Issue #020 — On the loneliness of running your own thing

Friend,

Nobody warned me about the loneliness.

There is a particular kind of loneliness that comes with running your own thing, and I do not think anyone in the genre of how-to-be-a-founder writing talks about it honestly. They talk about pressure. They talk about decision fatigue. They mention loneliness in passing, as a hazard, like a footnote. It is not a footnote. It is the texture of the work for long stretches.

The loneliness is not about being alone. I am not alone. I have a partner I love, friends I see, a small team. The loneliness is about which conversations are available.

Here is what I mean. When something hard happens in a regular job — a project lights on fire, a colleague is impossible, the strategy is not working — you have peers to vent to. People in your same shape. They get it. You do not have to explain the context. You can just say the brief came in at 4 p.m. on Friday and they nod, and the nodding is the medicine.

When you run your own thing, the equivalent peers exist, but you mostly cannot find them, and when you do, the things you most need to talk about — the cash-flow scare, the client who is making you doubt yourself, the question of whether the whole project is working — are also, often, the things you cannot say out loud. Saying them to your team would worry them. To investors would alarm them. To friends in regular jobs is a kind of unfair cognitive load. To your partner, sometimes, but the partner is not, and should not be, your founder peer.

So the conversations that would help most are the ones that are hardest to have, and most founders solve this by not having them, and instead carrying the thing alone, and calling the carrying resilience.

What I would tell my younger founder self: you do not need ten of these people. You need one. One person, in a similar shape, with whom you have agreed in advance that the rules of the conversation are different. Nothing is too dramatic. Nothing is held against you. You can say I am scared this whole thing is going to fail and they will not panic and will not fix and will simply receive it and tell you something true back.

Find the one. Cultivate it. Treat the maintenance of that relationship as core infrastructure, not as social life. It will outlast everything else.

Yours,
Enova