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I was writing an application to Daily Candy’s Make Your Mark contest and came to the question about what my inspiration is for the mark that I wanted to make (which I will not reveal yet for certain reasons).

I thought about it for a second and remembered an article that a good friend of mine YC sent on October 20th last year, which made me think hard about what I want to do in life. At that time, I had no idea who Paul Graham was. But now I think he’s a legend. This article changed my entire perspective on work and I can never go back to my former state after taking the leap into this new exciting world of discovering the kind of ‘work’ that makes me jump out of bed each morning.

Then just tonight, a young girl JF who’s been following my life story and old college blogs for years, messaged me for advice as she was lost on what she ought to do in life. She’s just finishing up her 2nd year in college and majoring in finance. She claims that she doesn’t know what she wants to do. This was what I responded:

“Girl, no one really ever knows what they want to do in life. You could be 10. 20. 30. 40 and still not know what you want to do. But what you DO know is what you DON’T want to do. And that’s sometimes enough.

Life’s like trial and error. You’ll just have to try different things and switch around quickly if you realize you don’t belong. Eventually, hopefully one day, you’ll discover something that you really like to do. That you LOVE to do.”

I forwarded her the link to Paul’s essay (copied below). Then I began to realize how similar this concept of trying to discover what you love is to Eric Ries‘ lean startup philosophy, which stresses on the process of (i) rapid hypothesis testing (ii) iterating or “pivoting” your model accordingly based on learned responses (ii) creating true value that people actually want (don’t build awesome features that nobody uses).

In real life, when applied to the idea of creating your career (which is essentially like creating your company), one should go out to the world as soon as possible to test if their ‘hypothesis’ about what they’ve chosen as a major is anything like what they thought it’s like in their minds. If you realize it isn’t, don’t fret, get upset or feel as though you’ve wasted your college degree. It’s sunk cost. No one knows what they want in life, remember? What makes you think a high school kid does?

Now, just ‘iterate’ quickly and repeat until you find something that is of true value to you and your community/society. At the end of the day, most people want to contribute back and do something that has an impact. Don’t fall into the trap of ‘building out perfect features before launching’ (as is the problem with most failed startup) i.e. don’t get sucked into a job because of prestige/money/laziness, thinking that you’ll hang onto it until you save up enough money or until you are ‘ready’ to take the leap to do something you love (eg. writing a novel). What if you then realize, at 40, that you don’t actually like writing novels? You wasted all those years only to now have to discover again, at 40, what you truly love doing?

This comparison between lean startup and what I now coin as a “lean career path” might seem like a stretch, but what the heck. I truly believe in it!

Here’s the full feature of Paul Graham’s essay. Quite a long read, but worth every minute.

How to Do What You Love
by Paul Graham

January 2006

To do something well you have to like it. That idea is not exactly novel. We’ve got it down to four words: “Do what you love.” But it’s not enough just to tell people that. Doing what you love is complicated.

The very idea is foreign to what most of us learn as kids. When I was a kid, it seemed as if work and fun were opposites by definition. Life had two states: some of the time adults were making you do things, and that was called work; the rest of the time you could do what you wanted, and that was called playing. Occasionally the things adults made you do were fun, just as, occasionally, playing wasn’t—for example, if you fell and hurt yourself. But except for these few anomalous cases, work was pretty much defined as not-fun.

And it did not seem to be an accident. School, it was implied, was tedious because it was preparation for grownup work.

The world then was divided into two groups, grownups and kids. Grownups, like some kind of cursed race, had to work. Kids didn’t, but they did have to go to school, which was a dilute version of work meant to prepare us for the real thing. Much as we disliked school, the grownups all agreed that grownup work was worse, and that we had it easy.

Teachers in particular all seemed to believe implicitly that work was not fun. Which is not surprising: work wasn’t fun for most of them. Why did we have to memorize state capitals instead of playing dodgeball? For the same reason they had to watch over a bunch of kids instead of lying on a beach. You couldn’t just do what you wanted.

I’m not saying we should let little kids do whatever they want. They may have to be made to work on certain things. But if we make kids work on dull stuff, it might be wise to tell them that tediousness is not the defining quality of work, and indeed that the reason they have to work on dull stuff now is so they can work on more interesting stuff later. [1]

Once, when I was about 9 or 10, my father told me I could be whatever I wanted when I grew up, so long as I enjoyed it. I remember that precisely because it seemed so anomalous. It was like being told to use dry water. Whatever I thought he meant, I didn’t think he meant work could literally be fun—fun like playing. It took me years to grasp that.

Jobs

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.

The main reason they all acted as if they enjoyed their work was presumably the upper-middle class convention that you’re supposed to. It would not merely be bad for your career to say that you despised your job, but a social faux-pas.

Why is it conventional to pretend to like what you do? The first sentence of this essay explains that. If you have to like something to do it well, then the most successful people will all like what they do. That’s where the upper-middle class tradition comes from. Just as houses all over America are full of chairs that are, without the owners even knowing it, nth-degree imitations of chairs designed 250 years ago for French kings, conventional attitudes about work are, without the owners even knowing it, nth-degree imitations of the attitudes of people who’ve done great things.

