My ambition is haunting me

Reckoning with the stories I told myself about success, and what comes next.

A few weeks ago, I ran my first reader survey. As I read through your thoughtful responses, I was struck by how many of you feel disillusioned by your career.

Me too.

You used words like “existential,” “burnout,” “uninspired,” and “broken.” The phrase I’ve been tossing around is “quarter-career crisis.” Word choices aside, I know we’re talking about the same thing.

I’ve squarely avoided this topic on False Start because it feels too vulnerable to share while I’m living it.

It’s easier to write about an experience after it’s over. Everything feels clearer in hindsight. Zoom out, connect the dots, and tie them together with a bow. The problem? Time erases the complexity of emotions. The memory of the feeling is not the same as the feeling itself.

I entered the workforce during the “lean in” era, devouring Sheryl Sandberg’s bestseller a month before I graduated from college. Instagram exploded after that, and with it came the birth of the “girlboss.” Sophia Amoruso was the poster child, but there were others, too. Payal Kadakia founded ClassPass in 2013. Emily Weiss launched Glossier in 2014. Ty Haney, Audrey Gelman, and many others followed suit.

The social posts, books, and interviews surrounding these women led me to believe that a successful career would bring me happiness, just as I thought it had for them. That’s a big assumption, but I was only privy to their highlight reels. Can you blame me?

To be clear, I don’t fault my role models for my misunderstanding. They don’t owe anyone complete honesty about the lows of their careers; the challenges that arose as their titles, salaries, and responsibilities grew. Besides, leaders often can’t share their most challenging moments due to legal and fiduciary reasons. There’s also the question of time and desire. Do they want to share? Do they have the space to? Even if they could speak about these topics, would it represent the whole of their experiences? Time and psychology tend to diffuse the truth.

There are two phenomena we can thank for that. The peak-end rule, coined by psychologists Daniel Kahneman and Barbara Fredrickson, states that memory is most influenced by feelings at the peak (the most intense moment) and the end of the experience. As such, recall is skewed, and we tend to forget the nuanced and shifting emotions that occur across time. Then, there’s the fading affect bias, which describes how the emotional intensity associated with negative memories fades faster than that of positive memories.

Combined, these make it difficult to share past experiences in full color. The career triumphs I consumed from my role models were incomplete stories. Unfortunately, my younger self used them to construct beliefs about professional success, mainly regarding how achievement would make me feel. It’s taken time and experience to learn that my expectations were more rooted in fable than fact.

Here’s what happened: I landed my first full-time job at 22 and enthusiastically climbed the ladder for over a decade. Finally, I achieved the fancy title and the salary. I was thrilled. Then came the existential dread. Panicked, I thought to myself, “This is it for the next thirty years?” Many contributing factors led me here — the chaos of early-stage startups, the pace of the marketing industry, and my own ambition — but my overidealized career expectations played a starring role.

I posted these pencils to IG in 2014. Says a lot.

The career crisis is, of course, a common and somewhat predictable experience: a person works their way up only to realize they’re unhappy. Sure, I could blame this on late-stage capitalism and call it a day. But that won’t help me design a career within the system that I can make peace with and derive fulfillment from.

I trust that eventually, I’ll look back on this phase of my life with gratitude. Though my professional frustration has already pushed me in a better direction, I’m still in the thick of it. The narrative I’ll one day tell will be different from the one I’m living right now. As the peak-end rule and fading affect bias influence my future reflections, they’ll never capture how I’m presently experiencing the reality of this life stage.

Still, I struggle to explain my career disillusionment — even to myself. Since I can’t explain it, I’ll tell you how it feels. I feel disconnected, as if I’ve snapped off a piece of my identity like a Lego. I feel weathered and jaded. I’m only 34; I shouldn’t be this tired. Without a goal to work towards, there’s nothing to anchor my ambition. It’s free-floating, swirling, haunting me. I’m both nostalgic for and resentful towards my younger self, who was single-mindedly focused on achievement.

In my twenties, I used external stories to shape my priorities. Now, I’m turning inward. My emotions, gut feelings, secret desires, and personal interests will guide me. The most important thing I can do is tell myself the truth and listen.

I’ll never discourage you from chasing traditional career achievements. The pursuit of a raise, promotion, title, and salary can be worthwhile. They can also be shiny objects that distract you from your true nature. Instead, I encourage you to get quiet. Pay attention. How do you feel?

Do you dread the work week? Is there a whisper that says, I don’t think this is for me? This effort feels meaningless. I’m not myself in this office. 10 years ago, mine said in a shy murmur, I want to work for myself. I want autonomy and independence. I ignored her for a while, but she’s only grown louder with time.