the thing about working for yourself that nobody says out loud

I thought the hard part would be the work. It's not the work.

For as long as I was planning an exit, I had a very specific image of what working for myself would feel like.

No calendar full of other people’s urgency. Mornings I shaped myself. A slow morning ritual I can take my time with and not have to apprehensively prepare myself for the morning meetings (that could have been an email). And the particular relief of not performing availability for hours at a time in meetings I attended out of obligation and left having said almost nothing that mattered.

I thought freedom would feel like space opening up.

It does. Some days it does.

But here's the thing I didn't see coming — and I'm still turning it over, trying to figure out what to do with it.

While I thrive in autonomy and value autonomous routines, there was an underlying loneliness that comes with it I wasn't prepared for. Not a devastating loneliness. More like the loneliness of eating at a restaurant you'd always wanted to try, alone. You're glad you went. And still you keep glancing toward the door.

What I didn’t think to account for was the rhythm problem.

When you work for yourself, you’re available all day. Which sounds like a benefit. And it is, mostly, until the middle of a Wednesday when everyone you want to reach is in their office hours, deep in their meetings, behind their inboxes. And you’re online. Posting. Putting something out. Watching it land into a feed that’s running on a clock you no longer keep.

Because they’re at their desks. And you’re not on that schedule anymore.

I spent years wanting off that schedule. It’s strange to be off it now and still feel its shape.

The other thing I didn’t think to replace was the colleague. I had someone I’d send half-formed thoughts to. Not emails — the kind of message that starts with “okay this is probably nothing but what if...” and they’d send back three words and somehow that was enough to unknot the whole thing. I didn’t realise how much of my thinking happened in that gap. The in-between space. The part that wasn’t formally the work but made the work possible.

That’s the part that doesn’t come with the freedom package.

So I've been sitting with a contradiction I didn't expect. I wanted to work for myself. I also want community. Company. The particular comfort of being in something with someone. The part where we bounce ideas and challenge concepts, because perhaps that is what connection is about. And I thought, for a long time, that those two things were incompatible. That choosing one meant giving up the other...

I’m not sure that’s true anymore.

I think what I’ve been calling the dream — building something on my own terms, the days that are fully mine — I don’t think that dream was ever about being alone. I think it was about being with the right people, in the right way, doing work that felt like it actually belonged to me.

That’s a longer project than I realised when I started.

But here’s what I’ve noticed. The days I feel most like myself aren’t the ones where I was most productive. They’re the days something got unstuck. A voice note from someone who’s also building. A reply that opens into something. Someone saying “I’ve been thinking about this too” — and suddenly the work feels real in a way it doesn’t when it’s just me and the document.

That’s the thing the office was accidentally doing. Making the work feel witnessed. Giving your half-formed ideas somewhere to land before they were finished.

I don’t want the office back. I want that part. On my own terms, with people I’ve actually chosen.

Which is different from how I used to do it — proximity and obligation, calling it community.

I’m learning to build the real version now. It’s slower. It’s better.