What a recipe for alienation. By the time they reach an age to think about what they’d like to do, most kids have been thoroughly misled about the idea of loving one’s work. School has trained them to regard work as an unpleasant duty. Having a job is said to be even more onerous than schoolwork. And yet all the adults claim to like what they do. You can’t blame kids for thinking “I am not like these people; I am not suited to this world.”

Actually they’ve been told three lies: the stuff they’ve been taught to regard as work in school is not real work; grownup work is not (necessarily) worse than schoolwork; and many of the adults around them are lying when they say they like what they do.

The most dangerous liars can be the kids’ own parents. If you take a boring job to give your family a high standard of living, as so many people do, you risk infecting your kids with the idea that work is boring. [2] Maybe it would be better for kids in this one case if parents were not so unselfish. A parent who set an example of loving their work might help their kids more than an expensive house. [3]

It was not till I was in college that the idea of work finally broke free from the idea of making a living. Then the important question became not how to make money, but what to work on. Ideally these coincided, but some spectacular boundary cases (like Einstein in the patent office) proved they weren’t identical.

The definition of work was now to make some original contribution to the world, and in the process not to starve. But after the habit of so many years my idea of work still included a large component of pain. Work still seemed to require discipline, because only hard problems yielded grand results, and hard problems couldn’t literally be fun. Surely one had to force oneself to work on them.

If you think something’s supposed to hurt, you’re less likely to notice if you’re doing it wrong. That about sums up my experience of graduate school.

Bounds

How much are you supposed to like what you do? Unless you know that, you don’t know when to stop searching. And if, like most people, you underestimate it, you’ll tend to stop searching too early. You’ll end up doing something chosen for you by your parents, or the desire to make money, or prestige—or sheer inertia.

Here’s an upper bound: Do what you love doesn’t mean, do what you would like to do most this second. Even Einstein probably had moments when he wanted to have a cup of coffee, but told himself he ought to finish what he was working on first.

It used to perplex me when I read about people who liked what they did so much that there was nothing they’d rather do. There didn’t seem to be any sort of work I liked that much. If I had a choice of (a) spending the next hour working on something or (b) be teleported to Rome and spend the next hour wandering about, was there any sort of work I’d prefer? Honestly, no.

But the fact is, almost anyone would rather, at any given moment, float about in the Carribbean, or have sex, or eat some delicious food, than work on hard problems. The rule about doing what you love assumes a certain length of time. It doesn’t mean, do what will make you happiest this second, but what will make you happiest over some longer period, like a week or a month.

Unproductive pleasures pall eventually. After a while you get tired of lying on the beach. If you want to stay happy, you have to do something.

As a lower bound, you have to like your work more than any unproductive pleasure. You have to like what you do enough that the concept of “spare time” seems mistaken. Which is not to say you have to spend all your time working. You can only work so much before you get tired and start to screw up. Then you want to do something else—even something mindless. But you don’t regard this time as the prize and the time you spend working as the pain you endure to earn it.

I put the lower bound there for practical reasons. If your work is not your favorite thing to do, you’ll have terrible problems with procrastination. You’ll have to force yourself to work, and when you resort to that the results are distinctly inferior.

To be happy I think you have to be doing something you not only enjoy, but admire. You have to be able to say, at the end, wow, that’s pretty cool. This doesn’t mean you have to make something. If you learn how to hang glide, or to speak a foreign language fluently, that will be enough to make you say, for a while at least, wow, that’s pretty cool. What there has to be is a test.

So one thing that falls just short of the standard, I think, is reading books. Except for some books in math and the hard sciences, there’s no test of how well you’ve read a book, and that’s why merely reading books doesn’t quite feel like work. You have to do something with what you’ve read to feel productive.

I think the best test is one Gino Lee taught me: to try to do things that would make your friends say wow. But it probably wouldn’t start to work properly till about age 22, because most people haven’t had a big enough sample to pick friends from before then.

Sirens

What you should not do, I think, is worry about the opinion of anyone beyond your friends. You shouldn’t worry about prestige. Prestige is the opinion of the rest of the world. When you can ask the opinions of people whose judgement you respect, what does it add to consider the opinions of people you don’t even know? [4]

This is easy advice to give. It’s hard to follow, especially when you’re young. [5] Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.

That’s what leads people to try to write novels, for example. They like reading novels. They notice that people who write them win Nobel prizes. What could be more wonderful, they think, than to be a novelist? But liking the idea of being a novelist is not enough; you have to like the actual work of novel-writing if you’re going to be good at it; you have to like making up elaborate lies.

Prestige is just fossilized inspiration. If you do anything well enough, you’ll make it prestigious. Plenty of things we now consider prestigious were anything but at first. Jazz comes to mind—though almost any established art form would do. So just do what you like, and let prestige take care of itself.

Prestige is especially dangerous to the ambitious. If you want to make ambitious people waste their time on errands, the way to do it is to bait the hook with prestige. That’s the recipe for getting people to give talks, write forewords, serve on committees, be department heads, and so on. 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.

Similarly, if you admire two kinds of work equally, but one is more prestigious, you should probably choose the other. Your opinions about what’s admirable are always going to be slightly influenced by prestige, so if the two seem equal to you, you probably have more genuine admiration for the less prestigious one.

