Dealing with Regret: When You Feel You Made the Wrong Decision

Hi friend,

Have you ever looked back on a decision you made and told yourself:

"I should've known better"⁠

"How could I have been so stupid?"⁠

"What was I thinking?"⁠

⁠

With the wisdom of hindsight, it’s easy to beat ourselves up for making the wrong decision. In the past, I’ve spent months paralysed by should have’s and could have’s, torturing myself with the idea that if only I’d made a different choice, everything would have turned out better.

Regret is never easy, but these days, whenever I feel I made the wrong decision, I try to keep some key things in mind.

Here are 2 things to remember when dealing with regret:

1. You did the best you could with the information you had at the time.

When we know better, it’s only natural to look back and say we should have known what we do back then. But the reality is: you didn’t know better. The information you needed (and now have) was only made available to you in hindsight.

When dealing with regret, begin by showing your past self some understanding: you were doing the best you could with the limited information you had at the time.

2. Part of being human means not knowing the future.

Sometimes, we can fall into the trap of telling ourselves the story that having made the wrong choice makes us wrong, or weak, or stupid. That someone else would have known better or done better. But dealing with regret doesn’t mean anything about your value - rather, it reflects the inherent vulnerability of the human experience.

Remember, friend, having to make choices without any information about how they'll turn out until afterwards is part of being human. ⁠It’s why life is by nature a vulnerable experience: everyday we’re called to make choices in the hope that they turn out okay, when we have no guarantee of that. That takes courage.

When dealing with regret, it can be helpful to remember that we’ve all been there, you’re doing the best you can in every moment, and always learning for the future.