What is ambition, actually?

Some reflections on my book draft now that I've handed it off

ChatGPT’s rendition of my book cover (giving Penguin’s cover artists a run for their money)

Dear readers,

At long last, the update I’ve fantasized about sending you for the better part of a year: I have now submitted a full book draft to my editor at Penguin. Here is how it felt:

At the urging of my editor (and everyone else who’s had to deal with me in recent months), I’m stepping away from the manuscript for a while, so I can approach it with fresh eyes when it hits my desk again.

Meanwhile, I thought I’d indulge in some general reflection on what my book is really about, and what writing it has taught me about ambition and about my own psychology.

A more fundamental sense of “ambition”

You might think, given I’m writing a book on the “psychology of ambition,” that I’d have long since nailed down a definition of “ambition.” But as I was fielding questions on the topic at a speaking event just last week, I realized I had been semi-deliberately toggling between two meanings of the term.

The first meaning is the one you’re more likely familiar with: “ambition” as in the desire to achieve outsize outcomes with respect to a given (usually professional) endeavor. This is much broader than the term’s original meaning, derived from the Latin “ambire” (to “go around”), which had a negative valence and referred to the obnoxious practice of walking around the city courting votes or political favors. But it still retains that underlying connotation of hustling to maximize whatever metric is conventionally used to measure attainment within one’s field or social circle (be it votes won, or dollars earned, or lives saved, or honors awarded).

On this definition, you are more “ambitious” if you want to become a doctor versus a nurse, for example, or a tenured professor versus a low-paid lab technician, or a company founder versus a hired manager versus an independent contributor (IC).

But this definition breaks down when you try to apply it to the lives of particular people: for instance, did Tony Fadell become “less ambitious” when he went from running his own startup (Fuse) to taking a product manager job at Apple? Not by his own account: he had founded Fuse because he wanted to create a consumer electronics device that “would hook up to the internet, but wouldn’t look or feel like a computer.” Working as a product manager at Apple allowed him to realize this ambition far more fully, first by leading the creation of the iPod and later the iPhone. Apple was, in his words, “the place where I finally grew up. I wasn’t just managing a team anymore. I was leading hundreds, thousands of people. It was a profound shift in my career and in who I was.”

Or was Kati Kariko being “less ambitious” when she chose to pursue an unpopular research topic (mRNA) that kept her at the bottom of the academic ladder for decades, rather than pursuing something more “fundable” and rapidly rising in status and salary?

For these and many other ambitious builders, eschewing the conventional metrics of “ambition” within their field was precisely the ambitious thing to do, given what their self-defined projects required.

This brings us to the second, more fundamental meaning of “ambition,” which I believe underlies the legitimate appeal of the first, and which is the real subject of my book: the desire and will to live one’s best life. The project of building a life for ourselves is, after all, our ultimate endeavor, of which all our more particular endeavors are part. And the more agency we exercise over the particular endeavors we pursue and the metrics by which we measure them, the better our lives will tend to go.

I’ve met startup founders who are living their best lives, and I’ve met startup founders who are far from it. I’ve also met plumbers who are living their best lives, and those who are far from it. Some plumbers I’ve met are living fuller, better lives than some of the most “successful” startup founders.

So then, you might ask, why do I bias so heavily toward startup founders when writing about ambition?

This is a question I’ve always had an intuitive answer to, but choosing what stories and examples to include in my book, and seeing the high proportion of founder stories, has forced me to grapple with it more explicitly.

The main reason my book features a lot of founders is because I’ve spent much of the past 5 years working with them. But more interesting, perhaps, are my reasons for choosing to work with them:

1. Because their chosen endeavor requires them to exercise agency over large swaths of their life (like how, where, and with whom they spend their time, what they prioritize, whether and how much they get paid, etc), thus naturally selecting for people who want to be ambitious in the more fundamental sense.

2. Because I’ve realized I can offer them a ton of value just by helping them reframe their understanding of “ambition” from the more concrete to the more fundamental sense.

3. Because their situation makes more starkly visible the facts and conditions of reality to which all of our lives are subject (like that death is the default, and that we are all making it up as we go), which in turn ought to motivate all of us toward greater ambition.

4. Because I personally love them. The founders in my life have consistently elevated and inspired me, and my life is better and fuller when I get to spend significant portions of my time with them.

Ambition begets ambition

When I ask repeat founders why they keep founding startups, the first (tongue-in-cheek) answer is often that they are “gluttons for punishment.” But what they actually mean, on further prompting, is that they are gluttons for growth. They’re never fully stimulated or satisfied unless they are pushing their own personal frontier in some way (akin to Lin Manuel Miranda’s portrayal of Hamilton, who “will never be satisfied”). For some of them this means finding new industries to master, or problems to solve, or leadership and management skills to develop as they scale. But whatever the particular dimensions along which they want to grow, their psychology necessarily comes along for the ride.

Some of them start caring about their psychology only once it becomes a rate limiter on the worldly ambition they want to achieve (e.g., they can’t scale their product any further unless they develop some people management and emotion regulation skills); others seek out the worldly ambitions primarily as outlets and forcing functions for the psychological growth they crave. But whatever their primary motivator, neither the worldly outcomes nor the psychological growth can function as “mere means” to the other; to achieve and sustain either, you need to care about both. Just look at what happens to lottery winnings or inherited fortunes when placed in the hands of someone who lacks the character traits to figure out what to do with them. If you want to be materially ambitious, you need to be psychologically ambitious, and vice versa. We build ourselves by building, and we can’t build except by building ourselves.

Likewise, in writing this book, I’ve needed to push my own psychological frontier forward in ways I couldn’t have previously imagined. As just one example, I’ve had to experiment with a hundred ways of triggering my mind to spit out creative and fluent prose “on demand,” which had been hard enough to effect even when I wasn’t operating within the confines of a pre-established book structure and a writing schedule tightly regimented to fit within the interstices between work and parenting. And I had to fight the frequent urge to get resentful of those constraints, forgetting why I had chosen to work within them and how beautifully they solved for everything else I want and value in my life. And I had to muster unprecedented levels of self-trust to get out of my own way of generating the sheer volume of text I needed to generate, absent any definitive feedback, while counting on myself to impose some kind of order on it afterward.

Once the book is published, I already know I’ll be up against another frontier, which is my long-endured but never-fully-tamed public speaking anxiety. Even as I type these words, I feel that familiar mix of sinking sensations and butterflies that have preceded so many of my worthiest projects; the telltale signs of “growing pains” ahead.

Whatever lies on your personal frontier, there are psychological hills you’ll need to scale as you venture into them. My book is about the framework and tools, not only for scaling those hills, but for choosing the frontiers and charting the paths most eminently worth scaling.

Or at least I think it is…. will let you know for sure when I re-read it some weeks/months from now! :D