The other big force leading people astray is money. Money by itself is not that dangerous. When something pays well but is regarded with contempt, like telemarketing, or prostitution, or personal injury litigation, ambitious people aren’t tempted by it. That kind of work ends up being done by people who are “just trying to make a living.” (Tip: avoid any field whose practitioners say this.) The danger is when money is combined with prestige, as in, say, corporate law, or medicine. A comparatively safe and prosperous career with some automatic baseline prestige is dangerously tempting to someone young, who hasn’t thought much about what they really like.

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. How many corporate lawyers would do their current work if they had to do it for free, in their spare time, and take day jobs as waiters to support themselves?

This test is especially helpful in deciding between different kinds of academic work, because fields vary greatly in this respect. Most good mathematicians would work on math even if there were no jobs as math professors, whereas in the departments at the other end of the spectrum, the availability of teaching jobs is the driver: people would rather be English professors than work in ad agencies, and publishing papers is the way you compete for such jobs. Math would happen without math departments, but it is the existence of English majors, and therefore jobs teaching them, that calls into being all those thousands of dreary papers about gender and identity in the novels of Conrad. No one does that kind of thing for fun.

The advice of parents will tend to err on the side of money. It seems safe to say there are more undergrads who want to be novelists and whose parents want them to be doctors than who want to be doctors and whose parents want them to be novelists. The kids think their parents are “materialistic.” Not necessarily. All parents tend to be more conservative for their kids than they would for themselves, simply because, as parents, they share risks more than rewards. If your eight year old son decides to climb a tall tree, or your teenage daughter decides to date the local bad boy, you won’t get a share in the excitement, but if your son falls, or your daughter gets pregnant, you’ll have to deal with the consequences.

Discipline

With such powerful forces leading us astray, it’s not surprising we find it so hard to discover what we like to work on. Most people are doomed in childhood by accepting the axiom that work = pain. Those who escape this are nearly all lured onto the rocks by prestige or money. How many even discover something they love to work on? A few hundred thousand, perhaps, out of billions.

It’s hard to find work you love; it must be, if so few do. So don’t underestimate this task. And don’t feel bad if you haven’t succeeded yet. In fact, if you admit to yourself that you’re discontented, you’re a step ahead of most people, who are still in denial. If you’re surrounded by colleagues who claim to enjoy work that you find contemptible, odds are they’re lying to themselves. Not necessarily, but probably.

Although doing great work takes less discipline than people think—because the way to do great work is to find something you like so much that you don’t have to force yourself to do it—finding work you love does usually require discipline. Some people are lucky enough to know what they want to do when they’re 12, and just glide along as if they were on railroad tracks. But this seems the exception. More often people who do great things have careers with the trajectory of a ping-pong ball. They go to school to study A, drop out and get a job doing B, and then become famous for C after taking it up on the side.

Sometimes jumping from one sort of work to another is a sign of energy, and sometimes it’s a sign of laziness. Are you dropping out, or boldly carving a new path? You often can’t tell yourself. Plenty of people who will later do great things seem to be disappointments early on, when they’re trying to find their niche.

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. 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.

Of course, figuring out what you like to work on doesn’t mean you get to work on it. That’s a separate question. And if you’re ambitious you have to keep them separate: you have to make a conscious effort to keep your ideas about what you want from being contaminated by what seems possible. [6]

It’s painful to keep them apart, because it’s painful to observe the gap between them. So most people pre-emptively lower their expectations. For example, if you asked random people on the street if they’d like to be able to draw like Leonardo, you’d find most would say something like “Oh, I can’t draw.” This is more a statement of intention than fact; it means, I’m not going to try. Because the fact is, if you took a random person off the street and somehow got them to work as hard as they possibly could at drawing for the next twenty years, they’d get surprisingly far. But it would require a great moral effort; it would mean staring failure in the eye every day for years. And so to protect themselves people say “I can’t.”

Another related line you often hear is that not everyone can do work they love—that someone has to do the unpleasant jobs. Really? How do you make them? In the US the only mechanism for forcing people to do unpleasant jobs is the draft, and that hasn’t been invoked for over 30 years. All we can do is encourage people to do unpleasant work, with money and prestige.

If there’s something people still won’t do, it seems as if society just has to make do without. That’s what happened with domestic servants. For millennia that was the canonical example of a job “someone had to do.” And yet in the mid twentieth century servants practically disappeared in rich countries, and the rich have just had to do without.

So while there may be some things someone has to do, there’s a good chance anyone saying that about any particular job is mistaken. Most unpleasant jobs would either get automated or go undone if no one were willing to do them.

Two Routes

There’s another sense of “not everyone can do work they love” that’s all too true, however. One has to make a living, and it’s hard to get paid for doing work you love. There are two routes to that destination:

The organic route: as you become more eminent, gradually to increase the parts of your job that you like at the expense of those you don’t.

The two-job route: to work at things you don’t like to get money to work on things you do.

The organic route is more common. It happens naturally to anyone who does good work. A young architect has to take whatever work he can get, but if he does well he’ll gradually be in a position to pick and choose among projects. The disadvantage of this route is that it’s slow and uncertain. Even tenure is not real freedom.

The two-job route has several variants depending on how long you work for money at a time. At one extreme is the “day job,” where you work regular hours at one job to make money, and work on what you love in your spare time. At the other extreme you work at something till you make enough not to have to work for money again.

