Welcome to the 55 Times Newsletter
Exploring the third phase of life
Last week I watched an SNL sketch about “Alexa Silver.” In it, the device’s main features are mediating arguments about room temperature and monitoring with precision what the neighborhood kids in the front yard are “up to.” (Alexa: “They’re just playing.”) I find it hilarious, maybe, because I saw something familiar.
There’s a subtle shift that happens as we age. A tendency toward crankiness. An impulse to monitor minor irritations with forensic precision. I’m 55 now, and I can feel the pull. Part of my motivation for starting this newsletter is to actively resist becoming that cantankerous old man. To maintain curiosity and generosity instead of succumbing to needless irritation.
The newsletter’s name came to me after my recent birthday. 55 Times. It brought back Sammy Hagar’s “I Can’t Drive 55,” which was everywhere when I was a new driver in high school. That age seemed impossibly distant then. Now here I am. The name also reflects my commitment to at least 55 weekly issues of the newsletter. We’ll see if I make it.
The Disorienting Part
It’s strange to look back on a career spanning over 30 years and realize that memories feeling relatively recent actually happened decades ago. When we’re younger, purpose seems clearer. Get into college. Do well. Get a job. Get promoted. Have kids. Build a family. For the most part, I’ve checked those boxes.
But purpose doesn’t end there. I still need to be a good husband, a decent father, a responsible son. Beyond those core commitments, though, I’m in new territory. My children have reached independence. The demanding years of practices, school runs, and constant presence are largely behind me. The time commitment has shifted dramatically.
Last Saturday morning I woke up with nowhere to drive anyone. No games. No events. No obligations requiring my presence. Just open time. I sat there for twenty minutes trying to remember what I used to do with Saturday mornings before kids. The feeling was simultaneously liberating and unsettling.
What Comes Next
For many of us, this period marks a transition. Retirement is close enough to merit serious attention. I’m looking forward to continuing productivity but also to greater independence and more time for personal projects. Health has become a bigger focus as I manage a few moderately serious conditions. These challenges, paradoxically, push me to think seriously about making Phase Three fruitful and productive rather than just comfortable.
I’ve been thinking a lot about Viktor Frankl’s Man’s Search for Meaning lately. The book centers on finding purpose, which feels especially relevant right now. Frankl observed that even in the most extreme circumstances, people who maintained a sense of purpose survived the concentration camps. Not always physically, but psychologically. That idea keeps surfacing for me.
What does purpose look like when the traditional markers are checked off? When your kids don’t need you at every soccer game? When your career trajectory has plateaued or concluded?
What to Expect Here
This newsletter will examine questions and choices around Phase Three. I’m thinking about personal finance (making the final push toward retirement and financial independence), personal growth and philosophy (what it means to be productive and useful in later years), productivity and technology (including observations on artificial intelligence), and family dynamics (what I’ve learned and what I might have done differently).
Some upcoming topics I’m planning:
I’ll dig into Frankl’s book and why it changed how I think about Monday mornings. I’ll look at “Your Money or Your Life” by Joe Dominguez and Vicki Robin, a personal finance cornerstone I keep revisiting. I’ll share what I’ve learned about frugal travel and credit card rewards, particularly for trips to Europe. I’ll discuss exercise and diet as they relate to energy and motivation. And I’ll examine other books and ideas that have shaped my thinking about this transition.
The goal isn’t to cover everything. It’s to be useful. To share honest reflections on navigating this phase as it happens, not after I’ve figured it all out.
Thanks for being here at the beginning.
Art V.
PS: If you’re in a similar life phase, I’d love to hear what you’re wrestling with. Send me a note and let me know what questions you are struggling with.