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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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The Imbalanced Problem with Work/Life Balance

Balancing is for your checkbook, gymnastics, and nutrition; not for your people’s work/life ratio.



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Balance…it requires an equal distribution of value between two or more subjects to maintain steady composure and equitable proportionality. (more…)

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How to Find the Courage to Start New

Change is scary, but it’s a normal part of life.



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It’s 2023, a new year, new you, right? But how do we start over? How do we make the changes in our lives that we crave so much to see?  (more…)

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Failing is More Important Than Succeeding

Failure is an integral part of life as life is incomplete without failures.



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People often consider failure a stigma.  Society often doesn’t respect the people who failed and avoids and criticizes their actions. Failure is an integral part of life as life is incomplete without failures. Not to have endeavored is worse than failing in life as at some stage of your life you regret not having tried in your life.  (more…)

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5 Indicators of Unresolved Attachment Trauma



Emotional Attachment Trauma

Trauma caused during specific stages of a child’s development, known as attachment trauma, can have lasting effects on a person’s sense of safety, security, predictability, and trust. This type of trauma is often the result of abuse, neglect, or inconsistent care from a primary caregiver.

Individuals who have not fully processed attachment trauma may display similar patterns of behavior and physical or psychological symptoms that negatively impact their adult lives, including the choices they make in relationships and business.

Unfortunately, many people may not even be aware that they are struggling with trauma. Research estimates that 6% of the population will experience PTSD in their lifetime, with a majority of males and females having experienced significant trauma.

Unresolved attachment trauma can significantly impair the overall quality of a person’s life, including their ability to form healthy relationships and make positive choices for themselves. One well-known effect of unhealed attachment trauma is the compulsion to repeat past wounds by unconsciously selecting romantic partners who trigger their developmental trauma.

However, there are other less recognized but equally detrimental signs of unprocessed developmental trauma.


Five possible indications of unresolved attachment trauma are:


1.  Unconscious Sabotage

Self-sabotage is a common pattern among individuals with unprocessed attachment trauma. This cycle often begins with hurting others, which is then followed by hurting oneself. It is also common for those with attachment trauma to have heightened emotional sensitivity, which can trigger this cycle.

This pattern can manifest in lashing out, shutting down, or impulsive behavior that leads to feelings of guilt, shame, and self-loathing.

Many people with attachment trauma are not aware of their wounds and operate on survival mode, unconsciously testing or challenging the emotional investment of those around them, and pushing them away out of self-preservation and fear of abandonment.

This can lead to a pattern of making poor choices for themselves based on impulsivity.


2. Persistent Pain

Chronic pain is a common symptom that can stem from early trauma. Studies have shown a connection between physical conditions such as fibromyalgia, headaches, gastrointestinal issues, insomnia, muscle aches, back pain, chest pain, and chronic fatigue with the aftermath of chronic developmental trauma, particularly physical abuse.
Research has found that individuals with insecure attachment styles, such as anxious, avoidant, or disorganized, have a higher incidence of somatic symptoms and a history of physical and emotional abuse in childhood compared to those with a secure attachment style.

3. Behaviors That Block Out Trauma

Trauma blocking practises are used to avoid the pain and memories connected with traumatic events.
Emotional numbing, avoidance, and escape via briefly pleasurable activities that distract from terrible memories or suffering are common examples. Unfortunately, this escape habit stops people from successfully processing and recovering from their trauma.
Furthermore, when the pain resurfaces, more and more diversions are necessary to continue ignoring it. This can be seen in compulsive behaviours such as drug or alcohol addiction, emotional eating, numbing oneself through relationships, workaholism, excessive or dangerous exercise routines, compulsive internet or technology use, or any other compulsive behaviour used to distract yoursef from intrusive thoughts and emotions.
These actions have the potential to prolong a cycle of avoidance and repression, preventing persons from healing and progressing.

4. A strong need for control

It’s understandable that some people may struggle with control issues in their adult lives, especially if they felt helpless or vulnerable during their childhood.
This can happen if someone had an overbearing caregiver who didn’t let them make their own choices, expected too much from them, or didn’t take care of them properly. As adults, they might try to control everything in their life to feel more in control and less anxious or scared. This might be because they didn’t feel like they had control over their life when they were a child.
It’s important to remember that everyone’s experiences are different and it’s okay to seek help if you’re struggling with control issues.

5. Psychological Symptoms That Are Not Explained

Individuals with a history of developmental trauma may experience a range of psychological symptoms, including obsessive-compulsive behavior, intense mood swings, irritability, anger, depression, emotional numbing, or severe anxiety.
These symptoms can vary in intensity and may occur intermittently throughout the day. People with this type of trauma may attempt to “distract” themselves from these symptoms by denying or rationalizing them, or may resort to substance abuse or behavioral addictions as coping mechanisms. This can be a maladaptive way of trying to numb their symptoms.

What to do next if you’re suffering from emotional attachment trauma?

Everyone’s experience of healing from trauma is unique. It’s important to be aware of whether you have experienced childhood developmental trauma and how it may be affecting your relationships as an adult. Sometimes, the effects of trauma can be overwhelming and we may try to push them away or avoid them.
If you notice that you’re engaging in these behaviors, it’s important to seek help from a trauma therapist who can support you on your healing journey. Remember, you’re not alone and it’s never too late to start healing.

There are several ways that people can work to overcome emotional attachment trauma:

  1. Therapy: One of the most effective ways to overcome emotional attachment trauma is through therapy. A therapist can help you process your experiences, understand the impact of your trauma on your life, and develop coping strategies to manage symptoms.
  2. Support groups: Joining a support group of people who have had similar experiences can be a great way to find validation, empathy, and a sense of community.
  3. Mindfulness practices: Mindfulness practices such as meditation, pilates, prayer time with God or journaling can help you become more aware of your thoughts, emotions, and physical sensations, and develop a sense of spiritual connection and self-regulation.
  4. Trauma-focused cognitive-behavioral therapy (TF-CBT): This is a type of therapy that is specifically designed to help individuals process and recover from traumatic events.
  5. Building a safety net: Building a support system of people you trust, who are there for you when you need them, can help you feel more secure and safe in your life.

It’s important to remember that healing from emotional attachment trauma is a process and it may take time. It’s also important to find a therapist who is experienced in treating trauma, who you feel comfortable talking with, and who can help you develop a personalized treatment plan.

If you desire to work with me on healing your wounds and unlocking the aspects of you that were never realized so you can achieve more success in your life then head over to and join my weekly LIVE online mentorship calls.
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