The two-job route is less common than the organic route, because it requires a deliberate choice. It’s also more dangerous. Life tends to get more expensive as you get older, so it’s easy to get sucked into working longer than you expected at the money job. Worse still, anything you work on changes you. If you work too long on tedious stuff, it will rot your brain. And the best paying jobs are most dangerous, because they require your full attention.

The advantage of the two-job route is that it lets you jump over obstacles. The landscape of possible jobs isn’t flat; there are walls of varying heights between different kinds of work. [7] The trick of maximizing the parts of your job that you like can get you from architecture to product design, but not, probably, to music. If you make money doing one thing and then work on another, you have more freedom of choice.

Which route should you take? That depends on how sure you are of what you want to do, how good you are at taking orders, how much risk you can stand, and the odds that anyone will pay (in your lifetime) for what you want to do. 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. But if you don’t know what you want to work on, or don’t like to take orders, you may want to take the two-job route, if you can stand the risk.

Don’t decide too soon. Kids who know early what they want to do seem impressive, as if they got the answer to some math question before the other kids. They have an answer, certainly, but odds are it’s wrong.

A friend of mine who is a quite successful doctor complains constantly about her job. When people applying to medical school ask her for advice, she wants to shake them and yell “Don’t do it!” (But she never does.) How did she get into this fix? In high school she already wanted to be a doctor. And she is so ambitious and determined that she overcame every obstacle along the way—including, unfortunately, not liking it.

Now she has a life chosen for her by a high-school kid.

When you’re young, you’re given the impression that you’ll get enough information to make each choice before you need to make it. But this is certainly not so with work. When you’re deciding what to do, you have to operate on ridiculously incomplete information. Even in college you get little idea what various types of work are like. At best you may have a couple internships, but not all jobs offer internships, and those that do don’t teach you much more about the work than being a batboy teaches you about playing baseball.

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?

Most people would say, I’d take that problem. Give me a million dollars and I’ll figure out what to do. But it’s harder than it looks. Constraints give your life shape. Remove them and most people have no idea what to do: look at what happens to those who win lotteries or inherit money. Much as everyone thinks they want financial security, the happiest people are not those who have it, but those who like what they do. So a plan that promises freedom at the expense of knowing what to do with it may not be as good as it seems.

Whichever route you take, expect a struggle. Finding work you love is very difficult. Most people fail. Even if you succeed, it’s rare to be free to work on what you want till your thirties or forties. 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.

Notes

[1] Currently we do the opposite: when we make kids do boring work, like arithmetic drills, instead of admitting frankly that it’s boring, we try to disguise it with superficial decorations.

[2] One father told me about a related phenomenon: he found himself concealing from his family how much he liked his work. When he wanted to go to work on a saturday, he found it easier to say that it was because he “had to” for some reason, rather than admitting he preferred to work than stay home with them.

[3] Something similar happens with suburbs. Parents move to suburbs to raise their kids in a safe environment, but suburbs are so dull and artificial that by the time they’re fifteen the kids are convinced the whole world is boring.

[4] I’m not saying friends should be the only audience for your work. The more people you can help, the better. But friends should be your compass.

[5] Donald Hall said young would-be poets were mistaken to be so obsessed with being published. But you can imagine what it would do for a 24 year old to get a poem published in The New Yorker. Now to people he meets at parties he’s a real poet. Actually he’s no better or worse than he was before, but to a clueless audience like that, the approval of an official authority makes all the difference. So it’s a harder problem than Hall realizes. The reason the young care so much about prestige is that the people they want to impress are not very discerning.

[6] This is isomorphic to the principle that you should prevent your beliefs about how things are from being contaminated by how you wish they were. Most people let them mix pretty promiscuously. The continuing popularity of religion is the most visible index of that.

[7] A more accurate metaphor would be to say that the graph of jobs is not very well connected.

Thanks to Trevor Blackwell, Dan Friedman, Sarah Harlin, Jessica Livingston, Jackie McDonough, Robert Morris, Peter Norvig, David Sloo, and Aaron Swartz for reading drafts of this.

For any aspiring entrepreneurs thinking about starting a company, I would highly recommend reading Paul Graham’s Essays, which can be found here: [paulgraham.com]

This is a must-read for any startup founder. Here’s an essay that gives you a flavor of what good stuff you can learn from Paul – a real look into what to expect in a startup!


October 2009(This essay is derived from a talk at the 2009 Startup School.)

I wasn’t sure what to talk about at Startup School, so I decided to ask the founders of the startups we’d funded. What hadn’t I written about yet?

I’m in the unusual position of being able to test the essays I write about startups. I hope the ones on other topics are right, but I have no way to test them. The ones on startups get tested by about 70 people every 6 months.

So I sent all the founders an email asking what surprised them about starting a startup. This amounts to asking what I got wrong, because if I’d explained things well enough, nothing should have surprised them.

I’m proud to report I got one response saying:

What surprised me the most is that everything was actually fairly predictable!

The bad news is that I got over 100 other responses listing the surprises they encountered.

