Never Retire: When Stability Starts to Scare You
How to stop treating peace like a jinx—and trust the life you built to keep working.
Last week, in When Your Dream Becomes Your Routine, I wrote about what happens when your big plan finally works—when you find yourself living the life you envisioned, and the dream becomes the day-to-day.
That post was about rhythm and structure. About how maintenance—when done right—can provide anxiety relief and even a sense of satisfaction. Maybe you have done something others only dream or talk about. So, in one respect, you absolutely should take a bow.
But that’s not the whole picture.
Because right next to that satisfaction lives something quieter and darker: the fear that the minute you start enjoying it, you’ll lose it.
That’s what we’ll look at today—the tension between gratitude and vigilance.
The way success itself can start to feel fragile.
The Anxiety of Arrival
Maybe you can relate, but I have been like this all of my life.
I get really into something worthwhile. Then I work really hard setting goals and laying the groundwork to reach them. I research, study, and plan. Then execute. It all goes off with barely a hitch. Of course, there are obstacles and tradeoffs made, but I end up where I want to be. Then, once I get there, the focus shifts to staying there (or better) and generates an only slightly different flavor of anxiety.
I can trace this behavior to when I was a child. I started working in radio when I was 13—in 1988. I spent the years leading up to that first gig at my hometown station doing things to make it happen. Calling the morning show each day to make a name for myself. Then, working with the Sunday night host—for free—to really get my foot in the door.
Once I completed what turned out to be part one, I spent my time trying to get a gig in the bigger city next to mine. Four years later, I got that gig—in Buffalo. And I immediately set the goal of getting a job in a different city as soon as possible out of high school. Before I turned 20—in 1995—I was on the road to do nights in Miami, where the process repeated itself.
Ever since—in myriad contexts—I have gone through similar, if not the same process. Thirty years of visioning where I want to be and not only dreaming about it, but doing what needed to be done to get there.
Ten months into what has been a wildly successful move to Spain, I find myself there again.
I wanted to turn 50 here. Did that. Now, the anxiety reappears. I hesitate to call it a successful move out of some irrational fear of jinxing it. And I have come to realize that, for me, the hardest part of stability isn’t managing it. It’s believing in it.
This is what Never Retire is really about—living inside the thing you worked so hard to build without letting fear, anxiety, and your penchant for keeping it all together run the show.
If this kind of reflection helps you navigate your own “after the arrival” moment, consider becoming a paid subscriber. You’ll get the rest of this post—(which includes photos from our trip to Rome)—and future deep dives into how to make stability last. Founding memberships—$100 or €90—get immediately converted into lifetime subscriptions.