What’s the best decision you ever made?

What’s the best decision you ever made? Not the one with the best outcome, necessarily, but the decision that you felt strongest about.

As Annie Duke recently shared on this episode of Maya Shankar’s “A Slight Change of Plans” podcast, decisions and outcomes are two different things. I shared a similar thought from Annie about a year ago, but her simple question that I used as a title has stuck in my head.

In the podcast, Maya worded it this way to Annie:

And I love the thought experiment that you give, which I think elucidates this concept well, which is when you ask people, “What’s the best decision you’ve ever made? What’s the worst decision you’ve ever made?” We tend to not focus on the process by which we made the decision or the inputs to that decision but instead what the outcome was. So what you found is you asked people, “What was the best decision?” Well, they tend to choose the thing that had the best outcome and and vice versa for the bad one. And it’s very possible that you made, actually, a really crappy decision, but you just lucked out, right? Like, chance worked in your favor, and new information appeared or whatnot, and you ended up with a good outcome.

But I think that is a really helpful thought experiment because, to your point, you might’ve very well made the decision to take on a pursuit or support a certain candidate. And it was a very smart choice given all the information you had at that moment.

Related to this are the decisions we make that we don’t realize we’re making. For example, if you’re considering taking a new job and end up staying where you are, that was a decision. The same for choosing to stay in a relationship versus breaking up. Choosing not to make a change is a decision in and of itself.

It’s tough to frame decisions that way, as it’s human nature to base the quality of a decision on the quality of the outcome. They’re related, for sure, but great decisions can go poorly and bad decisions can sometimes work out in your favor.

To take this further: What’s the best decision you ever made that had the worst outcome?