The Rich Roll Podcast - The Art of Non-Conformity: Chris Guillebeau on Living An Unconventional Life & The Power of Divine Moments

Episode Date: September 19, 2016

In the mid-1800's, this radical dude living alone in the woods famously wrote, the mass of men lead lives of quite desperation. What is called resignation is confirmed desperation. As set forth in th...e enduring Walden, the words of Henry David Thoreau were revelatory for the time. But it's an idea that more than holds up. Not only do I consider it daily, I would contend it perfectly encapsulates what has become the unfortunate, yet defining affliction of modern man. This week's guest has devoted his life to helping others avoid Thoreau's foreboding lament – a self-experiment in purposeful living he calls The Art of Non-Conformity. Ripe with wanderlust after a 4-year stint as a NGO volunteer executive in West Africa, Chris Guillebeau embarked on a multi-year quest to travel to every country in the world, all 193, before his 35th birthday. Along the way, he decided to share his adventures on a newly hatched blog. But what began as a rather ignored and somewhat turgid travelogue soon morphed into a globally revered portal chronicling the personal experience, lessons and wisdom earned and learned not just by Chris, but by a dynamic multitude of unconventional people overcoming conventional social mores around work, life and travel to achieve personal goals and greater life satisfaction. The blog exploded, capturing the intrigue, trust and fascination of people all across the world thirsty for the brass tacks steps and inspiration required to pursue more adventurous and personally fulfilling means of working and living outside traditional paradigms. With the success of the blog, it's not surprising that books soon followed. The Art of Non-Conformity* was translated into more than twenty languages. His second book, The $100 Startup*, was a New York Times and Wall Street Journal bestseller, selling more than 500,000 copies worldwide. His third book, The Happiness of Pursuit*, was also a New York Times bestseller. His most recent book, Born for This*, will help you find the work you were meant to do. When he's not writing bestselling books or traveling to parts unknown, you're likely to find Chris diligently working on his World Domination Summit — an annual gathering he founded six years ago that brings thousands of creative, remarkable people together. Everybody loves a good travel hack. The basic steps to launch a new business. Or the path to overnight success. If you're looking for Chris' answers to those questions, you're in the wrong place. I'm more interested in the man behind the work. What makes Chris tick. How he sees himself in the world. Enjoy! Rich

