People pay you for doing what they want, not what you want. But there's an obvious exception: when you both want the same thing. For example, if you love football, and you're good enough at it, you can get paid a lot to play it.

it's clear that Bill Gates truly loved running a software company. He didn't just love programming, which a lot of people do. He loved writing software for customers. That is a very strange taste indeed, but if you have it, you can make a lot by indulging it.

If you want to make a really huge amount of money — hundreds of millions or even billions of dollars — it turns out to be very useful to work on what interests you the most. The reason is not the extra motivation you get from doing this, but that the way to make a really large amount of money is to start a startup, and working on what interests you is an excellent way to discover startup ideas.

Many if not most of the biggest startups began as projects the founders were doing for fun. Apple, Google, and Facebook all began that way. Why is this pattern so common? Because the best ideas tend to be such outliers that you'd overlook them if you were consciously looking for ways to make money.

there's something like a midwit peak for making money. If you don't need to make much, you can work on whatever you're most interested in; if you want to become moderately rich, you can't usually afford to; but if you want to become super rich, and you're young and good at technology, working on what you're most interested in becomes a good idea again.

When you have trouble choosing between following your interests and making money, it's never because you have complete knowledge of yourself and of the types of work you're choosing between, and the options are perfectly balanced. When you can't decide which path to take, it's almost always due to ignorance. In fact you're usually suffering from three kinds of ignorance simultaneously: you don't know what makes you happy, what the various kinds of work are really like, or how well you could do them

Don't wait till the end of college to figure out what to work on. Don't even wait for internships during college. You don't necessarily need a job doing x in order to work on x; often you can just start doing it in some form yourself. And since figuring out what to work on is a problem that could take years to solve, the sooner you start, the better.

You'll become like whoever you work with. Do you want to become like these people?

If you choose a kind of work mainly for how well it pays, you'll be surrounded by other people who chose it for the same reason, and that will make it even more soul-sucking than it seems from the outside. Whereas if you choose work you're genuinely interested in, you'll be surrounded mostly by other people who are genuinely interested in it, and that will make it extra inspiring

The less sure you are about what to do, the more important it is to choose options that give you more options in the future. I call this "staying upwind." If you're unsure whether to major in math or economics, for example, choose math; math is upwind of economics in the sense that it will be easier to switch later from math to economics than from economics to math

The root of great work is a sort of ambitious curiosity, and you can't manufacture that.

The useful thing about defining good design as a form-context fit is that it tells you where you will find the form. The form is in the context. To find a good relationship, you do not start by saying, “I want a relationship that looks like this”—that would be starting in the wrong end, by defining form. Instead you say, “I’m just going to pay attention to what happens when I hang out with various people and iterate toward something that feels alive”—you start from the context.

The context is smarter than you. It holds more nuance and information than you can fit in your head. Collaborate with it.

If you want to find a good design—be that the design of a house or an essay, a career or a marriage—what you want is some process that allows you to extract information from the context, and bake it into the form. That is what unfolding is.

The opposite of an unfolding is a vision. A vision springs, not from a careful understanding of a context, but from a fantasy

Anything that increases the rate and resolution of information you get from the context will help. And anything that makes it easier for you to act on the context.

A common reason we filter information and become blind to the context is that we bundle things when we think. Thinking about our career, we might think in abstractions like “a job.” But really a career is made up of a bunch of different things like a salary, an identity, relationships, status, a sense of meaning, and so on. It is often easier to find a fit if you unbundle these things, and think about the parts that matter to you individually. Do you actually need more status? Or can you find a better fit if you go low status?

Another common reason the feedback loop of unfolding often works poorly is that people have decided on a solution already. They have turned on their confirmation bias. They have decided that a certain solution is off-limits. Let’s say you are 34 and haven’t found a partner but want kids. If we unbundle this, it is clear that the problem of having a kid and the problem of love are not the same thing, so you could solve your problem by having a kid with your best friend instead. But this feels weird. It is not the vision you have for your life. And it seems dysfunctional. Observe that feeling—it is, perhaps, a part of the context. There is some information there. But to unfold, do not write off any solutions. Leave them all on the table; let them combine and recombine. Many good ideas look bad at first. To increase the rate at which you understand the context, you want to develop a certain detachment. When the context thrashes one of your ideas, you want to say, “Oh, that’s interesting.” It takes practice. But it is worth getting better at. Reality is shy—it only reveals itself to those who, like honest scientists, do not wish it to be something else.

