What Nobody Told Me About Monday

Richard retired three years ago after a long career running a regional services business. He describes the first Monday clearly.

“I woke up at 5:45 because that’s what my body does. Made coffee. Sat at the kitchen table. And around 7:30 I realized nobody needed anything from me. Not one person.”

How did that feel?

“Like a vacation for about three weeks. Then like something was wrong with me.”

I asked what surprised him most.

“How much of my identity came from my calendar. My calendar was telling me who I was, and I didn’t know it. When it went blank, I didn’t have an answer.”

He talked about the small moments. Being introduced at a dinner party and not knowing what to say after his name. Offering an opinion at his kid’s house and realizing nobody was taking notes. Watching his wife, who had built her own daily rhythm over thirty years, adjust to having him home all day.

“She was patient. But she had a life that worked, and I walked into the middle of it.”

What replaced the work?

“Some things did. I joined a nonprofit board. I’m mentoring a couple of younger people. I golf more than I thought I would. But the thing that didn’t get replaced was the sense of building something. Of a problem I owned that I could see move.”

We talked about that loss specifically, because I think it’s the one executives underestimate most. Board seats and mentoring offer contribution, but often not ownership. For someone who spent decades accountable for results, advising from the side can feel thin.

“It took me a year to figure out I needed a project, not a role,” he said. “Something with a finish line that was mine.”

For Richard, that turned out to be helping a small local organization rebuild its operations from the ground up. Unpaid, time-limited, and entirely his to deliver.

I asked what he’d tell himself two years before retiring.

“Figure out what you’re actually going to do on Tuesday. Not ‘travel’ or ‘spend time with the grandkids.’ Tuesday. Write it down. If you can’t, you’re not ready yet, no matter what the spreadsheet says.”

Richard is doing well now, and he’d say so himself. But the adjustment took longer than he expected, and he thinks it could have gone faster with more deliberate preparation on the parts no one plans for.

What I took from this

Retirement planning is usually thorough on the financial side and thin on everything else: structure, purpose, identity, the dynamics at home. The executives who land well tend to treat those questions with the same seriousness they gave the money. Richard’s advice about Tuesday is the most practical thing I’ve heard on the subject.

I want to hear the real version of this story. If you’ve retired from a senior role in the past several years and are willing to talk honestly about the transition, I’d like to interview you for this series. Identities can be kept anonymous. You can reach me at jim@horizonlineadvisory.com.