PNTV: The Happiness of Pursuit by Chris Guillebeau (#150)
17 Dec 2025 · 11 min
Transcript of a Philosopher's Notes / Optimize podcast episode in which Brian Johnson reviews Chris Guillebeau’s book The Happiness of Pursuit. Johnson distills five core ideas around quests: (1) a quest’s defining features (specific outcome, end date, challenge, sacrifice, small steps), (2) finding a quest via calling or discontent, (3) flushing the “BS” and being authentic now, (4) the importance of belief/self‑efficacy, and (5) embracing the grind. He illustrates these with examples (Guillebeau’s goal to visit 193 countries, a runner doing 250 marathons in a year, and Johnson’s own quests) and closes with encouragement and platform promos.
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Hi, this is Brian. Welcome back to Philosopher's Notes tv. Today we've got another great book, the Happiness of Pursuit. The Happiness of Pursuit by Chris Guillebeau. Awesome title, great book. Kris is super smart, great writer, great storyteller and I really enjoyed this book. Excited to unpack it. Philosopher's Note, bunch of big ideas. Let's look at five of my favorite ideas. We'll start with the quest. This book is all about quests. Finding the quests that will give us inspiration and joy and meaning and mojo and happiness and all that good stuff. And via our pursuit of that quest, we will experience happiness. So what is a quest? Is a logical place to start. The quest is more than just a general self improvement kind of program. It has specific things that Kris identifies among them. You're very specific in your outcome. You have a very good sense of what you want to achieve. An end date by which you will do it. It's challenging, requires sacrifices, might be tied to a mission or a calling. And you got to achieve it via small steps. So uses some examples starting with his own. Kris said he wanted to travel to every single country in the world. 193 of them by the time he was 35. I think it took him around five years or so to do it. Less than a decade. He went to 193 countries. That's pretty awesome. Qualifies as a quest. He shared another story of a guy who did 250. 250 marathons in one year. 250 marathons in one Year. That's nuts. So when I read this book last week or whenever it was, I had the idea of I'm going to do 250 notes in 2015. Now I was pretty much committed to it, very confident I could do it. But when I read about this guy who did 250 marathons in a year, it put my 250 books that I'm going to read this year and do notes on and do videos like this on this year in perspective. 250 marathons. That's amazing. 193 countries. That's awesome. The other thing that Kris did for me is he really identified well what is my real quest. That's not quite the quest. That's just me getting back in the game, turning Pro, all in, etc. Right. But what's my bigger quest? For me, it's a thousand creating a thousand philosopher's notes by 2020. January 1, 2020. I hereby commit to doing that. That's my quest. So what's your quest? What's really something that could fire you up, that can challenge you? Kris helps us identify that in a really cool way, then tells us an amazing range of stories from everyday quests to, you know, some of the travel and adventure and heroic stuff, but fascinating stuff. So we want to identify our quest. Another way to look at it is to think about your calling. Joseph Campbell, our mythologist, we love, talked about the hero's journey. What a quest is, is basically a modern day hero's journey, kind of a mini hero's journey, right? Well, one way that we can experience our hero quest is via a calling. So Joseph Campbell likes to say, it's as if there's a phone ringing. There's a phone ringing and ringing and ringing and ringing. The question is, are you going to answer it? There's a calling waiting for you. Are you going to pick up the phone, your soul phone, and say, yep, got it. That is my mission. Should I choose to accept it, I accept. Let's do this calling. Do you have one? Are you paying attention to it? If you're ignoring it, can you step more into it? If you're kind of sort of committed, can you really go into it? Make a specific commitment to what you're going to do. That's your calling. Another way to find your quest is through discontent. You might be frustrated with certain things in your life or with certain things in the world. That's a great way to create a quest. It's our second big idea. The third big idea is a fun one.
Bs.
