Photo by Rostyslav Savchyn on Unsplash

4 Ways to Minimize Regret

Regret sucks. Let’s talk about some ways to make it suck less.

What You’ll Learn

  1. The Regret Minimization Framework
  2. Any Unasked Question is a No
  3. Make Mistakes of Ambition, not Sloth
  4. The Only Question

The Regret Minimization Framework

The Regret Minimization Framework is a fantastic tool. It is similar to an algorithm in Computer Science called Hill Climbing. Hill climbing is focused on finding local maxima (a fancy term for finding the highest point close to you.

Math is Fun Maxima Graph
thanks to math is fun

Given multiple choices, we want to take the option that results in the least amount of regret after it’s over.


You have 3 options that will take you one hour to complete. Doing one prohibits you from doing the others, adding an opportunity cost to all the choices.

Option A: Exercise (Regret score: 15)
Option B: Hanging out with your friends (Regret score: 20)
Option C: Watching Netflix (Regret score: 45)

In this case, it is best to spend the hour exercising. It incurs a cost of missing conversation with friends, and not getting ahead in our show, but minimizes the guilt felt at the end of the hour.

Hill climbing and regret minimization is not a perfect science. By focusing on local maxima, we miss chances to find optimal routes. But the ones we do find are good enough.

Any Unasked Question is a No

Anxiety is the sibling of regret. Regret criticizes choices made, and anxiety criticizes thoughts about choices. Anxiety is useful in doses. It prevents stupid decision making, for individuals and societies.

The sucky part is that if anxiety wins, regret will also win later.

Let’s say you want to ask your boss for a promotion. You’re anxious because you don’t want a light shined on the work you’ve done. So you don’t ask. 3 months later, your coworker is promoted to the role, and you regret not asking.

You’ve felt and acted on both the negative feelings of anxiety and regret. Ouch.

Any unasked question is a no, so go ahead and ask!

Make Mistakes of Ambition, not Sloth

“All courses of action are risky, so prudence is not in avoiding danger (it’s impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer.”
– The Prince, Machiavelli

The quote sums it up. There is no such thing as “no risk”. Make bold plays.

The Only Question

The final and easiest way to minimize regret is to ask yourself:

When I’m looking back at the end of my life, did I do everything I wanted?

Think in the long term. The short term has too many variables that pollute thinking. Long term thinking is values based, and since you can’t see how your plans play out, you’ll only have your values to guide you.

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