At Least My Old Boss Went Home at 6

It's 10:47pm on a Tuesday. I'm at my desk, still working.

Nobody asked me to be here. No boss is watching. No deadline is breathing down my neck. I could stop anytime.

And yet here I am, berating myself for not getting more done today. Wondering why I wasted twenty minutes at lunch. Planning to wake up earlier tomorrow to make up for it.

I fired my boss three years ago. Then I became one. A worse one.

The Monster Over Your Shoulder

When I worked for someone else, the enemy was clear. The micromanager. The unreasonable deadlines. The performance reviews that felt like interrogations.

I dreamed of freedom. Of working for myself. Of finally being able to set my own hours, my own pace, my own definition of "enough."

What nobody told me: the monster doesn't disappear when you leave. It just moves inside.

The voice that used to come from the corner office? It lives in my head now. And it doesn't have office hours. It doesn't take vacation. It follows me into the shower, into dinner, into 3am when I can't sleep because I'm mentally rewriting tomorrow's to-do list.

At least my old boss went home at 6.

Where This Shows Up

In writing: I'm finally free to write what I want. No editor dictating topics. No corporate messaging to parrot. Pure creative freedom.

So why do I berate myself for not writing enough? Not writing well enough? Not writing fast enough? I hit my word count and immediately think: that's it? I take a day off and feel guilty by noon. I became the unreasonable editor I always complained about.

In business: I escaped the 9-to-5 for freedom. No more punching clocks. No more asking permission. I can work whenever I want.

So I work 6am to midnight. I check email at my kid's soccer game. I take calls on vacation. I call it passion. I call it ownership. I call it everything except what it is: a worse job than the one I left, with a boss who never lets me clock out.

In life: There's no separation anymore. No weekend that's actually a weekend. No "done for the day" because the day never ends. The pursuit has no finish line because I keep moving it. Hit the goal? Raise the goal. Reach the milestone? There's another one right behind it.

I wanted freedom from external demands. I got freedom to demand infinitely more of myself.

Why the Internal Boss Is Worse

The external boss had limits.

There were labor laws. There was HR. There was the simple fact that they couldn't follow you home. At some point, you could close the laptop, leave the building, and be done. Even if you hated the work, you got evenings. Weekends. The blessed separation of "work" and "not work."

The internal boss has no such limits.

It knows your passwords. It knows your schedule. It knows exactly which insecurities to press. It can demand more at any hour because it lives in the same head you do.

And the worst part? It disguises itself as ambition.

You think you're being driven. You think you're being disciplined. You're just being tyrannized by yourself.

The Question I Keep Sitting With

How do you enjoy the work when you're also the one demanding more of it?

I don't have a clean answer. But I'm starting to notice something.

The external boss had boundaries because the structure forced them. Clock-in times. Clock-out times. Clear delineation of when work started and stopped.

The internal boss has no boundaries because I never built them. I tore down the external structure and replaced it with... nothing. Just open space that the internal boss was happy to fill.

Maybe freedom without boundaries isn't freedom. Maybe it's just a different kind of prison — one without walls, which makes it harder to see that you're trapped.

What I'm Trying Now

I'm experimenting with something embarrassing: pretending I have a boss again.

A reasonable one. One with office hours. One who says "that's enough for today" and means it.

Concretely, this means: a hard stop at 6pm. No email after dinner. Weekends that are actually weekends. A definition of "enough" that I'm not allowed to move once I set it.

It feels artificial. It feels like admitting I can't handle freedom.

But maybe that's the point. Maybe pure freedom isn't the goal. Maybe the goal is freedom with structure. Autonomy with limits. The power to direct yourself and also the wisdom to give yourself rest.

I'm still figuring it out. The internal boss is loud. But at least now I can hear it.

Try This Today

Notice the voice that tells you to keep working. Is it external or internal? And if it's internal — when does it let you stop?

If the answer is "never," consider building what the external boss had: a clock-out time. A finish line. A definition of "enough" that you're not allowed to move.

Freedom needs structure. Otherwise you're just trapped without walls.

What would your internal boss never let you do?