What If the Safe Choice Isn't the Right One?

What if the safe choice isn't the right one? Here's how a simple mental framework changed the trajectory of our lives.

In late 2020, at the height of COVID, my wife Adesuwa and I faced a pivotal decision. She had received two excellent medical fellowship offers: one in Chicago and another in San Francisco.

Chicago — safe, familiar, and predictable. San Francisco — a unique, national program, but full of uncertainties.

Chicago felt comfortable. It was home — we'd both built our lives there through business school and medical residency. San Francisco was exciting but the risks were significant, especially during the time of social distancing. We didn't know anyone there, and it might delay our plans to start a family or buy a home.

We started with the traditional approach: writing down the pros and cons. All signs pointed to Chicago. But then we asked ourselves a different question: "In 10 or 20 years, will we regret not taking this chance to experience life on the West Coast?"

This is the regret minimization framework. Surprisingly, this approach made our decision crystal clear. We chose San Francisco.

None of this would've happened if we hadn't used this framework.

In basketball, they say: "You miss 100% of the shots you don't take." This was our shot, and we took it. Because in the end, regret rarely comes from what we try and fail at — it comes from what we never try at all.