Never Retire: When Your Dream Becomes Your Routine
The quiet challenge of staying content when the plan actually worked.
After nearly three years of planning and another ten months of settling in, we’re here in Spain.
People love to say they’re thinking about moving here. They talk about sunshine, food, slower life. But most don’t have a path—and few realize how much work it takes to actually do it. Sometimes my wife and I stop and say we’re proud of what we’ve done.
We should be.
But—
Mission accomplished? Not quite.
Like with anything big you’re trying to do in life, you never really arrive. At least, I don’t think most people who read this newsletter just want to hang up their cleats and call it a day. We have more Bruce Springsteens in this group than lobsters on the beach.
I’ve always envisioned Never Retire to be a project where you and I—together with this community—brainstorm and evaluate ways to still be putting on our version of three-hour rock and roll shows at age 75.
Or something like that.
So let’s keep figuring out what you’ve got going, where you’re headed, and how it all fits inside this broader context.
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To start, it’s important to talk about something you don’t hear discussed too often.
When you’re finally living the thing you imagined—the life you planned and fought for—a shift happens. At first it’s all new and clumsy. You build new routines from scratch: when to shop, where to go, how to speak, how to rest.
Once those routines settle in, another kind of work begins—keeping them steady without letting them become a grind. Even good lives need maintenance. Even dreams generate admin. There’s stress in protecting something you’ve built—the kind that comes from success, not scarcity.
I am living that moment as we speak.
I’m thrilled to be here—happy that we executed our plan—but I spend time working and some time stressing to ensure we keep it rolling. This second act of life is giving us just what we expected—a much higher quality of life than what was possible in the United States. We live it every single day. But this doesn’t mean we’re suddenly different people who no longer have to pay attention to keeping a good thing going.
Some things that seem—and can be—so simple require thought and organization to sustain.
For example,
captured that balance many of us want to strike in one line that stuck with me:Coffee with my wife, a few focused hours of work, a bike ride midday… another shorter session after.
That’s where he said he wants to be—focusing on his music writing after retiring from his full-time job in a couple of years.
That’s not fantasy. That’s function—the pattern you reach when the experiment starts working and you’re responsible for keeping it alive.
My version looks slightly different but feels the same.
When the dream becomes your routine, the real task isn’t chasing change—it’s sustaining meaning. You’re running a better show maybe, possibly in a better environment, but it’s still a show.
Springsteen still sweats through the setlist. He’s still giving the crowd everything he’s got—just with fifty more years of road behind him.
That’s what Never Retire looks like in practice: purpose with pacing. The goal isn’t to work less; it’s to work in a way that lets everything else happen.
That’s what I hear in Kevin’s version too—not mindless ambition, but integration. The structure of a life that can absorb the stress of success without collapsing under it.
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I want to go deeper into what happens after the first year—what stability actually looks like once the adrenaline wears off. Because you shouldn’t have a honeymoon period.
Honeymoon periods are for the ill-prepared. They’re built on novelty, not understanding.
Olaf’s story from Switzerland and Kathi’s move from Brooklyn say it all: structure replaces novelty, and expression keeps the whole thing alive.