Chapter 13: The Regret Minimization Framework

The Regret Minimization Framework

Back in 1994, Jeff Bezos was sitting on a tough decision.

He had a cushy hedge fund job. Life was good. Safe. Stable.

But he had this idea (an online bookstore) and couldn’t shake the feeling that he needed to go for it.

So he asked himself one simple question:

"When I’m 80, will I regret not doing this?"

Would he regret leaving his comfortable job? Probably not.

Would he regret never taking the shot? Absolutely.

That was all he needed to know. So he quit and started Amazon.

The rest is history.

Why This Works

Most people make decisions based on short-term fears.

• What if I fail?

• What if it doesn’t work?

• What if people think I’m crazy?

But when you zoom out, you realize those fears don’t matter.

The Regret Minimization Framework flips the script.

Instead of asking, “What’s the safest choice?” ask yourself:

“What will I regret not doing?”

Suddenly, the decision is clear.

How I Used This in My Own Life

Last year, I was working through my own big decision:

Do I stay put in San Diego, where everything is comfortable and predictable?

Or do I move across the world, go all in on my own projects, and trust I’ll figure it out?

I pictured myself at 80.

Would I regret taking the leap, even if it didn’t work out? F*ck no.

Would I regret never trying? 100%.

So I did the damn thing.

And every day that passes I gain more conviction in that decision.

How to Use This Right Now

Got a big decision on your plate? Try this:

1. Picture the 80-year-old version of you. Imagine looking back on your life.

2. Ask: Which option will I regret NOT taking?

3. If the answer is clear, act on it. Future you will thank you.

Not every choice is life-changing, but the big ones—the ones that define your story—deserve this level of thinking.

Final Thought

99% of decisions aren’t permanent or fatal. But regret? That sticks.

So next time you’re feeling stuck, don’t obsess over the risks.

Consider what you will regret NOT DOING.

Because the only real failure? Never trying at all.

What’s one decision you’ve been putting off? And what would 80-year-old you say about it?

Personal Updates

If you’re reading this, I want you to know how much I appreciate you.

I took this leap into the unknown with a loose plan and a lot of conviction.

On Day 1, I told myself—if all that comes from this is inspiring one person to chase their own dream, it’ll all be worth it.

And every email, Instagram message, and text or call from a friend has reinforced that I’m on the right path.

I can feel the momentum building. More conviction in the direction I’m headed. More clarity on what this next chapter is evolving into.

So from the bottom of my heart—thank you.

I’m rooting for you. The best is yet to come🤘