Never Retire: How I Track Time Without the Guilt—And Still Get Paid

It’s not about productivity. It’s about sanity.

In the last Never Retire newsletter story, I talked about how movement—not motivation—keeps my days alive.

Never Retire: Movement Over Motivation

But here’s the question I think makes it difficult for people to understand how I work that I sometimes even wrestle with:

If I’m not time-blocking or planning every hour of my day… how do I know I’m actually getting anything done?

What happens on the front end before the results.

I plan my day—just not officially. And I casually track what happens—though “casually” might be misleading if you’re not naturally organized like I am.

Compared to how I used to operate—when I routinely worked 12-hour days and internalized the myth that the more I worked, the more valuable I was as a human—my current structure feels loose.

But this looseness is a necessary element of my day-to-day. It’s what keeps me out of the shame spiral of what didn’t happen.

I underpromise to myself. Then I either deliver—or overdeliver—on the actual work that needs to get done to maintain a solid flow and consistent income.

The big shift?

I reflect more than I plan. I think at the end of the day, not just the beginning. And that habit lets patterns emerge—and tasks get done—without a ton of pressure.

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How I Actually Track Time

This is simple, but it works.

I use to-do lists. Mostly, my to-do list reflects what I need to earn that day—or over the next few—to hit my monthly goal.

I have the advantage of—

• Getting paid a set rate per article

• Having a good sense of how much I will earn—on average—for stuff without fixed payments

• Building stuff where I’m not getting paid or making very little right now

Most days I will start work in the morning, knock out one or two stories and say to myself (or my wife)—fantastic, I made $XXX today. We don’t make our bed in the morning, but this is my equivalent of that day starter life coaches (still?) love.

Repeat this four to six days a week—we’re talking around 15 hours per week—and I have made what I need to make to be more than comfortable financially for the month with an eye on, but not obsessed with longer-term goals.

The rest of the day is gravy or time to do whatever I want. Which, more often than not, includes some work in the afternoon.

But sometimes that’s (also) the supermarket-market-bakery circuit. Sometimes that’s (also) sitting at a cafe for coffee and something to eat. Sometimes that’s (also) a bike ride—short or long.

Sometimes that’s all of the above.

Sometimes that’s blowing all or part of the day off.

Depends.

If you work doesn’t allow for this type of structure or income, you can tweak it.

We—or American culture at least—doesn’t like to talk about the reality that our workday is mostly made up of not working. It’s actually made up of the stuff that matters—fucking off, socializing with other people, walking aimlessly, drinking coffee, eating (hopefully, a slow) lunch, doodling, working on what you really want to be working on.

Office work is usually total bullshit—a lame ass dance between managers and workers who hide the reality that they’re both half-assing the day from one another.

If only we formalized that just a little. Rather than acting like we’re working when we’re blowing off work, wouldn’t it be nice to know going in that—

• I can fulfill my obligation in X amount of time, not get fired or lose a client, and earn what I need to survive and thrive.

• Then use the rest of the time to work on shit I really want to be working on. Myself. My real passion. The things I actually want to be doing to make money. Plans to move or make some other major life change. Whatever.

I can see how this might look as a 9-to-5 office worker (I once was myself), hourly worker, therapist, you name it.

The question is—can you?

That’s not rhetorical.

I genuinely wonder how transferable this is. Am I in my own little world here—or is there something useful in the way I work that you can adapt to your own situation?

You might not get paid per article. You might work fixed hours or punch a clock. But I bet there’s still space in your day that could be reclaimed. Maybe not all at once, and maybe not every day—but enough to matter.

And if you can’t see that space yet, maybe tracking your time—not planning it—helps you find it.

Because that’s really the point here.

I don’t track time to optimize for productivity. I track time to stay on track and good with myself. To notice what’s working. To remind myself that, yes, I did do something today. Maybe even a few things.

And when you string a bunch of those “I did something” days together, it turns into a life that actually works. It turns into a rhythm supported in a big way by where I live and what I choose to do with my life. What I chose to do some time ago.

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Why This Works Better

It’s not just the system I use. It’s the life I’ve built around it.

I live in a place—Valencia, Spain—where the rhythm of the day isn’t built around the grind. Where errands can double as a walk. Where I don’t need a car. Where people take their time in cafés and at the market and nobody cares if you’re being productive.

That matters. A lot.

But more than anything, I’ve designed a life that supports the work I want to do—and just as importantly, the way I want to do it. With room to move, to reset, to reflect. With the ability to adjust if I need a minute or a day.

That’s the part I want you to take from this.

Not the details of my structure, but the reality that you can build your own.

It might start with five minutes a day to track what you actually did. It might mean blocking one afternoon a week to work on something you actually care about. It might just be admitting that you’re burned out on overplanning and want to try something different.

It doesn’t have to happen abroad. But for me, living here gave me just enough distance to realize that most of what I thought was necessary… wasn’t. I started this in Los Angeles, and now—turning 50 this week—I’m in the (hopefully long) process of continuing it in Spain.

Thanks for reading.

If you're new here from a gifted sub or just checking Never Retire out, welcome.

I write about what it actually takes to make work and life fit together—especially when you're trying to do things differently. If you like this rhythm, stick around.