Risk Isn't That Risky

“You’re going to fucking die.” - David Senra

Dec 14, 2023

In 1994 at the age of 30, Jeff Bezos was the senior VP at a hedge fund in New York City.

Around this time, he told his boss about doing something wild: selling books on this new thing called the Internet. After a long walk, they concluded it was a good idea—but only for someone who didn’t already have a great job and stable life.

Still, Bezos left. Missing out on his juicy Wall Street bonus, he and his wife moved to Seattle to start Amazon.com in their garage.

But while he was still pondering leaving, he invented a way to make the difficult decision easy. He called it a “regret minimization framework.” The idea: imagine you’re 80 years old, reflecting back on your life. You want to have as few regrets as possible.

“I knew that when I was 80,” Bezos said, “I was not going to regret having tried this.”

“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. And I knew that would haunt me every day.” [1]

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Internal Suicide

I don’t think the billionaire regretted his decision.

And looking back on 2023, I don’t regret my decision to drop out of college.

When I was studying pre-med at Boulder, I had straight A’s. I was killing it in school. But I didn’t feel like I was where I really wanted to be. I felt like I was wasting my time memorizing Dopamine receptors.

And I wasn’t really around other curious, ambitious kids. I felt like an outsider. I wanted to learn—not party Thursday to Sunday. I read Seneca and learned productivity from Ali Abdaal, shoving back serious studying as much as I could. I started a newsletter to satiate my curiosity. I researched medicine and realized I didn’t want the limited lifestyle of a doctor. [2]

But I already finished three semesters. I was a month into my fourth.

Gearing up to take a Spanish test and a physiology quiz, my internal voice whispered something as loud as a whisper can be: I need to make a change. This path isn’t for me anymore. There’s something else out there. Trust your intuition.

Before I left, I walked myself through the regret framework. Like Bezos, I knew that I’d regret not leaving and trying something else. After all, it was also a reversible decision—colleges will probably always be there.

So with my stomach shivering on a Sunday morning at IHOP, I dumped the news on my parents. I dropped out. At first, I worried about what other people would think. Teachers, friends, classmates. An old professor even emailed me: Is everything alright, Baxter?

Why was I so worried about what other people thought about me? Why do we care so much about judgment and disappointing others?

Because we want external validation. Remember: we’re animals. We’re biologically programmed to crave social approval. But when you live for others, you commit internal suicide. [3]

And to prevent internal suicide, let me tell you a little bit more about regrets.

“You’re Going to Fucking Die.” - David Senra

In 2011, deathbed nurse Bronnie Ware wrote a book called The Top Five Regrets of the Dying. If there’s anybody to take advice from, it’s probably those close to the grave.

Their #1 regret:

"I wish I'd had the courage to live a life true to myself, not the life others expected of me."

This reminded me of an insight I heard from podcaster David Senra. Senra devotes his life’s work to reading biographies and sharing lessons from history’s greatest founders—both dead and alive. Bezos, Ford, Munger, and more great gods.

When thinking about risky decisions, Senra said, “everything you think is risky or scary is nothing compared to the end of your existence.” “You’re going to fucking die. You have one life, and you’re doing to die.”

In other words, fear is a liar. And risk isn’t that risky. [4]

Anytime I feel that twisting pit of fear in my stomach, I lean into it. I use fear as a cue to take action. At first it’s scary, but after a few months you’ll see—so worth it.

"The more important a call or action is to our soul's evolution, the more Resistance we will feel toward pursuing it." - Steven Pressfield, The War of Art

When I reflect on 2023 decisions like dropping out of Boulder, buying a one-way ticket to Sevilla, or sending a cold email to an author, all these changed my life trajectory.

If I died right now, I’d be stoked about my 2023.

For the first time in my life, I feel like I’m actually in control of my path. I’m going where I want—not where other people think I “should” go. I still don’t know exactly where I’m going, but that’s better than real regret.

I did things that I’ve always wanted to do. I vagabonded across Europe for 3 months. I saw Ludovico Einaudi perform live. I took an online writing course called Write of Passage. I read some banger books, like Greenlights and Mastery. And I’ve made some fast friends and mentors through the Internet.

If I make it to the age of 80, I know I won’t have regretted leaving college. I escaped internal suicide. I hope you find the courage to do the same.

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Notes

[1] I found this story in Bezos’ 2001 Interview

[2] There’s a great tip I heard from podcaster Danny Miranda on finding work you love: What do you do when you procrastinate?

If you binge TV or play video games, that probably doesn’t count. The question is more aimed at identifying things you’re naturally curious about. Things that you find interesting that others find a bit boring.

In college I loved reading about Stoicism, productivity, and psychology. I’d procrastinate by reading books. Looking back, that’s a good sign to be a reader and writer.

[3] I’m also not saying you should aim to do this alone. I think we still need a few staunch supporters to keep going.

Just beware of human nature:

In the psychology book Ca$hvertising, Drew Eric Whitman identified eight things that we’re biologically programmed to want. He called them the “Life Force 8.” Two of these are social approval and being superior.

[4] I heard this quote from entrepreneur Oliver Cookson on Ali Abdaal’s podcast.