Never Retire: Doubt Is Part of the Process

You don’t need to be certain. You just need to keep going.

If you’ve been reading Never Retire and thinking, “This all sounds good—but what about the money meets life part?”… We have touched on it and more is coming.

In the next few posts, more focus on Never Retire’s roots:

🇺🇸 Why traditional retirement in the U.S. is about as impossible as it ever has been

🇪🇸 What I actually spend and earn

🇪🇸 How I deal with uncertainty, risk, and structure in midlife

🇺🇸And how to stop chasing a broken system and build something better

If you want real-life numbers, honest trade-offs, and a reset on what retirement could look like now—subscribe:

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Every post I write builds on the one that came before it and leads into what’s next. We’re building an arc that defines Never Retire practically and conceptually.

Every few days, I wonder if what I’m doing is working.

Mainly with my recent Never Retire trajectory and the various projects I have going.

While so much feels right—freelancing, living in Spain, not wanting to return to America, and, at 50, still pushing forward in ways that feel exciting—I tend to doubt myself at the same time as being hard on myself.

This can lead to a flavor of anxiety like I described earlier this week. It can annoy the people around you and take some of the joy out of the things you enjoy doing. If you don’t check yourself and keep it in check.

That doubt hits hardest when I’m in the middle of something I care about and feel strongly about.

Like this recent run of Never Retire posts. I’ve felt momentum. I’ve felt clarity. I’ve felt proud of the work. But then I hit “publish” and immediately think: Was that too self-serving? Too much about me? Am I helping anyone—or just writing to feel like I am?

Sometimes the doubt passes. Other times, it lingers.

I start second-guessing the way I am presenting Never Retire as a concept, a series, a rhythm. I worry it sounds too cringy, too guru. I don’t want that. That’s not me.

So I start rewriting in my head. Not necessarily the words (though sometimes!), but the purpose.

I remind myself: I’m not offering answers. I’m not trying to be a life coach. I’m just showing how I work, live, and move through the second act of life—honestly, imperfectly, and as clearly as I can.

And doubt is part of that. Probably an essential part. Without doubt like this, there’s no—or not enough—self-awareness.

So maybe it shouldn’t provoke anxiety. This doubt is a sign that I care?

The doubt is also a way to keep in check the urge to look ahead too far. For example—in life generally and when you’re living in a place on a residence permit that requires a specific level of income to be earned in a specific type of way—the financial unknowns enter the picture alongside the creative uncertainty. I wonder if I can meet my ultimate goal of only doing Never Retire and Friki de Bici someday and only selectively taking work with private clients.

That’s a pressure I feel, even when everything else feels aligned. Pressure I put on myself because that’s the scenario I want, not the one I need. The way I work today as a freelancer is the reason why we were able to make it to Spain and covers the cost of doing life.

But I love the Friki project. I love making videos for it. Riding around Valencia, telling stories, noticing things—that part excites me.

It earns nothing right now.

But building it—alongside writing Never Retire—takes time.

Effort. Mental bandwidth.

All for a future I believe in, but can’t predict.

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Uncertainty = Doubt

When we’re uncertain, we instinctively doubt ourselves. Maybe it’s a way to give ourselves an out. To logically say I’m not going to continue building something because it might fail. To rationally conclude that there are safer bets out there than the one you’re making.

But that’s the definition of a boring life. It’s the type of mindset where people talk about doing things, but rarely, if ever, follow through.

Just a steady question in the background: Is this working?

Most people don’t talk about it. Especially once they’ve made a big move—geographically, professionally, creatively. You're supposed to act like it was all meant to be. Like you’re certain. Like you knew what you were doing the whole time.

But that’s rarely true. Doubt follows any meaningful shift. Especially when the structure of your life depends on ideas, writing, rhythm, or long-term bets you can't fully measure yet.

You can feel proud of what you’ve made and still wonder if it’s resonating.

You can love what you’re building and still get tired, frustrated, or unsure of how it will all come together.

None of that means you’re doing it wrong. It just means you're doing something that matters.

The work that actually means something to you will always come with uncertainty, which will lead to doubt that will trigger anxiety. The key is to recognize the emotional pathway, acknowledge it, then get back to work and get on with the joys of doing a life worth living because you made bold choices to begin with.

I know that a lot of people who read Never Retire are in some phase of making a significant life change—maybe a move abroad, a career change, or both. Doubt will enter the picture at every step of the process. The way I nip it in the bud is to put it in perspective.

Would I be happy with myself if—at age 50—I stuck with the status quo? Because the status quo has a way of maintaining itself. Of inducing stagnation and creating ruts that are difficult to shake out of, especially at or around middle age. If you have a comfortable life, it can be tough to opt for some level of discomfort in the name of growth, evolution, adventure, excitement—whatever. Particularly if you consider yourself a logical and rational person.

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You Don’t Have to Be Certain. You Just Have to Keep Moving.

That’s what I’ve learned—over and over—through every period of doubt.

It’s not about solving your life like a math problem. It’s about stacking days that work. Doing what you want to be doing—in part, so you have no regrets—even when the payoff feels far away.

For me, that means riding around Valencia telling stories. It means writing these posts even when I’m not sure who’s reading. It means showing up for the parts of my life that don’t yet make money, but matter because I care about them!

That’s what makes it sustainable. And that’s what Never Retire is built on.

Not a rejection of work, but a refusal to let doubt or convention stop you from doing the work you actually want to do and living the life you want to live now and for the duration.

One of my latest Friki de Bici videos on YouTube