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Today at a Glance
Question: What if you could know—with mathematical certainty—which life decision to make?
Quote: "I knew when I was 80, I was not going to regret having tried this. I knew the one thing I might regret is not ever having tried." - Jeff Bezos
Tool: The "Regret Minimization Framework" that made one man $200 billion
Question on Knowing What to Do
What if you could know—with mathematical certainty—which life decision to make?
Jeff Bezos had everything.
Spring 1994. Thirty years old. Senior vice president at a Wall Street hedge fund. Seven-figure salary. Manhattan penthouse. The American dream achieved before most people get their first promotion.
And he was about to throw it all away. For books.
Not writing them. Not reading them. Selling them. On something called "the Internet" that most people couldn't even define.
Here's how a 5-minute mental exercise turned a hedge fund VP into the world's richest man—and why you've been making decisions wrong your entire life.
Bezos worked at D.E. Shaw & Co., one of those Wall Street firms that prints money using math. His boss, David Shaw, was a former Columbia professor who'd figured out how to use computers to beat the market. Think of it as legalized money printing, but with algorithms.
Bezos was Shaw's golden boy. The youngest senior VP in company history. On track to make tens of millions before forty.
One day, while researching opportunities for the firm, Bezos found a statistic that broke his brain: Internet usage was growing at 2,300% per year.
Not 23%. Not 230%. Two thousand three hundred percent.
"Things just don't grow that fast," Bezos would later say. "Outside of petri dishes, nothing grows that fast."
He couldn't stop thinking about it. That number—2,300%—infected his mind like a virus.
So he did what any math nerd would do. He made a list. Twenty products that could be sold online. Books won. Why? Simple math: 3 million books existed in print, but the biggest bookstore could only hold 150,000. The Internet could hold them all.
Bezos knew he had to tell his boss.
"Jeff, let's take a walk," Shaw said.
This was their thing. Big decisions happened on walks through Central Park, not in boardrooms.
For two hours, they walked. Shaw understood immediately—this wasn't just about books. This was about the future of how humans would buy things. Everything.
Finally, Shaw spoke: "This is a brilliant idea. But it would be an even better idea for someone who didn't already have a good job."
Translation: You're about to become filthy rich here. Why risk it?
Shaw told Bezos to take 48 hours. Think it through. Make a rational decision.
That night, Bezos went home and tried something different. Instead of making lists or calculating odds, he imagined himself as an old man.
"I wanted to project myself forward to age 80," he later explained. "I wanted to have minimized the number of regrets I have."
Then he asked himself three questions:
How will I feel about this decision in 10 minutes?
How will I feel in 10 months?
How will I feel in 10 years?
10 minutes: Terrified. Walking away from guaranteed millions.
10 months: Either building something new or begging for my job back.
10 years: This is where everything changed.
"I knew when I was 80, I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet. I knew that if I failed, I wouldn't regret that."
Then the knockout punch:
"But I knew the one thing I might regret is not ever having tried. I knew that would haunt me every day."
The decision suddenly wasn't about success versus failure. It was about two different flavors of regret. And one tasted much worse than the other.
Bezos quit the next day.
He loaded his entire life into a beat-up Chevy Blazer. His wife MacKenzie drove while he typed a business plan on his laptop, using his knees as a desk. Destination: Seattle. Why? It had the most book readers per capita in America.
His parents invested their entire retirement savings—$300,000. When he explained the Internet, his mom asked, "What's that?"
They weren't investing in an idea. They were investing in their son.
Bezos set up shop in his garage. Built desks out of doors from Home Depot because real desks cost too much. When an employee suggested buying actual furniture, Bezos replied: "We should get knee pads instead."
It took him three weeks to realize the desks were the better idea.
The company was originally called Cadabra, like "abracadabra." His lawyer misheard it as "cadaver" on a phone call. Bezos immediately changed it to Amazon—the biggest river, for what he hoped would be the biggest store.
Years later, during the dot-com crash, Amazon's stock fell 95%. From $107 to $7. The media called it "Amazon.bomb." Analysts predicted bankruptcy within months.
But Bezos never second-guessed leaving Wall Street. Not once.
Why? Because he'd already run the only calculation that mattered.
Today, that calculation is worth $2 trillion.
Quote on the Science of Regret
"I knew when I was 80, I was not going to regret having tried this. I knew the one thing I might regret is not ever having tried." - Jeff Bezos
When Bezos imagined himself at 80, he accidentally discovered something scientists would later prove.
Cornell psychologist Thomas Gilovich spent 20 years studying what people regret. His finding changed everything we thought we knew about decision-making.
We regret what we didn't do twice as much as what we did.
But here's the twist: It gets worse over time.
Actions you regret fade. That business that failed? That relationship that crashed? The pain softens. Eventually, you laugh about it.
But things you didn't do? They grow. They compound. They become ghosts that haunt you at 3 AM.
