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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Stop Summarizing Books

Did the author not make themselves clear?

Was the book so awfully written that we need you to explain what the author failed to articulate?

Summarizing books is a waste of time that works.

It works because we’re getting busier. 200 pages? No time for that. 12 bullet points? Perfect.

And it’s a waste of time because none of your favorite authors summarized books before writing their first bestseller. Instead, they wrote until they wrote their first bestseller.

The point of reading a book is to experience the book through the lenses of your perception. To summarize books is to enable people to take more shortcuts.

Please don’t give me the key takeaways. Tell me why this book is worth the 9 hours it takes to read it.

If you have a counter argument, please, drop a comment and let me know. I love having my mind changed.

“But I don’t have any original ideas”

Right. Neither do I. Neither does anyone.

The idea doesn’t belong to you. It belongs to us.

Steven Pressfield pointed out that resistance is what gets us stuck. But resistance wasn’t his idea. He didn’t invent what it feels like to be stuck. Stuck creatives invented what it feels like to be stuck by feeling stuck. Then Steven Pressfield came along and used one word to express what it’s like to feel stuck. Resistance was only the word. The idea of being stuck belonged to the stuck creative.

Mark Zuckerberg didn’t invent the social creature. He didn’t invent a need to connect to other people. Facebook was his invention. A need for connection wasn’t his idea. It was our idea. We were social creatures before Zuckerberg came along. So Facebook worked.

We use Facebook because we want to feel connected.

We call it resistance because that’s what it feels like to be stuck.

We drink coffee because we don’t want to feel tired.

Original ideas are words and images that resonate with ancient feelings. Too often, the stuck creative focuses on the original idea first.

Humans have been around for a long time. You and I don’t have the omnipotence to invent a new need, personality trait, or desire. Nobody needs a $500 purse. Ancient nobility didn’t need a $500 purse, either. But what modern people and ancient nobility share in common is a need to feel luxurious. They need what the $500 purse will make them feel. The need to feel luxurious has been around since the age of kings and queens.

Is uniqueness dead? Are there no more final frontiers? Have The Simpsons claimed sovereignty over every new idea?

Of course not. You’re the final frontier. Nobody has expressed ideas in the way that only you can. Your idiosyncrasies are unique to you. Your personality is yours – nobody else’s.

The need to be original is why there’s more stuck creatives than unstuck creatives. The need to be original is a trap. We don’t have any original ideas. Opening up a gym so that people can get fit isn’t a new idea. We’ve been opening up gyms and getting fit since ancient Rome.

Instead of trying to come up with original ideas, let’s come up with unoriginal ideas instead.

Here’s some questions that’ll help with that:

What do you see that we don’t see?

What can you offer that nobody else can?

What’s your take on this?

What are your assertions?

Why is this so important to you?

What can you articulate that we find hard to express?

What would happen if you walked up to someone on the street and said, “Hey here’s my original idea”? What would they say? “Thanks, but what’s in it for me?” They’re not being selfish. You’d say the same thing. People want unoriginal feelings. Connection, luxury, status, alliance, anger, tension – those aren’t new feelings. They’ve been around forever. To disregard these essential elements of human nature is to be negligent of how people work.

You’re a person. You know how people work. Getting in your way means that you’re focusing too much on what you need.

Buy Me a Coffee at

Instant messaging and hiking

Instant messaging: you send a message, they respond. Instantly.

That’s not what happens when we publish an 800 word essay about a new self-help practice. Or a 16 minute video about a new meditation technique.

A good reader isn’t done reading after they’ve read the last word. The reading continues while the reader considers what they’ve read.

And if they try to apply what they’ve read? Expect to wait even longer to hear their feedback. Finding out if your advice actually works takes longer than reading your essay. Because of this, it takes longer than we think for our messages to spread.

But that doesn’t stop us from checking to see if anyone has liked our 800 word essay that we published 2 minutes ago. (If anybody has, your readers must be very good at speed-reading.)

So here’s a rule that might help ease any post-publishing nerves.

After you click publish, go take a hike.


My Most Ambitious Reading Project: The Collected Works of C.G Jung.


