In the summer of 2009, my wife and I sat at our kitchen table looking at two kids — ten and twelve — and a promise we’d made each other long before either of them existed. When the kids hit the sweet spot, we’d said, we’d take them somewhere far away for long enough that the place could change them. Not a long weekend with conference calls in the hotel lobby. A real trip. Italy. Summer of 2010.
There was just one problem. The business wasn’t ready for me to leave. And if I’m honest, neither was I.
I was running a jewelry company my wife had founded, and the previous year had nearly knocked us out. We were inching back, but everything felt fragile. My instinct when things feel fragile is to lean in, tighten my grip, talk faster, push harder. That instinct had served me for twenty years. It had also made me the guy who couldn’t take a real vacation — the guy who pretended to be off while dragging the office behind him like a carry-on.
I’ve come to believe that midlife hands you exactly these kinds of bills. The habits that built the thing you’re proud of are the same ones quietly stealing the life you actually want. You can keep paying that bill, or you can finally read it.
So I gave myself ten months to become a different leader. Not a different person — I’m still loud, still persuasive, still the guy who likes the microphone. But I had to put my strengths to a different use. I littered my office with sticky notes that said things like “Don’t tell. Ask.” and “What would you do?” I added a daily calendar reminder: “Be curious today.” When someone walked in with a problem, I made myself count to three before opening my mouth. Three seconds is just long enough to notice you were about to say something — and decide not to.
It was clumsy. Some days I nailed it, some days old Bill came roaring back with a smooth answer and a timeline. But over those ten months, the team started bringing different energy. Instead of “What should we do?” they’d say, “Here are the options, here’s the risk, here’s what we recommend.” Ownership is a muscle. I had been supervising so hard I was starving people’s muscles.
In June 2010, we got on the plane. I remember the moment the wheels left the runway — that shift when the rumble becomes a whoosh and your weight transfers from earth to air. That’s what it felt like inside me too.
We had a month of espresso in small cups, gelato, late dinners, and sailing in the bay of Naples. Meanwhile, back home, I’d open my email each morning to a short note from the daily huddle. A few numbers. Something that had gone well. Something that had gone sideways and what they were doing about it. Most days I wrote nothing back. A couple of days I wrote questions instead of answers. They chose. They executed. The company kept moving forward without me grabbing the wheel.
Here’s the part I didn’t see coming. That trip didn’t just give me a month in Italy with my kids at exactly the right age. It rearranged what was possible for the rest of my life. A few years later I was able to leave the company entirely and become a full-time coach — work I’d been quietly hungry for but couldn’t have done while I was still the keystone in the arch. When you stop being the only thing holding the building up, you get to walk out the front door and ask different questions about your life.
I think this is what the midlife shift actually asks of us. Not less ambition. Different ambition. Trade the swagger for steady rhythms. Trade hero for host. Trade “I am the business” for “I built something that runs.” Less struggle, more flow.
Italy was twelve years ago now. My kids are grown. I’m a grandfather. And the question I keep asking the leaders I coach is the same one Italy asked me: What would your life look like if the thing you built didn’t need you in every room?
You might find, like I did, that the answer is the trip you’ve been postponing — and the next chapter you didn’t know you were ready for.
-Bill
Bill Gallagher is an executive coach, host of the Scaling Up podcast, and author of the forthcoming book Busy Is Broken: Do Less, Scale More — a book for leaders who built something real and now suspect their own effort has become the thing slowing it down. Learn more at https://busyisbroken.com. Bill lives in the Oakland Hills with his wife Lori, where he’s usually found on the bay chasing wind on a wing foil board.