Abandon the idea that you are ever going to finish. Lose track of the 400 pages and write just one page for each day, it helps. Then when it gets finished, you are always surprised.

Forget your generalized audience. In the first place, the nameless, faceless audience will scare you to death and in the second place, unlike the theater, it doesn’t exist. In writing, your audience is one single reader. I have found that sometimes it helps to pick out one person—a real person you know, or an imagined person and write to that one.

If a scene or a section gets the better of you and you still think you want it—bypass it and go on. When you have finished the whole you can come back to it and then you may find that the reason it gave trouble is because it didn’t belong there.

If there is a magic in story writing, and I am convinced there is, no one has ever been able to reduce it to a recipe that can be passed from one person to another. The formula seems to lie solely in the aching urge of the writer to convey something he feels important to the reader.

a bad story is only an ineffective story.

So I do have kind of an extensive questionnaire, so we just touch on a few things, but one thing I think first and foremost is, what are your values? And I think it's really essential to do some sort of values clarification exercise. You can find a ton of them online. You can find a list of values and just pull out your core values and just compare them with each other because when you are aligned, it's great. Or when you're adjacent, it's also great. I might care a lot about excellence, Lenny, you might care a lot about learning. Fantastic. Those are great values that we can kind of, go together. I might care about excellence and you might care about work-life balance. Wow, let's talk about that because I think it's going to be really important as we go through our startup journey that we understand both of us, what does work-life balance mean and what does excellence mean?

One of the founders I worked with, he would text or Slack his co-founder on weekends and the co-founder wouldn't respond. And that was extremely frustrating to the person, to the co-founder I was talking to. And it turned out, after they finally addressed it, it really was about wanting to have some downtime and some, quote unquote, "Balance."

I'm so great at bringing things up." But the person who's close to you might say, "You seethe until you're ready to bring something up and it's really uncomfortable in the seething period." So it just gives you a little more self-awareness about how you actually handle conflict.

The other person might be a person who totally wants to talk about the conflict but wants to let it settle first and wants to also go through their own thinking process about what's important to them and might actually feel like they've resolved it themselves without having to have a conversation with you.

And if you're the person who's like, "Let's talk about it, let's talk about it, let's talk about it." And they're like, "I'm working through it myself." Now you have conflict over the conflict and it just turns into dynamic that's not necessary.

we introduced something new—a concept no one had tried before: We abandoned volume-based pricing, offering unlimited forms and responses for free We created a modern form-building experience—no drag-and-drop, just a beautifully simple interface that works like a text document

“Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.”

I will talk mainly about science because that is what I have studied. But so far as I know, and I've been told by others, much of what I say applies to many fields. Outstanding work is characterized very much the same way in most fields, but I will confine myself to science.

I spoke earlier about planting acorns so that oaks will grow. You can't always know exactly where to be, but you can keep active in places where something might happen. And even if you believe that great science is a matter of luck, you can stand on a mountain top where lightning strikes; you don't have to hide in the valley where you're safe.

Most great scientists know many important problems. They have something between 10 and 20 important problems for which they are looking for an attack. And when they see a new idea come up, one hears them say ``Well that bears on this problem.'' They drop all the other things and get after it.

The great scientists, when an opportunity opens up, get after it and they pursue it. They drop all other things. They get rid of other things and they get after an idea because they had already thought the thing through. Their minds are prepared; they see the opportunity and they go after it. Now of course lots of times it doesn't work out, but you don't have to hit many of them to do some great science. It's kind of easy. One of the chief tricks is to live a long time!

He who works with the door open gets all kinds of interruptions, but he also occasionally gets clues as to what the world is and what might be important. Now I cannot prove the cause and effect sequence because you might say, ``The closed door is symbolic of a closed mind.'' I don't know. But I can say there is a pretty good correlation between those who work with the doors open and those who ultimately do important things, although people who work with doors closed often work harder.

You should do your job in such a fashion that others can build on top of it, so they will indeed say, ``Yes, I've stood on so and so's shoulders and I saw further.'' The essence of science is cumulative. By changing a problem slightly you can often do great work rather than merely good work. Instead of attacking isolated problems, I made the resolution that I would never again solve an isolated problem except as characteristic of a class.

by altering the problem, by looking at the thing differently, you can make a great deal of difference in your final productivity because you can either do it in such a fashion that people can indeed build on what you've done, or you can do it in such a fashion that the next person has to essentially duplicate again what you've done. It isn't just a matter of the job, it's the way you write the report, the way you write the paper, the whole attitude. It's just as easy to do a broad, general job as one very special case. And it's much more satisfying and rewarding!

it is not sufficient to do a job, you have to sell it. `Selling' to a scientist is an awkward thing to do. It's very ugly; you shouldn't have to do it. The world is supposed to be waiting, and when you do something great, they should rush out and welcome it. But the fact is everyone is busy with their own work. You must present it so well that they will set aside what they are doing, look at what you've done, read it, and come back and say, ``Yes, that was good.'' I suggest that when you open a journal, as you turn the pages, you ask why you read some articles and not others. You had better write your report so when it is published in the Physical Review, or wherever else you want it, as the readers are turning the pages they won't just turn your pages but they will stop and read yours. If they don't stop and read it, you won't get credit.

I think it is very definitely worth the struggle to try and do first-class work because the truth is, the value is in the struggle more than it is in the result. The struggle to make something of yourself seems to be worthwhile in itself. The success and fame are sort of dividends, in my opinion.

He had his personality defect of wanting total control and was not willing to recognize that you need the support of the system. You find this happening again and again; good scientists will fight the system rather than learn to work with the system and take advantage of all the system has to offer. It has a lot, if you learn how to use it. It takes patience, but you can learn how to use the system pretty well, and you can learn how to get around it. After all, if you want a decision `No', you just go to your boss and get a `No' easy. If you want to do something, don't ask, do it. Present him with an accomplished fact. Don't give him a chance to tell you `No'. But if you want a `No', it's easy to get a `No'.

Amusement, yes, anger, no. Anger is misdirected. You should follow and cooperate rather than struggle against the system all the time.

I found out many times, like a cornered rat in a real trap, I was surprisingly capable. I have found that it paid to say, ``Oh yes, I'll get the answer for you Tuesday,'' not having any idea how to do it. By Sunday night I was really hard thinking on how I was going to deliver by Tuesday. I often put my pride on the line and sometimes I failed, but as I said, like a cornered rat I'm surprised how often I did a good job. I think you need to learn to use yourself. I think you need to know how to convert a situation from one view to another which would increase the chance of success.

I do go in to strictly talk to somebody and say, ``Look, I think there has to be something here. Here's what I think I see ...'' and then begin talking back and forth. But you want to pick capable people. To use another analogy, you know the idea called the `critical mass.' If you have enough stuff you have critical mass. There is also the idea I used to call `sound absorbers'. When you get too many sound absorbers, you give out an idea and they merely say, ``Yes, yes, yes.'' What you want to do is get that critical mass in action; ``Yes, that reminds me of so and so,'' or, ``Have you thought about that or this?'' When you talk to other people, you want to get rid of those sound absorbers who are nice people but merely say, ``Oh yes,'' and to find those who will stimulate you right back.

