Category: Retire Slowly

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…

No, that’s not a typo in today’s headline. I want to contrast decision-making with how we choose to live with our decisions. If you’re over 50, you’ve likely faced many crossroads where big decisions required careful thought. Whether it’s choosing a new career, retiring in a new city, or downsizing your home, the act of making the decision often feels…

When we hear the word “wealth,” our minds often jump straight to our investment accounts. While financial security is undoubtedly important, it’s just one piece of a larger puzzle. This idea is explored in the book “Die With Zero,” by Bill Perkins, which emphasizes the importance of spending down your financial wealth to maximize life experiences. He argues that there’s…

When I finish a big event, like a half marathon, I find myself in a bit of a post-race slump. After weeks or months of training, the race comes and goes, and suddenly I’m left wondering: what now? It’s tough to get back into the groove after achieving a goal like that. The motivation isn’t as strong, and I’m not…

Today I’d like to take a bit of a pause from writing about approaches to retirement and reflect a bit on the opportunities we have whether we’re working full-time, part-time or not currently working in the traditional sense. It strikes me that the question, “Why me?” is often asked in times of hardship, ‘bad luck’ or bad news.  When we…