The mental models we use to make our decisions define the small piece of life that we control.

How should we make life-changing decisions? How should we weigh the pros and cons? I’ve struggled to find a good way to piece these issues apart.

Logically, I want to make the decision most aligned with my purpose and values. I don’t think that’s enough though. How can I know that this decision won’t lead to the redefinition of these guides? I can’t.

That’s why I think I need something more. And I’m choosing regret.

Regret

In the past couple years, I’ve been redesigning my relationship with work. It started with regret. When thinking about what I’ve regretted most, I realized that I had rarely ever in my life looked back on something and wish I worked harder.

This is unusual. It seems that most people have times in their life where they didn’t work as hard as they could on something, didn’t get the result they wanted, and proceeded to regret not working as hard as they could.

I don’t feel that. When I look back on my most regretted moments, it’s the moments where I failed to have the courage to be vulnerable. It’s the moments where I chose to work over develop my closest relationships.

I love my work. I want a life where it’s an integral part of my flow. But I also recognize that I can feel too much of an obligation to it when it would be better both for myself and my work to simply step away and spend time with those I care about most.

When making a decision, I tend to ask myself: what would I regret more?

This is the question Jeff Bezos asked himself when he was deciding whether to leave his stable job to work on Amazon (at the time, it just sold books). While the way Bezos has run Amazon has been far from perfect (and sometimes downright immoral), I think most of us can look at his decision to leave his work to pursue his dream as the right one. He did what he wanted — not what he was expected to do.

Openness to Experience

Regret’s most powerful quality as a decision-making paradigm is that it typically has a bias towards courage and new experiences. Most of our regrets when it comes to decisions relate more to what we didn’t do as opposed to what we did. We wish we asked our crush out. We wish that we took a class in neuroscience. We wish we had the courage to make a new friend.

Often, regret arises when we were presented with an opportunity to be vulnerable, create connection, or simply take a risk and we turned it down — scared of consequences that were bigger in our mind than in reality.

Regret biases us towards courage. It encourages us to try new things. Because hey — maybe it will be life-changing.

Reflect on what you would most regret not doing

When I look back on the decisions I’ve made, there’s some big things I don’t regret. Studying for a neuroscience competition (even though I never competed), powerlifting, diving deep into the study of emergence, writing, confessing my feelings for my best friend are but a few.

When looking forward, it’s these moments I look back on. When did I go to sleep thinking “I’m glad I did that!”

Regret minimization keeps you on track. It keeps you in line with the you that you want to be. And so, next time you’re thinking about whether or not to do something, ask yourself what you’d regret more. Chances are, you’ll choose to be more courageous and vulnerable and take a step towards creating your best life.