I believed, in my early days, that you should spend at least as much time in the polish and presentation as you did in the original research. Now at least 50% of the time must go for the presentation. It's a big, big number.

Luck favors a prepared mind; luck favors a prepared person. It is not guaranteed; I don't guarantee success as being absolutely certain. I'd say luck changes the odds, but there is some definite control on the part of the individual.

If you read all the time what other people have done you will think the way they thought. If you want to think new thoughts that are different, then do what a lot of creative people do - get the problem reasonably clear and then refuse to look at any answers until you've thought the problem through carefully how you would do it, how you could slightly change the problem to be the correct one. So yes, you need to keep up. You need to keep up more to find out what the problems are than to read to find the solutions. The reading is necessary to know what is going on and what is possible. But reading to get the solutions does not seem to be the way to do great research. So I'll give you two answers. You read; but it is not the amount, it is the way you read that counts.

your dreams are, to a fair extent, a reworking of the experiences of the day. If you are deeply immersed and committed to a topic, day after day after day, your subconscious has nothing to do but work on your problem. And so you wake up one morning, or on some afternoon, and there's the answer.

You can't directly control where your thoughts drift. If you're controlling them, they're not drifting. But you can control them indirectly, by controlling what situations you let yourself get into. That has been the lesson for me: be careful what you let become critical to you. Try to get yourself into situations where the most urgent problems are ones you want to think about.

barring emergencies you have a good deal of indirect control over what becomes the top idea in your mind.

Turning the other cheek turns out to have selfish advantages. Someone who does you an injury hurts you twice: first by the injury itself, and second by taking up your time afterward thinking about it. If you learn to ignore injuries you can at least avoid the second half. I've found I can to some extent avoid thinking about nasty things people have done to me by telling myself: this doesn't deserve space in my head.

just take a shower. What topic do your thoughts keep returning to? If it's not what you want to be thinking about, you may want to change something.

people mix up two very different types of pivots and that it’s important to differentiate which path you’re on: Ideation pivots: This is when an early-stage startup changes its idea before having a fully formed product or meaningful traction. These pivots are easy to make, normally happen quickly after launch, and the new idea is often completely unrelated to the previous one. For example, Brex went from VR headsets to business banking, Retool went from Venmo for the U.K. to a no-code internal tools app, and Okta went from reliability monitoring to identity management all in under three months. YouTube changed direction from a dating site to a video streaming platform in less than a week. Hard pivots: This is when a company with a live product and real users/customers changes direction. In these cases, you are truly “pivoting”—keeping one element of the previous idea and doubling down on it. For example, Instagram stripped down its check-in app and went all in on its photo-sharing feature, Slack on its internal chat tool, and Loom on its screen recording feature. Occasionally a pivot is a mix of the two (i.e. you’re pivoting multiple times over 1+ years), but generally, when you’re following the advice below, make sure you’re clear on which category you’re in.

When looking at the data, a few interesting trends emerged: Ideation pivots generally happen within three months of launching your original idea. Note, a launch at this stage is typically just telling a bunch of your friends and colleagues about it. Hard pivots generally happen within two years after launch, and most around the one-year mark. I suspect the small number of companies that took longer regret not changing course earlier.

ou should have a hard conversation with your co-founder around the three-month mark, and depending on how it’s going (see below), either re-commit or change the idea. Then schedule a yearly check-in. If things are clicking, full speed ahead. If things feel meh, at least spend a few days talking about other potential directions.

Brex: “We applied to YC with this VR idea, which, looking back, it was pretty bad, but at the time we thought it was great. And within YC, we were like, ‘Yeah, we don’t even know where to start to build this.’” —Henrique Dubugras, co-founder and CEO

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.

I find it tremendously hopeful that “Stoner” is thriving in a world in which capitalist energies are so hellbent on distracting us from the necessary anguish of our inner lives. “Stoner” argues that we are measured ultimately by our capacity to face the truth of who we are in private moments, not by the burnishing of our public selves.

The story of his life is not a neat crescendo of industry and triumph, but something more akin to our own lives: a muddle of desires and inhibitions and compromises.

The deepest lesson of “Stoner” is this: What makes a life heroic is the quality of attention paid to it.

Americans worship athletes and moguls and movie stars, those who possess the glittering gifts we equate with worth and happiness. The stories that flash across our screens tend to be paeans to reckless ambition.

It’s the staggering acceleration of our intellectual and emotional metabolisms: our hunger for sensation and narcissistic reward, our readiness to privilege action over contemplation. And, most of all, our desperate compulsion to be known by the world rather than seeking to know ourselves.

The emergence of a robust advertising culture reinforced the notion that Americans were more or less always on stage and thus in constant need of suitable costumes and props.

Consider our nightly parade of prime-time talent shows and ginned-up documentaries in which chefs and pawn brokers and bored housewives reinvent their private lives as theater.

If you want to be among those who count, and you don’t happen to be endowed with divine talents or a royal lineage, well then, make some noise. Put your wit — or your craft projects or your rants or your pranks — on public display.

Our most profound acts of virtue and vice, of heroism and villainy, will be known by only those closest to us and forgotten soon enough. Even our deepest feelings will, for the most part, lay concealed within the vault of our hearts. Much of the reason we construct garish fantasies of fame is to distract ourselves from these painful truths. We confess so much to so many, as if by these disclosures we might escape the terror of confronting our hidden selves.

revelation is triggered by literature. The novel is notable as art because it places such profound faith in art.

We can finally define what it means for someone to be differently free from you. They are people who are playing just a slightly different game than you are. That difference makes them a reliable sources of non sequiturs in your life. Waiting for nature to present you with a parrot or a piece of corn to awaken you out of a finite game is a tricky, chancy business.

Differently free people change the equation in an interesting way. When you include a person in your life, it is because they have a definite worth (possibly negative) in whatever finite game you’re asleep in at the time. This means there is at least some overlap between their game and yours; some similarity between how you keep score and how they do. Some meaningful relationship (possibly adversarial)  between how you define winning and how they do.

This means you have a model of the person in your head. One that predicts how they will value things.

it is the parts that don’t overlap that matter. There are things that have a defined worth in their lives that are non sequiturs in yours, and vice versa. When you see through the eyes of a differently free person, you expect to see a landscape of presumptively valued things. A landscape based on your predictions of how they value things. When the other person appears to value something that doesn’t even register with you, for a moment, that thing turns into a non sequitur, a candidate parrot. It lingers just a little bit longer in your own mind than it would if you yourself saw it. Long enough that you do a double take and notice it consciously.

