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Winning Won't Make Us Happy

We were raised to be ambitious, and we're letting it destroy us.

Jason S. Canon
Jason S. Canon
4 min read
Winning Won't Make Us Happy

Ambition is killing us.

It promises happiness and never delivers. It keeps us bent toward hypothetical futures, distracted from our own time. It leaves us anxious and edgy and wanting. And yet it feels so very right.

We have been trained from childhood to set our sights high, to give 110%, to reach for the moon so that, even if we miss, we’ll still learn that motivational posters are full of shit. As adults, the thought of lowering our ambitions feels dangerous, even un-American.

If we’re not always wanting more, then who are we?

Over the next few weeks I want to examine the three ways that we typically discuss about ambition: we say that someone is ambitious when they’re after power or glory or superiority; they’re ambitious if they set difficult goals; and they’re ambitious if they’re driven. Each of these poisons contentment. Is there a better way? I’ll sketch one possibility at the end of the series.

The yearning of ambition can be found right there in the etymology: from ambitiō, "the act of soliciting for votes, running for public office, striving after popularity, desire for advancement". To be ambitious is not simply to wish the world into a better state; it is the desire to win. Ambition admits only success and failure. To see how this causes us harm, let’s begin by comparing ambition with another, better-known pathology.

Perfectionism has a well-established literature in clinical psychology. I know this because last year I found that, along with a warped sense of identity and purpose, perfectionism sat at the root of a long-term depression. I suspect I’m not alone in this — see if these conditions sound familiar:

  • Self-oriented perfectionism: individuals attach irrational importance to being perfect, hold unrealistic expectations of themselves, and are punitive in their self-evaluations.
  • Socially prescribed perfectionism: individuals believe their social context is excessively demanding, that others judge them harshly, and that they must display perfection to secure approval.
  • Other-oriented perfectionism: When perfectionistic expectations are directed toward others, individuals impose unrealistic standards on those around them and evaluate others critically.

Reader, I cannot describe the freedom in learning how I’d become entangled in these views, and how, upon learning this, their hold began to slacken. You’re only reading this because I’ve slipped free just enough to write.

Now note those symptoms again. Unrealistic standards; too critical of self and others; a belief that the world demands ever more from us. Do not these same qualities fly under the brighter banner of ambition? Do they not describe the idealized start-up founder or Hollywood auteur? Are they not, in fact, the very training that we’ve received since childhood?

We may call these traits "perfectionism" when we notice them in the present, applied toward this project or that goal, but we happily call them "ambition" when applied to the future, to the arc of one’s life or career. The results are the same in both cases: disquiet, ennui, regret. I know of no more devastating curse for one’s rival than to wish them more ambition.

One: Ambition as Domination

Andre Agassi was unhappy, and he was unhappy in a way that I'll never understand, because Andre Agassi had become the greatest tennis player in the world:

[Y]ou believe being the best will fill the void. I felt nothing. Every day is Groundhog Day and what’s the point? I declined in different ways. In some cases it was lack of work. In others it was the self-inflicted damage of drugs. I found many ways to hurt myself.

If you wanted to learn whether ambition will make you happy, you’d probably look first to elite athletes. After all, these are the people who go all in; Agassi dropped out of school in the ninth grade to go pro. We watch their performances, we cheer them on, in part because we want to see just how far the single-minded pursuit can take a human. Surely they’re justly rewarded for these efforts? Let’s do a quick Google search for "olympics depression" and see what we find:

Okay, so there’s no strong correlation between peak performance and success. Perhaps there are fringe benefits? Maybe, but probably not where they count — silver medalists actually live a bit longer than those who take the gold.

I have always implicitly believed that once I became the best—at writing, at thinking, at building furniture, whatever—I’d be happy. Not that I’d feel complete, of course. But you know, happy. Fulfilled. Like I’d conquered my foe and could rest now.

But that’s not what ambition looks like, or happiness for that matter. The rush of achievement doesn’t feel any better than the far simpler joys that we experience day to day. And when you account for all of the unhappiness that our striving takes from us along the way — it is, I’m told, a long way to the top if you wanna rock ‘n roll — ambition starts to feel like a bad bargain.

And yet we press on. Lo the voice of the power vests: Are you ready to crush the competition in Q2 bro? Are you ready to scale 10x after the SPAC? The boardroom knows no sweeter phrase than "market dominance". And to what end? Are the people who comprise the corporation any happier for it? Peer inside and find the same urges at smaller scale — a few doing all they can to "yes" their way to the C-suite; the rest left with a vague sense that they should be doing more; everyone feeling overextended and unbalanced. It’s the same dynamic in every industry, from sport to finance to academia. Everyone longing to get ahead. All of us breaking ourselves to feel just a little less broken.

It doesn’t have to be this way. I’m averse to ending these posts on a note so bleak, so let me hasten to add that not all ambitions are so noxious. Even better, all of our ambitions can be set aside at no great loss. The diagnosis is grim. The cure is radiant.

Further reflections next week.