There were very clear patterns in the responses; it was remarkable how often several people had been surprised by exactly the same thing. These were the biggest:

1. Be Careful with Cofounders

This was the surprise mentioned by the most founders. There were two types of responses: that you have to be careful who you pick as a cofounder, and that you have to work hard to maintain your relationship.

What people wished they’d paid more attention to when choosing cofounders was character and commitment, not ability. This was particularly true with startups that failed. The lesson: don’t pick cofounders who will flake.

Here’s a typical reponse:

You haven’t seen someone’s true colors unless you’ve worked with them on a startup.

The reason character is so important is that it’s tested more severely than in most other situations. One founder said explicitly that the relationship between founders was more important than ability:

I would rather cofound a startup with a friend than a stranger with higher output. Startups are so hard and emotional that the bonds and emotional and social support that come with friendship outweigh the extra output lost.

We learned this lesson a long time ago. If you look at the YC application, there are more questions about the commitment and relationship of the founders than their ability.

Founders of successful startups talked less about choosing cofounders and more about how hard they worked to maintain their relationship.

One thing that surprised me is how the relationship of startup founders goes from a friendship to a marriage. My relationship with my cofounder went from just being friends to seeing each other all the time, fretting over the finances and cleaning up shit. And the startup was our baby. I summed it up once like this: “It’s like we’re married, but we’re not fucking.”

Several people used that word “married.” It’s a far more intense relationship than you usually see between coworkers—partly because the stresses are so much greater, and partly because at first the founders are the whole company. So this relationship has to be built of top quality materials and carefully maintained. It’s the basis of everything.

2. Startups Take Over Your Life

Just as the relationship between cofounders is more intense than it usually is between coworkers, so is the relationship between the founders and the company. Running a startup is not like having a job or being a student, because it never stops. This is so foreign to most people’s experience that they don’t get it till it happens. 1

I didn’t realize I would spend almost every waking moment either working or thinking about our startup. You enter a whole different way of life when it’s your company vs. working for someone else’s company.

It’s exacerbated by the fast pace of startups, which makes it seem like time slows down:

I think the thing that’s been most surprising to me is how one’s perspective on time shifts. Working on our startup, I remember time seeming to stretch out, so that a month was a huge interval.

In the best case, total immersion can be exciting:

It’s surprising how much you become consumed by your startup, in that you think about it day and night, but never once does it feel like “work.”

Though I have to say, that quote is from someone we funded this summer. In a couple years he may not sound so chipper.

3. It’s an Emotional Roller-coaster

This was another one lots of people were surprised about. The ups and downs were more extreme than they were prepared for.

In a startup, things seem great one moment and hopeless the next. And by next, I mean a couple hours later.

The emotional ups and downs were the biggest surprise for me. One day, we’d think of ourselves as the next Google and dream of buying islands; the next, we’d be pondering how to let our loved ones know of our utter failure; and on and on.

The hard part, obviously, is the lows. For a lot of founders that was the big surprise:

How hard it is to keep everyone motivated during rough days or weeks, i.e. how low the lows can be.

After a while, if you don’t have significant success to cheer you up, it wears you out:

Your most basic advice to founders is “just don’t die,” but the energy to keep a company going in lieu of unburdening success isn’t free; it is siphoned from the founders themselves.

There’s a limit to how much you can take. If you get to the point where you can’t keep working anymore, it’s not the end of the world. Plenty of famous founders have had some failures along the way.

4. It Can Be Fun

The good news is, the highs are also very high. Several founders said what surprised them most about doing a startup was how fun it was:

I think you’ve left out just how fun it is to do a startup. I am more fulfilled in my work than pretty much any of my friends who did not start companies.

What they like most is the freedom:

I’m surprised by how much better it feels to be working on something that is challenging and creative, something I believe in, as opposed to the hired-gun stuff I was doing before. I knew it would feel better; what’s surprising is how much better.

Frankly, though, if I’ve misled people here, I’m not eager to fix that. I’d rather have everyone think starting a startup is grim and hard than have founders go into it expecting it to be fun, and a few months later saying “This is supposed to be fun? Are you kidding?”

The truth is, it wouldn’t be fun for most people. A lot of what we try to do in the application process is to weed out the people who wouldn’t like it, both for our sake and theirs.

The best way to put it might be that starting a startup is fun the way a survivalist training course would be fun, if you’re into that sort of thing. Which is to say, not at all, if you’re not.

5. Persistence Is the Key

A lot of founders were surprised how important persistence was in startups. It was both a negative and a positive surprise: they were surprised both by the degree of persistence required

Everyone said how determined and resilient you must be, but going through it made me realize that the determination required was still understated.

and also by the degree to which persistence alone was able to dissolve obstacles:

If you are persistent, even problems that seem out of your control (i.e. immigration) seem to work themselves out.

Several founders mentioned specifically how much more important persistence was than intelligence.

I’ve been surprised again and again by just how much more important persistence is than raw intelligence.

This applies not just to intelligence but to ability in general, and that’s why so many people said character was more important in choosing cofounders.

6. Think Long-Term

You need persistence because everything takes longer than you expect. A lot of people were surprised by that.

I’m continually surprised by how long everything can take. Assuming your product doesn’t experience the explosive growth that very few products do, everything from development to dealmaking (especially dealmaking) seems to take 2-3x longer than I always imagine.

