Why Most People Won't Make It, and Why That's Okay

A young founder told me last month, with the clean shining certainty of the very ambitious, that he was going to make it. I recognized the tone, because I have used it myself, more than once, with the same shine. I did not have the heart to ask him the question I have since learned to ask myself, which is: make what, exactly, and against whom?

That small phrase, “make it,” does an enormous amount of quiet work, and I have come to think most of that work is a kind of violence. It slips a scoreboard into your hand without telling you it has done so, and then it measures your one irreplaceable life against that scoreboard, and the reading it gives back, for almost everyone who takes it seriously, is failure. I want to defend a claim that sounds cruel and is in fact the opposite of cruel. Most people will not make it, in the sense that phrase intends. And that is not a tragedy, because the sense was rigged against them before they were born.

The shape of the world is a power law, not a bell curve

Begin with the arithmetic, because the arithmetic is the whole argument and everything humane follows from getting it right.

Many of the domains where we tell people to go and make it are not distributed like heights, clustered gently around an average, with the extremes rare and close by. They are distributed like earthquakes and city sizes: power laws, where a tiny handful of outcomes are astronomically large and the vast majority are small, and the average is a lie that describes almost no one. Startups are the cleanest example, which is why I know them in my bones. Most fail outright. Of the survivors, a small number generate almost all of the returns, so lopsidedly that a single winner in a portfolio can outweigh every other bet combined. Art is the same shape. Most books sell a few hundred copies and are forgotten within a decade; a vanishing few define the age. Music, streamed billions of times at the very top and essentially never at the long tail. Acting, science, any field where attention and reward concentrate.

This is structural. It is the geometry of tournaments, of networks, of anything that scales, and it has almost nothing to do with your worth as a person. I have watched genuinely brilliant founders fail and distinctly mediocre ones win, and when I am honest about the difference it was mostly not virtue. It was timing, and luck, and being the right shape for a moment that happened to arrive. The tail is thin because that is what a tail is. Telling everyone to aim for the tail and then treating the ones who land in the fat middle as failures is not motivation. It is a category error dressed up as a pep talk.

Survivorship bias runs the entire advice industry

There is a famous story from the Second World War about the statistician Abraham Wald and the returning bombers. The military wanted to add armor where the planes were most riddled with bullet holes. Wald pointed out the mistake that has since become a parable: they were only looking at the planes that came back. The holes on the survivors marked the places a plane could be hit and still fly home. The armor belonged where the survivors had no holes, because the planes hit there were the ones that never returned to be counted.

Almost everything we are told about how to succeed is a study of the bombers that came back. The memoirs are written by the winners. The stage at the conference holds the founder who made it, never the ten thousand who ran the identical playbook with the identical conviction and vanished without a book deal. The college dropout who became a billionaire is intensely visible; the dropouts who simply became unemployed are not invited to speak, because there is no lesson in a statistic. So we sample advice exclusively from the survivors and mistake it for a map, when it is closer to a lottery winner earnestly explaining his choice of numbers. Do what he did and you will mostly get what the ten thousand silent ones got. The survivors are not lying. They just cannot see the graveyard from up on the stage, and neither, listening to them, can you.

“Make it” smuggles in a single scoreboard

Now watch what the phrase actually does, because the trick is in the grammar.

“Make it” pretends there is one game. Winner take all, a single ladder, a single peak, and everyone is understood to be climbing the same one whether or not they ever agreed to. It quietly converts a whole human life into a percentile. It takes the tournament, which is a real thing with real winners and real prizes, and it claims, without ever arguing for the claim, that the tournament is the only thing. That is the sleight of hand, and it is so smooth that most of us never catch it being done to us. The tournament is one game. It is a legitimate game, and some people love playing it and should. But there are dozens of other games, most of them not zero-sum, most of them winnable by nearly anyone who chooses to play them well, and the phrase erases every one of them by pretending they do not count as making it. The cruelty is not in the tournament. The cruelty is in the word only, hidden inside a phrase that never says it out loud.

The people who raised me never made it, and they lived complete lives

Let me leave the abstractions and tell you about the men and women near Ambala, because they are the reason I stopped being afraid of this whole question.

My grandfather planted wheat and mustard on land his own grandfather had worked. He rose before the sun for sixty years. He read the sky the way I read a datasheet. He never appeared on any list of people who had made it, never gave an interview, never scaled anything, never had a title that would mean a thing to the young founder shining across the table from me. And he lived a life of such obvious weight and completeness that I have spent my educated, credentialed, mildly successful adulthood quietly measuring myself against him and coming up short.