My alternative to the heuristic, which many of you have heard in off-blog conversations, is that I am only interested in people as long as they are unpredictable to me. If I can predict what you’ll do or say, I’ll lose interest in you rapidly. If you can keep regularly surprising me in some way, forcing me to actually think in unscripted ways in order to respond, I’ll stay interested. It’s reciprocal. I suspect the people with whom I develop long-term relationships are the ones I surprise regularly. The ones who find me predictable don’t stick around. We’re not talking any old kind of surprise, but non sequiturs. Surprises that you can’t really relate to anything else, and don’t know what to do with. Mind-expanding surprises rather than gap-closing surprises.

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.

There’s a beautiful simplicity in devising a plan and then sticking to it without deviation. I didn’t have to make decisions every step of the way. I didn’t have to agonize over whether I should eat X or if I shouldn’t eat Y; I just had to color within the lines

There’s a beautiful simplicity in devising a plan and then sticking to it without deviation. I didn’t have to make decisions every step of the way. I didn’t have to agonize over whether I should eat X or if I shouldn’t eat Y; I just had to color within the lines.

your body doesn’t lie to you per se; it’s just that you’re ill-equipped to properly interpret your body’s signals.

Tom said it like this: “When you think you’re done, totally done — you have at least five more reps.”

…a certain level of discomfort is unavoidable when losing body fat. You will experience hunger, fatigue, and mood disturbance when using body fat to meet your body's caloric needs for extended periods.

the difference between a beginner lifter and a more advanced one isn’t just about having more strength or better technique; it’s about the ability of the mind to properly interpret the body’s signals.

There comes a point during a hard set of squats, for example, where it gets very uncomfortable. Your muscles are burning, you’re gasping for air. The less experienced lifter receives those signals and thinks “I have to stop now, or I’m going to get seriously injured.” The more experienced lifter gets the same signal, but they know it doesn’t mean they’re about to die; it means they’ve got five more reps

Many people try out careers in venture and then wind up leaving after a year when it stops feeling novel and starts feeling like they’re floating in lonely limbo without any markers of success. That’s because the craft of venture is not for people who derive their satisfaction from external indicators of progress — it’s for people who find the development of their relationships and refinement of their internal model of the world to be motivation enough to keep going.

If you derive satisfaction from refining a craft, don’t go into venture yet.

Here are five individual investor archetypes I’ve noticed can produce outsized returns in the early-stage venture game:Philosopher: hangs one’s reputation on their predictions about the futureHustler: simply outwork everyone else and are great at networkingHawk: most competitive, gets a thrill out of the fight to win a deal Friend: confidante and coach to founders, often founders’ first callCelebrity: a person widely respected for their work/knowledge/skill

A good archetype for you is whichever one you can sustain the longest. A great archetype for you is one that no one else is doing and you have some sort of signal works.

Some good advice I got: build your fund’s structure and strategy around allowing yourself to invest in whichever way you most enjoy and are naturally good at (admittedly, it will probably get harder and harder to stick to this as your fund scales).

Examples: if you like being a friend to founders and want your fund to function as Switzerland (i.e. not compete with anyone), write small checks. If you like to fight and are naturally hawkish, it might make sense to set yourself up to try to lead rounds. If complex problems and futuristic theories are what get you excited, investing in series A companies that fit into where you see the world going could be quite gratifying. If for some reason you love living in spreadsheets, consider growth investing (and don’t follow literally any of my advice).

In many ways, the job of the writer and the job of a VC are quite similar, in that they both ask you to produce an original end product (in the writer’s case, articulated ideas and stories; in the investor’s case, a differentiated portfolio with outsized financial returns) without much of a map for how you get there. The reason professional writers complain about writing so much is that it’s really difficult to wrangle your brain into producing uniquely interesting thoughts all the time, and highly frustrating when you consider it your job to do so. Making good investment decisions is similar; just with the added element of also being highly social. Taking the quality of your self talk seriously seems superfluous but is an investment that will result in better decisions.

A lot of the game of investing is won by getting people to think of you — a sign that you’ve built the kind of moat we call a strong brand. Remember: a fund is just a pile of money with a person on top to sell it. As an investor, putting down stakes in the ground about what you invest in saves you a lot of time in the long run because it allows people to self-select for fit

I’ve been surprised by how much it’s benefited my fund to make Moth’s brand (i.e. what I invest in and look for) difficult to summarize in a sentence. For small early-stage generalist funds like my own, quality matters much more than quantity. Quality deals almost always come from trusted sources who resonate with my taste, not from a list of random companies for which I have no context.

A brand is a promise to show up in the same way time and time again. Good brands are built on being decent and principled with all of the people you interact with.

Lastly and of utmost importance: remember that fear of failure fades into the background if you focus on leaving everyone you encounter along the way better than you found them.

VCs need to believe that your company could be a billion-dollar business and generally lack imagination — you need to paint a vivid picture of this path for them, starting with the striking protagonist character you play in your company’s story.Your alter ego should never lie, but it should be completely comfortable showing the fullest expression of your ambition to people who probably intimidate you. Fundraising is a snap judgment game — most VCs are trying to pattern-match you to a founder archetype who already won. They index primarily on IQ, self-belief, experience, and personability (in that order). A general rule of thumb is that to be taken seriously in SV, male founders would benefit from acting warmer, while female founders are taken more seriously when they act colder. Both benefit from acting a little entitled.

a VC’s job is to make a diversified portfolio of bets — you are only one. Most founders find being around VCs distracting and draining because they feel pressure to perform the role of ‘impressive person.’ If you can’t immediately capture value from your performance… why waste your energy?

don’t expect the average investor to provide much value beyond money and connections. This makes the 10% of investors who can be legitimately useful to your business worth their weight in gold. Develop litmus tests to identify the valuable ones quickly and avoid wasting your time trying to convince nonbelievers.

our goal here is to spend as little time fundraising as possible — which requires being strategic about the order in which you talk to investors and how you talk about where things stand as you progress through the raise. The combined force of controlling those two variables are what “generates momentum” during your fundraise process.

Make a list of all the investors you know and can get introduced to, ordering them by the ones you most want on board to the ones you couldn’t care less aboutTalk first to a few low-stakes investors at the bottom of your list to practice your pitch and identify common investor questions and critiques you’re going to getIf available to you, next get a few investors who already wanted to give you money on board so you have a dollar amount you can say you’ve raisedWork your way up your investor list, talking to the investors you most-want-on-board-but-still-need-to-convince last (this optimizes your odds they say yes)

This all goes by much faster if you court investors similarly to how hot girls treat their many potential suitors. If your raise is already a little taken and you exude an air that you don’t need them, mimetically-minded investors become much more interested.

If you’re anything like me, you will worry intensely about not making a fool of yourself. It will probably go ok, but not as amazing or illuminating as you’d hoped. You might leave and feel a deep sense of lostness set in. This is all very normal. In time you will see them in increasing clarity, often noticing the differences between your and their values and why you would not enjoy living their life at all.

the people on pedestals probably hate being there. It’s lonely, hard to trust that the intentions of the new people around you are pure, and you often feel like you’re constantly letting people down. In the end, idolization hurts everyone involved.