One reason founders are surprised is that because they work fast, they expect everyone else to. There’s a shocking amount of shear stress at every point where a startup touches a more bureaucratic organization, like a big company or a VC fund. That’s why fundraising and the enterprise market kill and maim so many startups. 2

But I think the reason most founders are surprised by how long it takes is that they’re overconfident. They think they’re going to be an instant success, like YouTube or Facebook. You tell them only 1 out of 100 successful startups has a trajectory like that, and they all think “we’re going to be that 1.”

Maybe they’ll listen to one of the more successful founders:

The top thing I didn’t understand before going into it is that persistence is the name of the game. For the vast majority of startups that become successful, it’s going to be a really long journey, at least 3 years and probably 5+.

There is a positive side to thinking longer-term. It’s not just that you have to resign yourself to everything taking longer than it should. If you work patiently it’s less stressful, and you can do better work:

Because we’re relaxed, it’s so much easier to have fun doing what we do. Gone is the awkward nervous energy fueled by the desperate need to not fail guiding our actions. We can concentrate on doing what’s best for our company, product, employees and customers.

That’s why things get so much better when you hit ramen profitability. You can shift into a different mode of working.

7. Lots of Little Things

We often emphasize how rarely startups win simply because they hit on some magic idea. I think founders have now gotten that into their heads. But a lot were surprised to find this also applies within startups. You have to do lots of different things:

It’s much more of a grind than glamorous. A timeslice selected at random would more likely find me tracking down a weird DLL loading bug on Swedish Windows, or tracking down a bug in the financial model Excel spreadsheet the night before a board meeting, rather than having brilliant flashes of strategic insight.

Most hacker-founders would like to spend all their time programming. You won’t get to, unless you fail. Which can be transformed into: If you spend all your time programming, you will fail.

The principle extends even into programming. There is rarely a single brilliant hack that ensures success:

I learnt never to bet on any one feature or deal or anything to bring you success. It is never a single thing. Everything is just incremental and you just have to keep doing lots of those things until you strike something.

Even in the rare cases where a clever hack makes your fortune, you probably won’t know till later:

There is no such thing as a killer feature. Or at least you won’t know what it is.

So the best strategy is to try lots of different things. The reason not to put all your eggs in one basket is not the usual one, which applies even when you know which basket is best. In a startup you don’t even know that.

8. Start with Something Minimal

Lots of founders mentioned how important it was to launch with the simplest possible thing. By this point everyone knows you should release fast and iterate. It’s practically a mantra at YC. But even so a lot of people seem to have been burned by not doing it:

Build the absolute smallest thing that can be considered a complete application and ship it.

Why do people take too long on the first version? Pride, mostly. They hate to release something that could be better. They worry what people will say about them. But you have to overcome this:

Doing something “simple” at first glance does not mean you aren’t doing something meaningful, defensible, or valuable.

Don’t worry what people will say. If your first version is so impressive that trolls don’t make fun of it, you waited too long to launch. 3

One founder said this should be your approach to all programming, not just startups, and I tend to agree.

Now, when coding, I try to think “How can I write this such that if people saw my code, they’d be amazed at how little there is and how little it does?”

Over-engineering is poison. It’s not like doing extra work for extra credit. It’s more like telling a lie that you then have to remember so you don’t contradict it.

9. Engage Users

Product development is a conversation with the user that doesn’t really start till you launch. Before you launch, you’re like a police artist before he’s shown the first version of his sketch to the witness.

It’s so important to launch fast that it may be better to think of your initial version not as a product, but as a trick for getting users to start talking to you.

I learned to think about the initial stages of a startup as a giant experiment. All products should be considered experiments, and those that have a market show promising results extremely quickly.

Once you start talking to users, I guarantee you’ll be surprised by what they tell you.

When you let customers tell you what they’re after, they will often reveal amazing details about what they find valuable as well what they’re willing to pay for.

The surprise is generally positive as well as negative. They won’t like what you’ve built, but there will be other things they would like that would be trivially easy to implement. It’s not till you start the conversation by launching the wrong thing that they can express (or perhaps even realize) what they’re looking for.

10. Change Your Idea

To benefit from engaging with users you have to be willing to change your idea. We’ve always encouraged founders to see a startup idea as a hypothesis rather than a blueprint. And yet they’re still surprised how well it works to change the idea.

Normally if you complain about something being hard, the general advice is to work harder. With a startup, I think you should find a problem that’s easy for you to solve. Optimizing in solution-space is familiar and straightforward, but you can make enormous gains playing around in problem-space.

Whereas mere determination, without flexibility, is a greedy algorithm that may get you nothing more than a mediocre local maximum:

When someone is determined, there’s still a danger that they’ll follow a long, hard path that ultimately leads nowhere.

You want to push forward, but at the same time twist and turn to find the most promising path. One founder put it very succinctly:

Fast iteration is the key to success.

One reason this advice is so hard to follow is that people don’t realize how hard it is to judge startup ideas, particularly their own. Experienced founders learn to keep an open mind:

Now I don’t laugh at ideas anymore, because I realized how terrible I was at knowing if they were good or not.

You can never tell what will work. You just have to do whatever seems best at each point. We do this with YC itself. We still don’t know if it will work, but it seems like a decent hypothesis.

