This past July, two days before my 37th birthday, I stood on the side of an uninhabited mountain and watched as the sun dropped behind a nearby ridge, the northern-California sky bursting to life in Technicolor yellows and blues. It should have been the most beautiful moment of the trip, but the splendor was lost on me. We were lost, and I was preoccupied with our safe return to camp.

Following our guide’s instruction, my party had packed for a five-hour trek: decent boots, shorts and T-shirt, a meal’s worth of calories, a few beers each. Now eight hours later, with base camp still beyond our sight, we were mostly without food, water, or sources of light. To complicate matters, our guide had literally fallen down drunk, and offered little instruction beyond a slurred, “Keep going straight.”

Ok, I knew this wasn’t life-or-death. I was not greeted by spirits. My previous 36 years did not flash before my eyes. I was in great company, and we’d be okay. But on that tortuous march home, I found myself in a deep, meditative state brought on by the intense darkness flanking us, my focus on every dimension of the ground below (a sprained ankle would have spelled disaster), the preternatural silence punctuated by the crunch of our boots in the brush.

I was overcome by thoughts of what awaited back home: my wife, our new place in Brooklyn, our dog, our friends and family; the passions I curated: playing music, reading, writing, chess, rock climbing. I though of the future, what we would become and beget.


But when my mind landed on career, I balked. Unlike other jobs I’d had in the past, I had reason enough to appreciate my current one: the people, the product, and the purpose were all undeniably positive. I love the industry and its concomitant quirks; I enjoy web and mobile development; I deeply respect and appreciate my colleagues. For some reason, the it brought a sense of gloom — and I knew it wasn’t isolated to that moment because I could feel the soreness of the subject, like a fresh but previously unnoticed bruise.

I realized then that my career had something the rest of my life didn’t: a ceiling. And worse yet, I had created it myself.

As the uncharted path crunched underfoot, I imagined the pre-defined career trajectory laid out before me and admitted how little desire I had for the points ahead. As a Vice President of a medium-sized public company, the options include: appending “Senior” or “Executive” to my title, dropping the “Vice,” and later achieving some Chief-level status. As I fluttered higher, I’d add responsibility, salary, equity, managees, and remove direct responsibility of products and design. After that obviously came CEO, and then CEO of something bigger, then Chairman of something much bigger, and…it frankly gave me anxiety even to imagine it.

It was painful, at first, the realization that this widely embraced definition of “success” didn’t appeal to me. Am I not smart enough? Is “business” beyond my capacity? Am I held back by a Freudian “death wish”? Should I have stayed in the relative obscurity of teaching or speechwriting? Am I immature or unrealistic? Did punk rock ruin me forever?

Middle management is said to be a means to an end, and staying in it is a fate to which one is “doomed.” Though a decade of hard work had earned me the means, what did it say about me that I was apathetic toward all of the ends?

It came down to ambition.

My predicament seemed to circle around this invisible force that (I’d been led to believe) drives every entrepreneur, leader, pro athlete, politician, astronaut, rock star, and chief-whatever-officer to wake up every day and rule the Earth with Type-A vigor and aplomb.

I questioned whether I lacked the right amount of ambition, or, worse, if I was altogether incapable of it — that I was, god help me, unambitious. I wondered if it was only by some cosmic accident that I’d made it this far in life, and my social perjury would be exposed in a matter of time. Whom had I fooled to get here, and what would be the consequences when my subterfuge was unveiled?

If I was going to understand myself, I needed to better understand this apparently important word and all its implications. And the more I looked into it, the less ambition seemed like a virtue, and more like a burden.

The modern usage of “ambition” suggests that it is binary: you’ve either got it or you don’t. “He’s so ambitious” serves as the antithesis to “he lacks ambition.” The former is sought after in job applicants and is rewarded in business; the latter is synonymous with lazy, deadbeat uncles. Bosses laud ambition, seeing in it something of themselves. (Indeed, the greatest compliment payable is “You could have my job someday,” as though one’s solitary aim in life should be advancement.)

In its contemporary application, ambition is the first variable in a formula that, when multiplied by hard work, results in success. And upon this precarious combination of variables depends, of course, one’s happiness. Something like:

(ambition x hard work) = success = happiness

What did it mean, though, if hard work alone made me happy? The intrinsic joy in doing didn’t contribute to the approved formula without ambition. And if I lacked ambition, then did the entire formula add up to zero? Was my success, like my career, “doomed”?

