The Learning Leader Show With Ryan Hawk - 690: Austin Kleon - Why Activated Leaders Win, The Analog Desk, Don't Call it Art, Stay Light, Professional Noticers, Lead with Curiosity, and How To Steal Like an Artist

Duration: 1h 0m
Broadcast on: 31 May 2026
Audio Format: other

The Learning Leader Show with Ryan Hawk

www.LearningLeader.com

New Book -- The Price of Becoming

www.LearningLeader.com/Becoming

Austin Kleon is the NYT bestselling author of Steal Like an Artist, Show Your Work, and Keep Going. He's a writer who draws, a former librarian, and one of the most original thinkers on creativity working today. His new book is Don't Call It Art: 10 Ways to Create Like a Kid Again.

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Key Learnings

Stay light. Bill Murray told ballplayers that if you stay light, loose, and relaxed, you can play at the highest level. Same with acting, writing, anything. Austin keeps a photo of Bill in his studio as a reminder.

Play is the work. A lot of Austin's best work requires a sense of play. It's hard to tell where one ends and the other begins.

Go to the analog desk first. Austin has a digital desk and an analog desk. Nothing electronic is allowed at the analog desk. He starts there with nothing and sees what comes.

Most people never give themselves the time, space, and materials to make something of what's swirling inside them.

People want to watch someone who is activated. "People will pay every night to show up and see somebody believe in themselves." (Kim Gordon, Sonic Youth)

The market for something to believe in is infinite. (Hugh MacLeod) The world is full of people just doing their thing. They're hungry to see someone on fire for something.

The writer's job: take what everyone is thinking and put it into words. "You gave me the words" is the highest compliment a reader can give.

Effortless is earned. People say the Friday newsletter looks easy. Austin's reply: Do it every Friday for 13 years, then call me.

A place to put things makes you notice more. Thoreau took morning walks knowing he'd write later, so he paid closer attention. Carry a camera, and you start seeing shots everywhere.

Live for the living, not for the writing. There's a tension between living your life and documenting it. Don't lose yourself to the feed.

Your attention is the most valuable thing you have. Everyone wants to take it. The real challenge of modern life is making sure you're the one who decides where it goes.

The best teachers are perpetual students. You realize what you know and don't know only when you try to teach it.

Toggle between knowing and not knowing. The moment you think you know what you're doing, the work gets stale. You start running on routine instead of need.

To be an amateur is to be a lover. The French root means "lover of." An amateur does it out of love, not material reward.

Every great CEO should be put in a room with a four-year-old. They'd both learn something. Kids knock the pompous certainty right out of you.

"I don't know. How do you think we should figure it out?" Austin's kids taught him it's less important to know everything than to know how to find out.

The leader isn't the one who speaks while everyone listens. The leader listens, asks questions, stays curious, and wonders how everyone is doing.

Look for who's having fun, not who's successful. Fun is underrated. Serious people have a serious time. Do it with lightness and it's contagious.

"A master in the art of living draws no sharp distinction between his work and his play." (Lawrence Pearsall Jacks) He hardly knows which is which. He simply pursues his vision of excellence through whatever he's doing and leaves others to decide whether he's working or playing. To himself, he always appears to be doing both.

Ask "What does the universe want to show me today?" A useful fiction. Tell yourself the world is trying to send you messages and suddenly you see a hundred of them.

Have the toy before you know what you'll do with it. Austin buys typewriters, then asks what to make. Get the bicycle first. In six months you'll know what kind you actually want.

Steal an idea someone only did once and turn it into a whole thing. Austin saw a single typewriter interview, made it a series, and has done more than 20.

Put the human hand in the work. Austin decided 20 years ago to make it obvious a human made his stuff. In the age of AI, it stands out more than ever. People want the imperfection.

Writing is thinking. People think you gather your ideas then write them down. The act of writing is the act of figuring out what you actually think. That's the hard part.

Differentiate yourself by reading a book outside your field. Swim a little further out than everyone else and you find new water.

Focus on what you can control. A writer controls only what's between the covers. Did you do a good job? Were you clear? Were you helpful? The rest isn't up to you.

Austin's champagne moment a year from now: his kids flourishing. The older he gets, the less the books mean and the more his family does.

Reflection Questions

Where is your analog desk? Do you have a space with no screens where you go to make something of what's swirling inside you?
Are you activated? When people watch you work, do they see someone on fire for it, or someone just going through the motions?
What's one idea from outside your field you could steal this week? Where could you swim a little further out and find new water?

More Learning

#676: Jesse Cole - Built for the Fans, Obsession & Excellence#687: Jim Collins - What to Make of a Life#241: Austin Kleon - How to Steal Like an Artist

Podcast Chapters

00:00 The Price of Becoming - Pre-Order Now!

