what this path costs

one of the saddest side effects of being a founder is that you can't really make friends at work.

12 October 2025 · first published on Substack

one of the saddest side effects of being a founder is that you can’t really make friends at work.

when you’re younger, school or college is where friendships form effortlessly. shared experiences, inside jokes, late nights, all of it.

but as you grow older, your workplace becomes that space. it’s where most people spend the bulk of their waking hours.

most of my friends have their “work friends”. the people they grab drinks with on fridays, vent to about their boss, or celebrate small wins with. it’s where they find community as adults.

and as a founder, you don’t really get that.


no matter how close you are to your team, there’s always this invisible layer of distance.

you can be friendly, but not really friends.

you can have deep conversations, but never quite as equals.

every interaction is filtered through the weight of responsibility: payroll, performance, vision, survival.

you’re the person who can hire, fire, promote, or disappoint.

and that changes the dynamics permanently, no matter how hard you try to make it not matter.


founders often preach culture, belonging, and connection.

but personally, you’re on the outside of it.

you build the playground, but rarely get to play in it.

you’re everyone’s emotional anchor, but you don’t get to lean on anyone in the same way.

the people who can truly empathize, other founders, are usually too busy fighting their own fires.

so you learn to carry it quietly.


building something meaningful is deeply fulfilling.

but there’s a quiet loneliness baked into it that few talk about.

it’s not the kind of loneliness that comes from being alone. it’s the loneliness of being surrounded by people who look to you for direction, not connection.

and every once in a while, when you see your friends laughing over drinks with their work friends, you feel that absence.

not with regret, but with a quiet recognition of what this path costs.