Pickup Sports Ramblings
Ideas, rants and raves from a lifelong pickup sports organizer.

Case Study: How We Cut 5 Hours of Weekly Admin from Our 3-on-3 Hockey Game
For a player, game day starts an hour before the puck drops. For the organizer, it starts 48 hours earlier. For over a decade, I’ve

The Art of Fair Teams: 5 Methods to Stop On-Ice Arguments Before They Start
It’s a ritual as old as the game itself. The players are warmed up, the pucks are gathered, and the organizer stands at center ice,

From Spreadsheets to Sanity: My 10-Year Journey to Automating My Hockey Game
For more than a decade, my 3-on-3 pickup hockey game has been a fixture in my life. It’s not a formal league, just a dedicated

HappyRoster vs. The Big Guys: Why League Apps Don’t Work for Pickup Sports
If you’re an organizer for a pickup game, you’ve probably done the search. You’re drowning in spreadsheets and group chats, you know there has to

The Sports Organizer’s Black Hole: How to Collect Money from Teammates Without Losing Your Mind
There are few tasks more awkward than having to chase your friends for money. That weekly text—”Hey man, just a reminder you still owe $15

“I’ll Let You Know”: How to Finally Solve the Pickup Sports No-Show Problem
Every organizer knows the feeling. It’s two hours before game time, and you’re staring at your phone, anxiously waiting for those last few confirmations to