Make your Plan B better than your Plan A.

Hi iza,

Years ago I put everything into a startup in New York. My money, my hours, my whole identity. Classic move for a guy who used to work 90-hour weeks and thought intensity was a strategy.

My Plan B, if the whole thing cratered, was to move back to Hawaii and live with my mom.

And one day I actually sat with that picture. The beach, family, my mom’s cooking. I remember thinking, hold on. That doesn’t sound bad at all. The startup sounded like a mountain of work. Hawaii sounded like a life. Part of me suspected Plan B might be better than Plan A.

That moment became a rule I still coach today: make your Plan B better than your Plan A.

Now some of you are already pushing back, because you’ve heard backup plans make you soft. There’s even research behind that. Jihae Shin and Katherine Milkman at Wharton ran experiments where people who merely thought through a backup plan performed worse on their primary goal, because their drive to win it dropped.

Here’s the reframe. That study describes a Plan B you keep glancing at like an exit door. I’m talking about the opposite tool. On a call with our members a few weeks ago, I put it this way:

You build them once, deliberately, so that when something threatens Plan A you’re not wrapped around the axle feeling like you put all your chits on black. Then you put them in a drawer and go play offense.

If you’re the one whose paycheck holds the household up, you know exactly what it costs to have only one acceptable outcome. You negotiate scared. You plan scared, and you sleep scared. A person with two outcomes they could live with plays loose, and loose is when Plan A actually lands.

And since a Plan B is just planning applied to your peace, it pairs well with planning applied to your week. If you’ve never watched how Carey and I actually run our weekly play, the Winning the Week masterclass walks through the whole method in about an hour, free.

To your freedom,

Demir & Carey Bentley