The Best Returns on Money I’ve Gotten

The best investments are rarely the flashy stuff. Comfort, time, peace of mind, knowledge acquisition, health, and saved hours compound faster than any status symbol. Here are some of the highest ROI things I don’t mind splurging on.

"Wisdom is the ability to go through life ready to change your mind."

I’m a big fan of Ryan Holiday. His work championing Stoicism has had a big influence on me, and he’s consistently one of the best at digging up timeless ideas from history and making them feel relevant today.

That said, I don’t think Wisdom Takes Work was written for someone like me. The book’s core message is that reading, writing, and deliberate thinking are the main ingredients for developing wisdom, which, frankly, is something I already live by. I found myself nodding along more than I was learning.

It’s a solid book that probably needed to exist, especially for people who haven’t yet built those habits. But because I’ve already read many of the sources Holiday quotes, it felt like a well-curated recap vs. a fresh perspective.

My only real gripe is one I’ve had with some of Holiday’s recent writing and online presence: his occasional political undertones. They’re subtle, but you can feel his disdain for a certain side of the aisle seep through. He’s free to write however he wants, of course, but I just think that edge kinda undercuts his whole reputation as the calm, "non-reactive" Stoic voice that drew me in to him to begin with.

I’ve been on the hunt for better ways to incorporate AI into my life — ways to improve my understanding, skills I can acquire, and resources for guidance. On a recent podcast, Seth Godin offered some fantastic advice. Among other gems, this was one of the most interesting use cases he offered:

For those who don’t get the meme, it’s actually straightforward and has a pretty cool backstory.

In WWII, engineers studied returning planes to see where to add armor. At first glance, you’d reinforce the spots riddled with bullet holes. But a mathematician realized the opposite was true — those planes survived despite being hit there. The planes that never came back were the ones hit in the untouched areas. Those were the areas that should be reinforced.

It's a classic example of survivorship bias, where you draw conclusions from only the visible “survivors,” ignoring the invisible failures. You see it everywhere. We copy the morning routines of billionaires, forgetting the thousands who followed the same routines and failed. We idolize college dropouts like Jobs and Zuck while ignoring the millions of dropouts who never made it. We look at long-married couples for “secrets,” overlooking the many who did the same things and divorced.

h/t @TheDimitriT

I wouldn’t have guessed it when I hit play, but this was one of the best podcasts I’ve listened to all year. Just read through the comment section to see how much people appreciate this conversation.

“This podcast, especially towards the last hour, makes me want to give both of them a big hug. Thank you gentlemen for being so real and relatable.”

I’ve always said that comedians are basically just philosophers who do comedy. Louis delves deep on this one, and it’s extremely refreshing to hear such public figures be humble and vulnerable with a great sense of humor through it all. Despite all he went through, he seems genuinely grateful to have arrived at a place of peace. I love how he interacts with Theo — he plays with everything he says while also keeping him on track (which not many people can do 😂).

More importantly, Louis C.K. is now an author! His novel, Ingram, is available on Amazon to pre-order through November 11.

Keith and Kyle sit down to discuss the life of Frantz Schmidt, a sixteenth-century executioner in ⁠Nuremberg, Germany⁠. Based on Schmidt's unique journal, the book explores his public role in executing and punishing people, his private struggles with his profession and religious faith, and his attempt to gain honor and avoid the social stigma of being an executioner.  A rare, detailed look into the era's criminal justice, social customs, and even medical practices, challenging the common perception of executioners as monsters. 

📚 Books discussed in this episode:

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Thanks for reading!