It was the third night of the conference. The day was filled with workshops, breakout sessions, and the kind of conversations that leave you full but drained. Dinner was wrapping up. The scheduled programming was done. My hotel room was just a short elevator ride away.

I’m an introvert and I know what my mind wants in moments like this…

Solitude. The couch. Maybe a show I’m behind on.

Then I scanned the courtyard where dinner had taken place.

Joey was at another table with Jayson, Simon, and Doug. There was an empty chair next to him. I’d been trying to catch up with Joey all week and hadn’t found the moment. The conversation at my own table had stalled out. And I was wearing a bracelet they give out at MMT that serves to remind us of the group’s core values.

Mine said “Lean In.”

We ended up talking for hours. Human history. AI. What’s coming for the species. The kind of wide-ranging, philosophical conversation I get almost no access to back home. It was the best conversation I had all week, and I almost didn’t have it.

Here’s what I keep noticing about myself, and maybe you notice it too. The version of me at 6:45, deciding whether to go back up to the room, is making a prediction about how the night will feel…

Tired. Draining. Not worth the effort.

But future me has a track record. And the track record says: when I lean in, I’m almost always glad I did. Not 60% of the time. Closer to 95%.

So why does the forecast keep winning?

I think it’s because the resistance feels like data, but it isn’t. It’s a feeling. The feeling shows up reliably, gets a vote, and then disappears the second I’m actually in the conversation. By the time I’m sitting next to Joey, the version of me who didn’t want to go has already left the building. He doesn’t come back to apologize for being wrong. He just shows up again next time, same forecast, same confidence.

I haven’t figured out a solution to this yet, but I’m working on trusting the version of me who’s grateful at 9:30 over the version of me who’s negotiating at 6:45.

I’ve started trying to give a little more weight to the track record and a little less to the forecast.