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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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Life

How Learning the Skill of Hope Can Change Everything

Hope isn’t wishful thinking. It’s a state of being and a skill that has profound evidence of helping people achieve success in life

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Hope as a skill
Image Credit: Midjourney

Hope isn’t wishful thinking. It’s a state of being and a skill that has profound evidence of helping people achieve success in life.

Wishful thinking, on the other hand, is like having dreams in the sky without a ladder to climb, having a destination without a map, or trying to operate a jet-engine airplane without instructions. It sounds nice but is impossible to realize. You don’t have what you need to make it happen!

What Real Hope Is

Real hope is actionable, practical, and realistic. Better yet, it’s feasible and can be learned.

One popular approach is Hope Theory. This concept is used by colleges to study how hope impacts students’ academic performance. Researchers found that students with high levels of hope achieve better grades and are more likely to graduate compared to those with less hope.

Hope can be broken down into two components:

  1. Pathways – The “how to” of hope. This is where people think of and establish plans for achieving their goals.
  2. Agency – The “I can” of hope. This is the belief that the person can accomplish their goals.

Does Hope Really Work?

According to Webster’s Dictionary, hope as a noun is defined as: “desire accompanied by expectation of or belief in fulfillment.”

As humans, we are wired to crave fulfillment. We have the ability to envision it and, through hope, make it a reality.

My Experience with Hope

For 13 years, I was a hopeless human. During my time working at a luxury hotel as a front desk agent earning $11.42 per hour, I felt the sting of hopelessness the most.

The regret of feeling my time was being stolen from me lingered every time I clocked in. Eventually, I decided to do something about it.

I gave myself permission to hope for something better. I began establishing pathways to success and regained agency by learning from self-help books and seeking mentorship.

Because I took action toward something I desired, I now feel more hope and joy than I ever felt hopelessness. Hope changed me.

Hope Actually Improves Your Life

Wishful thinking doesn’t work, and false hope is equally ineffective. Real hope, however, is directly tied to success in all areas of life.

Studies show that hopeful people tend to:

  • Demonstrate better problem-solving skills
  • Cultivate healthier relationships
  • Maintain stronger motivation to achieve goals
  • Exhibit better work ethic
  • Have a positive outlook on life

These benefits can impact work life, family life, habit-building, mental health, physical health, and spiritual practice. Imagine how much better your life could be by applying real hope to all these areas.

How to Develop the Skill to Hope

As acclaimed French writer Jean Giono wrote in The Man Who Planted Trees:
“There are also times in life when a person has to rush off in pursuit of hopefulness.”

If you are at one of those times, here are ways to develop the skill to hope:

1. Dream Again

To cultivate hope, you need to believe in its possibility. Start by:

  • Reflecting on what you’re passionate about, your values, and what you want to achieve.
  • Writing your dreams down, sharing them with someone encouraging, or saying them out loud.
  • Creating a vision board to make your dreams feel more tangible.

Dreams are the foundation of hope—they give you something meaningful to aspire toward.

2. Create an Environment of Hope

  • Set Goals: Write down your goals and create a plan to achieve them.
  • Visualize Success: Use inspirational quotes, photos, or tools like dumbbells or canvases to remind yourself of your goals.
  • Build a Resource Library: Collect books, eBooks, or audiobooks about hope and success to inspire you.

An environment that fosters hope will keep you motivated, resilient, and focused.

3. Face the Challenges

Don’t avoid challenges—overcoming them builds confidence. Participating in challenging activities, like strategic games, can enhance your problem-solving skills and reinforce hope.

4. Commit to Wisdom

Seek wisdom from those who have achieved what you aspire to. Whether through books, blogs, or social media platforms, learn from their journeys. Wisdom provides the foundation for real, actionable hope.

5. Take Note of Small Wins

Reflecting on past victories can fuel your hope for the future. Ask yourself:

  • What challenges have I already overcome?
  • How did I feel when I succeeded?

By remembering those feelings of happiness, relief, or satisfaction, your brain will naturally adopt a more hopeful mindset.

Conclusion

Hope is more than wishful thinking—it’s a powerful skill that can transform your life. By dreaming again, creating a hopeful environment, facing challenges, seeking wisdom, and celebrating small wins, you can develop the real hope necessary for success in all aspects of life.

Let hope guide you toward a brighter, more fulfilling future.

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Life

The 5 Stages of a Quarter-Life Crisis & What You Can Do

A quarter-life crisis isn’t a sign you’ve lost your way; it’s a sign you’re fighting for a life that’s truly yours.

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what is a quarter life crisis
Image Credit: Midjourney

The quarter-life crisis is a well-defined set of stages—Trapped, Checking Out, Separation, Exploration, Rebuilding—one goes through in breaking free from feelings of meaninglessness, lack of fulfillment, and misalignment with purpose. I detail the stages and interweave my story below. (more…)

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Life

Here’s The Thing About Learning, Unlearning, and Relearning

Stop hoarding and start sharing your knowledge and wealth for the benefit of humankind

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sharing your knowledge
Image Credit: Midjourney

Few people have the habit of hoarding their wealth without spending.  However, it limits their motivation as they tend to get into their comfort zones.  When people start spending money, then there will be depletion in their coffers. (more…)

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Life

3 Steps That’ll Help You Take Back Control of Your Life Immediately

The key to finding “enough” is recognizing that the root of the problem is a question of self-esteem and deservedness

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How to build self worth
Image Credit: Midjourney

“It’s never enough.” (more…)

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