How to do what you love? tl;dr of the popular Paul Graham essay

Bonus - Learn to apply a few tricks to find what you love

During my early days of fascination with startups (early 2010’s) I used to read a lot of general gyaan on the internet. Paul Graham stood out as a respectable voice spitting out some hard facts about startups and life. “How to do what you love” was one of the first essays I read and really the message hit home. Here’s a summarised version with some additional inputs

The first thing to note is that the idea of work is different from the idea of making a living. Making a living is a necessity but that is not the point of work

The definition of work was now to make some original contribution to the world, and in the process not to starve. And original contribution might be a higher bar, but a slightly lower bar is to become the “Best” at something.

Excellence in anything is a worthy pursuit.

But after the habit of so many years the idea of work still included a large component of pain. That’s what we have seen our elders do. And if you think work is supposed to be painful/difficult you're less likely to notice if you're doing it wrong. That about sums up most peoples work life.

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. The rule about doing what you love assumes a certain length of time. So this means 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. Generally a decade is a good enough timeframe

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.

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 do a handstand, 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, 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.

A simple test is to try to do things that would make your friends say wow. But this also implies having a great friend group that doesn’t try to pull you down. But generally doing something that impresses yourself is a good starting point

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? Prestige is like social convention. Like how it used to be 10 years back. Everyone who scored highly in 10 std boards must choose Science and become either a Doctor or an Engineer. Arts is for losers.

This is easy advice to give. It's hard to follow, especially when you're young. 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. I’d like to be be Sachin and it seems prestigious to play for India but am I ready to play 10 hours a day for min 10 years in 1st class cricket? The process should be appealing also.

Prestige is 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. Take startup founders for example. Being the founder of Flipkart or any large startup was looked down upon just 10-15 year back. Now it’s cool.

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. But a smarter way is to take that prestigious task up and try living that life for a short while. Always taste before you make a purchase. Though not all types of work might be open to this, but smaller exposures to all kinds of work are always possible

The larger danger is when money is combined with prestige, as in, say, government job or Doctor. 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 government servants in India 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?

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 dropout of school, you won't get a share in the excitement, but if your son falls, or your daughter gets lost in life, you'll have to deal with the consequences.

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. Then most are caught up in making a living. 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. Like Sachin. 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

There's a 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 years of experience 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.

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.

Just 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. Not everyone is Sachin.

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. Probably 16-20 is that age when you could be expected to have a slightly clear idea of what direction you might want to start moving in

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.

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 commodities 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.

Perhaps the single greatest constraint to doing what you love (assuming you found what you love) is ensuring your survival. The need to make a living is real in India and we are not like developed countries where we can survive indefinitely on government support.

So to find what you love, either you are Sachin and you know since childhood that Cricket is your thing, or be like Sherlock and deduce this by a process of elimination. Let your curiosity guide projects you work on and keep eliminating parts you don’t like and adding to parts that you like

Curiosity is a friend but make sure you survive till it reaches satiation

The good north star metric to guide you towards what you love is “Flow” If you really feel immersed in the work you do and find real joy there, then you are operating with flow.

And generally flow comes when you are close to “Mastery” in your domain. That’s when you are comfortable in your skin. Sometimes it might happen that you become a master in something that you don’t love. So don’t settle. Make sure you really enjoy it. Also becoming a master, means you are top 0.0001% in that field and that usually pays well enough to earn a living in most things.

Also do make sure you have friend group that gives you feedback on what you are good at and general constructive criticism. Remember getting to do the work you love is a privilege. But first you must figure out what you love. There is no point climbing the wrong ladder. Enough people are stuck in their careers like this

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