I loved law school.
There was joy in the study, in the debates, in the intellectual challenge of taking a problem apart and looking at it from every angle. I loved the conversations with classmates and the chance to sit with difficult questions long enough to understand the nuance.
Then I became a lawyer, and almost immediately, I knew something was wrong.
The practice of law felt nothing like law school. There wasn’t much time to read and reflect or savor the complexity of an issue. There was work to get out the door, deadlines to meet, clients to serve, and hours to bill. (Two thousand of them a year!)
My life was measured in six-minute increments.
I was also a trial lawyer, which meant spending a huge amount of time in conflict. That’s how the adversarial system works, of course, but year after year the contentiousness wore me down.
The problem was that I was really at it. And it paid really well.
So even though I wanted out, leaving didn’t feel simple. I had kids, a house, tuition bills and responsibilities. A therapist I worked with at the time called them the golden handcuffs, and the phrase fit perfectly.
The career that was making me miserable was also providing the income, security and identity that made leaving feel almost impossible.
And there was another trap I couldn’t see as clearly then: I had invested years becoming good at this.
Law school. The bar. Long days and late nights. Years learning how to try cases, take depositions, write briefs, negotiate settlements and advise clients.
Walking away from all of that felt wasteful.
That is how a lot of people stay stuck.
We assume that because we’ve invested heavily in something, we need to keep investing in it. Economists call this the sunk cost fallacy. The money is already spent. The years are already gone. Yet we keep allowing those past investments to determine what we do next.
But wait, there’s more! There’s another assumption underneath that one that may be even more powerful.
If I’m good at something, surely I’m “supposed” to keep doing it.
But competence and fulfillment are not the same thing.
You can be very good at work that is slowly hollowing you out. You can keep earning more money and still become less happy with the life that money is supporting.
From the outside, everything might look amazing. But on the inside you’re miserable.
It took me far too long to understand that.
I stayed in the practice of law for more than two decades.
Years later, I became an executive coach, and I absolutely love the work I get to do.
I love the conversations and the chance to help people see what they cannot quite see for themselves. I love sitting with a complicated business or life problem long enough for something useful to emerge.
And much of what made me a good lawyer came with me.
The ability to listen carefully, spot patterns, think strategically, ask difficult questions and help someone make sense of a complicated situation did not disappear when I left the law.
I didn’t throw away those years. I simply started using what I had learned in a different way.
I wish I had understood that sooner.
We often imagine a career change as starting over, but that’s not always what ‘s happening. More often than we realize, we carry a great deal with us. The skills, judgment and experience travel even when the profession itself does not.
Here’s what’s true: There nay be something in your own life right now that you are extraordinarily good at. People may admire you for it. They may depend on you for it, and it may pay you very well. But it doesn’t make your heart sing.
That doesn’t make the years you invested meaningless, and it doesn’t mean you made some terrible mistake by staying as long as you did. It may simply mean that the work served you for a season, and that the life you really want right now requires something different.
Just because you’re good at something doesn’t mean you should spend the rest of your life doing it.
I help people find the work and the life they love. If you’re even just the tiniest bit curious, email me: [email protected]













