Ambition is killing us.

It promises happiness but 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?

That yearning quality to 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. We know how bad it feels to fail. Can success guarantee flourishing?

Take Andre Agassi. Agassi was unhappy in a way that I'll never understand, because Andre Agassi was unhappy after having 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 brings happiness, you’d probably look first to elite athletes. After all, these people 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":

Okay, that's a lot of misery. Maybe there are fringe benefits? Not where they count. Silver medalists actually live a bit longer than those who take the gold.

I 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 happy. Fulfilled. Like I’d conquered something and could rest.

But that’s not how ambition works. It doesn't let us rest. It only keeps asking: what's next?

And when you account for all of the unhappiness that our striving takes from us along the way — I’m told that it's a long way to the top if you wanna rock 'n' roll — ambition starts to feel like a bad bargain.

But we keep striving. The boardroom knows no sweeter phrase than "market dominance". Walk the halls outside the boardroom and you find the same urges: a few people 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. All to what end?

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.

How revealing, then, how often wisdom traditions direct our attention less toward comparison and achievement and more toward humility and self-effacement. Recall "He must increase; I must decrease." (John 3:30) or the Buddha's advice to stop stressing ourselves out.

On this point they're insistent: happiness and freedom aren't found in winning, or losing, or simply going along. They exist in an entirely separate realm of values and pursuits.

If they were children of the '80s, the Buddhist arhat or the Christian desert father would probably quote War Games:

"A strange game. The only winning move is not to play."

Last revised 2026