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Regret minimisation framework: Making life's big decisions with confidence

An old man looking thoughtful

In 1994, a company called Cadabra, which sold books online, was founded in Washington. The founder of Cadabra, an investment banker at the time, left his well-paying and stable job to start the company, in what was considered a novel venture at the time, after asking himself this simple question: Will I regret this decision as I look back on my life at 80 years old?


A year later, that company changed its name from Cadabra to Amazon, the global consumer giant that has infiltrated and influenced the fabric of society in every corner of the world. In retrospect, it’s safe to say it was a pretty good decision. The man who made that decision was, of course, Jeff Bezos.


There are many learnings that can be taken from the Amazon story, but I’ve always been particularly drawn to the concept of what Jeff Bezos refers to as the “regret minimization framework”. The framework is simple: How can I minimise the number of regrets that I have when I'm looking back on my life at 80 years old? While not everybody will create one of the largest companies to have existed, we all make decisions, big or small, that have consequences for our future selves.


I find this structure to be especially helpful when considering the big jumps. Clearly, the decision of whether to cook dinner or have Uber Eats is not overly consequential to your life’s path. But changing jobs might be. Or starting a business. Or having kids. These are the big leaps that, while not all irreversible, certainly can have consequences in your life that reach far beyond that specific moment in time. These are the kinds of decisions that require the kind of long-term thinking prompted by the question: Will I regret this decision as I look back on my life at 80 years old?


I like the way that this question is framed. It’s aspirational and encourages a frame of mind that takes you outside of the current month, year, or even decade. It also doesn’t ask how much you stand to lose. I’m not saying to bet the house without some form of guardrails around the risk that significant decisions create, particularly those that are irreversible. That’s a topic for a different day. But I am supporting the use of a question that encourages a long-term vision.


You might ask why I’m personally so drawn to this principle. One of my greatest fears in life is that I fail to reach the innate potential that I have. I was listening to a podcast yesterday with Ed Mylett, and he framed up this fear in such a powerful way. He said something along the lines of this: “My biggest fear when I die and meet the man that I could have become is that we’re complete strangers.” That hit home big time for me. It's a thought that I live my life by every day. We’re always one decision away from becoming the best version of ourselves, which is an idea that is both incredibly freeing and equally frightening because you are the only one responsible for making the decision to move that one step closer.


I’ll end with this quote by Wayne Gretzky: “You miss 100% of the shots you don’t take.” Take the shot. If you miss, at least you’ll have tried. If you don’t try, you’ll never know what could have been. And that could end up being one of the biggest regrets of your life.

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