Never Retire: The Case for Light Work in Midlife
Because someday, even the doubt will seem funny.
I wrote my first Never Retire post on Substack four years ago this week. Back then, I didn’t know what shape this would take. I only knew that I wanted to share what it means to avoid stagnation and keep moving in midlife, particularly when you know you’ll Never Retire.
A lot has changed since 2021—me, my life, and this project. We’re nine months into our move to Spain and every single day I’m equally as grateful to be living here as I am humbled. Big life shifts like this naturally force a change in focus and perspective.
Evolving the project
As the philosophy behind Never Retire has evolved, so must the newsletter. I spent a long time proving that many of us are better off embracing the reality that we’ll Never Retire. I spent an equal amount of time chronicling the preparation for and settling in phases of my second act of life in Spain.
The shift to living abroad has given me a new lens. Today, I think of these posts as field notes—real-time snapshots of living abroad in Spain at 50. I pair them with numbers, routines, and trade-offs that make day-to-day life work and—bigger picture—keep you eager, enthusiastic, and engaged. These are the small observations that now feel most vital and helpful.
This week’s field note is about the power of making your work light.
I’m closing out my biggest month ever with my main freelance client. It’s steady and I’m grateful. But I know my real, long-term goal: to make the work I do for myself—Never Retire, Friki de Bici—my main income stream. Why? Because that work is more in my control. And, crucially, it’s more fun.
Take Friki de Bici: my next video is me riding three hours, only making left turns, never repeating a block. On paper? Pointless. In practice? It’s the kind of work that contributes to something bigger—a resilient body of work and a softer, freer life.
That’s the paradox of light work: it looks small, even silly, but it’s often the spark that scales. When you see it producing small wins—evidence that it can pay off—you realize how much control you actually have over your own trajectory.
I built a freelance writing career from nothing and established a presence on Medium, so it’s not too crazy to think I can take Never Retire to the next level and grow Friki de Bici into something out of nothing more than a bike and an idea. Someday, you’ll look back on any self-doubt you had today and—in the words of Bruce Springsteen, still on stage and constantly creating at 76—it will all seem funny.
And I see it in others, too—writers like Kevin Alexander, who works for an airline and shows up to write about music, or creators who carve out time for side projects that eventually become their main thing. Their light work isn’t a hobby, it’s the seed of something that compounds. It’s the work that gives you visibility into what your engaged second act can look like.
That’s the essential tension most of us feel: the work that pays vs. the work that pulls. The challenge isn’t abandoning the steady paycheck, it’s figuring out how to keep that foundation without letting it smother the spark—the light work—that actually makes you feel alive.
Because “light” doesn’t mean frivolous. Light work is what keeps you positive when everything else feels like a bit of a pain in the ass (even though you know you’re lucky to have it). Light work not only lets you build something lasting, but it provides a glimpse of what it might look like to stay engaged—accelerating fresh, new projects—right when other people your age are starting to slow down.
From this perspective, traditional retirement looks like a bad idea.
The question, then, isn’t whether you should chase light work. It’s when will you be ready to transition. To make that light work your full-time gig—whatever that looks like for you.
For me, the biggest roadblock is patience—trusting that the time for the next transition will come. Just like the move to Spain, which felt so far away until it suddenly wasn’t.
That’s the thing about the work you’re most excited and passionate about: you do it long enough, and one day, it stops being just your “passion project.” It becomes the foundation.
Next Field Note
Light work doesn’t just stay light. Do it long enough and it becomes the foundation.
In the next post, I’ll share how my freelance writing career started as a side experiment, took detours that looked pointless at the time, and eventually built into a sustainable living—and how you can spot the same potential in your own “light work.”
