Book the flight before the calendar clears

Happy Sunday!

I flew back to California last week, and the first night I stood in my mom's kitchen at 11 PM eating leftovers out of the pan she'd cooked them in, while she stayed up past her bedtime to keep me company. That's the moment the whole trip was for.

I booked the flight in February

I bought it without knowing what May was going to look like, which clients would be on fire, or which weeks I'd want to pull back into. I booked it anyway, because I've learned the hard way that if I wait for the quarter to calm down before I put a trip on the calendar, the trip never happens.

The quarter never calms down

That's the part nobody tells you when you start a company. There is no week where the inbox is clear, the roadmap is settled, and nothing is mildly on fire. If you make travel contingent on that week showing up, you're going to skip a lot of birthdays.

So at some point I stopped asking whether I had time, and started booking the flight first and letting the work bend around it. That sounds dramatic for a $400 Southwest fare, but it's the most accurate way I can describe it.

The plane ticket is the system

A flight on the calendar is non-negotiable in a way that "I should really see them more" is not. You can talk yourself out of intention every Monday morning, but you cannot talk yourself out of a boarding pass you already paid for.

The same week I was home, I flew to EDC with four friends I've known since freshman year at UC Irvine, when we were all 18. Same logic, same move. I bought the festival pass in November when I had no idea what work would look like in May, and bought it anyway.

At 2 AM on the second night, somewhere near the bass stage, I realized I would not have been there if I had waited to see how the quarter was shaping up. The version of me checking Slack in November would have passed. The version of me with a ticket in hand just showed up.

A date is a decision

This is the same principle as anything else that matters in a business. If it's not on the calendar with a date attached, it doesn't exist, whether that's hiring plans, quarterly offsites, the AI experiment you keep meaning to run, or the audit you keep meaning to do on your own account.

Intention without a date is a feeling. A date is a decision.

The trip itself is the artifact. The decision happened months ago, sitting on my couch with a credit card, choosing a weekend on a calendar I couldn't yet see.

I booked the next one before I left the airport. I don't know what August looks like yet, and that's the point.

Hope you have a great Sunday. Go book the thing you've been putting off.

- Raymond