I Retired, Now What? Take a Running Assessment, Of Course

Paul Yee
6 min readJul 21, 2023

Last month, after more than two decades in corporate finance, I closed the books for the final time. I hung up the spreadsheets. I retired.

An unexplored world awaits

At age 50, I have many years left to live, and now, thanks to my stubborn frugality and a whole lot of luck, I can spend them doing things that give me joy. I haven’t felt this much anticipation since my wife was pregnant with our first child (who last time I checked can now legally drink). As I peer over the edge of our soon-empty nest, a vast world beckons below.

Despite the fastidious planning that got me to this point, I find myself ill-prepared. I thrive on structure: in my world, everything has its place, and I chase down errant items and return them to their proper cubbies. Not surprisingly, I spent my first few days of retirement ripping through our “honey-do” task list. Reorganizing cabinets, however, can only eat up so much time, and I quickly depleted the ways to deplete my energy. I started to feel like how my calendar looked: empty.

Of course, as my logical side is quick to note, that’s the whole point. “Retiring” shouldn’t mean “tiring again.” It’s instead an opportunity to decelerate, undergo a factory reset, and enjoy a fully refurbished life of your choosing. A mentor advised me to wait at least six months before making any new major…

--

--