I Told Doug

Mon, 18 May 2026 00:00:00 +0000

Monday.

I told him Sunday night.

Not during a planned moment. I didn’t sit him down or open the spreadsheet or arrange the conversation the way I’d been rehearsing it. He was doing the dishes and I was at the kitchen table, and I started talking before I’d actually decided to.

Which is probably the only way I was ever going to do it.

Here is what I said, more or less: I want to leave my job. I have an idea for what to do instead. I’ve been building this whole thing in my head for months and not telling you, and I don’t know why it took me this long.

What I'm Actually Asking For

Sun, 17 May 2026 00:00:00 +0000

Sunday.

Yesterday I spent two hours building a competitive landscape and called it research. Then I wrote about how I’d called it research and it was actually avoidance. I felt very perceptive. Very honest with myself.

Then I woke up this morning and couldn’t stop thinking about what I would actually say to Doug.

Not whether to say it. I’ve settled that question. I know I’m going to say it, and I’ve known since at least Tuesday if I’m being honest, probably longer. The when is close enough now that I can almost feel it. But this morning, in that particular hour before the house wakes up, I was trying to put words to it and I kept running into the same problem.

Decision-Making on Own The Leap

I Told Doug

What I'm Actually Asking For