When our startup failed, I didn’t know what to do next.

I’ve always been busy running somewhere but never had the time to think hard about where I was heading.

Now I had all the time in the world. So I embarked on a journey to figure out what to work on.

I dug deep. Over the past six months, I devoured hundreds of books, articles, and videos on how to choose what to work on (or, more generally, what the fuck should I do with my life).

Most of them sucked. But the winners changed my life.

Instead of you wasting years searching for the best stuff, I’ve created this curriculum of the 13 essential reads to choosing what to work on.

These are less the 1% that made the cut. I’ve read virtually all of these twice or more.

1. How to Get Rich, by Naval Ravikant


This is the one thing I urge everyone to read no matter what they do. I believe they should teach this in schools. Naval explains how to create wealth. He covers everything from choosing what to work on to applying maximum leverage by building tech companies. Read and listen to it 3-5 times to fully understand the thought behind it.

What stuck: “The way to retire is actually to find the thing that you know how to do better than anybody, and you know how to do that better than anybody cause you love to do it. No one can compete with you if you love to do it. Be authentic, and then figure out how to map that to what society actually wants, apply some leverage, put your name on it, so you take the risks but you gain the rewards, have ownership, and equity in what you do, and then just crank it out.”

My Favorite Quotes:

  • You won’t get rich renting out your time, because you can’t earn non-linearly.
  • Making money isn’t about luck. It’s about becoming the kind of person who makes money.
  • Tools and leverage are what create this disconnection between inputs and outputs.
  • The easiest way to figure out if something is viable or not is by doing it. At least do the first step, and the second step, and the third, and then decide.
  • Specific knowledge is the knowledge that you care about.
  • It’s better to read a great book really slowly than to fly through a hundred books quickly.
  • The five most important skills are of course, reading, writing, arithmetic, and then as you’re adding in, persuasion, which is talking.
  • There’s no actual skill called business. Avoid business schools and magazines.
  • It’s the number of iterations that drives the learning curve.
  • People will forgive failures as long as you were honest and made a high integrity effort.
  • Product and media are the leverage of new wealth. Create software and media that work for you while you sleep.
  • Investment books are the worst place to learn about investment.
  • You can save yourself a lot of time if you pick the right area to work in.
  • When you have your inspiration, do it right then and there.
  • Be impatient with actions, but patient with results.
  • The product progress is the resume for the entrepreneur. It is the unshakable, unfakeable resume.
  • Networking is overrated even early in your career.
  • A busy calendar and a busy mind will destroy your ability to do great things in this world.
  • Sometimes when we search our egos, we want to be something that we are not.
  • If you survey enough people all the advice will cancel to zero.
  • If you want to be a philosopher king first become a king then become a philosopher. Not first become a philosopher and then become a king.

2. Advice for Ambitious 19 Year Olds, by Sam Altman


Build the right systems around you to maximize serendipity.

What stuck: “If you start a company, only do so if you have an idea you’re in love with.”

I can’t emphasize this enough.

My Favorite Quotes:

  • The critical point is that you want to do the thing that is most likely to get you on a path to do something great.
  • No matter what you choose, build stuff and be around smart people.
  • The best people always seem to be building stuff and hanging around smart people, so if you have to decide between several options, this may be a good filter.
  • Working on something good will pull you along a path where good things keep happening to you.
  • If you join a company, my general advice is to join a company on a breakout trajectory.
  • Don’t let salary be a factor.
  • If you start a company, only do so if you have an idea you’re in love with.
  • If you fail at an idea that you really loved and could have been great, you’re unlikely to regret it, and people will not hold it against you.
  • One big con is that it’s easy to start a company for the wrong reasons—usually so that you can say you’re starting a company—and this makes it easy to cloud your judgment.
  • keep your personal burn rate low and minimize your commitments.
  • Think about risk the right way. You only have to be right once. The risk is not getting on the path where you get to be right that one critical time.

3. How to Do What You Love, by Paul Graham


Avoid prestige. We often choose things to work on based on what other people think. Try different things. Always produce.

What stuck: “It might be a good rule simply to avoid any prestigious task. If it didn't suck, they wouldn't have had to make it prestigious.”

