


12 Jun 2026 · 4m · 3 chapters

The episode argues that life and work shouldn’t be only about productivity; small, sometimes “weird” activities can make you feel alive and present, and that AI adoption should be approached without guessing.
Chris Guillebeau (author/entrepreneur known for travel and “side hustle”/purpose-driven work).
Don’t sit on the sidelines with AI; competitors are using it now. Find small joys that others may not understand, and say yes to them. Example: “Jan” in the Netherlands books cheap flights within Europe every Wednesday for decades, never leaving the airport—he finds it peaceful. Another example: the host walks 6–7 hours to a restaurant 17 miles away, then remembers it as a “core memory,” despite intending to be productive.
Written by AI. May contain mistakes.
Exploring the importance of having fun and the small joys in life.
“You have to think about how to be of service and also how to have fun and enjoy life yourself, which is also something that I don't historically do a good job of like, I want to have fun.”
Discussing how unproductive activities can lead to memorable and fulfilling experiences.
“But of course it was actually very meditative and kind of fun.”
The importance of accepting spontaneous decisions that seem irresponsible.
“There's a cornbread appetizer that's usually like shared among people.”

Get the gist, explore an idea or ask about something said.
On The Daily Stoic, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Ryan Holiday: You know, most businesses are asking themselves these days, how do we make AI work for us? There's a lot of possibilities. Guessing is risky. There's maybe a steep learning curve. But I think we all understand that sitting on the sidelines is not an option because you know your competitors are using it right now. Well, with NetSuite by Oracle, you can put AI to work today. NetSuite is the number one AI cloud ERP trusted by over 43 ,000 businesses. It's a unified suite that brings your financials, inventory, commerce, HR, and CRM into a single source of truth. From software and IT services to healthcare, equipment manufacturing, financial services, and many other great American industries, NetSuite delivers a customized solution for your businesses.
0:46Ryan Holiday: And it's not some bolted-on tool. It's AI built into the system that runs your business, whether you're a big one or a small one. If your revenues are at least in the seven figures, get their free business guide, Demystifying AI, at netsuite.com. That guide is free to you at netsuite.com. Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world.
1:22Chris Guillebeau: You have to think about how to be of service and also how to have fun and enjoy life yourself, which is also something that I don't historically do a good job of like, I want to have fun. I'm going to do, you know, I actually wrote about it. It's like, how do I practice having fun? Right. It's a whole chapter about this. And I like had the story of this guy in the Netherlands named Jan, who for like 30 years, every Wednesday, he would go to Amsterdam Schiphol Airport and book a flight somewhere within Europe, wherever was cheapest, he'd fly to Stockholm or Barcelona or somewhere. And he would just kind of hang out and he would like walk around the terminal and he'd fly back and he - Never leave the airport?
1:56Chris Guillebeau: Never leave the airport. Okay. It's so interesting. This is what he liked to do. He just like, he found it really peaceful, enjoyable, relaxing, and so on. So it's so easy to criticize that, you know, be like, he never, he traveled so much and never traveled at all. Right. But it's a small thing that made him happy, you know? And I think, you know, if we can all find like small things that make us happy, even if they seem weird to other people or strange or like, why would you do that? Then our lives are going to be better. And I was thinking about his story one day when I went for a walk. I found this restaurant I wanted to go to that was like 17 miles from my house.
2:27Chris Guillebeau: I thought about it for maybe like a few days in advance, but not too long. And I was like, I should walk there. You know, I was like, I should walk to this, you know. And so one day I was like, okay, what do I have this afternoon? Not that much, nothing that I can't do later. And so I did. I got it like right after lunch, I left and I walked like six or seven hours. And it's funny because I thought, well, I'm going to try to get some stuff done on the walk, you know, like make some phone calls or whatever. But then your phone battery dies, you know, cause you're on GPS the whole time, like tracking.
2:53Chris Guillebeau: And I was like, oh, this is not going to actually be a very productive experience. But of course it was actually very meditative and kind of fun. And, you know, also silly, but like, it's like, this is a thing I'm just doing for myself. And I'm not even going to like blog about this. I'm not like, Hey everybody, I'm out on a walk for six hours, you know, I'm just doing this thing. And I, so I went to the restaurant and, and then like went home and then like for days afterwards, I'm like, what a cool thing. You know, what a fun thing that I did. It's a weird core memory.
3:17Ryan Holiday: I bet you felt very alive.
3:18Chris Guillebeau: Yes, exactly. Yeah. Exactly. And so there are things you can do to feel more alive.
3:22Ryan Holiday: Yeah.
3:23Chris Guillebeau: And I have been trying to lean into that myself and I hope that other people will.
3:26Ryan Holiday: Yeah. Instead of going, Hey, I got across these 15 restaurants off a list. I got to do this. you i'm sure you're not just you probably felt alive because you were present you were only doing that thing however silly and inexplicable that thing that was the attraction yes right that
3:44Chris Guillebeau: was the that was the thing yeah did you walk back no i took an uber back and then the whole way 15 minutes exactly that's what's funny i was like this is but i'm passing all the way all the places that i walked you know and i was like oh that's just fun so that was probably when you pass by those places now, you can tap into that feeling for even just a fleeting second. Yeah. And this is two years ago. And I still remember this weird memory and it wasn't that hard of a choice to make. And it's not like I was like every Wednesday from now on, I'm going to walk 17 miles. I don't have to do that.
4:17Chris Guillebeau: I can just be like, what are things like that that I can respond to and say yes to? How was the food? The food was really good. It was really delicious. Cornbread. There's a cornbread appetizer that's usually like shared among people. And I ate the thing. Sure, you just worked it off. Yeah, exactly. You could do whatever you wanted.
4:33Ryan Holiday: I think as you get older, you have less time and also tolerance for doing inexplicable things because they seem irresponsible or hard to justify or even just hard from a scheduling standpoint. But that's kind of what life is. Those are the things that you remember.
4:58You
Heading into the weekend, here’s a reminder that not everything you do has to be useful, efficient, or productive. In this bonus episode, Ryan and Chris Guillebeau talk about making space for fun, following strange impulses, and doing the small things that make you feel more alive.
Watch the full episode with Chris Guillebeau here: https://www.youtube.com/watch?v=SHyEgbTg-BA
Chris Guillebeau is the New York Times bestselling author of The $100 Startup, Side Hustle, and The Happiness of Pursuit, which have sold over one million copies worldwide. During a lifetime of self-employment that included a four-year commitment as a volunteer executive in West Africa, he visited every country in the world (193 in total) before his thirty-fifth birthday. His latest book, Time Anxiety: The Illusion of Urgency and a Better Way to Live, Chris offers a bold path for redefining our relationship with the clock.
Check out Chris’ new book Time Anxiety: The Illusion of Urgency and a Better Way to Live and grab copies of The $100 Startup, Gonzo Capitalism, The Art of Non-Confirmity, 100 Side Hustles at The Painted Porch: https://www.thepaintedporch.com
Follow Chris on Instagram @193Countries and on X @chrisguillebeau.
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