I looked deeper only to find that ambition wasn’t always the cool kid in school. In fact, in its heyday the word was more often synonymous with sin and sickness than success.

“Ambition…is a great man’s madness,” wrote John Webster in The Duchess of Malfi, “lunatic beyond all cure.” In addition to the totally rad usage of “lunatic” as an adjective, Webster’s 17th-century epic describes ambition as being fueled by “the wild noise of prattling visitants.” His disdain for it is palpable, linking it as he does to the admiration of superficial idiots.

And just a few decades later, the ultimate backfire of ambition was described by John Milton; the “ambitious aim” of his infamous antagonist was “to set himself in glory above his peers.” Milton was, of course, writing about Satan. (Spoiler alert: it doesn’t work out for the ol’ Fallen One.)

And it’s no surprise that Johns Milton and Webster would have held ambition in such poor regard: the word was invented for politicians.

Two centuries prior, “ambition” was born of the Old French ambīre, meaning “to go around (canvassing for votes).” Any modern voter can easily hear the glad-handing and baby-kissing in that definition. Rather than illuminating an admirable virtue, the Latin instead evokes the tsk-tsk-ing of a mother commenting on one’s shameful self-promotion. (Hardly the quality of a star employee.)

For a while, at least, ambition’s pejorative roots seemed to have turned people off from using it; textual usage dropped dramatically after the 19th century. I suppose being infamously linked to Satan will do that to a word.

But these Latin roots must have atrophied: web-search and textual trends indicate a measurable increase in its usage over the past decade. In forgetting its meaning, though, we seem to have added our own modern backspin to it, associating it instead with anyone who dreams big, who has vision.

Still, the word “ambition” remains cumbersome. First, it has no verb counterpart. It is not done but merely possessed. One can only “have ambition” or “be ambitious”; as a noun it is passive, and as an adjective it is vague. (Thankfully, “to ambish” has not been bastardized into existence yet.) And unlike other qualities one can possess — happiness, acumen, integrity — ambition is unearned. One needs only to will it to exist, creating ambition from nothing save for an insatiable desire for more.

By this measure, ambition is not only binary, but also quantitative: each individual’s level of ambition can be easily plotted on a single line. Like IQ, we each fall measurably before some and after others, and a line in the middle demarcates the unambitious and the ambitious.

So it’s relative not to one’s own life, but to the ambition of others: my high school classmates who never left our hometown are less ambitious than, say, Elon Musk. It looks not unlike the red and blue of our two-party political system — and I’m jammed somewhere in the unacceptable territory of “moderate.”

I believe these are dangerous misconceptions. First, this absolutism makes one’s happiness dependent upon the degree of their ambition. It says that if my ambition is too slight, my success will suffer. Had I only that insatiable desire for more, then perhaps I could have achieved greater success and happiness. Otherwise, all my hard work yields diminishing returns and happiness remains forever elusive without ambition.

Further, it gives those who have ambition the power to define it for others. After all, what more could an ambitious person want than to be plotted ahead of his peers on a line? It is a self-fulfilling prophecy for those already quite full of themselves. Worse yet, doing so gives the self-proclaimed ambitious control over everyone else’s happiness formula. It allows them to say, “He’s not successful because he’s not ambitious. No wonder he’s unhappy.” How convenient.

But, no. We easily invalidate the formula with its classical usage: in Paradise Lost, Lucifer’s ambition earned him the favor of just enough of Heaven’s angels to lose mythology’s most epic battle. It certainly was not without hard work, but success (luckily) evaded the devil’s grasp.

Reluctant to rely on the 17th century? Fair enough. Consider our own modern-day pinnacle of ambition: Donald Trump. Though obviously convinced he’s tremendously qualified to be President, the candidate seems to be continuously thwarted in spite of (if not because of) his ambition. Trump’s unrelenting desire for more invokes Webster’s “madness” — a strain of megalomania that would be almost sad were it not so obnoxious. Meanwhile, Trump’s soaring ambition may yet lead him to his greatest public embarrassment: a landslide electoral victory for his opponent. (Or, conversely: to our nation’s untimely demise.)

