Image: César Astudillo

In 1994, Jeff Bezos was working at a Wall Street hedge fund, making great money in what he called a “stable career path.”

But he had a crazy idea. One that would require him to quit his job for a riskier path. He wanted to start a business selling books online.

“[I wanted] to participate in this thing called the Internet that I thought was going to be a really big deal.”

His wife supported him, but his boss advised him against it:

“This actually sounds like a great idea. But it would be a better idea for someone who didn’t already have a good job!”

You know the story from here. And if you’re among the 64% of American households or 65 million customers worldwide who regularly shop on his site Amazon, you’re part of the story.

Bezos and Amazon are having a bit of a moment right now. The left-field Whole Foods acquisition. Bezos being dubbed the richest man in the world – for a few hours at least. The internet exploding over his biceps exploding.

So I thought it timely to share a powerful lesson I learned from Bezos in the vein of our recent theme: how to decide.

Jeff Bezos’s decision to launch Amazon may seem like a ‘duh’ decision now, but please remember what the internet looked like in 1994:

And we all know how that decision turned out:

How did Bezos ultimately decide to veer off his so-called “stable career path” to start something wild like Amazon.com?

As Bezos weighed his big decision to quit, he searched for a decision making framework that could pierce through short-term considerations to give him a longer-term view. Considerations like: 

What about my upcoming annual bonus? 

Haven’t I invested too much time in my current career to ditch it now? 

What if the new thing fails and I lose momentum in my current career?

What Bezos discovered wasn’t quite as nerdy as the criteria-based spreadsheet method I explored earlier – but it’s close. He came up with something he called the Regret Minimization Framework. Here’s how he describes 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. And 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. And I knew that that would haunt me everyday. So when I thought about it that way, it was an incredibly easy decision.”

Regrets of the Dying

I learned about Bezos’s Regret Minimization Framework while writing an essay about quitting in the early days of the Escape School. In deconstructing my own decision to leave IBM and pursue a dream of long-term travel, I realized how big a role potential regret played.

So the first I’d heard of regret as a decision making tool wasn’t from Bezos, but an Australian palliative nurse named Bronnie Ware.

In 2012, Ware published a book documenting her quest to understand the top regrets of her dying patients.

The #1 regret?

“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

“This was the most common regret of all. When people realise that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honoured even a half of their dreams and had to die knowing that it was due to choices they had made, or not made. Health brings a freedom very few realise, until they no longer have it.”

The other four top regrets?

2. I wish I hadn’t worked so hard.
3. I wish I’d had the courage to express my feelings.
4. I wish I had stayed in touch with my friends.
5. I wish that I had let myself be happier.

Hating What You Do Is Harder

Bringing it back to quitting (or any big decision to leave something in favor of a new or uncertain path), a chorus of questions like these chime in:

What might happen in the next year or two if I quit?

Is it stupid to take a pay cut or work for free to pursue something new?

What if this new thing isn’t the right thing?

These are scary questions. But asking them comes from too short-term of a mindset. It’s this mindset that Bezos attempted to pierce through. Thinking instead of potential regrets helps us look beyond short-term hiccups and forces us to ask the more important (and even scarier) question: What happens if I don’t quit?

As I weighed my decision to leave IBM, I become less concerned about what would happen in the next one, two, or three years if I quit. I projected myself into the future and asked: what might happen in the next 10, 20, or 30 years if I don’t quit? If I don’t do the things that were burning in my heart?

Quitting something that’s not working is tough. Traversing a new, uncertain road is just as hard. Sometimes even harder. But it’s a different kind of hard.

Designer Debbie Millman has a name for avoiding these tough choices: settling.

“If you are considering settling because going after what you want seems too hard to do, remember: hating what you do every day is even harder.”

You may not aspire to build the next Amazon like Bezos, but you might be running toward a similarly personal ambition. Maybe toward a long-forgotten dream or a bucket-list item. Or toward a more creative life. Or toward a life you can truly call your own. Or toward a future you, one you know you have the potential to become.

That’s the power in potential regrets.

Near the end of your days, when you’re 80, will your life be measured in the regrets you didn’t have the courage to act upon, or in the bold moves (and perhaps mistakes) you had the courage to make?

More Resources

Here are some resources on decision making from readers (thank you!):

Next week I’ll dig into using intention as a decision making tool – less for long-term decisions, more for in-the-moment situations. Subscribe below to get it first.


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