He had standing. When there was a dispute in the village, people came to him, because across six decades he had been fair, and being known to be fair for six decades is a kind of wealth that does not appear on any balance sheet I know how to read. He raised children who came back to see him, which anyone who has watched families fracture will tell you is not a small or automatic achievement. He was competent at a difficult thing and he did it with his whole body until his body gave out. And when he died the road filled with people, hundreds of them, who had walked in from the surrounding villages, not because he was famous, he was not, but because he had been useful and honest and kind within arm’s reach of them for a lifetime, and they had come to say so. If your definition of success cannot see that funeral for what it plainly was, a life landing exactly on target, then it is your definition that is broken, and not his life.

What the tournament optimizes for, and what it cannot see

The tournament sees rank, and rank is all it can see. It is blind, structurally and permanently, to almost everything that a human being on their deathbed actually turns out to have cared about.

It cannot see the texture of an ordinary Tuesday: work you are quietly good at, a walk you take, a meal with someone who knows you. It cannot price being genuinely excellent at a craft that will never be famous. It cannot price being needed by a small number of people who depend on you and would be lost without you. It has no column for loving and being loved, for keeping your word across decades until your word becomes the thing people build on, for raising a child who turns out decent. These are not consolation prizes handed to the people who lost the real contest. On the honest accounting of a human life, they are the main entries, the ones that are there at the end when the rank has long since stopped mattering to anyone including you. The tournament simply has no way to record them, and so it acts as though they are worth nothing, and we, taking our sense of the score from the tournament, half believe it. That half-belief is the quiet poison. It is worth naming so you can stop drinking it.

This is not sour grapes, and ambition is not the enemy

I want to be careful here, because the argument I am making has a lazy cousin, and I do not want to be mistaken for him. The lazy cousin says ambition is bad, striving is ego, wanting to win is a spiritual failing, and you should content yourself with less. That is not my claim, and I find it faintly dishonest, usually a way of pre-forgiving a defeat one has not yet even attempted to avoid.

Striving is good. Building things is one of the great human joys and I would not surrender it. I built a company. I wanted to win, badly, and I would do it again tomorrow, and if you have a real shot at the tail and it calls to you then by all means go and take your swing at it with everything you have. The error is not wanting to win. The error is the belief that the tournament is the only game, so that losing it means you have failed at life itself. You can lose the tournament and win at very nearly everything that turns out to matter. And, less comfortably, you can win the tournament and discover you skipped all the rest to do it, which is its own well-documented tragedy, the one they make the sad films about, the man at the top of the ladder realizing it was leaning against the wrong wall. Both failures come from the same original mistake: believing the single scoreboard was real.

A good life was never a percentile

So here is the reframing I actually live by, and I offer it without any promise that it is easy.

Separate the games you cannot control from the games you largely can. The tail, the tournament, the concentration of fame and fortune into a few winners: these turn on luck and timing and forces indifferent to your effort, and staking your sense of your own life on that outcome is staking it on a coin the mathematics has already told you will mostly come up tails, for almost everyone, by construction. Then there are the other games: craft, character, love, contribution, the quality of your attention to the people directly in front of you. These are not lotteries. They pay out in proportion to what you put in, they are open to nearly anyone who chooses them, and they are, not coincidentally, the ones that were quietly running the whole time under all the noise about making it. Aim hard at those. Hold the tournament loosely, play it if it delights you, but do not hand it the authority to tell you whether your life was worth living, because it is not qualified to judge and it never was.

The half that was always the point

Most people will not make it, if making it means the summit of the tournament, and that is not pessimism, it is just what the word most is doing in the sentence. It is arithmetic. Someone has to stand at the median. The median is not a failure state to be escaped. It is the wide, ordinary ground where nearly all of human meaning has always actually lived, and where it lives still.

My grandfather could not have told you what a power law was. He understood the important half of this essay far better than I do, understood it in his hands and his habits rather than his vocabulary. He planted trees whose shade he knew he would not sit in. He kept his word until his word was worth more than most men’s contracts. He was useful, every day, to people who were within reach of needing him. And when he was gone the road filled with people who had walked a long way to say so. He made nothing, by the magazine’s meaning of the word. He made a life. That was always the game worth being certain you had actually played, and it is the one game where most people, if they will only stop measuring themselves by the other one, can still quietly and completely win.