Never Retire: The Hidden Downside of Freelancing and Being Your Own Boss

There are two ways to be self-employed and work from home. I do both. But one is way better than the other.

My most important resource is time. If you support my livelihood as a freelance writer, you free up time I would normally dedicate to other paying work to focus on my newsletters.

I wrote that in the Never Retire newsletter the other day as I asked for your support to help launch my forthcoming Friki de Bici Substack. And thanks for the support. It feels great to see it coming in. Much appreciated! I am looking forward to sharing my plan for Friki de Bici (Bike Geek).

My wife and I have big ideas to make it more than a Substack. I will write up additional details about the project this week. But—to do everything I want to do with it—requires time. And—it’s not a cliche—but time is money.

This is one of the biggest challenges self-employed freelancers who work from home face—but rarely talk about. Maybe it's denial. We don’t want to admit that following our passion, doing what we love, and being our own boss can quickly lose their romantic shine.

In some ways, being self-employed can start to resemble the—dare I say—9-to-5 grind. To be clear—I am not complaining. I am in a great situation that I manage to keep in check. However, if you intend to go out on your own as part of a Never Retire strategy, ensure (A) you know what you’re getting into and (B) you’re able to keep things from sliding.

I bring this up because too many freelancers never consider this reality. Then, they act as if it’s not happening, simply by refusing to acknowledge it. They’re operating in much the same way they did when they were an employee.

An illustration of what I mean in a minute, using my work and latest project as an example.

But—yes, by all means—please help support Friki de Bici at whatever amount you can using the button below.

I already purchased the frikidebici.com domain.

I am about to get this thing off of the ground in March and April, before kicking it into high gear in May/June as part of our San Francisco/Barcelona/Paris/Amsterdam trip with our daughters.

A paid subscription to the Never Retire newsletter does the same trick. As we continue to blend how life really is on the ground in Spain with discussions on how to Never Retire. Whatever that means to you and in your situation. For me, it absolutely means doing work I love—following my passions—at the same time as trying to not spend too much time on the more formal work tasks that—at the moment—pay the bills.

So—no doubt—it’s a familiar cycle. The 9-to-5 employee looking for a way out so they can do what they love. How is this any different from what happened to me on Sunday morning? Even if on a smaller, much easier-to-swallow scale.