Retire by Degrees

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 […]

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 […]

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 […]

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 […]

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’ […]

How are you doing with your New Year’s resolutions from just a few weeks ago? Often the goals we set at the beginning of a year are ambitious, but then they fall by the wayside. In a recent Wall Street Journal article, Ron Shaich, billionaire entrepreneur and investor, offered a more practical alternative: the “premortem.” […]

Yes, there’s really such a thing as coaches for your retirement – and there are even multiple certifications for professional coaches.  What do these retirement coaches offer? Retirement coaches help you navigate the transition from work to retirement by addressing both practical and emotional aspects. They assist their clients in clarifying goals, finding purpose, and […]

Throughout my career in information technology, I’ve witnessed the rise of Agile software development practices, emphasizing flexibility and iterative progress. These replace older approaches where a complex, multi-year project was planned out in detail…but those efforts were rarely successful…requirements changed, people changed and there were many things we learned along the way. I realized that […]