Beware of intellectual dementors and clout demonsIntellectual dementors will try to eat your ideas and interestingness — not necessarily to copy you, but to wring your brain dry to amass knowledge themselves. They often play mini IQ games/tests of will in conversation and masquerade as investors while never actually investing. Clout demons are similar, but view people less as brains and more as stepping stones towards supreme social status. The power move to protect yourself from both is to simply abstain from playing their games — give as little info on yourself and your ideas as possible and reflect their questions directly back at them.

People will help you if you ask for what you want clearly and concisely

Knowing what you want requires a lot of upfront soul-searching, followed by strategic and long-term thinking once you’ve committed to a thing (I can’t really demystify this more). Once you’re all in, I highly recommend diligently keeping a list somewhere of the top three things you currently need help with so when people ask, you’re ready.

You don’t want to make people feel like you’re using them but you do want to use your social capital for things you care about. General rule of thumb: ask for things either 1) after a positive interaction or 2) completely out of the blue with a concisely written and compelling email/text. Tone matters because you don’t want to sound desperate and you do want to show you know how to play the game (write like the founder you most admire talks).

once we’ve taken action on behalf of something, our brain assigns more value to said thing. Tim Keller: “The feeling of love follows the action of love.” Love is a strong word here, but the point stands — help people help you. Startups are long-term games, so it only makes sense to do them with people you truly want to be around for a very long time.

Forget trying to decide what your life’s destiny is. That’s too grand. Instead, just figure out what you should do in the next 2 years.

Try to define yourself by what you love and embrace, rather than what you hate and refuse.

Where you live—what city, what country—has more impact on your well being than any other factor. Where you live is one of the few things in your life you can choose and change.

Once a month take a different route home, enter your house by a different door, and sit in a different chair at dinner. No ruts.

Every now and then throw a memorable party. The price will be steep, but long afterwards you will remember the party, whereas you won’t remember how much is in your checking account.

Most arguments are not really about the argument, so most arguments can’t be won by arguing.

invent your own definition of success. Shoot your arrows first and then paint a bull’s eye around where they land. You’re the winner!

There should be at least one thing in your life you enjoy despite being no good at it. This is your play time, which will keep you young. Never apologize for it.

You have 5 minutes to act on a new idea before it disappears from your mind.

The patience you need for big things, is developed by your patience with the little things.

When you are stuck or overwhelmed, focus on the smallest possible thing that moves your project forward.

For steady satisfaction, work on improving your worst days, rather than your best days.

Your decisions will become wiser when you consider these three words: “…and then what?” for each choice.

If possible, every room should be constructed to provide light from two sides.  Rooms with light from only one side are used less often, so when you have a choice, go with light from two sides.

There is a profound difference between thinking less of yourself (not useful), and thinking of yourself less (better).

Always ask yourself: what would change my mind?

Becoming one-of-a-kind is not a solo job. Paradoxically you need everyone else in the world to help make you unique.

If you need emergency help from a bystander, command them what to do. By giving them an assignment, you transform them from bewildered bystander to a responsible assistant.

The most common mistake we make is to do a great job on an unimportant task.

Don’t work for a company you would not invest money in, because when you are working you are investing the most valuable thing you have: your time.

Fail forward. Failing is not a disgrace if you keep failing better.

Do not cling to a mistake just because you spent a lot of time making it.

For small tasks the best way to get ready is to do it immediately.

What others want from you is mostly to be seen. Let others know you see them.

When you try something new, don’t think of it as a matter of success / failure, but as success / learning to succeed.

use your honesty as a gift not as a weapon. Your honesty should benefit others.

A good sign that you are doing the kind of work you should be doing is that you enjoy the tedious parts that other people find tortuous.

Celebrating the success of others costs you nothing, and increases the happiness of everyone, including you.

To tell a good story, you must reveal a surprise; otherwise it is just a report.

a long horizon allows you to compound small advances into quite large achievements.

Often ideas are rejected because of the tone of voice they are wrapped in. Humility covers many blemishes.

When you are right, you are learning nothing.

Very small things accumulate until they define your larger life. Carefully choose your everyday things.

If you are impressed with someone’s work, you should tell them, but even better, tell their boss.

Humility is mostly about being very honest about how much you owe to luck.

The beginning is almost never the most compelling or important part. It's just the bit you thought of first, based on your subjective chronology.

Signposting what you're going to write about is good, but starting with an exhaustive list of definitions is extremely boring.

Invoking paleolithic people is an overplayed way to convince us your topic is cosmically important.

Openings need tension – paradoxes, unanswered questions, and unresolved action

Good openings propose problems, pose questions, drop you into an unfinished story, or point at fundamental tensions within a topic. Ideally within the first paragraph or two.

"Good writing starts strong. Not with a cliché ("Since the dawn of time"), not with a banality ("Recently, scholars have been increasingly concerned with the questions of..."), but with a contentful observation that provokes curiosity."A Sense of StyleStephen Pinker

Creating tension in non-fiction work is trickier because your story is (hopefully) constrained by reality. You are not at liberty to invent suspicious murders, salacious extramarital affairs, or newly-discovered-magical-powers to create tension and mystery. You have to deal with the plain, unexotic facts of the world.

Your job becomes much harder if you pick topics with no tension, problems, or puzzles within them. To paraphrase Williams, it is more of a failure to pose an uninteresting problem, than to poorly articulate an interesting one

Your interest in the topic is your best directional clue for finding the tension or interesting paradox. Your urge to write about the thing hopefully comes from a place of curiosity. You have unanswered questions about it. It feels important or consequential for unexplained reasons. You think you've seen things in it other people haven't. Pay attention to that interest.

Problems are a destabilising condition that has a cost for a community of readers that needs a solution. Destabilising condition is just a fancy word for “change” here – a change in the status quo. Put another way, a problem is an expected turn of events, that has undesireable consequences, for an audience who will care about it, that we want to explore solutions to.

Williams is speaking to a community of academic writers in his book. They're trying to present scientific and research problems in plain, objective language, which isn't necessarily what we want to do with narrative writing like blogging or personal essays. We have a little more liberty to put interesting padding around the change, consequences, and solution, such as telling an opening anecdote, or drawing readers in with characters, rich details, and sensory descriptions.

Williams suggests we try to state our problem and then ask a series of so what?'s to get at the underlying problem

For your writing to be worth reading, you need to be exploring something of consequence for someone

When McPhee writes, after first immersing himself in his raw material (field notes, interview transcripts, official documents) for weeks, he then draws a structure for the work. The structure lays out the major themes and scenes he'll work through, in the order that will make them most compelling and coherent.

Developing a structure requires navigating the tension between chronology and theme. Chronology is what we default to, but themes that repeatedly appear want to pull themselves together into a single place. The themes that really matter should be in your opening. Even if the moment that best defines them happens right before the end of the timeline.

resist the urge to add immediate value. Instead we have to hold space for a more vulnerable, honest and open relationship with our client - to allow them to open up more fully and to work on things that are useful, even if not in scope.

