Today’s Fast Summary:

• The Regret Minimization framework operates on delayed gratification. Regret lives in the future, not the present.

• When facing a difficult decision, ask yourself, “Which action would my 80-year-old self most regret not having taken?” The answer you come to is your next step.

• Fear setting is a means of avoiding self-destruction. It’s a way to assess possible outcomes.

| Level Up Your Soft Skills

Today’s newsletter is brought to you by Wave AI, a leading edge coaching platform.

Top talent use coaching to deal with the challenges they face in the workplace around leadership, impact, and productivity (Managing time and priorities, building trust, increasing productivity, or communicating).

Current apps and methodologies for professional growth are outdated, especially for tech leaders.

Wave is developing an innovative way to improve your skills by building daily routines. In a measurable way.

Leads and managers from Amazon, Stripe, Google, or Strapi are already using the beta.

Join the waitlist and claim 1 free month

A few years ago, I was working at a prestigious global investment bank. I’d worked extremely hard to get the job and had a great setup with kind and highly competent colleagues, as well as ‘relatively’ reasonable hours.

The problem was: When I examined myself, I knew my heart wasn’t in it. I knew it wasn’t where my future lay. Most importantly, I felt that by staying, I would set a precedent for myself to ‘settle for less’ for the rest of my life.

Nonetheless, the decision to leave was a challenging one. Leaving was synonymous with a significant reduction in my earnings and no clear idea of what was next for my career.

I needed a method to rationalise my decision’s long-term implications, not just its short-term ones.

Enter The Jeff Bezos’s Regret Minimization Framework.

After graduating from Princeton University, Jeff Bezos got a job at an investment firm. He enjoyed a large, six-figure salary and rose through the ranks, becoming a Senior Vice President in only four years.

In 1994, Bezos’ job was studying how to profit from the internet. It was then that he had an epiphany: The internet would be one of the greatest drivers of profit in human history, and he wanted to be part of it.

Bezos calculated the benefits and drawbacks of leaving. He asked himself, “At the end of my life, will I regret having done this?

For Bezos, the answer was yes, so he left the company and started Amazon, now valued at $2 trillion.

He would’ve had a bright future in banking, but he used his framework to shift his focus.

The Framework in Action

Bezos’ Regret Minimization Framework is simple.

When facing a difficult decision, ask yourself:

“Which action would my 80-year-old self most regret not having taken?” or, “Will I regret foregoing this opportunity?”

The answer you come to is your next step.

The framework operates by tapping into delayed gratification. Regret lives in the future, not the present. To eliminate it, think past your present doubts.

It’s a highly transferable, lifelong model. It lends well to the following:

• Academics (college decisions, assignments, trying new extracurricular activities, etc)

• Business and professional environments (leaving your job, managing your tasks, seeking novel opportunities)

• Family and personal matters (starting a family, buying a home, etc)

For example, you’re deciding whether or not to go to graduate school. You research programs, scholarships, and fellowships, but you’re unsure whether or not you should apply.

On one hand, graduate school would be a lot of work, and comes with it a hefty opportunity cost and loss of earnings.

On the other, it would improve your employability and long-term earnings potential.

Ask yourself, “Will I regret going to graduate school?”

Many have a difficult time finding an answer. But that’s an answer in and of itself. Hesitance is a sign you’re leaning toward making a change.

This framework operates on honesty. If you aren’t honest with yourself, you won’t come to any conclusions. Or, the conclusions you come to won’t reflect your true motivations.

Answer the question quickly.

How Can You Tell When You’ll Regret Something?

The largest qualm I hear about this model is that regret is ambiguous. Most people are familiar with regret, but foreseeing it is tricky.

Try these methods to reconcile this.

1. Reflect on your values. Does the decision you come to align with your core values? What about your long-term goals? If not, it’s likely you’ll regret it in the future.

2. Consider past experiences. Reflect on similar situations from your past. How do you feel about those decisions? Were you satisfied with the outcome? Use this information to inform your decision.

3. Consult others. Seek advice from those you trust, or from those who have experience in the area. Their insights can help you minimize regret’s potential.

4. Confirm with other decision-making frameworks. Apply other frameworks like decision trees or expected utility theory to think through each potential outcome.

5. Trust your intuition. Don’t ignore your gut feelings. Intuition is a powerful source of information.

6. Give yourself some time. Don’t make decisions impulsively. Take time to think through your options and consider possible consequences.

7. Uncertainty is inevitable. You cannot predict the future. Accept inherent uncertainty and focus on using the information you have available.

