Never Retire: Not a Smaller Life—Just a Different One
What readers from Brooklyn to South Africa are teaching me about aging well
The comments I received over the weekend on the last post—from Brooklyn to Switzerland to Madison—encouraged me. They hit exactly what I’ve always wanted Never Retire to be: a real community of people building second acts that actually work.
It’s not a philosophy so much as a reminder that life doesn’t end at retirement or a particular age. This life can happen abroad—or not. Never Retire is about staying vibrant and engaged at the very point when so many people start to complain, coast, and stagnate.
The people who subscribe here aren’t daydreamers or escapists. You’ve already done the work. You just want the next chapter to feel as deliberate as everything that came before it.
Olaf, from Switzerland, gearing up for a semi-retirement experiment in South Africa, reaffirmed what really matters when you change countries—not the sunshine or cheap wine, but structure. Finding a café, a few neighbors, a rhythm that makes you part of the place.
Kathi, preparing to move from Brooklyn to Spain, said it best:
Never Retire means I still have interests that engage me. I’m still out in the world—not having a smaller life, just a different one.
That’s the line. That’s the energy.
Kevin in Wisconsin described the kind of day I recognize right away—coffee with his wife, a few focused hours of work, a bike ride midday. That’s the shape of a life worth waking up for.
Reading all of this, it’s clear we’re all after the same thing: stability, autonomy, and purpose—but not as abstractions. As systems. Routines that make good days repeatable.
That’s exactly where I’m focused. Spain didn’t “fix” my life. Like many of you, I came from a good life in Los Angeles. Spain just gave me a better backdrop to test whether these ideas hold up against the real stuff—taxes, weather, money, feeling vibrant and alive, and the quiet what’s next? that never really goes away.
They hold up. But it takes work to make them last.
That’s what Wednesday’s paid post will dig into—what it actually looks like when your second act stops being an adjustment and starts being real life lived.The systems and rhythms that make this all sustainable.
If you’ve been following this journey for a while, now’s the perfect time to go deeper.
Never Retire has never been about quitting work. It’s about building a life that keeps paying off—emotionally, financially, and creatively—long after the hustle stops feeling romantic.
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Founding membership: one-time $100 (€90). Pay once. Never again.
My wife’s second act starting to take shape in the ceramics studio. She did this mug for a client!
A different life. I love that thought.
There is an old expression that it changes as good as a rest. As I pondered that this morning I realised that Won might want to articulate that in a more precise way. Namely that a change in location is as good as a rest. It would seem harder and perhaps less fulfilling to change things significantly exactly where you are today . So that speaks to moving somewhere else and discovering new things.