While giving advice can help you be seen as knowledgeable, it doesn’t necessarily build trust.

“You should…” It’s a simple sounding phrase but it gets you in trouble more often than not. It’s problematic for two reasons: it assumes a control of client resources and it’s too prescriptive in form

We typically don’t have a complete view of everything that the company is working on, we don’t have a detailed understanding of how long things actually take or the full range of dependencies required for them.

Example: working with a client where I wanted to re-design a landing page on their site to improve it. Unfortunately I was under-estimating the number of people who need to be involved since the landing pages were still owned by the product team and are technically part of the same codebase as the full tech product. So a “small” change required detailed security scrutiny and QA before going live. Making “simple” changes was not in fact simple at all here.

Example: working with the NYTimes cooking team I suggested that they should re-tag their content. This kind of “you should…” recommendation seemed straightforward but neglected the political considerations - the team had just spent 6-figures on re-tagging all their recipes - so to ask for further budget to re-do a task they had just done would lose them face internally. A “straightforward” change that actually carried a bunch of political baggage.

Some other types of complexity that you might be under-estimating with regards resource allocation: Regulation/compliance complexity - which either prevents you even doing your recommendation or makes it slower. Technical complexity - while something might be technically easy, doing it with the client’s existing technology might be hard. Data complexity - a simple seeming request on the surface (make a landing page for every neighborhood) might actually depend on a robust, maintained data set that doesn’t yet exist. Maintenance complexity - even if the initial request to create something or do something is not resource intensive, it might come with an implicit agreement to continue to maintain it - expanding the resources allocated. Production complexity - where what you’re proposing isn’t that expensive or resource intensive to do, but the client (for whatever reason) has a higher quality threshold, making the recommendation more expensive/slower/harder than you anticipated. Narrative complexity - where what you’re recommending seems reasonable but either the company has tried it before, or a competitor has tried it before or there’s a general sense that “this doesn’t work”. Which can make your recommendation extremely hard to actually get done.

When we say “You should…” we’re essentially offering a problem diagnosis AND a solution at the same time. The consequence of this is that we’re essentially asking the client to accept or reject both together.

most of your work would be more effective at actually changing clients if you stopped to clearly separate the diagnosis from the solution.

if you’re asking “You should…” to the client, stop and examine if you’ve properly defined the situation and provided evidence for the problem, to help the client deeply internalize the problem and win over the necessary stakeholders before you propose any kind of solution.

A good mental exercise to ensure you’re doing the work here is to ask yourself: what happens if the client takes no action? What is the consequence of the current trajectory, or the null case of no investment?

By showing what’s possible, clients are able to feel more invested in designing the solution with you, rather than just being told what to do.

clients deeply appreciate you clearly separating out expert opinion and judgment from evidence-based analysis.

A good process for the advisor to follow is: Give them their options Give them an education about their options (including enough discussion for them to consider each option in depth) Give them a recommendation Let them choose

Taking a collaborative stance with your client is powerful. There are many aspects of consulting that are almost combative by nature - like pointing out problems the client has (that the client was complicit in creating!).

I find in my own work that senior executives are often blocked by some inability to see what’s actually going on - and that telling them is useless! Instead you need to help them see it for themselves.

Because of their distance from the day to day work, senior executives are especially prone to replacing some version of reality with a compressed narrative. And when this compressed narrative is wrong in some key way you need to return to first principles to show them (not tell them!).

Your sense of “what’s going on” with a client is intermediated by your point of contact and it turns out that your client is an unreliable narrator.

When a client comes to you asking for a “content strategy” or support “hiring a VP marketing” it all seems so straightforward, rational and well defined. But as you unpack the layers of the onion you begin to realize why it’s been so hard for the client to help themselves. And that’s when the emotional and political complexity of the problem starts to come into view.

if the work is done effectively, it requires that the consultant be both involved enough in the dynamics so as to experience their impact and detached enough so as to analyze what is transpiring. These demands make imperative the use of oneself as tool.

always work on the next most useful thing. This mantra helps remind me that consulting isn’t about being right, it’s about being useful.

I delivered what I think is good quality work with a deeply researched and evidence-based 66-page strategy for producing content and…. Nothing happened? They were happy enough with the work product but it didn’t lead to any material change in their strategy or an ongoing consulting relationship. In hindsight the key mistake here was not asking myself enough what the next most useful thing was. I think if I’d been more honest about what would add value and show momentum for the client it would have been either a) condensed one or two slide summary of the content opportunity for their fundraising deck and/or b) supporting their VP marketing recruitment effort.

Either you’re telling the client “draw some circles” and the client is frustrated the advice is too basic and high level. Or you’re telling the client to “draw the rest of the fucking owl” and are ignoring the detailed reality of the situation and the limitations of teams, resources and capabilities.

Or worse, the client asked you for help drawing owls but what they’re really doing is painting a woodland scene…

Think about this image next time a client comes to you for help drawing owls - your first response shouldn’t be “Oh, that’s easy, first you draw some circles”, it should be “Show me how your owls look today. What do you think is holding you back from drawing better owls? And why is drawing owls important to you right now?”

Remember - it’s about adopting a collaborative, trusted stance with clients. And that might require resisting your initial urge to give advice. Instead you need to listen to the full emotional and political situation and then work with the client to re-examine reality in new and surprising ways. Always work on the next most useful thing. And that doesn’t always involve doing what the client asked for.

As the “am I ready?” question continues to ricochet off myself and others, I’m finally viewing it for what it is: a clever, creative way to procrastinate self-actualization. If you’re asking yourself whether you’re ready, or finding reasons why you aren’t, it’s a sign you have let the gap grow too wide between idea and action. Your mind is probably convincing you that there is some existential reason for that buffer, when in reality, you’re just scared to do a new thing wrong or to look weird doing it. That’s okay. Now that you’ve noticed your inaction, you can act. You are as ready as you’ll ever be, because ready-ness is not measured by thinking, it’s measured by starting.

If you keep waiting for permission from some external source long after anyone is responsible for giving it to you, your ideas and ambitions will whither while you become bitter that no one is letting you do what you wanted to do. But in the end: it’s your responsibility to give yourself permission. This doesn’t need to be daunting. It can be the most liberating epiphany of all to realize that you can start now.

are you ready? to be in the relationship? to start the business? to say i love you to your partner? to forgive the person you resent? to have the hard conversation? to tell the truth? to publish the piece? to admit you were wrong? to create the life you imagine? to do what scares you?

what I’ve leapt at before I felt ready has consistently lead to the most expansive journeys of my life. Pursuing jobs I was too young for. Applying for scholarships that seemed impossible to get. Reaching out to people that I had no business knowing.

The whole notion of needing to be ready is highly corrosive to action. Because how can we really measure ready-ness? What if the only measure of “being ready” is just… starting? Trying? Doing the thing. What if ready is something you prove to yourself you are while you’re making the attempt, instead of trying to prove it before you start? What if being ready is not something you can cognitively analyze, but something that can be only demonstrated through action.

