Retire by Degrees

Something can look simple from the outside, but the experience often turns out a little different than expected. Take riding in a Waymo. You open the app, summon a driverless car, and hop in. Sounds straightforward enough. But then you have to figure out which car is yours when it arrives & what the exact pick-up location is, how to…

I was catching up with my friend Dave the other night. He’s been retired for about three years, a little ahead of many of our friends who are just starting to think about their own timelines. Later he sent me something that’s taken shape for him over these first few years — a Retirement Hierarchy of Needs. He’s realized that…

I’ve talked with a surprising number of people who know exactly how many days remain until their retirement. “415 days.” “Just two more years.” “I’ve got a countdown app on my phone.” I always smile because I remember doing the exact same thing—but not for retirement. For Christmas! When I was a young child growing up in Iowa, Christmas seemed…

Many people approaching retirement tell me they feel overwhelmed by artificial intelligence (AI). The concern often sounds like: “I’ve spent decades building my career. Now AI is changing everything. Do I really want to learn another major technology at this stage?” It’s a fair question — but it’s also a moment to rethink what this stage of life is really…

I’ve been writing about the topic of phased retirement for more than three years now. During that time, I’ve explored the practical side of retirement planning, the emotional side of stepping away from a career, and the reality that retirement doesn’t have to be an on/off switch. It can be gradual. Intentional. Personal. It can come in many flavors. Last…