How to Pick a Career (That Actually Fits You) - Wait But Why


72 bookmarks. First posted by dotcoma 11 days ago.


Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
yesterday by mattl
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.

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.

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.

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.

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.

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… [more]
career  what-to-do-with-my-life  life-advice  success  work 
yesterday by lwhlihu
Our career path is how we spend our time, how we support our lifestyles, how we make our impact, and even sometimes how we define our identity. Let’s make sure we’re on the right track.
career  life  work  advice 
2 days ago by robknight
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
3 days ago by mauty
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 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?
work 
3 days ago by jbertsche
How to Pick a Career (That Actually Fits You) - Wait But Why
from twitter
4 days ago by kctipton
"This post isn’t me giving you career advice really—it’s a framework that I think can help you make career decisions that actually reflect who you are, what you want, and what our rapidly changing career landscape looks like today. You’re not a pro at this, but you’re certainly more qualified to figure out what’s best for you than our collective un-self-aware great uncle. For those of you yet to start your career who aren’t sure what you want to do with their lives, or those of you currently in the middle of your career who aren’t sure you’re on the right path, I hope this post can help you press the reset button on your thought process and get some clarity."
howto  career  advice  timurban  article  tools  framework 
4 days ago by eugenexxv
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
4 days ago by urbansheep
You’re not a pro at this, but you’re certainly more qualified to figure out what’s best for you than our collective un-self-aware great uncle.
5 days ago by leonbarnard
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. via Pocket
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5 days ago by dubo
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
6 days ago by tonyandrewmeyer
You’re not a pro at this, but you’re certainly more qualified to figure out what’s best for you than our collective un-self-aware great uncle.
6 days ago by ShawnLi
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers.
Archive  pocket 
6 days ago by cronco
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. via Pocket
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6 days ago by Pheelmore
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. via Pocket
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7 days ago by joostw
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers.
Archive 
7 days ago by dvand5
Unpacking your desires and values
psychology  work 
7 days ago by magnusc
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
7 days ago by adamlogic
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
8 days ago by nertzy
the was longer than it needed to be.

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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.10 (You should be especially wary of cement feet—psychologists believe that people at the end of their lives are most likely to regret living by inertia: a commonly voiced regret is “I wish I had quit earlier,” and the most common advice of the elderly is, “Don’t stay in a job you dislike.“)
8 days ago by hoboyobo
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
8 days ago by wenxin
How to Pick a Career (That Actually Fits You) - Wait But Why, Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…, via Instapaper
Instapaper 
8 days ago by paulp
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
8 days ago by TuckerMax
Our career path is how we spend our time, how we support our lifestyles, how we make our impact, and even sometimes how we define our identity. Let’s make sure we’re on the right track.
career  work  advice  business  life  howto 
8 days ago by catichenor
another Wait But Why gem. just a great way to think about your life & career. Very long, but worthwhile.
life 
9 days ago by adamtait
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
9 days ago by ihatemornings
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
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9 days ago by breau
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers.
9 days ago by davidmatas
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
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9 days ago by simondoggett
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
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9 days ago by louderthan10
How to Pick a Career (That Actually Fits You) - Wait But Why via Instapaper https://waitbutwhy.com/2018/04/picking-career.html
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9 days ago by tobbe
Hey readers! Quick note before we jump in: This is a post about something I’ve been wanting to write about forever: careers. Society tells us a lot of things…
from instapaper
9 days ago by sricha27
How to Pick a Career (That Actually Fits You)
from twitter
9 days ago by jonbstrong
You’re not a pro at this, but you’re certainly more qualified to figure out what’s best for you than our collective un-self-aware great uncle.
career 
11 days ago by dotcoma