Rich Hebron: The Slow Life, Rethinking Homelessness, French Pressed Meditation, Museums, Books, Chicago, and Defining Success (#30)

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Today on the show I’m joined by my buddy Rich Hebron (@richhebron). Rich Hebron is a writer, illustrator, and public speaker from Chicago, Illinois. His podcast Rich Conversations is available on Spotify, Apple podcasts, and YouTube.

I love this guy. Rich Hebron is a true renaissance man. In three words? Playful. Wise. Open. Rich Hebron is like an open treasure chest in the middle of an urban park. You walk through the city, distracted by the sights and sounds. But then you discover the park, like that big park in New York City. Sitting in that park is an open treasure chest. You peek inside. It’s full of ancient wisdom on how to live life to the fullest. That’s Rich Hebron.

When Rich was 22 years old he voluntarily lived homeless to see what it was like. He remembers those experiences to this day. And in this episode he shares what he learned about homelessness, and how we need to rethink what it means to live without permanent housing.

Rich brings the sort of joy to a conversation that reminds me why I love talking to people. This is only round one of a hundred more episodes we’ll have together.

Please enjoy this wide ranging conversation about books, museums, dinosaurs, life, death, rethinking homelessness (Rich spent months living homeless), and, of course, so much more.

Cheers, and here’s to your good health this week.

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Shopping is about trying stuff on

Aristotle wrote, “It is the mark of an educated mind to be able to entertain a thought without accepting it.”

And it’s the mark of a conscious materialist to be able to walk around Walmart on Black Friday without frothing at the mouth.

Nothing wrong with shopping. Especially good shopping. Good shopping means slow shopping. Conscious shopping. Shopping for more of what you need, and less of what you wish you had.

Let’s apply this to our brains.

We can shop around, consciously, for new habits, thoughts, goals, beliefs. We can try on the 30-day jogging habit like we try on the Leopard Skin Pillbox Hat. And if we don’t like it, if we find out it’s not for us, we can choose something else. We can do Aristotle proud. We can entertain without accepting. Besides, that’s what shopping is for. Trying stuff.

P.S I realize now you can’t try on a plasma screen TV.
(Do they still make TV screens out of plasma? Isn’t that dangerous?)


We all have the capacity to learn. To learn to ride a bike. To learn a language. To learn to solve complicated math problems.

But what we often lack is the capacity for commitment. The follow through. The jump. The starting as you mean to go on.

And just as we have the capacity to learn a language, we have the capacity to learn how to follow through with our plans.

“You will lose points if you make too many mistakes”

The instructions on my online Japanese homework read: “you will lose points if you make too many mistakes.”

I’m sorry?

Isn’t that how we learn?

By making mistakes?

And how many mistakes is too many? It doesn’t matter if a kid falls off his bike 500 times. Give them the chance to get back on 512 times, if that’s what it takes to teach him how to ride a bike.

I understand that this is to discourage students from doing badly on purpose. That’s called brute-force cheating, and it doesn’t teach students anything besides how to cheat.

But what if instead of penalizing students for making mistakes, we encouraged them to make as many mistakes as they need?

This problem wouldn’t exist if we designed courses that were impossible to cheat. As long, of course, as we also encourage them to understand why it matters to make mistakes.

0.0001%* Of Your Life

If you’re learning something new, ask yourself:

How much of my life have I spent not doing this?

26 years of not speaking in Japanese.

37 years of not surfing.

81 years of not writing a memoir.

Of course it’s hard. Of course you’re forgetting steps, falling off your board, and faltering up the stairs. Of course you want to quit. But do you realize that you’ve only spent a miniscule fraction of your life trying to improve at this? And that you’ve spent the other 99.99something% doing other stuff?

The time you haven’t spent improving at this will always outnumber the time you’ve spent working hard to get better.

There’s a fight going on inside of you between an archetypal David and Goliath. In one corner of the ring we have You With Experience. And in the other corner, we have You With No Experience.

You With Experience has 4 days of Japanese grammar tutorials fresh in his head. This is you. You are David. You are naïve. Undisciplined. Untrained. Nobody expects you to win. The odds are against you.

You With No Experience has 26 years of Not-Knowing-Jack-About-Japanese Grammar Experience under his belt. This is also you. You are your own Goliath. You’ve been training your entire life in the ways of not knowing jack about the が particle.

Who do you think will win?

* Guesswork with a very rough ballpark estimate, maybe, perhaps.