Still in the Chair

David is 58, a chief commercial officer, and by every external measure he’s at the top of his game. His numbers are good. His team is strong. His CEO relies on him.

“And I’m bored out of my mind about half the time,” he says.

I asked him which half.

“The half that’s about protecting what we’ve already built. Forecast reviews. Budget defense. Explaining a variance for the fourth time to someone who doesn’t care. The other half, developing people, figuring out a new market, I’d still do for free.”

This conversation happens quietly inside a lot of senior careers. Nobody has left. Nobody has been pushed. But the gap between the title a person holds and their appetite for the work inside it keeps widening, and there’s rarely a forum to talk about it. You can’t say it to your boss. You often can’t say it to your team. Sometimes you can’t say it at home, because the income and the identity are both tied up in the answer.

“What would you drop tomorrow if nobody noticed?” I asked.

He laughed. “The travel. The quarterly board prep. Probably a third of my meetings.”

And what would you add?

“More time with the people two levels down. I learn more from them than from anyone else in the building.”

I pushed on whether he’d ever raised that with his CEO.

“No. Because the minute I say I want less of something, I’m signaling I’m on my way out. And maybe I am. I just don’t know yet.”

That uncertainty is the real subject. David isn’t in crisis. He’s in the middle of a slow recalculation, and the risk for someone in his position is waiting for an event, a reorganization or a health scare or an acquisition, to make the decision for him.

We talked about what a deliberate version of this would look like. Not a resignation letter. Something smaller: a clear-eyed inventory of where his energy goes, a conversation with his spouse about what the next five years could hold, and a test or two, like a board seat or a mentoring commitment, that would tell him whether the work he loves can live outside his current title.

“I’ve spent thirty years being deliberate about the business,” he said. “I’ve never been deliberate about this.”

We ended on the question I find most useful at this stage: who are you still trying to prove something to?

He took a long time with that one. “My father, probably. He’s been gone twelve years.”

What I took from this

Senior leaders in this stage often have more options than they realize and less clarity than they’d admit. The work is naming what you’d keep, what you’d shed, and what you’ve been carrying out of habit or old obligation. That can happen deliberately, on your own timeline, instead of waiting for circumstances to force it.

I want to hear the real version of this story. If you’re in a senior role and quietly reconsidering what the next chapter should look like, I’d like to interview you for this series. Identities can be kept anonymous. You can reach me at jim@horizonlineadvisory.com.