My Favorite Quotes:

  • The test of whether people love what they do is whether they'd do it even if they weren't paid for it—even if they had to work at another job to make a living.
  • Is there some test you can use to keep yourself honest? One is to try to do a good job at whatever you're doing, even if you don't like it. Then at least you'll know you're not using dissatisfaction as an excuse for being lazy. Perhaps more importantly, you'll get into the habit of doing things well.
  • 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.
  • "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.
  • 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. That was probably part of the reason I chose computers. You can be a professor, or make a lot of money, or morph it into any number of other kinds of work.
  • It's also wise, early on, to seek jobs that let you do many different things, so you can learn faster what various kinds of work are like. Conversely, the extreme version of the two-job route is dangerous because it teaches you so little about what you like. If you work hard at being a bond trader for ten years, thinking that you'll quit and write novels when you have enough money, what happens when you quit and then discover that you don't actually like writing novels?
  • But if you have the destination in sight you'll be more likely to arrive at it. If you know you can love work, you're in the home stretch, and if you know what work you love, you're practically there.

4. You and Your Research, by Richard Hamming


If you do not work on an important problem, it's unlikely you'll do important work. It's not the consequence that makes a problem important, it is that you have a reasonable attack.

My Favorite Quotes:

  • Each of you has one life to live.
  • The particular thing you do is luck, but that you do something is not.
  • Newton said, “If others would think as hard as I did, then they would get similar results.”
  • Once you get your courage up and believe that you can do important problems, then you can. If you think you can't, almost surely you are not going to.
  • When you are famous it is hard to work on small problems. The great scientists often make this error. They fail to continue to plant the little acorns from which the mighty oak trees grow. They try to get the big thing right off. And that isn't the way things go.
  • People are often most productive when working conditions are bad.
  • Knowledge and productivity are like compound interest. Given two people of approximately the same ability and one person who works ten percent more than the other, the latter will more than twice outproduce the former.
  • The misapplication of effort is a very serious matter. Just hard work is not enough - it must be applied sensibly.
  • Great contributions are rarely done by adding another decimal place. It comes down to an emotional commitment.
  • Everybody who has studied creativity is driven finally to saying, “creativity comes out of your subconscious.” Somehow, suddenly, there it is. It just appears. Well, we know very little about the subconscious; but one thing you are pretty well aware of is that your dreams also come out of your subconscious. And you're aware 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. For those who don't get committed to their current problem, the subconscious goofs off on other things and doesn't produce the big result. So the way to manage yourself is that when you have a real important problem you don't let anything else get the center of your attention - you keep your thoughts on the problem. Keep your subconscious starved so it has to work on your problem, so you can sleep peacefully and get the answer in the morning, free.
  • “If what you are doing is not important, and if you don't think it is going to lead to something important, why are you at Bell Labs working on it?”
  • You can't always know exactly where to be, but you can keep active in places where something might happen.
  • 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.
  • 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.
  • By changing a problem slightly you can often do great work rather than merely good work.
  • It is a poor workman who blames his tools - the good man gets on with the job, given what he's got, and gets the best answer he can.
  • 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.

Transcript: https://blog.samaltman.com/you-and-your-research.

5. Competition is For Losers, by Peter Thiel


Avoid competition. We go for things that lots of other people are going for.

What stuck: “You could say that a track in law school is a low risk track from one perspective, but it may still be a very high risk track in the sense that maybe you have a high risk of not doing something meaningful with your life.”

My Favorite Quotes:

  • We always think of the losers as the people who are not good at competing. We think of losers as the people who are slow on the track team in high school or do a little less well on standardized tests, and don't get into the right schools. So we always think of losers as people who can't compete and I want us to really rethink and re-value this and consider whether it's possible the competition itself is off.
  • We find ourselves very attracted to competition and in one form or another we find it reassuring if other people do things.
  • So much of people's identities got wrapped up in winning these competitions that they somehow lost sight of what was important, what was valuable.
  • Competition does make you better at whatever it is that you're competing at because when you're competing you're comparing yourself with the people around you. I’m figuring out how to beat the people next to me, how do I do somewhat better than whatever it is they're doing and you will get better at that. I'm not questioning that, I'm not denying that, but there often comes this tremendous price that you stop asking some bigger questions about what's truly important and truly valuable.
  • Don't always go through the tiny little door that everyone's trying to rush through, maybe go around the corner and go through the vast gate that nobody is taking.

Transcript: https://genius.com/Peter-thiel-lecture-5-business-strategy-and-monopoly-theory-annotated.

