The calendar was full and I was lonely

Happy Sunday!

I had a week recently where my calendar was the fullest it's been all year, and I felt more alone in it than I have in months. Back-to-back calls, two founder dinners, a panel thing on a Wednesday night, and by Friday I couldn't tell you a single conversation that wasn't, in some small way, a pitch.

That's the part nobody warned me about when I started this company.

The trap

The problem isn't that you don't see people. It's that everyone you see has a reason to be in the room with you. They want to partner, hire you, get hired by you, learn from you, sell you something, or compare notes on the same problems.

None of it is bad, and some of it is genuinely useful. But it adds up to a strange kind of isolation where every relationship has a business shape to it.

I've watched a lot of founders, including me, try to fix this with more of the same. More dinners, more DMs, another conference. The logic is that if you're lonely, the answer is more contact, and the contacts you have access to happen to be other operators.

I think that's actually the trap. Past a certain point, more business surface area is what's making you lonely.

The parallel circle

The reframe that's been sitting with me is that I don't need more business friends. I need a parallel set of relationships where I'm a human first. People who don't know my MRR, who wouldn't notice if the company doubled or died, who don't see me as a node in their professional graph.

Both sides actually matter. The business circle keeps me sharp and gives me people who understand what a Tuesday actually looks like, and the human circle is what keeps me from disappearing entirely into the work. Most founders I know are heavy on one side and starving on the other, and I've been on both sides of that imbalance in the same year.

For me, the second circle has come from places that have nothing to do with email or retention. A climbing gym where most people have no idea what I do, a bathhouse on a Saturday afternoon, a tennis court, a bench in a park with old friends who knew me before any of this.

None of those are scenes I went looking for as a "founder." They're just places I show up as a person, and the relationships built there have a totally different texture.

What I haven't figured out

I want to be careful here, because I haven't cracked this. One half of me wants to lean all the way in and work seven days a week, because the company genuinely is the most interesting problem in my life. The other half knows that the weeks I do that are the weeks I feel most isolated, even with a packed calendar.

I'm not going to pretend that tension goes away. What I do know is that more meetings is not the cure for loneliness. The cure is the people who don't show up on my calendar at all.

That's the part I'm still building, slowly, alongside the company. Some weeks I lean too far the wrong way and feel it by Friday, but I notice the difference now, and naming it, even just to myself, has made the lonely weeks a little less confusing.

Talk soon,

- Raymond

P.S. Take some time this week to reflect — not on the business, on yourself. What do you actually like as a human, separate from what you do for a living? The list might be shorter than you expect. That's the work.