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Jeff Bezos Life Changing Decision Making Approach



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Nearly two decades ago, Amazon’s now-iconic CEO explained why he chose to leave a cushy, secure banking gig on Wall Street and roll the dice on founding an online bookstore. We know now that Jeff Bezos’ gambit would ultimately pay off — but back then, such a pivot was dangerously risky. Bezos was aware of the potential for failure, but in his mind, the potential for regret was far greater.

During a rare interview, Bezos shared the philosophy that drove him to chance disaster — a decision-making approach he calls the regret minimization framework. “I wanted to project myself forward to age 80 and say, ‘Okay, now I’m looking back on my life. I want to have minimized the number of regrets I have,’” Bezos recounted.

“I knew that when I was 80 I was not going to regret having tried [Amazon]. 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. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision.”

Needless to say, Bezos’ bet paid off. In the space of two decades, the founder went from personally labeling shipping boxes to overseeing a business whose revenue, at last count, stretches above $321 billion. Jeff Bezos saw an opportunity, felt inspiration, took a risk, and received a reward. His regret minimization framework allowed him to overcome fear of failure and serious doubts in order to create the potential to achieve massive success. 

There is no question that I have followed Bezos’ philosophy in countless business and personal decisions; however, it was never with the clarity and simplicity he articulates. I am sure that there are many who would, from the outside, view some of my decisions as overly optimistic, imprudent, and, in some cases, outright ridiculous. Some have worked out exceptionally well, some have been unmitigated disasters, and with some it is still too soon to tell.

But regardless of the outcome, I know that I made the best decision I could given the facts at hand and my long-term aspirations prevailing at that moment. I never employed the elegance of a formal “regret minimization framework,” but the underlying impetus was the same as the one Bezos described. I never want to be in a situation where I second-guess myself for not trying something I believed in.

“What we need to do is always lean into the future; when the world changes around you and when it changes against you – what used to be a tail wind is now a head wind – you have to lean into that and figure out what to do because complaining isn’t a strategy.” – Jeff Bezos

In a previous article, I wrote that the most important part of business decision-making isn’t about coming up with the idea, but about executing on that idea. As President Teddy Roosevelt espoused, it’s about getting into the ring and trying. In my opinion, trying and failing is far better than never trying. Regret minimization is about eliminating the question of, why didn’t I at least try? Who wants to face that question, whether in regard to business or personal issues, five or ten years from now — or, as Bezos described, when you’re 80 years old and looking back?

Practicing regret minimization is not about asking, “When will I succeed?” Instead, it’s about living with yourself and knowing that you tried. 

Of course, there is a world of difference between starting a company at the inception of the Internet Age and launching one in the middle of a global pandemic. Covid-19 has utterly disrupted our lives. People from every corner of the country have been shaken from their familiar routines; they have lost their jobs, been isolated from their friends and family members, and faced seemingly endless months of uncertain anxiety. 

The upheaval has forced people to ask questions they never thought that they would need to answer — or, at the very least, that they wouldn’t need to answer quite so soon

Should I start a new business?

Should I relocate?

Should I retrain myself?

Should I start buying or selling something meaningful?

Against current circumstances, it can be easier to say no. It seems safer to stay indoors and off the metaphorical road, remaining in place until the situation improves. It is easy and convenient to think the pandemic can’t last forever, but that really isn’t the story emanating from Covid. The trends and changes impacting our personal lives and business affairs will likely never fully reverse. The size, speed and severity of these changes present opportunities and challenges that were literally unimaginable just a couple of years ago.

Technology acceleration and adoption in areas like retail, healthcare, and entertainment have created drastic changes in how and where we work and play. The world is in a massive flux that might almost be equivalent to the internet revolution that drove Bezos decades ago. Regret minimization is about sitting around with your grandchildren telling them about how you felt and lived during this time of tectonic change. Who wants to look back and admit they were so paralyzed by uncertainty and fear that they didn’t try to capitalize on what were obvious future trends? 

“All of my best decisions in business and in life have been made with heart, intuition, guts… not analysis.” – Jeff Bezos

In some areas the changes are so substantial that it is almost unbelievable and easier to deny. A small but poignant example was Gregg Lemkau, the Co-head of Investment Banking at Goldman Sachs saying in a recent CNBC interview that he doubts the IPO roadshow will ever return. At the onset of Covid, industry experts predicted that the inability to travel would create a pause or even a freeze in mergers and acquisitions and public offerings. Instead, the exact opposite has occurred. Participants on all sides quickly realized — albeit out of necessity — that these could all be done more efficiently, virtually. 

If you are involved with business hospitality, you can pretend everything will revert once Covid is behind us or acknowledge the new reality is permanent. Regret minimization is alleviated by not having one’s head in the sand as it relates to your career or business activities. Simply accepting the status quo during a time of massive flux will inevitably lead to regrets for many. The business leaders and entrepreneurs who emerge from this crisis triumphant will be the ones who did what Bezos did in 1996. The people who thrive will be those who stay attuned to the reshuffling of industries and make the most of business opportunities and career paths when they appear. 

It is critical to emphasize that pursuing what seems like a compelling opportunity or pathway has no guarantee of success and that is not what regret minimization is about. Ultimately, succeeding is irrelevant. It’s about engaging and trying, regardless of the outcomes. In the end it is about assessing where the greatest regrets lie: potentially failing or failing to pursue?

Jeff Greenstein is an American entrepreneur and private investor based in Seattle, Washington. He is currently the President of YIS Capital, an active philanthropist and passionate collector of contemporary art. His work has previously been published in VentureBeat, TriplePundit, and Thrive Global.

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