The reframe I am now internalizing is that ready is a felt state you can consciously bring yourself to.

You can imagine what the version of you that is ready would feel like and fill yourself up with those feelings. Or to make it even simpler: you can just start. If it doesn’t work, you can ask why, integrate your learnings, and try a different way. Or move on. Or whatever. But action—action!—is the path to ready-ness, not more thinking.

limiting beliefs. Poor attempts at protecting me from some imagined danger. Blocks created by my mind, designed to keep my ideas inside me and keep my creativity away from the world—away from reaching you. I’m now weeding out this ready-ness block and seeding the belief that the ability to imagine is the only sign of ready-ness you need.

You can go back later to refine what you’ve done. But by then, you’re already in the act. You’ve done it instead of remaining stuck in thought. So, the next time you find yourself wondering if you’re ready: don’t. Instead: start. We become ready by trying, not by thinking. Because ready-ness is a question of boldness, and as Bradbury so eloquently reminds us: intellect doesn’t help you very much there.

When I first started meeting founders, I wanted to help with anything and everything. Unfortunately, that's neither realistic or possible. For example, I have many responsibilities at my day job that must come first. Over time, I have honed in my pitch to be explicit about how I can and can't help. See the notes above about ways to be helpful, and find your own unique combination of value to bring to the table.

My contract typically looks like this: We agree to meet ~X hours per quarter/half/year Multiply by Y contracting rate Y ⨉ X = some dollar amount Z Divide Z by the startup's latest price per share to arrive at a number of advisor shares to grant

Be founder-friendly! It's a big deal and a lot of paperwork to get a smaller check or advisor on the cap table (unless they already have a lot of operational infrastructure in place) – this usually means being relaxed about the commitment paperwork or helping out pro-bono for the first few hours while they work through the logistics.

Finding founders you work well with can be a numbers game; you won't be sure what you like doing until you've met a handful of founders, done several advisory meetings, and poked at different types of problems. It's okay to dip your toe and warm up to the process before committing a lot of time and energy to this. I started slow, and have been steadily sharpening my own intuition about what kinds of products and founders get me excited, and where I can add unique value

If you don’t have the opportunity to “do great things”, focus on consistently achieving small wins. These small things in fact do not need to be done in a great way, but a good way, repeatably

Essentially, as someone achieves new successes in various aspects of their lives, their baseline shifts to reflect that new level and therefore, their expectations and desires are re-established as well. There is no net gain in happiness and thus, it becomes even more difficult to stay “level-headed” during these down moments.

The best things in life often aren’t miracles, but well-thought out approaches that are sustainable. The same thing is true with businesses, marriages, and just about anything with repeatable elements. If you invest time into solving for what leads to success continuously, you will reap those benefits for years to come

“Moving fast and breaking things” is not a strategy, unless you are clearly defining a process of learning so that in the future, you can “move fast and break less of the same things”.

try testing things intentionally every month or even every week. Pilot a lot and then double down when you have found your path towards “good”. You may ask, “what makes good, good?”. Ask yourself the question: “If I were to continue this every day for the next year, would I be in a better place?” If the answer is yes, you have a path towards “good”.

“It is easy to get bogged down trying to find the optimal plan for change: the fastest way to lose weight, the best program to build muscle, the perfect idea for a side hustle. We are so focused on figuring out the best approach that we never get around to taking action” - James Clear, Atomic Habits

Do not look for perfection or even greatness, but instead signs of “good” and start making tangible progress.

Most startups end up doing something different than they planned. The way the successful ones find something that works is by trying things that don't. So the worst thing you can do in a startup is to have a rigid, pre-ordained plan and then start spending a lot of money to implement it. Better to operate cheaply and give your ideas time to evolve.

Successful startups are almost never started by one person. Usually they begin with a conversation in which someone mentions that something would be a good idea for a company, and his friend says, "Yeah, that is a good idea, let's try it." If you're missing that second person who says "let's try it," the startup never happens. And that is another area where undergrads have an edge. They're surrounded by people willing to say that.

Look for the people who keep starting projects, and finish at least some of them. That's what we look for. Above all else, above academic credentials and even the idea you apply with, we look for people who build things.

You need a certain activation energy to start a startup. So an employer who's fairly pleasant to work for can lull you into staying indefinitely, even if it would be a net win for you to leave.

Most people look at a company like Apple and think, how could I ever make such a thing? Apple is an institution, and I'm just a person. But every institution was at one point just a handful of people in a room deciding to start something. Institutions are made up, and made up by people no different from you.

What goes wrong with young founders is that they build stuff that looks like class projects. It was only recently that we figured this out ourselves. We noticed a lot of similarities between the startups that seemed to be falling behind, but we couldn't figure out how to put it into words. Then finally we realized what it was: they were building class projects.

Class projects will inevitably solve fake problems. For one thing, real problems are rare and valuable. If a professor wanted to have students solve real problems, he'd face the same paradox as someone trying to give an example of whatever "paradigm" might succeed the Standard Model of physics. There may well be something that does, but if you could think of an example you'd be entitled to the Nobel Prize. Similarly, good new problems are not to be had for the asking.

real startups tend to discover the problem they're solving by a process of evolution. Someone has an idea for something; they build it; and in doing so (and probably only by doing so) they realize the problem they should be solving is another one.

Professors will tend to judge you by the distance between the starting point and where you are now. If someone has achieved a lot, they should get a good grade. But customers will judge you from the other direction: the distance remaining between where you are now and the features they need. The market doesn't give a shit how hard you worked. Users just want your software to do what they need, and you get a zero otherwise. That is one of the most distinctive differences between school and the real world: there is no reward for putting in a good effort. In fact, the whole concept of a "good effort" is a fake idea adults invented to encourage kids. It is not found in nature.

unfortunately when you graduate they don't give you a list of all the lies they told you during your education. You have to get them beaten out of you by contact with the real world.

really what work experience refers to is not some specific expertise, but the elimination of certain habits left over from childhood.

One of the defining qualities of kids is that they flake. When you're a kid and you face some hard test, you can cry and say "I can't" and they won't make you do it. Of course, no one can make you do anything in the grownup world either. What they do instead is fire you. And when motivated by that you find you can do a lot more than you realized. So one of the things employers expect from someone with "work experience" is the elimination of the flake reflex—the ability to get things done, with no excuses.

Fundamentally the equation is a brutal one: you have to spend most of your waking hours doing stuff someone else wants, or starve. There are a few places where the work is so interesting that this is concealed, because what other people want done happens to coincide with what you want to work on.

So the most important advantage 24 year old founders have over 20 year old founders is that they know what they're trying to avoid. To the average undergrad the idea of getting rich translates into buying Ferraris, or being admired. To someone who has learned from experience about the relationship between money and work, it translates to something way more important: it means you get to opt out of the brutal equation that governs the lives of 99.9% of people. Getting rich means you can stop treading water.