The faster you can collide your ideas against reality, the faster you get feedback.

The school system is centered around visions, not unfolding. You are asked to make decisions about realities that are five, ten years down the line, and you get no feedback on your decisions.

you’re less torn by anxious attachments when you recognize how something must naturally and necessarily unfold.

Knowledge is freedom from getting mad at facts.

Detachment does not mean you don’t care what happens. It just means you don’t care whether a specific thing happens or not. You want to know the outcome of the coin-toss (you care), but you don’t care whether it is heads or tails even if you’ve bet on heads (you’re not attached to a specific outcome). The important thing is that something happens, which means you’ve successfully kept play going, but without keeping score.

Emotional Self-Management: I like to think of this as accepting the emotions you have instead of having emotions about having emotions in an endless stack.

Fear. Not fear, plus anxiety about fear, plus guilt about anxiety about fear, plus shame about displaying guilt about experiencing anxiety about having fear. This is emotional focus. Instead of retreating from an emotion through layers of additional emotions until you find one you can deal with, you experience the actual emotion for what it is.

I will never know where I am going to hit until I actually throw the dart. If I spend a ton of time thinking about how I am going to throw the dart and never throw it, I might be doing a whole lot of work that isn’t actually helping.

Self-oriented perfectionism refers to having unrealistic expectations and standards for oneself that lead to perfectionistic motivation. In other words, we lie to ourselves: "If only I could do just a little bit better." (Perfectionism, in this case, somehow became my one great excuse for procrastination: because of my intention to perfect, I can always keep polishing my stuff instead of putting it out in the world.) Socially prescribed perfectionism is characterized by developing perfectionistic motivations due actual or perceived high expectations of significant others. That is, we get told these lies by the ones that matter most to us. Parents who push their children to be successful in certain endeavors (such as athletics or academics) provide an example of what often causes this type of perfectionism, as the children feel that they must meet their parents' lofty expectations. Other-oriented perfectionism is having unrealistic expectations and standards for others that in turn pressure them to have perfectionistic motivations of their own. Which means, sadly, that we tell these lies back to others, although sometimes unconsciously.

Excellencism is a term coined by the psychologist Patrick Gaudreau. It means still setting high standards but not beating yourself up about it if you do not meet them. Hank Green summarizes this pretty well: 80%. Do your best to get it 80% of the way to as good as you can make it and go no further. Just do not try to get it to 100%. There are healthier goals than perfect and getting it done is already success. Because your thing is always going to look imperfect to you, the chance of you learning more from those 80% feedback is always higher. You may learn from perfecting those 20%, but you also may not.

Throwing that dart requires courage. Not beating yourself up requires courage. Especially when you just started and are still new to whatever you are doing. You just know that your thing is objectively not that good, not even close to being excellent. And you might fail, miserably sometimes, but remember this: failure is not weakness. Have compassion for yourself the same way that you would have compassion for someone else. Accept your own occasional failure the same way that you would accept someone else’s. If it makes you feel any better, imperfection is what makes us human. And there is nothing wrong with that.

The same applies to writing. For example, when one topic doesn’t seem to fit a narrative structure, it often feels like a problem I need to “get out of the way”. It’s much better to wonder: “Hm, why do I have this strong instinct that this point’s related? Is there some more powerful unifying theme waiting to be identified here?”

Often I need to improve the framing, to find one which better expresses what I’m deeply excited about. If I can’t find a problem statement which captures my curiosity, it’s best to drop the project for now.

I’m much less likely to flinch away when I’m feeling intensely curious, when I truly want to understand something, when it’s a landscape to explore rather than a destination to reach. Happily, curiosity can be cultivated. And curiosity is much more likely than task-orientation to lead me to interesting ideas.

Savor the subtle insights which really do occur regularly in research. Think of it like cultivating a much more sensitive palate.

