The gist of it:

Regret minimization is a decision-making principle that encourages individuals to make choices in a way that minimizes the potential for future regrets.

It's often associated with life and career decisions, particularly when making choices that involve risks or significant changes.

The idea is to make choices that align with your long-term goals, values, and desires, so you are less likely to look back with regret in the future.

How to use it:

Regret minimization encourages you to think about your future self and what you would regret or appreciate looking back years from now. It promotes decision-making that benefits your future well-being.

So when faced with a particularly difficult decision:

1. Project yourself forward into the future.

2. Look back on the decision.

3. Ask "Will I regret not doing this?"

4. Act accordingly.

The goal is to minimize the number of regrets in life.

Deep Dive

“Most failures are one-time costs. Most regrets are recurring costs. The pain of inaction stings longer than the pain of incorrect action.”

- James Clear

When Jeff Bezos had the idea for Amazon, he told everyone he wanted to start an online store to sell books. At that point, he had a great job at a hedge fund where he made Senior Vice-President at age 30. It was inherently risky to give all of that up for a startup.

To help him make his decision, he used a mental model called the Regret Minimization Framework. It’s a very simple but powerful concept which got him to take action on his startup idea and turned a difficult decision into an easy one.

It starts by asking yourself - “In X years (a point in time in the distant future), will I regret not doing this?”

If the answer is yes, do it!
If it’s a no, don’t bother.

The idea is simply to project your present self into the future and look back at your decision from that perspective. This forces you to think beyond the moment and away from all the fears, doubts and unknowns that you would never be able to look past otherwise.

Instead, you fast forward into the future and assess your decision from that perspective; and this presents the decision in a completely new light.

 For Bezos, he thought of when he would be 80 and if he would regret not trying to start this company. Yes or no. His answer was quite clear.

As Bezos puts it:

I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried.

Sources:
Jeff Bezos uses a simple framework for making big decisions. Here’s how it works
The Bezos Regret Minimization Framework