Use Fear Setting

Your answer might scare you, and that’s okay.

Jeff believed that Amazon only had a 30% chance of success at its inception. Bezos was terrified, and now he runs one of the most successful companies in the world.

Had he stayed in his position, you wouldn’t have next-day delivery and easy shopping at your fingertips.

Fear is normal. Embrace it.

However, fear can impede the model’s effectiveness. Try fear setting to take action against fear.

Fear setting is a means of avoiding self-destruction. It’s a way to assess possible outcomes.

Before you begin, answer, “What if I [insert major decision to be made]?”

I’ll use my own predicament as an example.

I asked, “What if I left my job?”

The following is a breakdown of fear-setting in practice.

1. Define.

Ask yourself, “What are the 10-20 worst-case scenarios that might happen if you choose to leave your job?”

Consider these scenarios in as much detail as possible. Visualize the scenario that is preventing you from taking action.

For example, I might’ve been unable to get another job.

Additionally, I might have had to make adjustments to my lifestyle.

Acknowledge fear and establish a conservative perspective.

2. Prevent.

Consider what you can do to prevent each of the worst-case scenarios.

In my example, I could maintain my contacts in the industry and save money to ensure I can continue with my given lifestyle.

Visualize what you can do before the decision is finalized. Put that into action.

3. Repair.

Ask yourself, “How can I repair the damage if the worst-case scenario really happens?”

For example, I could re-apply for my position, ask contacts for referrals and recommendations, or accept a different lifestyle temporarily.

Visualize the repair process.

4. Think Positively

When you’re finished considering the negative implications, flip the script. Go through the model again, but limit yourself to the benefits of the decision.

Ask yourself, “What are the benefits of an attempt or partial success?”

This time, consider the financial, spiritual, physical, relational, and emotional benefits of your decision.

In my case, I was one step closer to knowing what I wanted to do with my career. I was much happier.

5. The Implications of Inaction

Ask yourself, “If I avoid this action or decision, what would my life look like in 6 months, 12 months, or 3 years?”

Visualize the outcome in as much detail as possible.

Then, compare the cost of inaction to the potential benefits of partial or total success.

You’ll find that success’s benefits typically far outweigh those of failure or inaction.

Minimize Regret

The Regret Minimization framework is among the best decision-making tools in your toolkit.

After I used this model for myself, my choice became among the easiest I’ve ever made.

The long-term is always more important than short-term happiness. I knew leaving was the best thing for my future, and that’s the basis I valued most highly.

I was terrified, but I’ve never been happier with my life.

Ultimately, I would be nowhere near as happy as I am had I not asked myself,

“Will I regret this when I’m 80?”

This week, we’re going to try putting fear setting into action. Before completing the exercise, choose a decision you’ve been deliberating on for some time. This decision can be anything—leaving a job, leaving a relationship, moving to a new city, etc. As always, write down your responses and be honest with yourself. Honesty is paramount to this exercise’s success.

1. Employ ‘Define.’ 

   a. Ask yourself, “What are the 10-20 worst-case scenarios that might happen if you choose to do what you’ve been pondering?” Name each scenario and list them.

   b. Think about the scenarios in great detail. Consider all facets (professional, emotional, personal, relational, and financial) of the potential outcome.

2. Prevent it. 

   a. Consider what you could do to prevent each negative event you listed.

   b. Under each, list the ways in which you could prevent each negative event. Ensure you’re visualizing each in detail.

3. Repair afterward. 

   a. If the worst-case scenario happened, how could you fix it?

   b. Revise what you wrote. Write in concrete, declarative sentences. Visualize the repair process.

4. Flip the Script.

   a. This time, exercise the decision’s benefits. Ask yourself, “What are the benefits of an attempt or partial success?” Consider the financial, spiritual, physical, relational, and emotional benefits of your decision.

   b. Next, consider inaction. Ask yourself, “If I avoid this action or decision, what would my life look like in 6 months, 12 months, or 3 years?” Visualize the outcome of inaction in as much detail as possible.

   c. Finally, in a pros/cons format, compare the cost of inaction to the potential benefits of your own partial or complete success.

Use regret minimization to make your biggest, most challenging personal and professional choices.

You’ll be more than happy you made a choice.

Conclusion

I’d love to hear from you:

• Which decision are you wrestling with?

• Did Bezos’s story empower you? How so?

Tweet at me (@_alexbrogan) or respond to this email — I’ll try to respond to everyone.

Have a wonderful, Wednesday all.

Until next time,

Alex

Interested in starting your own newsletter?