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Someone close to me recently shared that they didn’t consider themselves ambitious. Surrounded by friends who are actors and writers and comedians, people whose day jobs merely provide financial support for deeper, abiding artistic interests, this person (let’s call them Jordan) compared their own life to the map of a video game. Jordan doesn’t dream of some future prize in the form of a promotion or a published book. They’re only able to see what’s immediately in front of them.
I was surprised to hear Jordan view this as a negative. My curse is the opposite: I’m always optimizing for some future state, which means I constantly feel behind. Or as my college boyfriend put it before I flew to the UK for graduate school, crying as I asked him in the 115 degree Las Vegas heat whether our relationship would survive 5,000 miles and eight times zones of long distance, I’m “always thinking six chess moves ahead.”1
Fighting the Ambition Monster
One of the reasons I left my corporate job last year was because I was tired of living this way. Since then, I’ve been trying to be less of an ambition monster. I’m focusing more on the day to day, on what activities feel good to me right now, and fretting less about what this means for the job title I’ll have five or 10 years down the line. I’m getting more comfortable with the idea that I won’t know what’s next until it’s right in front of me—until I get there, wherever there is, on the video game map.
In other words, I’m trying to live life the way Jordan does, optimizing for the short-term instead of fretting uselessly about the long-term. After all, your sixth chess move depends on what the person sitting across the table does in the interim, which is entirely outside of your control. And in real life, the rules of the game might even change before your next turn. Careers exist today that didn’t exist 20 or 10 or even five years ago. One of my favorite magazine editors now leads Meta’s fashion business; a friend of a friend landed a book deal after going viral on TikTok.
Counterintuitively, this approach has made me more ambitious, not less. But ambition has taken on a new form. I want to do so much more than get promoted to Senior Director or take another company public. I want to publish a novel, grow my comms consultancy into a high six figures business, profile up-and-coming tech founders in the style of a techno-optimist Taffy Brodesser-Akner, coach tech founders through inflection points, adapt my novel into a TV show, ghostwrite op-eds and books for the spikiest minds of our generation…. But I’m also comfortable knowing that the list will evolve as I do.
The Grass Is Always…Well, You Know
The fact that Jordan and I have opposite impulses and yet both feel like our factory settings are suboptimal reflects a broader trend I’ve noticed among my cohort lately: We’re all convinced we’ve made the wrong tradeoffs. I don’t mean we all hate our lives, just that the grass indeed always looks greener.
Another of my friends is a playwright. They dove into the arts right after college, earning an MFA from a well-known program and, more recently, inking a flashy deal with a media juggernaut. Like many of my friends in the arts, this friend tutors to pay the bills, but lately they’ve been flirting with the idea of a corporate job. The stability (and the healthcare) sound appealing.
When they mentioned this to me, I laughed at the irony—in my view, they were living the dream, while I’d spent years letting everything take a backseat to my corporate job. The playwright and I admitted we both envied another friend, an actor who works a tech behemoth and genuinely seems to enjoy their work while also leaving it at the office. I have no doubt that the actor, too, would laugh if we told them we thought they’d negotiated the perfect balance between art and work, the same way Jordan would be shocked to know I admire the way they zealously use their PTO.
I suppose this is all to say that no one has it figured out, least of all me. Lately I find myself perusing job postings on LinkedIn, daydreaming about returning to office life. In my fantasies, I’m usually a senior individual contributor, getting a healthy paycheck to write missives for a brilliant, quirky executive. I eat subsidized meals as I catch up on office gossip with my work friends. I fly business class to Cannes and Davos. All of this pays for a respectable amount of time spent writing for myself, my day job never infringing on my artistic pursuits.2
And then it will be a beautiful day in Brooklyn, a hyperbolically spring day, warm but not humid, the flowers blooming pink and white, and I will take the long way to a coffee with a founder whose business I might invest in, and I will be so grateful I am not spending 10 or 12 or 14 hours straight facing a monitor that looks like an army battle station.
I know corporate life isn’t what I want right now. I have found something like balance between my client work, which I love, and writing my novel (which right now I kind of hate, but I mostly love). And yet the most energized I’ve felt in the last year was when I interviewed at a venture capital firm that boasted heated Japanese smart toilets and some of the smartest people I’ve ever met. I’m not sure what to make of these contradictions.
But I am certain the only way to untangle these questions is to live them. To apply one of my favorite writing maxims to life, “Writing a novel is like driving a car at night. You can see only as far as your headlights, but you can make the whole trip that way.”
We lasted for two more years, through an MPhil dissertation and a disastrous presidential election. In retrospect, I wish we hadn’t! But I’d already planned out those next chess moves factoring him in. It wasn’t until my whole vision for my future came crashing down at the Javits Center on Election Day 2016 that I reevaluated.
Hahahahaha