I never would have imagined choosing between chocolate cake, key lime pie and bread pudding would be so hard.
I was at dinner with my business co-founder at the time, recapping our day of meetings with potential partners. We had orders from vendors. All our hard work was finally paying off.
This was a nice spot. Twenty dollar cocktails, big steaks and great service. The waiter cleared our plates and returned to take our dessert order.
Him: “Ummmm…I don’t know,” looking at the menu for the third time and back to me. “What are you going to get?”
Me: “Bread pudding.”
Him: “Ok…yeah. I’ll do that too then.”
My partner who had spent the afternoon negotiating deals couldn’t pick a dessert.
You may shake your head and say you’d never be like that, but let me ask you - when was the last time you had a conversation where you went back and forth on where to eat?
Most people are bad at decision making. Mainly because they’re afraid. Afraid to make someone uncomfortable with a lunch pick, and - with bigger choices - about being wrong.
So they hedge. They try to get someone else to make the call (NOT MY FAULT!). Or they ask their favorite AI (STILL NOT MY FAULT!).
Choosing not to decide is a choice. Why not just choose what you want?
And how do you choose what you want? With big decisions - like a new house or job or hire - the key is to know what you ultimately want. What’s the outcome you desire? When you know your destination, you make choices based on what route seems likely to get you there.
When you make a decision that doesn’t work you can always make another decision and get on a different track.
Being a better decision maker starts just like you going to the gym for the first time. You’re not picking up the heavy dumbbells day one. Go light. Five pounds today. Fifty in six months.
Start with your next dinner conversation. When someone asks, tell them you’re in the mood for ____.
Own it.
I’ve written a book called Dump the Drawer, about why capable people hand off choices they’re qualified to make. Out October 2026.