He Could Have Already Retired

It was around lunchtime on a Thursday when the email came through marked confidential. A colleague of mine who led another degree program in my department was leaving after five years.

I opened it and paused. When someone leaves, my mind usually runs through the same few options. A better offer somewhere else, something that didn’t work out, or something that had been building quietly for longer than anyone realized.

But as I kept reading, it became straightforward. He was taking a new role closer to home and on paper it made complete sense.

And still, something about it didn’t sit right with me.

Over the past few years, I had watched him build something from the ground up. An online degree program shaped by decades of executive experience and a real ability to teach what he knew. It wasn’t just the output that stood out, but how much range the work required. Teaching, building connections, learning AI tools, working through accreditation. All of it happening at once and without all the fanfare.

During one of our department meetings, I remember saying out loud how hard he was working, well into the years most people start pulling back. He shrugged and kept moving.

A few days later, we met to talk through his departure and the question I had been wanting to ask him came out a little more directly than I intended.

Why are you still working this hard when you don’t have to?

There was no “I just need something to keep me busy.” He said he believed he could still make a difference by educating the next group of healthcare leaders. After all these years, the problem still had his attention. And more than that, the work still felt like it was going somewhere.

I didn’t have much to say after that. I just sat there and listened.

At that stage in life most people start choosing less. Fewer commitments, a lighter schedule and a gradual shift toward protecting what they’ve already built. The math makes sense, and no one really questions it.

What I was witnessing felt different.

He was choosing more. Not because he had to, but because something in the work still pulled at him. From what I could tell, the financial side was settled, and the reputation was already there. There was nothing left to prove to anyone.

I really think there’s a difference between someone who is still working hard and someone who is still moving toward something.

I’ve seen both. I’ve sat in the meetings where everything looked productive on paper. The work was getting done, the calendar was full, and nothing obvious was falling behind. But if you stayed with it long enough, you could feel something change. The work hadn’t stopped, but it had quietly turned into something being maintained rather than built.

He wasn’t doing that.

A few years ago, I had a clear direction. I was moving toward a pathway in institutional leadership, and I could see what the next chapter was supposed to look like.

Then the pandemic came and pulled that plan apart in ways I didn’t fully appreciate at the time. Six years later, I’m still deciding what I’m actually moving toward instead.

This kind of uncertainty doesn’t show up all at once. It just stays with you across enough Monday mornings that you start to question whether the pull you used to feel was real, or whether you just got good at following through on what was already in front of you.

I’ve been thinking about this for a while.

On most mornings I’m up early before anything else starts. It’s quiet, and I’ll spend that time writing or thinking through the same problem I haven’t quite landed on yet. Something there still matters, even if I can’t fully name it yet.

In one of our final conversations the topic shifted to a book I’ve been meaning to write for a few years. Since he had already done it, I paid close attention.

“Start with the problem. Be clear about who it affects. Then show how you would actually work through it.”

Then he paused.

I didn’t need more ideas. What I needed was to decide what problem I was willing to stay with for the next few years. He said it like it was obvious. It probably was.

Simple enough to hear. Harder when you’re still figuring out what that problem truly is.

From what I’ve seen, it’s rarely a lack of ability that pulls things off track. Everything else just fills in around it too quickly.

Responsibilities expand, the calendar fills, and the work that needs getting done shows up faster than the work that requires real thinking. The urgent thing wins on any given Tuesday, and the other work waits another week.

I think you know the kind of work I mean. The kind of work that asks more of you, carries no immediate deadline, and won’t create a visible problem if it gets pushed again. Except it keeps getting pushed, and at some point pushing becomes the pattern.

Eventually you look at your calendar and realize most of what’s there is something you’re managing rather than building toward. Meetings you’ve run a hundred times, problems you’ve already solved, work that moves without much resistance. There’s a steadiness to that and for a while it genuinely feels like progress.

After enough time it starts to feel like you’re just keeping something in place.

The people who still feel a real pull in their work ten or fifteen years in don’t seem to have found the perfect path early and stayed on it. From what I can tell they just kept choosing to stay engaged with something that’s important, even when the role stopped requiring it and the calendar never made it easy. They kept coming back to it when most people quietly moved on.

Watching my colleague take that new role didn’t land the way I expected. Unsettling was probably closer to the truth, which turned out to be the more useful response. It made me ask whether the work I’ve been maintaining was starting to overtake the parts that could still move me somewhere.

Look at your calendar this week. Find one commitment that feels like maintenance and one that still feels like motion. If the second one isn’t there, that’s probably the thing worth paying attention to.

When did your work stop feeling like somewhere you were going and start feeling like something you were managing?

And do you remember deciding that or did it just slowly happen over time?

If someone came to mind while you were reading this, feel free to pass it along.

Until next time.