The Ghost in the Room

Podcast

Feb 14

I didn’t become a lawyer because I wanted to be one.

I became one because a professor suggested I take the LSAT. I did well. And suddenly, the track appeared beneath my feet.

That’s how it works. You don’t decide so much as you step forward, and then momentum does the rest. Law school is expensive, it’s hard to get in, and yet — once you’re in — it’s somehow the path of least resistance. The groove is well-worn. The blinders go on. And before long, you’re not making choices anymore. You’re just moving.

I wanted to be an artist. I always wanted to be an artist. But I went for the shiny thing instead: the firm, the money, the prestige, the respect. The wife, the kids, the summer camp, the golf club. And if I’m being totally honest? I was looking for something I thought I could get from the outside. Something that — if I trace it all the way back — was really just approval.

That worked. Until it didn’t.

I spent 12 years as an entertainment lawyer. Built a real practice. A partner, associates, an office, clients I’d known for at least a decade. By every external measure, I’d made it.

But there’s this thing I’d call “epistemological dissonance” - when you know something for a long time and can’t make yourself act on it. I knew back in law school. First month, maybe second. Standing in the foyer on the phone with my mom, thinking: this was a huge mistake. These are not my people.

I didn’t leave. I saw the shiny thing and I went for it again.

Every time I had a chance to get out, I doubled down. It’s what you do when something is uncomfortable and the alternative is terrifying. You cling harder to what you know.

The shift, when it finally came, wasn’t dramatic. It was a fight with a long-term client. Someone I’d worked with for over ten years. I was treated poorly in a way I couldn’t shrug off — and I fired them.

That was hard. It still kind of is.

But then something cracked open. Because if I could fire one client... I could fire them all. I didn’t have to keep doing this. I actually had a choice.

That realization — so obvious in retrospect, so invisible when you’re inside it — changed everything.

I left law at 40. Sat at my birthday dinner with my parents and my wife, already having made the leap, thinking: my god. I just left this stable, painful profession. What the hell am I doing?

The career ended. But the identity didn’t. Not right away. For a long time after, when people asked what I did, I’d say: well, I used to be a lawyer. Still framing myself through something in the past. Because it was the most stable thing I could name. The most legible thing. The thing that oriented other people.

Which, when I finally looked at it clearly, had nothing to do with me. That was about their comfort.

Here’s what I’ve come to understand about identity change: it requires mourning. You have to let something die before the new thing can begin. And the old identity — the career, the title, the version of yourself that knew exactly who it was — it doesn’t disappear. It becomes a ghost.

And a ghost deserves a little respect.

Not because it’s still running the show. But because it has wisdom. It earned things. It taught things. I would have zero credibility with the lawyers and executives I work with now if I hadn’t lived through what I lived through. The wounded healer isn’t a metaphor. It’s the whole framework.

In this conversation with , we go deep on all of it — the quarter-life crisis that preceded the midlife one, the year I actually left law to teach yoga and take pictures, what it looks like to help people get unstuck without pushing them toward any particular answer, and why leaving a profession isn’t always the solution - but staying in it unconsciously definitely isn’t either.

If you’re in the middle of something - I think you’ll find something useful here.

Thoughts? Leave a comment (that helps get this work out there) or send me a note here.