11. Don’t Worry about Competitors

When you think you’ve got a great idea, it’s sort of like having a guilty conscience about something. All someone has to do is look at you funny, and you think “Oh my God, they know.”

These alarms are almost always false:

Companies that seemed like competitors and threats at first glance usually never were when you really looked at it. Even if they were operating in the same area, they had a different goal.

One reason people overreact to competitors is that they overvalue ideas. If ideas really were the key, a competitor with the same idea would be a real threat. But it’s usually execution that matters:

All the scares induced by seeing a new competitor pop up are forgotten weeks later. It always comes down to your own product and approach to the market.

This is generally true even if competitors get lots of attention.

Competitors riding on lots of good blogger perception aren’t really the winners and can disappear from the map quickly. You need consumers after all.

Hype doesn’t make satisfied users, at least not for something as complicated as technology.

12. It’s Hard to Get Users

A lot of founders complained about how hard it was to get users, though.

I had no idea how much time and effort needed to go into attaining users.

This is a complicated topic. When you can’t get users, it’s hard to say whether the problem is lack of exposure, or whether the product’s simply bad. Even good products can be blocked by switching or integration costs:

Getting people to use a new service is incredibly difficult. This is especially true for a service that other companies can use, because it requires their developers to do work. If you’re small, they don’t think it is urgent. 4

The sharpest criticism of YC came from a founder who said we didn’t focus enough on customer acquisition:

YC preaches “make something people want” as an engineering task, a never ending stream of feature after feature until enough people are happy and the application takes off. There’s very little focus on the cost of customer acquisition.

This may be true; this may be something we need to fix, especially for applications like games. If you make something where the challenges are mostly technical, you can rely on word of mouth, like Google did. One founder was surprised by how well that worked for him:

There is an irrational fear that no one will buy your product. But if you work hard and incrementally make it better, there is no need to worry.

But with other types of startups you may win less by features and more by deals and marketing.

13. Expect the Worst with Deals

Deals fall through. That’s a constant of the startup world. Startups are powerless, and good startup ideas generally seem wrong. So everyone is nervous about closing deals with you, and you have no way to make them.

This is particularly true with investors:

In retrospect, it would have been much better if we had operated under the assumption that we would never get any additional outside investment. That would have focused us on finding revenue streams early.

My advice is generally pessimistic. Assume you won’t get money, and if someone does offer you any, assume you’ll never get any more.

If someone offers you money, take it. You say it a lot, but I think it needs even more emphasizing. We had the opportunity to raise a lot more money than we did last year and I wish we had.

Why do founders ignore me? Mostly because they’re optimistic by nature. The mistake is to be optimistic about things you can’t control. By all means be optimistic about your ability to make something great. But you’re asking for trouble if you’re optimistic about big companies or investors.

14. Investors Are Clueless

A lot of founders mentioned how surprised they were by the cluelessness of investors:

They don’t even know about the stuff they’ve invested in. I met some investors that had invested in a hardware device and when I asked them to demo the device they had difficulty switching it on.

Angels are a bit better than VCs, because they usually have startup experience themselves:

VC investors don’t know half the time what they are talking about and are years behind in their thinking. A few were great, but 95% of the investors we dealt with were unprofessional, didn’t seem to be very good at business or have any kind of creative vision. Angels were generally much better to talk to.

Why are founders surprised that VCs are clueless? I think it’s because they seem so formidable.

The reason VCs seem formidable is that it’s their profession to. You get to be a VC by convincing asset managers to trust you with hundreds of millions of dollars. How do you do that? You have to seem confident, and you have to seem like you understand technology. 5

15. You May Have to Play Games

Because investors are so bad at judging you, you have to work harder than you should at selling yourself. One founder said the thing that surprised him most was

The degree to which feigning certitude impressed investors.

This is the thing that has surprised me most about YC founders’ experiences. This summer we invited some of the alumni to talk to the new startups about fundraising, and pretty much 100% of their advice was about investor psychology. I thought I was cynical about VCs, but the founders were much more cynical.

A lot of what startup founders do is just posturing. It works.

VCs themselves have no idea of the extent to which the startups they like are the ones that are best at selling themselves to VCs. 6 It’s exactly the same phenomenon we saw a step earlier. VCs get money by seeming confident to LPs, and founders get money by seeming confident to VCs.

16. Luck Is a Big Factor

With two such random linkages in the path between startups and money, it shouldn’t be surprising that luck is a big factor in deals. And yet a lot of founders are surprised by it.

I didn’t realize how much of a role luck plays and how much is outside of our control.

If you think about famous startups, it’s pretty clear how big a role luck plays. Where would Microsoft be if IBM insisted on an exclusive license for DOS?

Why are founders fooled by this? Business guys probably aren’t, but hackers are used to a world where skill is paramount, and you get what you deserve.

When we started our startup, I had bought the hype of the startup founder dream: that this is a game of skill. It is, in some ways. Having skill is valuable. So is being determined as all hell. But being lucky is the critical ingredient.

Actually the best model would be to say that the outcome is the product of skill, determination, and luck. No matter how much skill and determination you have, if you roll a zero for luck, the outcome is zero.

