Useful, but not okay.

On learning that I'm okay, even when I'm not being useful.

Jan 08, 2026

Welcome to issue #050 of Unsubscribe. Each week, I send one essay that helps you step off the default path to build a life you love, supported by work you enjoy.

Every day, I block off noon to 3 p.m. for deep work.

Three hours with no meetings, no calls, no distractions. And most days, I finish everything I need to do in about two hours, which means I have an hour of empty time just sitting there on my calendar.

You’d think I’d enjoy that. But instead, I feel this pull. This urge to grab tomorrow’s tasks and drag them into today.

The logic sounds reasonable in my head: if I can pull Tuesday’s work into Monday, and Wednesday’s into Tuesday, then I’ll create this glorious five-day weekend stretching out in front of me. Wednesday, Thursday, Friday, Saturday, Sunday. Pure open time with nothing hanging over me.

But here’s what actually happens: I never stop pulling. I finish today’s work, pull in tomorrow’s. Finish that, pull in the next day’s. The open time I’m chasing never actually comes because I keep dragging the future into the present and filling it before I get there.

I’ve done this for years. I’m working on it, and I’ve gotten significantly better. Most Fridays now, I don’t work at all. But recently, something happened that made me realize this isn’t really about productivity or time management or discipline.

It’s about something deeper that I’ve never fully examined.

Last week, I got the flu. And for maybe the second or third time since Jennifer and I got together 14 years ago, I took a nap in the middle of the day. I was just completely exhausted, so I lay down and slept for two hours and fifteen minutes.

When I woke up, she told me two things that have been rattling around in my head ever since.

First, she said it was the first time she could remember in a decade that I had taken a nap. A decade. I’ve gone an entire decade without sleeping in the middle of the day, and I never really noticed until she pointed it out.

Second, she said she didn’t know whether to wake me up. She knew I needed the sleep, but she also knew I’d probably be irritated with myself for “wasting” part of the day. Because apparently I talk about that a lot.

I had to really sit with that for a second. I was sick. I had the flu. My body desperately needed rest. And my wife had to genuinely debate whether letting me sleep would make me angry at myself.

That’s when I started to realize something might be off about how I relate to rest and productivity and my own sense of worth.

I’ve been thinking about this constantly since it happened. Not just the nap thing, but all of it. The pulling work forward. The inability to sit with open time. The low-grade guilt I feel whenever I’m not producing something.

And I’ve started paying attention to what happens in my mind and body when I try to do nothing.

I feel antsy. Unsettled. I look at open time and freeze. What do I do with this? How should I spend it? What’s the right choice? And when I freeze like that, when the openness becomes overwhelming, I retreat back to what’s comfortable. And what’s comfortable is generally work.

Work has rules. Work has a finish line. Work gives me that small hit of completion that my brain has learned to crave. Doing nothing has no finish line, and I think that’s what terrifies me about it.

I keep coming back to the same memory. July 11th, 1995. The day I turned 14, my father dropped me off at the McDonald’s in Chesterland, Ohio, and told me it was time to get a job. I’ve worked nearly every day since. By 16, I was a manager at Burger King, wearing a shirt and tie, managing men and women three and four times my age. I remember how proud my parents were of that.

By 19, I snuck into a career fair for Ohio State graduates while I was still a sophomore and somehow landed two job offers from companies that thought I was about to graduate. I had to go back and tell them I still had two years left. One of them hired me anyway when I finally graduated.

Achievement was what got me praised. Output was what made people proud of me. Being useful was what made me feel like I mattered. And I learned those lessons early.

But there’s another piece to this that I don’t talk about much.

I was overweight as a kid. Uncool. Picked on constantly in middle school and into my freshman and sophomore years of high school. I got beaten up a lot. There was one kid, Mike, who waited for me outside of math class and punched me in the stomach every single day in front of all the other kids.

When I got older and learned to stand up for myself, I started looking for ways to feel secure and important and worthy of respect. Some kids had athletic ability. Some had social status or good looks or whatever else made you cool in high school. I had achievement.

So I leaned into it. Hard. It became more than just a strategy for getting ahead. It became a chip on my shoulder, a way to prove that I mattered, a way to make sure nobody could ever make me feel small again.

And somewhere along the way, I think I started believing that I’m only okay if I’m being useful.

Jennifer is different from me in this way, and I notice it all the time.

She’s content naturally. She looks around at our life, at our three dogs, our house, and our financial security, and she just feels grateful. That’s her default state. She doesn’t have to do anything to feel okay. She is just okay.

My default state has always been restless. Searching for the next thing that will finally make me feel like I’ve done enough. I’m 44 years old. I’ve built a business I’m proud of. I have zero debt and more financial security than I ever imagined I’d have. And for most of my adult life, I’ve still felt like I had to keep producing to deserve any of it.

But something has started to shift.

I used to think I had a productivity problem. That I needed better boundaries, or better systems, or more discipline around rest. But once I realized it was never really about productivity, and was actually about permission, things started to change.

I never gave myself permission to just exist without producing something. I never believed I was allowed to rest without earning it first. I combined my output with my “okay-ness” so completely that I didn’t know where one ended and the other began.

Now that I can see it, I can work on it. And I have been.

Last year, Jennifer and I went on what we thought would be a short hike at Minnewaska State Park. We got a little lost and ended up being gone for about six and a half hours, just wandering around, finding new paths and waterfalls and rock formations, with no real plan or destination.

It didn’t feel like a waste. It felt like one of the best days I’d had in years. I didn’t produce anything. I didn’t check anything off. I just existed out there in the woods with Jennifer, and I felt completely okay.

That was the first time I realized the voice in my head might be wrong.

Since then, I’ve been collecting more moments like that. I’ve gotten better at noticing when the pull to be productive is actually just discomfort with being still. I’ve started letting empty hours stay empty instead of filling them with tomorrow’s work. Most Fridays, I do absolutely nothing, and I don’t feel guilty about it anymore.

But just yesterday, I caught myself doing it again. I finished my work by 1 p.m. and had two completely open hours. And within five minutes, I was pulling Thursday’s tasks into Wednesday. The old pattern was running on autopilot. But I stopped myself this time, closed my laptop, and went out for coffee. But the urge was there, just as strong as ever.

I’m not going to tell you the voice is gone, because it isn’t. I still catch myself pulling work forward. I still feel that twinge when I sit still for too long. But the voice is a lot quieter now. And when it speaks up, I recognize it for what it is: an old belief that helped me survive when I was younger but doesn’t serve me anymore.

I’m learning that I don’t have to earn my okay-ness. I can just have it.

Jennifer’s known this her whole life. It took me about 44 years to start figuring it out. But I’m getting there.

And if you’re someone who’s spent your whole life believing that your worth comes from your output, I want you to know that you can unlearn it too. It’s not easy, and it doesn’t happen overnight, but it starts with noticing.

Once you see the pattern, you can interrupt it. And once you interrupt it enough times, it starts to lose its grip on you.

So here’s what I’m wondering this week.

When you’re not being useful to anyone, when you’re not producing or achieving or checking something off a list, when you’re just sitting there existing without having earned it first, do you feel like you’re allowed to be there?

And if the answer is no, what would it take to change that?

Leave a comment and tell me. I read every response.

I appreciate your time.

When you’re not being useful to anyone, when you’re just sitting there existing without having earned it first, do you feel like you’re allowed to be there?

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