In both examples, our antagonist demonstrates that ambition is as blind as it is limitless: one would not be satisfied to rule a business empire when he could rule a country; the other unsatisfied as a citizen of Paradise when he could reign over it. But in neither example does ambition — even at such dramatic scale — guarantee success, so we must consider the formula flawed.

If we believe ambition to mean “desire for more” then by itself it can never be satisfied. Ambition begets ambition, and any amount of success creates a demand for more. Left unchecked, ambition would be a divisor in our modern formula: if my ambition is too great, I can never achieve happiness, since none of my hard work will ever be enough.

Just as the infinite cannot be achieved or completed, nor can it be contained in definition.

Therefore, ambition should not be treated a standalone quality — and certainly not a “virtue” — like courage or intellect. I find more similarity in a word like “wherewithal,” which cannot be possessed outright or alone: one cannot simply “have wherewithal” or “be wherewith.” One must “have the wherewithal to” — and always with a specific end in mind. Similarly, ambition should be made relative to one’s specific desires, and especially pointed toward something achievable.

This new definition liberates our happiness from the grips of greed’s slippery slope. It becomes personal and specific — irrespective to the ambition of others, and dedicated to an achievable aim. Most importantly, freed from ambition, now hard work alone can lead to success and happiness.

So what is it then, if not ambition, that drives us to sail to the New World, to map the Western Territory, to put a man on the moon?

I defer instead to “aspiration.” Though often mistaken for a synonym of “ambition,” its etymology is much more nuanced. It means literally “to breathe in,” but it was used in the context of invoking knowledge and truth. Instead of ambition’s blind desire for immeasurable greatness, aspiration emboldens one with the spirit of achieving a specific task.

I refer now to my third John of the day: Kennedy, speaking to Rice University in 1962:

We choose to go to the Moon in this decade and do the other things, not because they are easy, but because they are hard; because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one we intend to win.

Though the speech (penned by the brilliant Ted Sorensen) hints at Manifest Destiny, Kennedy refuses to rely solely on the “Sure, why not?” argument. Ambition alone would not suffice; the mere desire for more would not carry us to the moon. It was instead the satisfaction of doing the hardest work imaginable, of striving to reach what was previously believed to be unreachable. As a nation, we aspired to reach the moon: we collectively invoked the spirit of that epic journey, held the moon in our hearts, and shared in the joy of reaching it. I’ll take that any day over “going around canvassing for votes.”

Three weeks after I got home from that hike out west, the New York Timespublished a piece about James Altucher in which he declared, “I have ambition to have no ambition.”

I was a somewhat new fan of Altucher’s blog and had recently begun reading his book Choose Yourself, so it felt like a cosmic nod that he of all people would construct a paradox that poked fun at a subject with which I currently struggled.

I felt my new formula had been validated — and that I had been vindicated — by those seven words. His coup de grâce granted me permission to regain control of my own trajectory, to eschew the foregone conclusion of ambition’s greased rails and free myself from expectations set by others.

When we returned from the hike that night, I collapsed, exhausted, onto my cot and pulled the sleeping bag up over my mud-covered clothes. I cinched the bag’s hood to fend off the cold, but left a small porthole through which to view the night sky. At 6,000 feet up, miles from the nearest man-made light, the stars were intense, dense, and dizzying.

I felt high from adrenaline. I was exhausted. I was pissed off. I was proud of my crew. I was scared of what might have happened. I shuddered to think of what could have been lost. I watched a satellite crawl in a steady arc across the sky and wondered how it felt to soar at 28,000 miles per hour.

I breathed deeply once, twice, taking in the cool night air of the California wild. I breathed again, aspiring, taking in the dirt and trees and rocks and sky, and then slept hard until sunrise.

I didn’t know it then, but challenging ambition would help me begin replacing it with aspiration. I reject the label “unambitious” — that’s a convenient judgment cast by shameless self-aggrandizers. No, I was becoming ambitionless. And this spiritual alchemy empowered me to aspire — and not to reach for ambiguous heights or to obtain the immeasurable more, but to find something personal and meaningful and great, and shoot for it.

And now it’s just about finding that something.