These quotes about luck are not from founders whose startups failed. Founders who fail quickly tend to blame themselves. Founders who succeed quickly don’t usually realize how lucky they were. It’s the ones in the middle who see how important luck is.

17. The Value of Community

A surprising number of founders said what surprised them most about starting a startup was the value of community. Some meant the micro-community of YC founders:

The immense value of the peer group of YC companies, and facing similar obstacles at similar times.

which shouldn’t be that surprising, because that’s why it’s structured that way. Others were surprised at the value of the startup community in the larger sense:

How advantageous it is to live in Silicon Valley, where you can’t help but hear all the cutting-edge tech and startup news, and run into useful people constantly.

The specific thing that surprised them most was the general spirit of benevolence:

One of the most surprising things I saw was the willingness of people to help us. Even people who had nothing to gain went out of their way to help our startup succeed.

and particularly how it extended all the way to the top:

The surprise for me was how accessible important and interesting people are. It’s amazing how easily you can reach out to people and get immediate feedback.

This is one of the reasons I like being part of this world. Creating wealth is not a zero-sum game, so you don’t have to stab people in the back to win.

18. You Get No Respect

There was one surprise founders mentioned that I’d forgotten about: that outside the startup world, startup founders get no respect.

In social settings, I found that I got a lot more respect when I said, “I worked on Microsoft Office” instead of “I work at a small startup you’ve never heard of called x.”

Partly this is because the rest of the world just doesn’t get startups, and partly it’s yet another consequence of the fact that most good startup ideas seem bad:

If you pitch your idea to a random person, 95% of the time you’ll find the person instinctively thinks the idea will be a flop and you’re wasting your time (although they probably won’t say this directly).

Unfortunately this extends even to dating:

It surprised me that being a startup founder does not get you more admiration from women.

I did know about that, but I’d forgotten.

19. Things Change as You Grow

The last big surprise founders mentioned is how much things changed as they grew. The biggest change was that you got to program even less:

Your job description as technical founder/CEO is completely rewritten every 6-12 months. Less coding, more managing/planning/company building, hiring, cleaning up messes, and generally getting things in place for what needs to happen a few months from now.

In particular, you now have to deal with employees, who often have different motivations:

I knew the founder equation and had been focused on it since I knew I wanted to start a startup as a 19 year old. The employee equation is quite different so it took me a while to get it down.

Fortunately, it can become a lot less stressful once you reach cruising altitude:

I’d say 75% of the stress is gone now from when we first started. Running a business is so much more enjoyable now. We’re more confident. We’re more patient. We fight less. We sleep more.

I wish I could say it was this way for every startup that succeeded, but 75% is probably on the high side.

The Super-Pattern

There were a few other patterns, but these were the biggest. One’s first thought when looking at them all is to ask if there’s a super-pattern, a pattern to the patterns.

I saw it immediately, and so did a YC founder I read the list to. These are supposed to be the surprises, the things I didn’t tell people. What do they all have in common? They’re all things I tell people. If I wrote a new essay with the same outline as this that wasn’t summarizing the founders’ responses, everyone would say I’d run out of ideas and was just repeating myself.

What is going on here?

When I look at the responses, the common theme is that starting a startup was like I said, but way more so. People just don’t seem to get how different it is till they do it. Why? The key to that mystery is to ask, how different from what? Once you phrase it that way, the answer is obvious: from a job. Everyone’s model of work is a job. It’s completely pervasive. Even if you’ve never had a job, your parents probably did, along with practically every other adult you’ve met.

Unconsciously, everyone expects a startup to be like a job, and that explains most of the surprises. It explains why people are surprised how carefully you have to choose cofounders and how hard you have to work to maintain your relationship. You don’t have to do that with coworkers. It explains why the ups and downs are surprisingly extreme. In a job there is much more damping. But it also explains why the good times are surprisingly good: most people can’t imagine such freedom. As you go down the list, almost all the surprises are surprising in how much a startup differs from a job.

You probably can’t overcome anything so pervasive as the model of work you grew up with. So the best solution is to be consciously aware of that. As you go into a startup, you’ll be thinking “everyone says it’s really extreme.” Your next thought will probably be “but I can’t believe it will be that bad.” If you want to avoid being surprised, the next thought after that should be: “and the reason I can’t believe it will be that bad is that my model of work is a job.”

Notes

1 Graduate students might understand it. In grad school you always feel you should be working on your thesis. It doesn’t end every semester like classes do.

2 The best way for a startup to engage with slow-moving organizations is to fork off separate processes to deal with them. It’s when they’re on the critical path that they kill you—when you depend on closing a deal to move forward. It’s worth taking extreme measures to avoid that.

3 This is a variant of Reid Hoffman’s principle that if you aren’t embarrassed by what you launch with, you waited too long to launch.

4 The question to ask about what you’ve built is not whether it’s good, but whether it’s good enough to supply the activation energy required.

5 Some VCs seem to understand technology because they actually do, but that’s overkill; the defining test is whether you can talk about it well enough to convince limited partners.

6 This is the same phenomenon you see with defense contractors or fashion brands. The dumber the customers, the more effort you expend on the process of selling things to them rather than making the things you sell.

Thanks: to Jessica Livingston for reading drafts of this, and to all the founders who responded to my email.

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