Jung was a juggernaut.

Inspired by Poor Bjorn’s post about his reading the entire “Story of Civilization” by Will Durant, I’d like to share with you what I consider to be my most ambitious reading project: to read through the entire collected works of C.G Jung (The Bollingen Series as translated by RF.C Hull. Can you believe that just about every word that Jung wrote was translated by one person?)

There are 20 volumes in total (the last 2 are an index and bibliography) containing Jung’s commitment to think through millennia of myth and symbolism to explain what every good psychologist is supposed to explain: why we do what we do. 

So far, I’ve only read ‘Two Essays on Analytical Psychology’ which I found to be absolutely fascinating. Highly recommended for anyone even slightly interested in the nuances of human behavior.

This is going to take a long time. Not only because of the length of the books, but because the content in many of his books is difficult to understand (anima and animus, the mana personality, the syzygy –  to name just few esoteric concepts) and he frequently references other authors like Gothe, Freud, Nietzsche, Lao Tzu, and many other ancient scriptures and texts. And finally, because many of Jung’s sentences are so profound that it’s like being punched in the gut when you’re not prepared. You just have to take a minute to let the depth of what you’ve just read sink in. These are books that you can’t speed read.

But this goal has no due date. It’s part of a larger goal of mine, which is to read all the great books in the subjects that interest me the most. To name a few, this includes all the great books by Dostoevsky, Freud, Carl Rogers, Nietzsche, Seneca. On the business/productivity/21st century skill side, this includes all the great books by Tim Ferriss, Seth Godin, Ryan Holiday, Ray Dalio, Jocko Willink, and many others.

Is there a subject that you’re so passionate about, so enthralled by, that you want to read everything that was ever written on it? Let me know. I’d love to hear from you.

Penguin Latte 01: Zen and The Art of Motorcycle Maintenance

Today, I’m launching the first episode of the Penguin Latte Podcast.

In this podcast, I’ll be sharing with you thought provoking ideas from the fields and practices of Psychology, business, marketing, self-development, art, minimalism, meditation, and everything in between.

This is a podcast about the ideas and stories that challenge you to be your best self.

Ultimately, this is a podcast about quality.

Here’s the first episode.

And here are the show notes.

Zen and The art of Motorcycle Maintenance

The Art of Learning by Josh Waitzkin

Josh Waitzkin’s recommended books on Philosophy (how I discovered Zen and The Art)


Wabi Sabi and Essentialism – Two Approaches to Quality

Everything and everybody is calling out for our attention. Respond to this email, take this job offering, apply to this college, read this book instead of that one, start a blog; no, don’t start a blog, don’t make another podcast, don’t get a regular job because freelancing is in vogue.

We no longer listen with our ears. We listen with our attention. And our attention is tone-deaf because of the incessant noise of everything and everybody demanding it. What and who should we listen to?

Ourselves. Our voice. The voice that we know best. The voice that’s drowned out by all the other voices.

Okay –  but how? How can we tell which demands for our attention – inner and outer – are worth ignoring? And when doing our work, how can we know what to keep and what to discard? How can we know what we’re trying to say? How can we know what our message really is?

Authors Beth Kempton and Greg McKeown know how.

In Wabi-Sabi, Beth Kempton approaches these questions from a more spiritual and poetic perspective, tying in stories from her life in Japan with rich observations on what it means to live a life of ‘imperfect imperfection.’ Her book reminds me how important it is to be okay with imperfections, especially when it comes to personal branding. (Emphasis should always be placed on the word ‘personal’) Though, the personal brings the imperfections – but that’s exactly what makes your work standout.

In Essentialism, Greg McKeown approaches these questions from the world of business and productivity. Essentialism is a framework that challenges us to be okay with cutting out the fluff from our work, to say no to many of the demands for our atrention.

Essentialism is a timeless book. No matter what project I start, I face the same problems as the last project: what should I keep, what should I discard? Should I make this? Who should I connect with? What if I’m not good enough? Why am I hindering my progress by ruminating on these questions?

These two books taught me that ‘enough’ is something I get to decide.

Have you read these books? Drop a comment. I’d love to hear from you.