“I see it all perfectly; there are two possible situations — one can either do this or that. My honest opinion and my friendly advice is this: do it or do not do it — you will regret both.” ― Søren Kierkegaard

Regrets haunt us all.

In those late nights when sleep won’t come, when the world is dark and quiet, when I feel alone, when I feel like shedding my skin and jumping out of my body, regrets fill my head.

Why didn’t I put my ego aside and apologize?

Why didn’t I work harder at it?

Why did I keep pushing them away when they were trying to help? Why couldn’t I see how stupid I was acting?

Over the course of our life, we’ll make millions of choices.

Each choice opens and closes different paths. Each path not taken is a potential regret.

It’s impossible to explore every path.

No matter what we do, there will always be some road we didn’t take.

Regrets are an unavoidable part of life.

The key lies in minimizing the number of Big Regrets we end up with.

One tool we can use to help us in this pursuit is the “regret minimization framework”.

When you are 80, will you regret this?

When I’m 80, am I going to regret leaving Wall Street? No. Will I regret missing the beginning of the Internet? Yes. — Jeff Bezos

Before founding Amazon, Jeff Bezos was making a name for himself on Wall Street.

By the age of 30, he had it all.

He was one of four senior vice presidents at D. E. Shaw & Co., a successful and growing hedge fund, and he had recently gotten married.

He had found success in both his private and his work life.

Yet, while looking for new business opportunities for D. E. Shaw, he became entranced by the growth of the Internet.

He tried to convince his partners at D. E. Shaw to implement his idea of selling books on the Internet, but he didn’t get their buy-in.

And so, using what he called a “regret minimization framework”, he realized he had to try to make his vision a reality or he would regret it for the rest of his life.

A few months later, Bezos quit his job at D. E. Shaw and moved to Seattle to begin working on Amazon.

You won’t know if you don’t try

Failure sucks, but the pain that is failure does not exceed the pain that is not trying at all. See, I regret my failures, but I would regret more a failure to try.
— Casey Neistat

In March 2015, Casey Neistat started posting daily vlogs on his YouTube channel.

He quickly became a YouTube celebrity.

By August, he had 1 million subscribers. A year later, 4 million.

Yet in November 2016 he canceled his daily vlogs to devote his time to Beme, a social media video app he was working on.

Not long after, CNN acquired Beme for $25 million, hoping to use Neistat’s reach, influence, and creativity to reach younger viewers.

The whole project was a huge failure.

Beme shut down in early 2017 and Neistat left CNN sometime during the summer of 2017.

Now Casey’s back.

A few days ago, Casey announced that his daily vlog was returning.

He failed in his Beme-CNN project, but it wasn’t for a lack of trying.

And while he’ll regret this failure, he’ll never have to wonder “What if?”

How I’ve used the regret minimization framework

During my senior year of college, I had to pick between two job offers.

The first was a Fortune 500 company where I had interned the previous summer.

There were many reasons to take this job.

I had enjoyed the work I had done over the summer and I already knew the people I’d be working with.

The offices were a half an hour away from my home, so I would have been able to stay close to my family and my girlfriend.

The other choice was Amazon.

Working at Amazon would have required me to move to the other side of the country.

I didn’t know the people or the company culture.

I’d see my family maybe once a year and my girlfriend still had a year left in college and there were no guarantees we’d make the long distance work.

But I knew I would regret not taking the chance to work at Amazon.

Working at a technology company that operates at the scale of Amazon had been my dream for years.

In the end, I joined Amazon.

While I miss my family every day and can’t wait for my girlfriend to join me, I’m glad I made this choice. I know I would have regretted it otherwise.

We’re not robots

We need to forgive ourselves. For all the things we didn’t do. All the things we should have done. You can’t get stuck on the regrets of what should have happened. — Mitch Schwartz

The regret minimization framework can be a big help when making decisions.

It helps push us towards what will fulfill us and not just what’s comfortable.

It forces us to take a bird’s-eye view on our lives, to see the big picture, to make a conscious decision of where we want to go rather than to have Life or some external party make this decision for us.

But we’re human, not robots. We’re still going to make mistakes. We’re still going to have regrets.

So don’t dwell on your regrets too long. Let them wash over you and let them go.

Forgive yourself.

The two questions you need to ask yourself

I think Bezos’ regret minimization framework can be summed up in two questions, with the experiences of Bezos himself and Casey Neistat serving as great examples for each question:

1. Will I regret not doing this 10, 20, 50 years from now?
2. If I fail, will I still be glad I gave it a go? Will I regret not having tried this?

You’ll always have regrets.

But which regrets you end up with is up to you.

Choose wisely.

As always, thanks for reading.

How You Can Use Regret To Guide Your Decisions was originally published in The Ascent on Medium, where people are continuing the conversation by highlighting and responding to this story.