5 min read
The premise of this month's experiment is that I'm letting AI help run things. Planning, content, the daily grind of keeping a business moving while pregnant, parenting a six-year-old through summer, and trying not to burn out before October.
So before July even started, I sat down with Claude and asked it to plan the whole month.
What followed was about three hours of back and forth. Not three hours of the AI spitting out a calendar while I watched. Three hours of actual conversation, correction, refinement, and a few moments where I had to say "no, that's not how this works."
Here's what that actually looked like.
I didn't start with a simple ask. I gave it everything.
A brain dump covering who I am, what I'm running, my energy patterns, my family situation, three distinct phases of July travel, specific dates, goals, Sophie's camp schedule, a UK trip, a redeye flight, the whole thing. It was long. It was detailed. I figured the more it had upfront, the less we'd have to untangle later.
The first thing it did was ask questions. Not generic ones. Specific things that would actually change the shape of the plan — whether I had sessions already booked (I didn't), which days the Disney park visits were (one confirmed, one TBD), whether I batch-film content or create day to day (day to day, with proactive filming before known light days), what the newsletter situation actually was.
That part surprised me a little. I expected it to just run with what I gave it. Instead it stopped and identified the gaps before building anything. That's not a small thing. A plan built on assumptions you never checked isn't a plan, it's a guess.
The three-phase structure of July came back immediately and it was correct: Orlando through July 10, home with camp from July 14 to 23, UK from July 25 through August 2. It named the camp window as the best focused work period of the month without me having to say that explicitly.
It also flagged something I hadn't fully sat with yet. The World Cup final is July 19. That means the entire tournament — all that daily knockout content I'd been planning — lives almost entirely in Phase 1. By the time camp starts, it's over. Knowing that changed how I thought about what to create and when.
A few things.
It blocked time for writing client playbooks speculatively — before any sessions were booked. That's not how I want to work right now. I'm not going to hold a two-hour block every week on the off-chance something comes in. Block the time when the session books, not before.
It also treated the July 12 flight home as a travel day. We drove. And we didn't drive home on the 12th — we left on the 11th, stopped overnight, and arrived home on the 12th. Two days of driving, not one. That changed the last real Orlando work day to July 10, and it changed the content plan for those days: film everything on the 10th, edit and post from the road.