6. Zero to One, by Peter Thiel


The most contrarian thing of all is not to oppose the crowd but to think for yourself. The best projects are likely to be overlooked, not trumpeted by a crowd; the best problems to work on are often the ones nobody else even tries to solve.

What stuck: “Leanness is a methodology, not a goal. Making small changes to things that already exist might lead you to a local maximum, but it won't help you find the global maximum. You could build the best version of an app that lets people order toilet paper from their iPhone. But iteration without a bold plan won't take you from 0 to 1. A company is the strangest place of all for an indefinite optimism: why should you expect your own business to succeed without a plan to make it happen?”

My Favorite Quotes:

  • “What important truth do very few people agree with you on?”
  • Most answers to the contrarian question are different ways of seeing the present; good answers are as close as we can get to looking into the future.
  • “How much of what you know about business is shaped by mistaken reactions to past mistakes?”
  • If you want to create and capture lasting value, don't build an undifferentiated commodity business.
  • Competition can make people hallucinate opportunities where none exists.
  • Winning is better than losing, but everybody loses when the war isn't one worth fighting.
  • If you focus on near-term growth above all else, you will miss the most important question you should be asking: will this business still be around a decade from now? Numbers alone won't tell you the answer; instead you must think critically about the qualitative characteristics of your business.
  • Why should you expect your own business to succeed without a plan to make it happen?
  • Once you think that you're playing the lottery, you're already psychologically prepared yourself to lose.
  • An entrepreneur makes a major investment just by spending her time working on a startup. Therefore every entrepreneur must think about whether her company is going to succeed and become valuable.
  • To say that there are no secrets left today would mean that we live in a society with no hidden injustices.

7. How To Be Successful, by Sam Altman


Pick the right thing to do (this is critical and usually ignored), focus, believe in yourself (especially when others tell you it’s not going to work), develop personal connections with people that will help you, learn to identify talented people, and work hard.

What stuck: One of the most powerful lessons to learn is that you can figure out what to do in situations that seem to have no solution. The more times you do this, the more you will believe it. Grit comes from learning you can get back up after you get knocked down.”

My Favorite Quotes:

  • You should aim for your life to follow an ever-increasing up-and-to-the-right trajectory. It’s important to move towards a career that has a compounding effect—most careers progress fairly linearly.
  • I am willing to take as much time as needed between projects to find my next thing. But I always want it to be a project that, if successful, will make the rest of my career look like a footnote.
  • The biggest competitive advantage in business—either for a company or for an individual’s career—is long-term thinking with a broad view of how different systems in the world are going to come together.
  • Show up in person whenever it’s important.
  • Almost everyone I’ve ever met would be well-served by spending more time thinking about what to focus on.
  • An effective way to build a network is to help people as much as you can.
  • Eventually, you will define your success by performing excellent work in areas that are important to you.

8. The Days Are Long But the Decades Are Short, by Sam Altman


One of my favorite essays ever. I read it once or twice a year to reflect if I’m still moving in a direction.

What stuck: “Do new things often. This seems to be really important. Not only does doing new things seem to slow down the perception of time, increase happiness, and keep life interesting, but it seems to prevent people from calcifying in the ways that they think. Aim to do something big, new, and risky every year in your personal and professional life.”

My Favorite Quotes:

  • Do what makes you happy and fulfilled—few people get remembered hundreds of years after they die anyway.
  • Don’t do stuff that doesn’t make you happy (this happens most often when other people want you to do something).
  • Don’t spend time trying to maintain relationships with people you don’t like, and cut negative people out of your life. Negativity is really bad.
  • Don’t let yourself make excuses for not doing the things you want to do.
  • When in doubt, kiss the boy/girl.

9. The Knowledge Project, by Naval Ravikant and Shane Parrish


Find out the people who need you the most, to find out the business that needs you the most, to find the project and the art that needs you the most. There is something out there just for you. What you don’t want to do is be building checklists and decision frameworks built on what other people are doing. You’re never going to be that. You’ll never be good at being somebody else.

What stuck: “Socially, we’re told, “Go work out. Go look good.” That’s a multi-player competitive game. Other people can see if I’m doing a good job or not. We’re told, “Go make money. Go buy a big house.” Again, external monkey-player competitive game. When it comes to learn to be happy, train yourself to be happy, completely internal, no external progress, no external validation, 100% you’re competing against yourself, single-player game. We are such social creatures, we’re more like bees or ants, that we’re externally programmed and driven, that we just don’t know how to play and win at these single-player games anymore. We compete purely on multi-player games. The reality is life is a single-player game. You’re born alone. You’re going to die alone. All of your interpretations are alone. All your memories are alone. You’re gone in three generations and nobody cares. Before you showed up, nobody cared. It’s all single-player.”