You don't get money just for working, but for doing things other people want. Someone who's figured that out will automatically focus more on the user. And that cures the other half of the class-project syndrome. After you've been working for a while, you yourself tend to measure what you've done the same way the market does.

the most important skill for a startup founder isn't a programming technique. It's a knack for understanding users and figuring out how to give them what they want. I know I repeat this, but that's because it's so important. And it's a skill you can learn, though perhaps habit might be a better word. Get into the habit of thinking of software as having users. What do those users want? What would make them say wow?

To write about something hard to explain, write a detailed letter to a friend about why it is so hard to explain, and then remove the initial “Dear Friend” part and you’ll have a great first draft.

To be interesting just tell your story with uncommon honesty.

Most articles and stories are improved significantly if you delete the first page of the manuscript draft. Immediately start with the action.

Each technology can not stand alone. It takes a saw to make a hammer and it takes a hammer to make a saw. And it takes both tools to make a computer, and in today’s factory it takes a computer to make saws and hammers. This co-dependency creates an ecosystem of highly interdependent technologies that support each other

On the other hand, I see this technium as an extension of the same self-organizing system responsible for the evolution of life on this planet. The technium is evolution accelerated. A lot of the same dynamics that propel evolution are also at work in the technium

Our technologies are ultimately not contrary to life, but are in fact an extension of life, enabling it to develop yet more options and possibilities at a faster rate. Increasing options and possibilities is also known as progress, so in the end, what the technium brings us humans is progress.

Libraries, journals, communication networks, and the accumulation of other technologies help create the next idea, beyond the efforts of a single individual

We also see near-identical parallel inventions of tricky contraptions like slingshots and blowguns. However, because it was so ancient, we don’t have a lot of data for this behavior. What we would really like is to have a N=100 study of hundreds of other technological civilizations in our galaxy. From that analysis we’d be able to measure, outline, and predict the development of technologies. That is a key reason to seek extraterrestrial life.

When information is processed in a computer, it is being ceaselessly replicated and re-copied while it computes. Information wants to be copied. Therefore, when certain people get upset about the ubiquitous copying happening in the technium, their misguided impulse is to stop the copies. They want to stamp out rampant copying in the name of "copy protection,” whether it be music, science journals, or art for AI training. But the emergent behavior of the technium is to copy promiscuously. To ban, outlaw, or impede the superconductivity of copies is to work against the grain of the system.

the worry of some environmentalists is that technology can only contribute more to the problem and none to the solution. They believe that tech is incapable of being green because it is the source of relentless consumerism at the expense of diminishing nature, and that our technological civilization requires endless growth to keep the system going. I disagree.

Over time evolution arranges the same number of atoms in more complex patterns to yield more complex organisms, for instance producing an agile lemur the same size and weight as a jelly fish. We seek the same shift in the technium. Standard economic growth aims to get consumers to drink more wine. Type 2 growth aims to get them to not drink more wine, but better wine.

to measure (and thus increase) productivity we count up the number of refrigerators manufactured and sold each year. More is generally better. But this counting tends to overlook the fact that refrigerators have gotten better over time. In addition to making cold, they now dispense ice cubes, or self-defrost, and use less energy. And they may cost less in real dollars. This betterment is truly real value, but is not accounted for in the “more” column

it is imperative that we figure out how to shift more of our type 1 growth to type 2 growth, because we won’t be able to keep expanding the usual “more.”  We will have to perfect a system that can keep improving and getting better with fewer customers each year, smaller markets and audiences, and fewer workers. That is a huge shift from the past few centuries where every year there has been more of everything.

“degrowthers” are correct in that there are limits to bulk growth — and running out of humans may be one of them. But they don’t seem to understand that evolutionary growth, which includes the expansion of intangibles such as freedom, wisdom, and complexity, doesn’t have similar limits. We can always figure out a way to improve things, even without using more stuff — especially without using more stuff!

the technium is not inherently contrary to nature; it is inherently derived from evolution and thus inherently capable of being compatible with nature. We can choose to create versions of the technium that are aligned with the natural world.

Social media can transmit false information at great range at great speed. But compared to what? Social media's influence on elections from transmitting false information was far less than the influence of the existing medias of cable news and talk radio, where false information was rampant. Did anyone seriously suggest we should regulate what cable news hosts or call in radio listeners could say? Bullying middle schoolers on social media? Compared to what? Does it even register when compared to the bullying done in school hallways? Radicalization on YouTube? Compared to talk radio? To googling?

Kids are inherently obsessive about new things, and can become deeply infatuated with stuff that they outgrow and abandon a few years later. So the fact they may be infatuated with social media right now should not in itself be alarming. Yes, we should indeed understand how it affects children and how to enhance its benefits, but it is dangerous to construct national policies for a technology based on the behavior of children using it.

Since it is the same technology, inspecting how it is used in other parts of the world would help us isolate what is being caused by the technology and what is being caused by the peculiar culture of the US.

You don’t notice what difference you make because of the platform's humongous billions-scale. In aggregate your choices make a difference which direction it — or any technology — goes. People prefer to watch things on demand, so little by little, we have steered the technology to let us binge watch. Streaming happened without much regulation or even enthusiasm of the media companies. Street usage is the fastest and most direct way to steer tech.

Vibrators instead of the cacophony of ringing bells on cell phones is one example of a marketplace technological solution

The long-term effects of AI will affect our society to a greater degree than electricity and fire, but its full effects will take centuries to play out. That means that we’ll be arguing, discussing, and wrangling with the changes brought about by AI for the next 10 decades. Because AI operates so close to our own inner self and identity, we are headed into a century-long identity crisis.

What we tend to call AI, will not be considered AI years from now

What we are discovering is that many of the cognitive tasks we have been doing as humans are dumber than they seem. Playing chess was more mechanical than we thought. Playing the game Go is more mechanical than we thought. Painting a picture and being creative was more mechanical than we thought. And even writing a paragraph with words turns out to be more mechanical than we thought

out of the perhaps dozen of cognitive modes operating in our minds, we have managed to synthesize two of them: perception and pattern matching. Everything we’ve seen so far in AI is because we can produce those two modes. We have not made any real progress in synthesizing symbolic logic and deductive reasoning and other modes of thinking

we are slowly realizing we still have NO IDEA how our own intelligences really work, or even what intelligence is. A major byproduct of AI is that it will tell us more about our minds than centuries of psychology and neuroscience have

There is no monolithic AI. Instead there will be thousands of species of AIs, each engineered to optimize different ways of thinking, doing different jobs

Now from the get-go we assume there will be significant costs and harms of anything new, which was not the norm in my parent's generation

The astronomical volume of money and greed flowing through this frontier overwhelmed and disguised whatever value it may have had

The sweet elegance of blockchain enables decentralization, which is a perpetually powerful force. This tech just has to be matched up to the tasks — currently not visible — where it is worth paying the huge cost that decentralization entails. That is a big ask, but taking the long-view, this moment may not be a failure

My generic career advice for young people is that if at all possible, you should aim to work on something that no one has a word for. Spend your energies where we don’t have a name for what you are doing, where it takes a while to explain to your mother what it is you do. When you are ahead of language, that means you are in a spot where it is more likely you are working on things that only you can do. It also means you won’t have much competition.