We want to flush it. Chris tells a great story of a friend of his who's a hospice worker who obviously works with people at the end of their lives. And she said the one thing that she noticed was that there's absolutely no BS at the end of their lives. They're just not pretending. They're not going to do anything to please anybody else in a silly artificial way. There's no bs. They've gotten rid of all that. And Chris's question is, why do we need to wait? Why do we need to wait till the end of our lives to let it all go? That all the stuff that just doesn't matter, to let go of all the bs, right? Imagine, go forward, your last breath. You're going to have a certain level of freedom. It's going to be painful and challenging and scary to even imagine that, but there's a certain freedom if you just let go of all the little Petty things. Why do we need to wait? Let's flush the BS now. It's a good idea. Alright. The fourth big idea here is we need to believe. Now. When you want to go for a big quest, whether it's traveling to every country in the world, Kris had his fair share of critics. Why are you going to do that? 250 marathons in a year. Every doctor will tell you that's just impossible. And the guy goes and does it. You're going to have people who don't believe in your dreams on whatever scale it is. But it's important that you believe. Again, Henry Ford. Whether you think you can or you think you can't, you're right. If you don't think you have a shot to rock your quest, well, you're not going to period. You're not even going to dream. As Chris says, if you want to do the unimaginable, the first step is imagining it. You need to believe that you can do it to move through the inevitable obstacles that we're going to talk about more in a moment and do it. Scientists call this self efficacy, which we talk about often. Whether you think you can or you think you can't, you're going to be right. They've studied wrestlers and seen that those who believe in themselves win more often than those who don't. Not complicated, but we really want to embrace this. In the note, I share a story of my own process. When I was 24 years old, I had just dropped out of law school. The only thing I knew I wanted to do was to coach a little league baseball team. I did that in the process. I had an idea. This is 1998 and I could see that in a matter of time every single team and league in the world, Little league baseball teams, AYSO soccer teams, Pop Warner football teams, bowling leagues, etc. Every one of them would be online.com boom, number one, right? Nothing was online yet. I could only find a couple dozen baseball websites. But I had this vision that we'd have a million teams using our system in five years. And I had the opportunity to talk to a friend of mine's dad who was super, super successful, chairman of a very large company. And I came was raised in a blue collar family. So it's a big deal for me to be able to talk to somebody of his stature. We talked. I told him my enthusiasm, what we're going to do and how we're going to do it, not how we're going to do it because I didn't know how we were going to do it, but a million teams in five years. He listened to me and he said, well, Brian, the first most important thing that you need to identify in a business is the need. What's the need here? The reality was that, well, no teams were using the web yet. I thought they would have a need and I thought that would be pretty awesome. But that wasn't a passing score in this conversation with this guy. Then he proceeded to tell me that I have no business experience, I just dropped out of law school. I literally just moved back out of my mom's house. I had no contacts, I had no money. All of which was true. And he told me, and I quote, take another hit off of that pipe, now I don't smoke anything. But I heard that and I said, really? He was being super nice. He wasn't even trying to be mean spirited. He was just trying to support me and protect me. But inside I just had this thought of, oh yeah, okay, so cool, I'm going to go get at it. Fast forward. We wind up doing all of that.comv1 and the kind of era where a 24, 25 year old entrepreneur can raise $5 million. Did that, hired the CEO of Adidas to replace me as a CEO, wound up selling it to a company that went public. And I like to jokingly say that he was actually right. We didn't get to a million teams in five years, we got there in four. So there you go. That's my little story of one of my quests and the importance of believing. Kind of fun. And Chris tells us, look, when you're able to do that, it makes for fun stories like that. You want to be able to move through the objections you're naturally going to get. If you're doing anything worthwhile, you're going to have people saying it's not possible and go do it. It makes for a fun story 15 years later. It's not always fun at the moment, but it makes for a fun story. So then, final big idea here is the grind. So one of the ways that Joseph Campbell tells us to figure out our calling is to follow our bliss. That's a great way to discover your calling. Do what you love to do, right? But Campbell also says that at the end of his life he said, you know, I wish I had added follow our grunt. Follow your grunt. Follow your bliss. Follow your grunt. It isn't all sunshine and rainbows and dancing on unicorns over those rainbows, etcetera, et. Butterflies, etcetera. A lot of it's the Grind. Chris tells some great stories about the Odyssey odysseus. He spent seven years in prison out of his 20 year journey. He was in prison for seven years. He had all these heroic encounters, but he also spent countless months in the grind. Sailing wasn't exciting. There's nothing sexy about that. When we go on a quest, we need to embrace the grind and realize that we need to also embrace our grind. There's the day in and day out monotony of doing what needs to get done. To travel to 193 countries to do 250 marathons. Mind boggling. For me to create 250 than a thousand of these notes. A lot of it is not the sexiest stuff in the world. It's just showing up day in and day out. We need to embrace that small incremental action steps that we take consistently over time leads to huge results. So there you go. Super quick look at the happiness of pursuit. Really fun book. If you're looking for a quest, I think you'll love the book. Looking to optimize yours and be inspired by other people going out and crushing it. Get your quest on, follow your calling or your discontent. Flush the bs. Believe. You've got to believe. You always have that. How do you like them apples story once you get through it? And then the grind, embrace that too. Follow your bliss, follow your grind and get out there and rock it. Hope you enjoyed. I look forward to sharing more with you soon. Have another awesome day. See you.
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