If you like it, you’ll enjoy watching Joe Rogan’s podcast with Naval as well.

My Favorite Quotes:

  • A really good book costs $10 or $20 and can change your life in a meaningful way.
  • I probably read one to two hours a day. That puts me in the top .00001%.
  • I don’t have time is just another way of saying, it’s not a priority.
  • Happiness to me is mainly not suffering, not desiring, not thinking too much about the future or the past, really embracing the present moment and the reality of what is, the way it is. Nature has no concept of happiness or unhappiness. To a tree, there is no right or wrong. There is no good or bad.
  • I think it can literally destroy your happiness if you spend all your time living in delusions of the future.
  • There is actually nothing but this moment. No one has ever gone back in time and no one has ever been able to predict the future successfully in any way that matters. Literally, the only thing that exists is this exact point where you are in space at the exact time that you happen to be. Like all the great profound truths, it’s all paradoxes. Any two points are infinitely different. Any moment is perfectly unique. That moment itself slips by so quickly that you can’t grab it.
  • I think all the benefits in life come from compound interest, whether in money or in relationships or love or health or activities or habits. I only want to be around people that I know I’m going to be around with for the rest of my life. I only want to work on things that I know have long-term payout.
  • The moment you tell somebody else something that’s not honest, you’ve lied to yourself. Then you’ll start believing your own lie. Then that will disconnect you from reality and take you down the wrong road.
  • You’re meant to do something. You’re not just meant to lie there in the sand and meditate all day long. You should self-actualize. You should do what you are meant to do.
  • The idea that you’re going to change something in the outside world and that is going to bring you the peace and everlasting joy and the happiness that you deserve, that is a fundamental delusion that we all suffer from, including me. The mistake over and over and over is to say, “Oh, I’ll be happy when I get that thing, whatever that is.” That’s the fundamental mistake that we all make, including me, 24/7, all day long.
  • The advantage of meditation is not that you’re suddenly going to gain the superpower to control your internal state, it’s that you will recognize just how out of control your mind is.
  • Who really sits there, years later, and goes back and looks at all their trip photos and gets nostalgic? Go take your next trip. I just don’t believe in anything from the past. Anything. No memories. No regrets. No people. No trips. Nothing.
  • I don’t believe that I have the ability to say what is going to work. Rather, what I try to do is I try to eliminate what’s not going to work. I think being successful is just about not making mistakes. It’s not about having correct judgment. It’s about avoiding the incorrect judgments.
  • I don’t believe in specific goals. Scott Adams said, famously also, “Set up systems, not goals.” Use your judgment to figure out what kinds of environments you can thrive in and then build a system to create that environment around you so that you’re statistically likely to succeed.
  • If you stop trying to figure out how to do things the way other people want you to do them, then you get to listen to that little voice inside of your head that wants to do things a certain way and then you get to be you.
  • “Easy choices, hard life. Hard choices, easy life.”
  • No one in the world is going to beat you at being you. You’re never going to be as good at being me as I am. I’m never going to be as good at being you as you are. Certainly listen, absorb, but don’t try and emulate. It’s a fool’s errand. Instead, each person is uniquely qualified at something. They have some specific knowledge, capability, and desire that nobody else in the world does. That’s just purely from the combinatorics of human DNA and development.

10. Don’t Follow Your Passion, by Ben Horowitz


Passions are hard to prioritize, they change over time, and you’re not necessarily good at your passions. On the other side, “What are you good at?” is a much easier question to answer.

What stuck: “And you know what everybody wants to hear? What they already believe to be true. And so the last thing they want to hear is an original idea that contradicts their belief system. So it’s very hard to even bring that kind of stuff up. But those are the things; those are the only things — things that YOU believe, that everybody around you doesn’t believe — that when you’re right that create real value in the world. “

My Favorite Quotes:

  • Don’t listen to your friends. Think for yourself.
  • What you’re passionate about at 21 is not necessarily what you’re gonna be passionate about at 40. Now, this is true for boyfriends as well as career choices.
  • Find the thing that you’re great at, put that into the world, contribute to others, help the world be better and that is the thing to follow.