“Why is this so hard? Because you’re utterly habituated to steady progress—to completing things, to producing, to solving. When progress is subtle or slow, when there’s no clear way to proceed, you flinch away. You redirect your attention to something safer, to something you can do. You jump to implementation prematurely; you feel a compulsion to do more background reading; you obsess over tractable but peripheral details. These are all displacement behaviors, ways of not sitting with the problem. Though each instance seems insignificant, the cumulative effect is that your stare rarely rests on the fog long enough to penetrate it. Weeks pass, with apparent motion, yet you’re just spinning in place. You return to the surface with each glance away. You must learn to remain in the depths.”

Depth of concentration is cumulative, and precious. An extra hour or two of depth is enormously valuable. I reliably get more done—and with more depth—in that 6-7 hour morning block than I’d previously done in 9-10 hours throughout the day.This feels wonderful. By 2PM, I’ve done my important work for the day. I know that no more depth-y work is likely, and that I’ll only frustrate myself if I try—so I free myself from that pressureI notice that some part of me feels ashamed to say that I’m “done” working at 2PM. This is probably because in my previous roles, I really could solve problems and get more done by simply throwing more hours at the work. That’s just obviously not true in my present work, as I’ve learned through much frustration. Reading memoirs of writers, artists, and scientists, I see that 2-4 hours per day seems to be the norm for a primary creative working block. Separately, and I don’t want to harp on this because I want this essay to be about quality, not quantity, but: I think most people are laughably misled about how much time they truly work. In a median morning block, I complete the equivalent of 1225-minute pomodoros. When I worked at large companies, getting 8 done before 6PM was a rarity—even though I’d assiduously arrange my calendar to maximize deep work!. I take meetings; I exercise; I meditate; I go on long walks. I’ll often do shallower initial reads of papers and books in the afternoon, or handle administrative tasks. Sometimes I’ll do easy programming work. It’s all “bonus time”, nothing obligatory. My life got several hours more slack when I adopted this schedule, and yet my output improved. Wonderful!

no internet on my phone before I sit down at my desk. I don’t want anyone else’s thoughts in my head before I start thinking my own.

If I spend a working interval flailing, never sinking below the surface, the temptation is to double-down, to “make up for it”. But the right move for me is usually to go sit in a different room with only my notebook, and to spend the next working interval writing or sketching by hand about the problem.

Administrative tasks are a constant temptation for me: aha, a task I can complete! How tantalizing! But these tasks are rarely important. So I explicitly prohibit myself from doing any kind of administrative work for most of the morning. In the last hour or two, if I notice myself getting weary and unfocused, I’ll sometimes switch gears into administrative work as a way to “rescue” that time.

I’ve noticed that unhealthy afternoon/evening activities can easily harm the next morning’s focus, by habituating me to immediate gratification.

most of the benefit just seems to come from regularly reflecting on what I’m trying and what’s happening as a result. It’s really about developing a rich mental model of what focus and perseverance feel like, and what factors seem to support or harm those states of mind.

Sometimes I just need to execute; and then traditional productivity advice helps enormously. But deep insight is generally the bottleneck to my work, and producing it usually involves the sort of practices I’ve described here.

No one is ahead or behind. No one is best or better. Every day you’re alive, you have a new opportunity to enjoy existence on this strange planet.Unfortunately, right now you’re tripping. You’re confused about reality and time and it’s panicking you. And nothing will make you more special than learning to appreciate the perfect ragged textures of this moment, right now.

I’m still catching up on my teen years where most of my opportunities at experimentation faltered in the face of my strict and demanding father, and the depression that resulted from that upbringing. I know that time is relative and doing something at 20 or 30 is not less impressive than doing it at 40 or 50. But my brain decided these rules don’t apply to me.

Take a sledgehammer to your tiny little anxious window on the world and let some air and some light in. There’s no race and no finish line. You’ve escaped the depressions and oppressions of the past and it slowed you down, sure, but now you’re here, free from those burdens, and you can sing and dance and learn guitar. There’s no hourglass running out. No alarm will go off if you don’t learn everything in time or win all of the awards quickly. No one is watching and measuring. No one holds a secret key to happiness. Success doesn’t make everything perfect in every way.

