Regret Minimization Frameworks & Uncomfortable Truths

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Idea: Regret Minimization Framework

Before Jeff Bezos founded Amazon, he faced a pivotal moment. He had a comfortable finance job, but couldn't shake the idea for an online bookstore. He asked himself:

"When I'm 80 years old, what will I regret more - trying this or not trying this?"

This question led Bezos to create the Regret Minimization Framework, an invaluable tool for overcoming fear and making bold long-term choices.

Here's how it works:

  • Imagine your 80-year-old self, reflecting back on your life's trajectory.

  • What pivotal decisions along the way make you most proud?

  • Which ones do you wish you’d made differently?

  • Use these insights to guide your choices right now.

This simple yet profound framework helps pierce through short-term thinking. We often make choices chasing immediate gratification that lead to long-term regret.

Think of the companies that failed to adapt - Kodak dismissing digital cameras or Blockbuster ignoring streaming. In retrospect, their choices seem comically short-sighted. But in the moment, steering into uncertainty feels daunting.

Here's the key insight: regret often stems more from inaction than failure itself. Bezos knew trying to build Amazon carried risks, but he'd regret not pursuing his vision even more. Better to dare and fall short than die wondering "what if?"

The regret minimization framework builds on several powerful concepts:

  • Second-order thinking - considering how today’s choices ripple into future outcomes

  • Premortem analysis - envisioning your endeavors collapsed, then course correcting anticipated failure points

  • Surrogate regret - learning vicariously from others' regrets

To apply it, reflect on your own past choices to extract timeless principles about yourself. What worked? What didn't? Why?

Anticipate future opportunities and ask, "will I one day regret not doing this?" Get clear on your goals and let possible regrets guide you.

Channel your wiser future self - what would 80 year-old you advise doing right now? What bold vision or endeavor would they tell you to begin, even if success isn't guaranteed?

Of course, minimizing all regret is likely impossible. But regularly reviewing decisions through this lens leads to bolder choices aligned with your long-term fulfillment. It helps balance risks and rewards, instead of defaulting to safety.

So simplify the complex by asking, "what will I regret more?" Let possible regrets guide you, not paralyze you. Make choices that your future self will high-five you for.

Question: Uncomfortable Truths

“What uncomfortable truths about myself am I avoiding?”

This question stopped me in my tracks recently. It cuts through the layers of rationalization my ego hides behind. Forces me to confront aspects of myself I’d rather suppress. Parts that feel messy, undesirable or incongruent with my ideal self-image.

We all have inner demons. Behaviors rooted in childhood stories or past traumas. Fears that limit us. Outdated beliefs about who we are. Impulses misaligned with our values.

It’s easier to avoid facing them. But each time we look away, we grant these demons more power over our lives. By avoiding uncomfortable truths, I give these shadows control over my thoughts, emotions and actions. I become a slave to their whims, acting in ways I know contradict my vision.

Several psychological models reveal why we shy away from self-examination:

  • Cognitive dissonance theory shows how we rationalize contradictions to reduce inner tension.

  • Attachment theory traces avoidance to childhood bonding patterns.

But the root cause is simple: it’s excruciatingly uncomfortable to admit we’re not who we want to be.

Still, hiding from our inner demons only allows them to dictate our fate, as Jung put it. Great leaders know this. They skillfully excavate their own shadows. They courageously unearth limiting beliefs, unhealthy tendencies and suppressed traumatic memories from their subconscious. Only then can they nullify their demons’ control.

As Holocaust survivor Viktor Frankl wrote: “Everything can be taken from a man but one thing: the last of the human freedoms - to choose one's attitude in any given set of circumstances.”

So how do we develop this level of fierce self-honesty?

First, bluntly ask: What truth about myself have I been avoiding? What impulse doesn’t align with my values? Sit with these insights, unpack their roots. This kind of sincere self-inquiry rewrites neural pathways and transforms self-sabotaging behaviors.

Of course, excavating our shadows is intense inner work, requiring ruthless courage and honesty. But once we confront buried aspects of ourselves, we unlock our full creative power. We stop unconsciously sabotaging ourselves. We step into radical self-responsibility.

