The Time My Friend Told Me to Get My License

A friend once asked me how much my commission was going to be. I told her I don't charge anything. She said, “Of course you don't charge — but how much money are you making off my curated joy?” I genuinely had never thought about it that way.

I didn't set out to do any of this. It started the way most things like this start — with my own family and friends, and me being the one who couldn't leave a trip half-planned.

There was my husband's 40th — a surprise trip to Las Vegas I didn't even start planning until around December 10th, for a birthday on January 15th. Twenty people flew in from all over the country and pulled it off without him knowing a thing.

There was the year I planned a work trip to “the convention” in Orlando — fifteen-plus people, upper management, three different hotels, two toddlers, and my mother, all moving as one unit. The next year the same convention was in Barcelona, and that trip was four people, three of us landing on three different flights, all converging at Nobu Barcelona. I flew Turkish Airlines business class for that one. Completely worth it.

Somewhere in the middle of all that I became a mom who runs 5Ks and 10Ks — but only at Disney. It started during the pandemic and never really stopped. I got loud about it, the way you get loud about something you love, and eventually I was planning Disney trips for anyone who'd let me. There is a right way and a wrong way to vacation at Walt Disney World, and I will die on that hill.

Which brings me back to my friend. After I helped her plan one particular trip, she asked about my commission, I told her there wasn't one, and she looked at me like I'd lost my mind. “Reagan, you are not a travel agent,” she said. I told her no, I'm not — I'm just giving you the game on what to book and how to actually enjoy it. She burst out laughing. “Girl, if you don't go get your license and make money. Out here giving it away for free.”

Well. That's how we got here.

The free advice in the group chat isn't going anywhere — ask me anything, anytime. But if you want the whole thing handled, the flights and the hotels and the parts that go wrong so you never have to see them, that part I do for real now.