Retire by Degrees

As I think about my phased retirement and explore new activities, one idea that keeps coming up is serving on a paid board. I’d love to leverage the experience I’ve gained over the years—especially in areas like leadership, technology, and strategy. A friend of mine does this kind of work and recently gave me a few board profiles to review…

It’s summertime—the season of shorts and flip-flops, long hours of daylight, and a break from the usual routines. But soon enough, school will be back in session. For college students, that means new classes and freshly printed syllabi, each one a roadmap for the next four months. Assignments, deadlines, goals—all neatly laid out. It’s funny how, for much of life,…

If you’ve worked with financial planners or read books about your retirement finances (books like “Die With Zero,” by Bill Perkins that I’ve referenced here before) you’ve likely heard them talk about retirement in three distinct stages: But here’s the thing: you don’t know how long your Go-Go years will last. That’s why it’s so critical to think about and…

We often hear the question: What will they say about you when you’re gone? While legacy is important, perhaps the more pressing question is this: Who will you be when the meetings and emails stop? As you retire (or begin winding down from full-time work) and your calendar opens up and the calls for your expertise quiet down, how will…

“Take the Risk or Lose the Chance” I saw this on someone’s T-shirt on a train in Italy last week when I finally reserved some time for a 2-week vacation to explore Europe with my wife. It’s just a simple phrase—but even on vacation there can be unexpected insights that make us think and inspire us. This certainly did for…

For many senior leaders, retirement isn’t just a change in schedule – it’s a profound shift in their identity. Moving from the center of strategic decisions and organizational influence can feel disorienting, even diminishing. The end of an executive career often means stepping away from the very status, purpose, people and structure that defined daily life for decades. That’s why…