Set a firm date. Say, “Guys, it doesn’t matter if you can’t take off work, we’re going on this day.” If you tell them they don’t have an option, they make it work somehow.
Take turns organizing. We did the Turn-Up Teepee trip for New Years in Joshua Tree with maybe 20 of us. Solange and [video director] Melina Matsoukas orga- nized it all. Solange is a Cancer and Melina is a Virgo, so that’s two very organized people.
Use Airbnb. Know what you want going in. I like to stay in airy places that look like the jungle and feel friendly.
Divide the bill equally at the end of the trip. Have one person handle one section of the trip (snack, gas and tolls, hotels), save the receipts, and then split it all up.
Assemble a good mix of personalities. I can’t imagine going on an all-girls trip; I would lose my brain. Having a guy there balances out the attitudes. You want calm, creative people.
The bigger the group, the shorter the trip. With a big group we always aim for three days, because after the third day everybody’s ready to smack somebody. When it’s a smaller group, it’s more chill and relaxed and you can plan something a little longer.
Utilize the group text. For the Joshua Tree trip, we started a 15-person group text message. It was the funniest thread ever, with memes and GIFs. Someone dressed their dog up in heels and was like, “This is going to be me.”