Where to play and how to win.
That is the whole of strategy in seven words, and I love it more than anyone should love a sentence out of a business book. The two men who wrote it down meant it the way a coach means it. A field, an opponent, a scoreboard. Fine. I keep snagging on the verb anyway…
They could have written where to dominate. Where to invest. Where to work, or where to deploy resources (a phrase that has never once gotten anybody out of bed on a Saturday). Any of those would describe the same market on the same map. They picked play, the only word on that list that expects you to lose now and then and keep going.
Lose where you meant to dominate and you failed. Lose where you meant to invest and you get a write-down, followed by a meeting about the write-down. Get tagged and you’re it, which is just a new job inside the same game. The loss is one of the moves.
Since the start of this year I’ve been running my year in themed weeks. Poetry, cooking, stand-up, woodworking, stocks, nature, video editing, gardening, meditation, improv, watercolor, motorcycle, candlemaking, manga. Every week gets the same seven slots, from reading something, to cold-emailing a local practitioner, to teaching my daughters, to a big closing number I named the Wow capstone. Seven days on one small field. Then the lines get painted somewhere new.
The scoreboard is honest, which means it’s ugly in spots. Woodworking was a wipeout, nothing built. But there was a broken bowl I hand-carved (and hand-broke?). History and geography got abandoned with the supplies ordered and never used. The gardening planter box got pushed a full year. Each of those cost me exactly the week I gave it and not an hour more.
Lined up side by side, the losses share a fingerprint. Anything that needed a new tool, shop space, or somebody else’s calendar tended not to happen. I didn’t find out I’m bad at wood. I found out where my field actually ends, which no amount of planning had told me.
Play is the only one of those verbs that pays out when you lose.
The winning half surprised me too. The Wow capstone was supposed to be the fireworks, and it was the slot I skipped most. The fake Netflix special never got filmed. The maker’s mark never got made. What I kept instead was smaller. Poems on index cards pinned to a tackboard. A binder of handwritten recipe cards. A frame of pressed leaves. A jar of improv prompts from a living-room showcase. I had defined winning as fireworks, and the game kept handing me ticket stubs.
The bar runs on the same logic. One location, on purpose, no second pot. Inside that one room, 90s Week, Plant Week, a tap list that refuses to sit still. The field stays fixed so the play can move. Plenty of companies run it the other way around, picking where to dominate, defining winning as the launch, and then wondering why nobody on the team will try anything that might not land.
If you lead anybody, hand them a field before you hand them a target. Edges they can see, small enough that a loss inside them costs a week instead of a reputation. Then watch who starts leaping.
My daughters had this figured out on poetry week. They loved tracking down every item on the scavenger hunt and never quite grasped the part where the items turn into a poem. The poem was my idea of how they’d win. They had already picked where to play.
Stay Positive & Go Lose A Week (You’ll Gain Much More)