Bottom line, it’s not enough to perfectly analyze business models or market trends. Successful leaders also courageously confront their inner worlds - their self-deceptions, childhood stories and contradictory impulses.

Who are you, really? It’s time to dig deep and find out.

Quote: Expect Failure

"Success is the ability to go from one failure to another with no loss of enthusiasm.” – Winston Churchill

Failure gets a bad rap. We're conditioned to avoid it at all costs. One F on a test and your parents freak out. Mess up at work and you get reprimanded. Strike out asking someone on a date and your friends ruthlessly tease you.

We're taught that failure is something to be ashamed of. The opposite of success. A dead end.

But Churchill flips that notion on its head. Success isn't the absence of failure - it's the ability to fail, again and again, with undying zeal.

Failure is fertile soil. An essential ingredient for growth. Each fumble and flop provides an invaluable chance to learn. To experiment. To expand the boundaries of what you're capable of. Failure forces you to get creative, determined, and scrappy.

The most successful people fail more than anyone else. They plunge headfirst into the unknown, fall flat on their face, dust themselves off, and jump back in. Failure is feedback that propels them forward. It's rocket fuel for reaching new heights.

Next time you "fail," see it as one step closer to success. Let curiosity conquer fear. Reframe the situation into a captivating game and play to win. Study those who have gone from zero to hero and realize that failure paved their way.

Wallowing in shame, doubt, and self-pity after a failure leads to decay. Continuing to act in enthusiasm leads to emerging skills, wealth, and fulfillment.

Become addiction to progress, not perfection. Thrive off adversity. Let perseverance in the face of failure become an art form.

The bigger the failure, the more meaningful the rebound


1. Mike Mandell - Principal Attorney at Mandell Law

YouTube | Spotify | Apple

Mike Mandell is a lawyer, social media influencer, and founder of Mandell Law, a firm that transforms the process of legal advocacy. He is also known as the #1 Lawyer on TikTok, where he has amassed over 7 million followers by sharing legal advice and tips in an entertaining and informative way. He also has a strong presence on Instagram, Twitter, and YouTube, where he posts videos, podcasts, and testimonials about his work and life. He is on a mission to connect with a younger, internet-savvy audience and educate them about their legal rights and options.

2. Dr. Emily Bashah - Founder of Bashah Psychological Services

YouTube | Spotify | Apple

Dr. Emily Basha is a renowned psychologist, author, and podcast co-host who specializes in clinical and forensic psychology. She has a private practice in Scottsdale, Arizona, where she provides cutting-edge psychotherapy, psychological evaluations, and expert testimony for various legal cases. She has worked on high-profile cases involving domestic terrorism, capital offenses, and first-degree murder, as well as immigration, civil, and family law matters. She has testified in federal, state, and local courts, and has consulted for the FBI, the Department of Homeland Security, and the Department of Justice.

3. Dr. Steven G. Rogelberg - Chancellor’s Professor at UNC Charlotte

YouTube | Spotify | Apple

Dr. Steven G. Rogelberg is a Chancellor’s Professor at UNC Charlotte and a leading expert in Organizational Science, Management, and Psychology. He boasts a distinguished career with over 150 publications addressing topics from team effectiveness to leadership. He is also the author of the bestselling book The Surprising Science of Meetings, which has been featured on various media outlets such as CBS This Morning, NPR, BBC, and Forbes, as well as his latest book Glad We Met: The Art and Science of 1:1 Meetings. Dr. Rogelberg is a sought-after speaker and consultant who has worked with many Fortune 100 companies and served on multiple advisory boards.

Article: The Long View

I just discovered one of my new favorite writers. Vicki Tan. She was a product designer at companies like Spotify, Headspace, Lyft, and Google and she’s currently taking a break to bless us with some writing on behavioral science / psychology. She wrote an article breaking down a (in her words) metaphysical design framework to help us design better possible past/present/futures that create the human experience we want, for all time.

Here’s some of the questions she asks (and answers).

  • How do we navigate decision-making processes more effectively?

  • What guides our initial choices in determining what to build?

  • What do we invest our time and resources in?

  • How do we decide what to improve or get rid of?

Read it here.

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