01:33 Meet Austin Kleon

02:53 The Bill Murray Photo: Stay Light

05:42 The Analog Desk: Where the Real Work Starts

08:51 People Want to Watch Someone Activated

15:22 Why "It Looks Easy" Is the Whole Point

16:28 The Newsletter as a Forcing Function to Notice

20:46 Who Owns Your Attention?

24:39 How Austin's Kids Became His Teachers

29:06 Why the Best Creators Stay Amateurs

31:33 Curiosity Is the Real Leadership Skill

34:09 What Does the Universe Want to Show Me Today?

35:02 Look for Who's Having Fun, Not Who's Successful

38:30 Do You Love to Write, or Love to Have Written?

41:00 The Typewriter Interviews: Stealing an Idea Done Once

47:18 The Interplay of Analog and Digital

49:02 AI and Why the Human Hand Wins

51:23 The Champagne Question: Family Flourishing

55:47 Walk-Ins Welcome

58:06 EOPC

My next book, The Price of Becoming, will be out in a few months, available for pre-order right now at learningleader.com but in the meantime, I've been sending it to authors that I really look up to. A lot of them have been on this podcast. One of them is Daniel Pink, best-selling author of To Sell Us Human, Drive, Win, The Power of Regret and many others. Just ask them what he thought. Ask them if you'd write a blurb, an endorsement for the book, maybe one that I would put on the cover, and this is what he sent back to me. Dan Pink says, "The price of becoming refuses to sell you a shortcut." Instead, Ryan shows how small, daily deposits, 100 shots, 500 words, a single, tough conversation compound into something that looks like an overnight success to anyone who wasn't paying attention. This is a clear-eyed, powerful book. I'm super grateful for people like Dan Pink to have read it and shared his thoughts. I would love it if you would go to learningleader.com and pre-order the book right now or just go straight to Amazon and pre-order The Price of Becoming. Thank you so much. Welcome to The Learning Leaders Show presented by Insight Global. I am your host, Ryan Hawk. Thank you so much for being here. Go to learningleader.com for show notes of this and all podcast episodes. Go to learningleader.com. Now on to tonight's featured leader. I love Austin Cleon, New York Times best-selling author of "Steal Like An Artist." Show your work and keep going. These are books that have sold more than 2 million copies worldwide. Austin is a writer who draws a former librarian and one of the most original thinkers on creativity working today. His new book is called Don't Call It Art. 10 ways to create like a kid again. During our conversation we discuss why watching someone who is fully activated and loves their work is one of the most contagious and attractive things in the world. Then the analog desk, why you should consider having a separate space with no screens and what it unlocks that digital work and not Austin has one of these and we go deep on that. And then he tells a cool story about why he goes out into the world and doesn't look for people who are "successful." Instead, he looks for people who are having fun and then tries to learn from them. Ladies and gentlemen, please enjoy my conversation with Austin Cleon. I love the fact that you have a picture of Bill Murray up in your studio. As a reminder, why do you have a picture of Bill Murray up? Well, you know, Bill Murray, it's this really goofy picture I found in the magazine and I think he has like a, he's got his belly exposed and he's like drawing a crown on it. The really important part of the picture is there's this post-it and it says stay light and it was a speech that he gave these ball players one time. He said, you know, if you can stay light and loose and relaxed, you can play at the highest level. And he said that was true of like baseball acting or whatever. And I just like always really took that to heart because I found it in my own work. If I can stay light and have a sense of, you know, just to keep that sense of lightness, of play, of flow, I do better, you know, keeping that sense of playfulness. And so that's why I keep it up in the studio. One of the things that I watch your videos, I feel like you just have such a welcoming style. Hey, y'all, you know, like bringing your inside the studio. It's so you've got all the stuff behind you, right? You get all these things going on. And it seems that you embody that spirit well of welcoming people into your creative space on you have an analog desk and you have all these separate areas where you could actually make art. I love just hear more about your overall philosophy of how you have designed your space to be welcoming, not only for yourself, but for other people as well. Oh, yeah. Well, that's a fun thing. So when I first started out, I didn't have much of a space. I mean, I was making I think my first book I did in the basement of the law school where I was a web designer and and riding the bus back home. I mean, that's how a lot of that first a poetry book was made. And then, you know, as I kind of like, it continued on and on, I think I had a nice office in our house when my kids were little and then we had another kid and I had to move out to the garage and they worked into garages for a while. It's at this place that we're in right now. I actually built this. This is in my backyard in Austin, Texas. And it's it's the first space I've ever actually created for myself. There's a funny story about this. When I had this built and it was pristine, it had like, you know, nice new floors and new walls and it just it was like, wow,

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