Transcript: https://a16z.com/2015/05/28/some-career-advice-for-all-you-recent-graduates/.

11. Commencement Address MIT 2013, by Drew Houston


Do what you’re obsessed with. Sometimes that little voice in your head knows best. Surround yourself with the best people. Where you live matters.

What stuck: ”I just moved to San Francisco, and one night I couldn’t sleep, so I’m on my laptop and was on the internet, and I ran into this page and I read: there are 30,000 days in your life. And at first I’m like yeah, whatever, obviously, but then I was like huh, and I remember I tabbed into the calculator, and I typed it I’m like 24 times 365, I’m like oh my god, I’m like 9,000 days down, what the hell I have been doing. And by the way, you guys are 8,000 days down.”

My Favorite Quotes:

  • I was fascinated, I was like possessed, I was like, I just couldn’t stop thinking about this thing, I would think about it in the shower, I’d think about it, you know, waking up in the middle of the night, and I was like the switch went on, and I was a machine.
  • The happiest and most successful people that I know, they’re not just in love with what they do, they’re obsessed, and they’re not just obsessed, but they’re obsessed with solving an important problem. Something that really matters to them.
  • And what scares me is that both Dropbox and this poker bot started out as distractions. Like that little voice in my head was telling me what to do all along, and the whole time I’m telling it to shut up, so I can get back to work. I almost missed it. But sometimes that little voice knows best.
  • You are the average of the five people you spend the most time with. So think about that for a second, like who would be in your circle of five?
  • And your circle is gonna grow, to include your co-workers, and the people around you where you live. And where you live matters. There’s only one MIT, and there’s only one Hollywood, and there’s only one Silicon Valley. And this isn’t a coincidence.
  • Bill Gates’ first company made software for traffic lights. Steve Jobs’ first company made plastic whistles that allowed you to make free phone calls. Neither of these companies were successful, but it’s hard to imagine these guys are too worried about it.
  • My grandma always ends our calls with the same one word, excelsior, meaning ever upward. And that’s what I wish for you. Instead of trying to make your life perfect, give yourself the freedom to make it an adventure, and go ever upward.

Transcript: http://news.mit.edu/2013/commencement-address-houston-0607.

12. Advice, by Patrick Collison


Go deep on multiple things. Try to get a sense for which kinds of things you enjoy doing. Develop your own worldview. Read a lot. Make things.

What stuck: “There are a lot of forces that will push you towards following train tracks laid by others rather than charting a course yourself. Make sure that the things you're pursuing are weird things that you want to pursue, not whatever the standard path is. Heuristic: do your friends at school think your path is a bit strange? If not, maybe it's too normal.”

My Favorite Quotes:

  • Try to go deep on multiple things.
  • One of the main things you should try to achieve by age 20 is some sense for which kinds of things you enjoy doing.
  • A large fraction of what people around you believe is mistaken. Internalize this and practice coming up with your own worldview.
  • Operating in a space with a lot of uncertainty is a very different experience to learning something.
  • The internet is one of the biggest advantages you have over prior generations. Leverage it.
  • Don't make the mistake of judging your success based on your current peer group.

13. Stanford Commencement Address, by Steve Jobs


Follow your curiosity and intuition. Don't lose faith. Find what you love. Do what you believe is great work. Keep looking. Don't settle. Live each day as if it was your last. Remember that you'll be dead soon. Your time is limited. Don't waste it living someone else's life. Follow your heart and intuition. Everything else is secondary.

My Favorite Quotes:

  • Much of what I stumbled into by following my curiosity and intuition turned out to be priceless later on.
  • Again, you can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.
  • I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.
  • I’m pretty sure none of this would have happened if I hadn’t been fired from Apple. It was awful tasting medicine, but I guess the patient needed it. Sometimes life hits you in the head with a brick. Don’t lose faith.
  • I’m convinced that the only thing that kept me going was that I loved what I did. You’ve got to find what you love. And that is as true for your work as it is for your lovers. Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it. And, like any great relationship, it just gets better and better as the years roll on. So keep looking until you find it. Don’t settle.
  • When I was 17, I read a quote that went something like: “If you live each day as if it was your last, someday you’ll most certainly be right.” It made an impression on me, and since then, for the past 33 years, I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.
  • Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything — all external expectations, all pride, all fear of embarrassment or failure — these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.
  • Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma — which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.

Transcript: https://news.stanford.edu/2005/06/14/jobs-061505/.