Jacob has multiple advanced degrees. For the last 12 years, he’s led a large organization as its executive director.
And he’s been extraordinarily successful.
He’s built an amazing team. The organization has grown and thrived under his leadership. By every metric, and certainly by all outward appearances, Jacob has had a great run.
There’s just one problem.
He’s done.
Not burned out exactly. Not unhappy. He just knows he’s taken the organization about as far as he wants to take it. The work that once energized him doesn’t anymore.
He wants a new career.
But he has absolutely no idea what it should be.
I see this all the time in my coaching work. People arrive at my doorstep after 15 or 20 or 30 years of doing something they’ve become very good at. They know they want a change, sometimes desperately, but they can’t for the life of them figure out what comes next.
Part of the problem is that success has a way of narrowing our field of vision.
You’ve spent years becoming known for something. You have a title that carries weight. You’ve built a reputation and a network around the work you do. The money may have been pretty good too.
Eventually, all of that gets tangled up with identity.
I remember this from my years practicing law.
I’d walk into a networking event and inevitably someone would ask, “What do you do?”
“I’m a lawyer,” I’d say.
If I wanted to sound particularly impressive, I could upgrade that to: “I’m a trial lawyer.”
There was a lot packed into those few words. Education. Status. Expertise. Years of experience. And, whether I wanted to admit it or not, ego.
The trouble is, I wasn’t a lawyer.
I practiced law.
There’s an enormous difference.
When we identify too closely with a role, it becomes difficult to imagine ourselves outside it. We look at the future and think we have to find another box that somehow accommodates the person we’ve been.
But a career isn’t a box. And your job title has never captured the whole of you.
Over the years, you’ve acquired ways of thinking, solving problems and navigating difficult situations. You’ve learned things about people. You’ve discovered what you’re unusually good at, often without noticing because those abilities have become second nature.
None of that disappears when you leave your office and hand back the keys.
I wish I’d understood that sooner.
When I wanted to leave the practice of law, I could see everything I would be giving up. I wasn’t nearly as good at seeing what I could take with me.
Years later, when I became an executive coach, I discovered that much of what I’d learned as a lawyer came along for the ride. I knew how to listen carefully, I could hear what wasn’t being said; I knew how to get underneath a problem and ask questions that might reveal what was really going on.
And here’s the truth: My old career wasn’t wasted time. It had been preparing me for work I couldn’t yet see.
Which brings me back to Jacob.
He and I could have started by looking at job postings. We could have inventoried his credentials and searched for roles where an experienced executive director might fit.
Instead, I asked him a different question.
“What draws you here?” I said, putting my hand over my heart. “What tugs at your heart?”
Because I’ve come to believe that the heart often knows long before the résumé does.
Finding what’s next may require loosening your grip on the person you’ve worked so hard to become. Not abandoning that person. Just making room for someone else who has been quietly emerging along the way.
You may not know the title yet.
That’s OK.
Start with the tug.













