This is the second part in my new series, Don’t Work, where I share my story about what happened when I took time away from work, and my central identity disappeared. Check out my last series, Work in Progress, covering my lessons learned from a 12-year journey from startup to public company.

“Who am I, without work?”

They say there’s two sides to every story.

There was the story of my career growth and origins of my strong work identity.

Now here is the story of my unraveling.

After years of pounding away at a startup-now-public-company, I decided to take some time off. I envisioned a brief hiatus followed by the launch of my own business.

I had all the momentum in the world - supportive mentors, potential investors, and a war chest to survive the inevitable ups-and-downs of launching a new thing.

My list of business ideas were neatly organized in a spreadsheet, ranked by potential, all lined up to evaluate. What was missing was just a little time and head space to recharge and explore. This, I thought, was so I could hit my next big chapter with renewed ambition.

But that’s not what happened next.

As months passed, things changed. I changed.

Inside the emptiness of time away, removed from the day-to-day intensity and structure of the working world, a slew of dormant questions and insecurities surfaced.

Among them, none were as unsettling as the one that forced me to confront an uncomfortable reality: “who am I, without work?”

This is the unraveling of my work identity…

I. I’m not my company

"When a hundred men stand together, each of them loses his mind and gets another one." Friedrich Nietzsche

Maybe some of you feel proud of being part of your company or team. When the company does well, you feel better. And when it does poorly, you feel poorly.

As an early employee of a startup, the company felt like it was part of me.

The fact that the company had done so well was a sense of pride. I felt partly responsible for creating something innovative and consequential.

When I stopped working, that all went away.

Watching it flourish had brought me self-worth, but stepping away made me realize how deeply intertwined my identity had become with its success.

Leaving the company meant relinquishing…

• the influence I once had over its direction. Suddenly, I found myself on the outside looking in, no longer shaping its future.

• being part of the inner circle, without access to important people (or being thought of as one myself).

• day-to-day relationships aligned with that group. People moved on faster than I thought. I became irrelevant, quickly.

And without a “next thing” lined up, there was no other organizational anchor to hold onto. That part of me was just empty - a blank line on a resume.

In retrospect, this was a fragile way to base my worth. What if things hadn’t turned out so well? To be whipped around by the fate of something I influenced (a bit), but ultimately was outside my control?

We value “community” and being part of something bigger than ourselves. That’s all good.

But the tradeoff is when our identities become enmeshed inside these external, impermanent entities, we are subject to their direction, their outcome, their worth.

Shedding my organizational identity was the first step. But there was more coming…

II. I’m not my position

"Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like." Paul Graham

While working, I was a Very-Important-Person!

Senior Vice Peasant of this and that. Able to approve a few thousand dollars in budget without approval. Plane tickets in Economy Plus. Yeah, that important.

But seriously, people cared about my opinion and seniority. My title was high. I held organizational power, both in terms of the hierarchy and also the soft power of relationships and reputation accumulated over time.

I had the authority to shape decisions that impacted the future of the company and teams. People’s livelihood at Privia depended on my judgment over them.

I also was relatively young for my position, which of course was nice fuel for the ego. 

It felt good to be important.

And I expected to leverage that Very-Important-Person status into becoming an Even-More-Important-Person in my next venture. It was the next rung in the ladder.

But when I stopped working, it all fell off. Where were all the people and projects I could command? What decisions of consequence remained?

The further I drifted away from work, the less I could identify with my old title and importance, even only a few months removed.

What started as “I am…” became “I recently was…” then “I used to be…”

In this positional vacuum, I began to ask myself who I was without my position? And whether any title, expertise, or status would make me feel whole?

• If not SVP, then what about CEO?

• What about Founder?

• What about Founder/CEO of a small company?

• Or must it be a big company? How big?

“What if, instead of being an early employee/SVP of a $2B company, I was a Founder/CEO of a $10B company? Now that sounds like a Super-Important-Person!” - actual thought that went through my head

If all this sounds stupid and self-absorbed, you’re right. It was.

But it’s hard to disassociate yourself from your positional status at work. Yes, my position was an artificial fiction, but still a foundation I stood upon.

Seeing this absurd line of questioning revealed its pointlessness. There was no status big enough because there’d always be another.

While the position granted me authority and recognition, it was missing lasting fulfillment and a broader sense of identity.

I was ready for the next level down…

III. I’m not a worker

"They intoxicate themselves with work so they won’t see how they really are." Aldous Huxley

This last layer is a biggy. And a difficult one to explain because it was, and still is, so enmeshed in my identity.

For my company and positional identities, it made basic sense that when you leave, you can’t take those things with you.

But who was I, if I did not work at all?

When I stopped work, a bunch of hidden stories emerged. The questions came from the outside, but they also came from the inside. 

From the outside, even when I explained my sabbatical as temporary, people would still look at me a little strange:

• “Aren’t you too young to not work?”

• “You need to set up the next thing before you leave your current thing.”

• “It’s good to take time off, but don’t for too long or you’ll become irrelevant.”

• “Taking time off is nice and all, but when are you getting back to work?”

  (actual things said to me)

While these were uncomfortable questions, nothing compares to the inner dialogue. The battle royale within myself providing unending lectures, imploring me to do this-or-that:

• It told me to “be productive” and to “be useful.” That a solid output was the ultimate measure of a good day (and good life).

• It told me that work is my “legacy.” That I should “make an impact” or (more absurd) “make a dent in the universe.” When I die, I go, but my work remains.

• It told me that not working was “unsustainable.” What would happen to the economy if everyone stopped working like you?

• It told me that when people don’t work, they’re a loser. The unemployed! The leeches and bottom dwellers of society.

These are scripts that so many of us believe to be objectively true: we are here to work and we are our work.

But it didn’t take much to poke holes in the logic. For example, were my children worthless because they didn’t work? Is a part-time worker, part-time worthless? How long, after I die, must my work last for it to be worthwhile?

Shall I keep going?

Seeing these stories emerge, and playing through this absurd line of questioning, was an unsettling, yet important step in my evolution.

While I’m still figuring this part out, I can see the worker identity as it is: a mirage.

IV. What remains?

“And your way, is it really your way? […] What, moreover, can you call your own? The house you live in, the food you swallow, the clothes you wear — you neither built the house nor raised the food nor made the clothes. […] The same goes for your ideas. You moved into them ready-made.” Henry Miller, credit to Maria Popova, Henry Miller on Originality

Some of you may even be thinking that I’m insane for sharing all this. I get it.

But these stories about ourselves can be easily skipped over, simply because they are so pervasive. And because they are so pervasive we take them for granted.

Where did these beliefs come from? Did people always think this way? Are there other ways?

While I understand my story better, I’m nowhere near the bottom of it all.

What I do know is that when I strip these identities down, peel away layers of the onion, I’ve realized something a bit frightening: I want these identities. They serve me in some way.

Yes, some identities are put onto us by others. But we decide whether to keep them. And they can crowd out what we might put in their place.

What we put there and how to do it, is what I’ll cover in the remainder of the series.

Next up, I will explore the counterintuitive value of disappearing. Subscribe to stay tuned.