When Gilovich surveyed thousands of people about their deepest regrets:
76% were things they DIDN'T do
Only 24% were things they DID
And the pattern intensified with age:
20-somethings: Equal regret for action and inaction
40-somethings: 2x more regret for inaction
60-somethings: 3x more regret for inaction
80-somethings: Almost exclusively regret inaction
The science gets darker.
USC neuroscientists put people in brain scanners and watched what happens when we experience regret. The results were shocking.
Your brain processes a missed opportunity exactly like an actual loss. Neurologically, they're identical. Losing $10,000 and not making $10,000 you could have made look exactly the same in your brain.
With one cruel difference.
Actual losses have closure. You lost. It's over. You move on.
Missed opportunities never close. They create what psychologists call "open loops"—mental processes that never complete. They sit in your brain, consuming energy, forever.
Northwestern researcher Neal Roese found this pattern in every culture studied. American, European, Asian—everyone shows the same pattern. The regret of inaction compounds like interest on a debt you can never pay.
But the most important discovery came from Hamburg researcher Stefanie Brassen.
She studied people who aged successfully—staying happy and sharp into their 80s. They all shared one trait.
They weren't the people who succeeded at everything.
They were the people who tried everything that mattered to them.
Their brains had literally rewired around action instead of avoidance.
Which brings us back to Bezos, running his mental calculation.
He wasn't optimizing for success. He was optimizing for regret minimization.
And that changed everything.
A Useful Tool: The Regret Minimization Framework
Bezos calls it his "regret minimization framework."
It takes 5 minutes. It will change your life.
Here's exactly how it works:
Step 1: Make It Binary
Your brain hates gray areas. Convert your decision to a clear yes/no with a deadline.
Bad: "Should I think about maybe changing careers?" Good: "Will I quit my job by March 31st to start my business?"
Specificity forces clarity. Vague questions produce vague lives.
Step 2: Three Time Horizons
Set a timer. 90 seconds per horizon. Write without stopping.
10 Minutes From Now: How do I feel? What am I dealing with? What's the story in my head?
10 Months From Now: What's daily life like? What problems are gone? What new problems exist?
10 Years From Now: What story do I tell about this? What would I tell my current self?
Critical: Write from the future looking back. Not "I will feel scared" but "I felt scared for two weeks, then..."
Step 3: Do the Math
Rate each scenario from 1-10:
Action Regret: If I do this and fail, how much will I regret it in 10 years?
Inaction Regret: If I don't do this, how much will I regret it in 10 years?
The Differential: Inaction minus Action
Positive number = You must act
Negative = Don't act
Zero = Need more data
Bezos's calculation:
Action Regret: 2/10 ("I tried something bold")
Inaction Regret: 10/10 ("I watched from the sidelines")
Differential: +8 (Overwhelming signal to act)
Step 4: Pre-Mortem
If your differential is positive, assume you'll act. Now assume you'll fail.
List three likely failure modes:
Biggest risk → How to prevent it
Second risk → How to prevent it
Third risk → How to prevent it
This isn't pessimism. It's vaccination. You're building immunity to failure.
Step 5: Burn the Ships
Within 24 hours, do something irreversible:
Send the resignation
Pay the deposit
Tell everyone
Book the ticket
Cortés burned his ships when he reached the New World. No retreat possible.
Bezos told his parents before his boss. Once your parents know you're quitting Wall Street to sell books online, there's no graceful exit.
The Hidden Pattern
Every avoided decision makes the next one easier to avoid. Cowardice compounds.
But courage compounds too. Every action makes the next action easier.
Bezos didn't just use this framework once. He used it for everything. AWS? "What would we regret not trying?" Prime? Same question. Alexa? Same question.
The framework became a philosophy. The philosophy became an empire.
Your Permission Slip
Right now, you're sitting on a decision.
You know the one. It's been eating at you for weeks, months, maybe years.
You've made lists. Asked everyone. Researched yourself into paralysis.
But you haven't run the framework.
Because you already know what it will tell you.
Here's what Bezos understood: You're not afraid of failure. You're afraid of the space between now and potential failure. That temporary discomfort.
But your 80-year-old self doesn't care about temporary.
Your 80-year-old self only cares about one thing: Did you try?
Not "Did you succeed?" Just "Did you try?"
Bezos could have stayed at D.E. Shaw. He'd be worth hundreds of millions today. Safe. Comfortable. Successful.
But he wouldn't be Bezos.
And you, choosing safety, aren't becoming you.
Every decision you delay is a vote for who you were instead of who you could be.
The 10-minute you wants comfort. The 10-month you wants security. The 10-year you wants stories.
Listen to the 10-year you.
Open a document. Right now. Write the question. Run the calculation.
The framework takes 5 minutes.
The regret lasts forever.
You're choosing one of them right now.
Whether you realize it or not.
This is such a powerful reminder, Scott. The regret minimization framework really reframes decision-making, focusing on action over fear. So often we overanalyze, but stepping back and thinking about our 80-year-old self makes it clear what truly matters. Definitely going to try this for my next big decision.