Your 20s are the perfect time to do a few things that are unusual, weird, bold, risky, unexplainable, crazy, unprofitable, and looks nothing like “success.” The less this time looks like success, the better it will be as a foundation

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.

There comes a frustration when you know you're a unique human being who knows some things about the world, but somehow the writing isn't showing that. That's the most maddening thing. That’s the gateway to style, really—to say, "I'm going to accept all those things about me that I normally deny." The way to do that is to see when the prose lights up. If you're writing in a certain mode and the prose is boring, that means you're keeping yourself out of it somehow, whereas when the prose lights up and even you can't help but read your own prose, that means you're letting yourself in.

The working world expects so much of your soul. That’s where our lives are taking place, actually, in the pressure cooker that work makes on our grace.

"I want you to recreate your reading experience. When did you start to love or hate this piece of writing? Go down to the phrase level.” That's actually how it works. If you pick up a book in a bookstore, a book that's gotten a lot of great reviews, written by someone who's one year younger than you, god forbid—you read it, and instantly you're opining about it. That's a really valuable thing for a young writer: what do you really love about prose, and what do you hate about it? It’s maybe the one part of our lives where we get to be so opinionated without being obnoxious.

We have crazily refined micro-opinions about things. That, I think, is the hidden superpower. The pathway to the uniqueness we're talking about is turning down your inner nice guy who’s always trying to like everything. Turn that down, and when you read a bit of prose, watch that little needle flicker. That's where a person's uniqueness lies. If you then make a career of radically honoring those little preferences with every sentence, pretty soon the whole book has your stamp on it, which is ultimately what we're looking for. When I pick up your book, I want you to be there. I want you specifically to be there. And the way you get yourself in there is by those 10,000 micro-choices.

Science and technology are understood to be great because they get you a job, but this very essential human thing of asking, "What are we doing here, and how should I behave?"—that has somehow become considered a bit of an indulgence. And it isn't.

These Russians remind us that a really good story is eternal. That Tolstoy story in the book, “Master and Man,” is about power dynamics. You could easily make that story a commentary about racism, because whatever it is that's actually behind racism, which is power, is totally opened up in that story. I've been trying to think that whatever the pandemic is "teaching" me will come out eventually. It'll come out in some form. It won't be a story about face masks, but somehow it'll be there.

When any person walks into a grocery store, they're basically writing a novel. They see a woman with two little kids, and they make a story up about her, even if they don't realize it. It's called projection. A novel or a short story is not something foreign to us. We do it all the time. We generalize without very much information, and we make assumptions about the world, about, "This is how we stay alive." If we're good at it, we not only stay alive, but we stay alive compassionately, and we become better at being patient with other people. By imagining their circumstances, we make a more spacious universe. That's a skill you have to practice.

if we practice the opposite of it, which I’d argue we practice every time we're on social media about politics—then what we're doing is short-circuiting the process of generous projection. We're projecting hateful caricatures of each other. Obviously that has an effect on our neurology. It makes us more anxious, more nervous, more accusatory, quicker to act.

Now, that moment where I felt drawn to her was every bit as real as the moment where I felt aversion to her. That's a short story. That energy is short-story energy, which is, “I thought I knew her, and I thought I knew what I thought of her. But just by abiding there a little bit, I found out that I was capable of a little bit more.” That's essentially what reading is. It's not a complete antidote, but I think we all could all stand a little more of it. Sometimes you have to act. Sometimes you have to arrest people who go into the Capitol. That's a no-brainer. But even in that process, if you have some fellow feeling for them, you're going to do a better job.

Another test you can use is: always produce. For example, if you have a day job you don't take seriously because you plan to be a novelist, are you producing? Are you writing pages of fiction, however bad? As long as you're producing, you'll know you're not merely using the hazy vision of the grand novel you plan to write one day as an opiate. The view of it will be obstructed by the all too palpably flawed one you're actually writing."Always produce" is also a heuristic for finding the work you love. If you subject yourself to that constraint, it will automatically push you away from things you think you're supposed to work on, toward things you actually like. "Always produce" will discover your life's work the way water, with the aid of gravity, finds the hole in your roof.

anything you work on changes you. If you work too long on tedious stuff, it will rot your brain.

If you're sure of the general area you want to work in and it's something people are likely to pay you for, then you should probably take the organic route.

In the design of lives, as in the design of most other things, you get better results if you use flexible media. So unless you're fairly sure what you want to do, your best bet may be to choose a type of work that could turn into either an organic or two-job career.

By high school, the prospect of an actual job was on the horizon. Adults would sometimes come to speak to us about their work, or we would go to see them at work. It was always understood that they enjoyed what they did. In retrospect I think one may have: the private jet pilot. But I don't think the bank manager really did.

My path to merging onto the VC highway involved exploring basically every other option before finally circling back to reconsider this route with renewed appreciation

I’m a generalist at heart — I know I can do most things decently well (or at least figure them out) but what I actually excel at is understanding people, packaging their stories, and making them feel seen. What kind of craft is that?

Without a product in mind ‘company’ never seemed right and ‘non-profit’ felt unnecessarily limiting.

most advice bestowed on young people overrotates on being someone far before we have enough data points to know who that someone should be

most advice bestowed on young people overrotates on being someone far before we have enough data points to know who that someone should be.

I think most people live the majority of their lives trapped in place by a fear of rejection that probably feels worse to stew in than actually experiencing the rejection they fear so dearly itself.

If you were magically given 10,000 hours to be amazing at something, what would it be? The more clarity you have on this response, the better off you’ll be.

Scott Adams popularized the idea of finding the intersection of 2-3 things you’re best at even if you’re not best at any of them individually. He wasn’t neither the best cartoonist nor the best writer nor the best entrepreneur, but he was the best combination. It could be a combination of expertise, relationships, sensibilities, and skills that you’ve accumulated over the years. If you’re just starting out, ideally it picks up where your childhood left off. Now, I spent my childhood trying to make the NBA. So if like me, you misallocated your childhood in the skills department, you have to be more creative. Later on, I realized I could apply the self-discipline and systems thinking I deployed when trying to be good at basketball into other fields, and found some that better fit my natural abilities.

If you’re a generalist, you want to be the best at the intersection of a few different skills, even if it’s a few disparate things. The challenge is it's easy to lie to yourself & say that you're a generalist when in reality you've tried a bunch of things and you've flaked out when things got hard and then tried something else.

Some people who you think are generalists have also specialized. Malcolm Gladwell for example writes about lots of topics, but he's mastered the art of translating academic work for a mass audience. Tyler Cowen self-defines himself as specializing as a generalist, but he spent a couple decades going deep on economics.

A personal moat is a set of unique and accumulating competitive advantages in the context of your career. Like company moats, your personal moat should be a competitive advantage specific to you that's not only durable, but compounds over time.