedicated to helping young, high-potential people

make big career choices—is an awesome resource. The site is run by super
smart, thoughtful, forward-thinking people, and can be digested in video or
book format in addition to on their site.

I’ve been reading Seth Godin’s blog for years. Seth has a lot of wisdom in his
head, and he doles it out in little bite-sized nuggets each morning on his blog
(which I receive by email). A lot of Seth’s advice applies to career choices.
Here’s an example (which I adapted into one of the cartoons in this post).

Eric Barker’s blog is full of actual data that can help with career choices,
like this post on what makes a career fulfilling or this one on the
importance of mentors.

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More Wait But Why human deep dives:

The Marriage Decision: Everything Forever or Nothing Ever Again

Why Procrastinators Procrastinate

And a post about getting wiser

And a few less self-reflect-y Wait But Why posts on:

Awkward social interactions

The history of everything

Colonizing Mars

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