I remember the moment pretty clearly.

I was looking at the people ahead of me, the ones I was technically working toward becoming, and I had this quiet realization.

Oh shit. I don’t want their jobs.

I don’t want their problems. I definitely don’t want their lives. And geez. I don’t really want to be at those tables anymore.

Which is a slightly inconvenient realization when you’ve spent 15 years doing everything “right” to get there.

Nothing was technically wrong. I wasn’t miserable. I liked working hard, liked being good at something. I really liked growing and leading people. Building things, solving problems. But somewhere along the way I’d learned what I needed to learn from that world. And now I felt like a puppet. A cog. And I couldn’t see a future I was excited about.

I didn’t just want a new job. I wanted to be around, well different people.

And by different, I don’t mean less ambitious. I am ambitious. Annoyingly so, probably.

I mean people doing life a little more gently. A little more in tune with themselves. People who still cared about building things, but also cared about staying true to their values, not just the $.

Because the world I was in had started to feel ruthless. So much about the numbers. So little about the actual people. The higher I got, the more I saw how decisions were made, how things were packaged, how much energy went into politics and saying things the “right” way instead of just saying what was true.

Every year the same compensation conversations. The same weird corporate dance. Being forced back into the office post-COVID made me crazy. The badge swipes. The counting. I can’t.

There is something especially soul-sucking about being a grown adult with children, a mortgage, and a 401k and still having a building swipe decide whether you worked enough that week. Especially when you woke up at 5:30am to take calls with the Singapore office and give up your Sunday to fly west.

At some point I thought: I cannot keep being a smiling little messenger pigeon for things I don’t believe in and for leaders I don’t agree with.

The Slow Drift Into Someone I Didn’t Recognize

So I started asking different questions.

Who do I actually want to be around? What rooms do I want to be in? Whose problems do I want to help solve? What kind of ambition feels good in my body?

And the slightly obnoxious answer was: not the rooms I was currently in. And not the rooms I’d end up in if I stayed on that track.

That track looked lonely to me. It looked impressive, sure. But lonely. And if I’m really telling the truth, I could also see how it might feed the worst parts of me. The ego. The part that wants the title, money and power.

I could feel it happening. I was getting harder in ways I didn’t like. Less playful. Less present. More irritated. More impressed by things I didn’t even respect.

How did I get so lost in autopilot that I let that happen?

The Question I Kept Avoiding

For a long time, I kept asking: what’s the worst that could happen if I leave?

Very adult. Very responsible. Let’s put it on a mug.

But eventually I had to ask a different one: What’s the worst that could happen if I stay?

That one opened my eyes. Because the worst-case scenario of leaving was mostly financial. And yes, money matters. Hugely.

But the worst-case scenario of staying felt like slowly becoming someone I didn’t want to be. Less present. Less playful. Less connected to herself. More resentful. More polished. More impressive, maybe.

Less alive. And that cost started to feel too high.

I also started asking the flip side: what’s the best case if I stay? If I leave? Those answers were clarifying

But here’s the thing nobody tells you about that realization. It doesn’t come with a plan. I had two fears tangled up together, and they were both real.

The first one was obvious: how would I make money? What would I actually do?

The second one was sneakier: what if I left one machine and slowly built another one, except this time I was the machine. The operator, the marketer, the bookkeeper, the customer service department, and the person crying into a laptop at 11pm making less money.

I had heard enough founder stories to know that “build your own thing” can very quickly become: congrats, your new boss is now your worst self.

I didn’t want that either.

So I didn’t wake up one day with a perfect plan. That’s not what happened. Next week I’ll tell you what happened instead.

Oh and by the way, I’m hosting something small. A day in Serenbe, June 12, for people sitting with exactly this question. Spots go to the list first. Join here.

xx, Gina