The backup plan wins

We treat contingency planning like an admission of doubt. Real conviction, we tell ourselves, means committing fully to the one plan. Then deadline day arrives, the plan collapses in the final hour, and we discover what that conviction was hiding: a refusal to prepare...

What fantasy football has taught me

I love Fantasy Premier League. Genuinely. It engages me, frustrates me, and gives me real joy in ways that surprise people who don’t play. Part of it is the strategy. Part of it is the constraints: a fixed budget, a limited number of moves, rules that...

The CEO’s #1 job

We confuse busyness with strategy. We fill the calendar with reviews, standups, pipeline calls, and board prep, and we tell ourselves we are leading. We are not. We are managing. The two are not the same, and the gap between them is where companies stall. The...

Who declared victory?

Imagine a sport with no scoreboard. No defined winner. No agreement on what the game even is. We’d call that chaos. We’d never watch it. We’d certainly never play hard for it. Yet we build organizations exactly this way. We set vague goals and call...

Pack your bags

We plan vacations obsessively. Itineraries, reservations, who’s coming, when to leave. We treat projects like chores. Same energy. Same stakes. Often bigger consequences. The founder who maps a project like a trip, knowing the destination, the milestones,...