You need to smash that replica of your father’s exacting standards that lives inside your mind and start living on your own terms. Reinvent you expectations of yourself from the ground up. Don’t recreate the oppressive world you grew up in. Invent a new universe where you can breathe freely and explore and treat every new year as a blank slate, a new era to explore and play and learn.

If the big lie seems too hard to address or remedy, I would get a therapist and find a path forward by talking through it. Don’t underestimate what a big piece of your pain and struggle this is. Clearing that piece of deception out of the way will make it easier for you to get the most out of the next few years and make honest, open connections with the people around you. Embrace the challenge of getting out from under that lie permanently.

so much of what you’re struggling with right now is wrapped up in external expectations and timelines and shame. Right now, you’re tripping on this punishing storm outside your door that has nothing to do with you. It’s time to figure out what kind of a space you want to create INSIDE, safe from all of that noise.

When you commit to honesty and commit to slowing down and savoring the luxury of being alive as much as you can, when you commit to drinking in knowledge and embracing beauty and delighting in the unpredictable weirdos around you, you will be misunderstood regularly.

When you’re open, you aren’t constantly glancing at your watch and policing yourself and telling little lies to excuse your behavior. You show up and tell the truth.

What is our purpose on this planet? Do we have a responsibility to one another? Who even are we?Answering those questions alone is asking a lot of a person. The easier option is to choose from the platter of social-strata-acceptable possibilities we’re presented with for education, occupation, geographical location, personality, etc, and call it a day.

if you spend all your time constantly sketching (probably quickly outdated) pictures of your thinking on the bigger questions we’ve all been tasked with answering, you neglect the actual doing that would reveal answers with richer hues

incredible opportunities are unlocked by constructing a digitally consumable caricature of yourself that makes you legible to literally anyone in the world. It’s probably the most far-ranging bat signal possible to find people who think and feel similarly to you.

There’s simply so much friction in the process of turning belief into action online — meaning that most of the time all you actually get from internet attention is internalized impossible-to-attain expectations for yourself and an extremely confused ego.

If you care about personally choosing the shape, scale, and direction of your impact on the world, you might find that playing off-the-shelf games turns out to be a remarkably risky bet. There’s just no money/time-back guarantee that any of the off-the-shelf options will continue to fit you as your desires evolve. And maybe that’s ok — but continually reinventing yourself is a tiring and time-consuming task that too often leads you away from the real “calling”-finding-and-defining work.

In my book, big things are only worth committing to if the answer to the question “would you do this thing even if no one was watching?” is an immediate and unequivocal yes

What I regret most in my life are failures of kindness. Those moments when another human being was there, in front of me, suffering, and I responded . . . sensibly. Reservedly. Mildly. Or, to look at it from the other end of the telescope: Who, in your life, do you remember most fondly, with the most undeniable feelings of warmth? Those who were kindest to you, I bet.

When young, we’re anxious — understandably — to find out if we’ve got what it takes. Can we succeed? Can we build a viable life for ourselves? But you — in particular you, of this generation — may have noticed a certain cyclical quality to ambition. You do well in high-school, in hopes of getting into a good college, so you can do well in the good college, in the hopes of getting a good job, so you can do well in the good job so you can . . . And this is actually O.K. If we’re going to become kinder, that process has to include taking ourselves seriously — as doers, as accomplishers, as dreamers. We have to do that, to be our best selves.

Do all the other things, the ambitious things — travel, get rich, get famous, innovate, lead, fall in love, make and lose fortunes, swim naked in wild jungle rivers (after first having it tested for monkey poop) – but as you do, to the extent that you can, err in the direction of kindness. Do those things that incline you toward the big questions, and avoid the things that would reduce you and make you trivial.

Gatekeepers could see themselves not only as talent hunters for their own organization, but also as managers of society’s collective supply of ambition. We could demand that they consider it a responsibility to waste as little of their applicants’ ambition as possible. That they strive to redirect and allocate that ambition wherever it is most needed.

In practice, there isn’t any single solution. Rejection is a facet of life, and everybody needs to figure out their own strategies to cope with it. The most I can offer is that it’s better when you’re aware of how it works. It isn’t enough to know, on an abstract level, that rejection is typically random and impersonal — but it helps.