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Starting point is 00:00:00 For me the goal is genuine empowerment and affirmation and I think there's value in that. Like helping people understand their self-worth, helping people understand their potential and not just understand it but then actually do something about it, taking the action that we touched on briefly earlier. That to me is the value. Whenever it has shifted to become like this personality based thing then that feels a little bit less comfortable. For me personally, I will deflect a lot of that stuff. If people have a question about how to ask for a promotion at work or how to start their little side business while they have their day job,
Starting point is 00:00:40 great, I can tell you exactly how to do that. That's author and entrepreneur Chris Guillebeau, this week on The Rich Roll Podcast. The Rich Roll Podcast. Hey, everybody. How are you guys doing? Greetings. Welcome to the show or welcome back. My name is Rich Roll. I am your host. This is the Rich Roll Podcast, the show where I go deep and long form with some of the most compelling, some of the most thought-provoking, some of the most inspiring thought leaders and paradigm-breaking positive changemakers all across the globe. These are not interviews, not merely interviews. They are conversations, conversations intended to elucidate the wisdom, the experience, the
Starting point is 00:01:27 practices, the knowledge, the approaches of all of these remarkable people as sort of a vehicle to inspire and incite you and me to unlock our innate potential to unleash our collective best, most authentic selves. How's that for a mission statement? You guys like that? In any event, thanks so much for tuning in, for sharing the show, for reviewing the show, for subscribing to the show on iTunes, and of course, for always using the Amazon banner at richroll.com for all your Amazon purchases. Doesn't cost you a cent extra, but Amazon kicks
Starting point is 00:01:58 us some loose commission change, and that really goes a long way towards helping us do what we do here. So we really appreciate everybody who has made a habit, made a practice out of doing that. If you're inspired to support the mission even further, now you can do that. We have a Patreon page, and you can find that by clicking on the Patreon banner. That's right next to the Amazon banner on every episode page at richroll.com. richroll.com. All right, I got a really cool show for you guys today. But before I get into that, I wanted to kind of share a quick thought with you guys. Julie and I just got back from a weekend in Tucson. We were attending the MindBodyGreen Revitalize Conference, which was really extraordinary. It was basically 200 wellness leaders and wellness
Starting point is 00:02:47 seekers and wellness pioneers congregating at this beautiful resort in the desert nestled up against this mountain to basically cultivate community around shared common ideas, to have talks and panels and meditation sessions and eat together and what else go on hikes and trail runs, etc. And it was just a beautiful event. It's the third year in a row that they've done it. And I just came back, I came back revitalized, what can I say, it was really amazing. But I think one of the highlights for me, beyond just really seeing my friends and being able to kind of go deeper with a lot of people and meet new people
Starting point is 00:03:26 and really kind of tap into this community. I remember at one of the dinners looking around the room and I think I saw no less than like 10 people that have been on the podcast. There was Jason Waka, Dr. Joel Kahn, Charlie Knowles, Light Watkins, Doug Evans from Juicero, David Flynn, one of the happy pair guys, and his brother, but his brother had to leave early because his wife was having
Starting point is 00:03:49 a baby. That's a whole other story. Hilary Biscay, Rebecca Soni, Marco Borges from 22 Days Nutrition, Ben Greenfield was there. I'm sure I'm forgetting somebody else, but the bottom line was it was really cool to look around and see all these people who have, you know, basically trusted me to share their story with you guys. And today's conversation is no different. It's a conversation that's long, long overdue. I've been a fan and an admirer of
Starting point is 00:04:17 Chris Guillebeau for a long, long time. And I finally got the opportunity to meet him in person in Portland when I was up there a couple weeks ago. And what came out of this definitely does not disappoint. All right, so if Chris is brand new to you, how to describe this guy? Well, on a surface level, I think it's fair to say that he is quite the accomplished multi-hyphenate, taking it back a few years. After a four-year stint as a volunteer executive in West Africa, Chris took a stab at blogging. a four-year stint as a volunteer executive in West Africa, Chris took a stab at blogging. And he did it initially just to chronicle this quest that he had set out for himself to travel to every country in the world, all 193 of them, and get it done before his 35th birthday. Spoiler alert, he made it. We talk about it in the podcast, so you can look forward to that. But in any event,
Starting point is 00:05:02 as his quest matured and he was kind of checking the boxes on these countries that he was visiting, so did his writing. And his Art of Nonconformity blog, which is where he shares how unconventional, quote-unquote unconventional people battle against conventional beliefs in work, life, travel, in order to achieve personal goals, well, this blog exploded. And what happened is he ended up cultivating this vast global audience of people thirsty for not only the brass-tack steps of how to travel the world, but the inspiration required to pursue more adventurous and more personally fulfilling means of working and living outside traditional paradigms. And so it's not surprising that as his blog continued to blow up and increase in readership, that books would follow. So his first book was called The Art
Starting point is 00:05:51 of Nonconformity. It was translated into more than 20 languages. His second book, The $100 Startup, was a New York Times and Wall Street Journal bestseller, selling more than half a million copies worldwide. His third book, The Happiness of Pursuit, was also a New York Times bestseller. And his most recent book, Born for This, is all organized around helping you find the work you were meant to do. And in furtherance of Chris's devotion to cultivating community around all of these powerful ideas, six years ago, he founded something called the World Domination Summit, which is this really cool gathering of creative, remarkable people, and like thousands and thousands of people attend this event. It's pretty amazing. And this is a really special
Starting point is 00:06:29 conversation. It's less about Chris's book specifically and much more about what makes Chris tick, like how he sees himself in the world, the importance of purpose, of cultivating community, of giving back, and the strength required to continually grow and evolve. And so throughout this conversation, we get pretty honest, we get raw, we get real, we went deep, we get a little emotional at times. And these, of course, are all of my favorite things to do. It's why I do the podcast, and it doesn't always happen with every guest. But at the end of this, I really felt like I found a new friend, a new confidant, which is really special. And it's why
Starting point is 00:07:10 I think this episode really stands out. So enough about that. Let's drop into Portland and tap into the psyche of one of my new favorite people. Enjoy this conversation with Mr. Chris Guillebeau. conversation with Mr. Chris Guillebeau. This is long overdue. We should have made this happen quite a long time ago. I apologize to you for that, but I'm glad that we're finally sitting here together. Here we are. Yeah, we have lots of points of commonality and interest and lots of mutual friends. We shared an editor, a book editor, and Rick Horgan, the fabulous Rick Horgan. friends we shared an editor a book editor and rick horgan the fabulous rick horgan how many books did he uh work on with you uh rick and i did the hundred dollar startup and the happiness of pursuit together and he's as you said fantastic guy yeah he's an incredible gift for vocabulary he always has the right word for everything and uh he's truly wonderful he was my editor on on
Starting point is 00:08:02 finding ultra and i just felt so privileged. I mean, that was my first book, and I had no idea what I was doing. And I just couldn't even believe that he was interested in editing my book. I remember I had an initial call with him when I was pitching the book, and he wanted to do it. And I told my book agent. I couldn't believe I had a book agent. Yeah, same. I couldn't believe I was having any of these conversations or that anyone was interested at all.
Starting point is 00:08:27 But I said to her, so Rick's not really going to edit my book, right? He's just going to assign this to some junior editor who's like a year out of Vassar, right? She's like, no, he's going to edit it. And then when I was writing, I was very sheepish about bugging. Like I didn't want to bug him unless I could send him know, had, we could send him a, you know, a copious amount of work or whether it was something super substantive. So I actually don't feel like I took as much advantage of his wisdom and knowledge as I could have.
Starting point is 00:08:56 Did you get any 10 page memos from him? I did. He does this single spaced, you know, dear Chris, you know, and then it goes on and on and on and on. And it's all, it's all frustratingly helpful in the sense that, you know, he's providing all this constructive feedback and I read it and I'm like, damn, unfortunately he's right. Right. In the sense that I have to go back and do a lot of work, but all for the better product, hopefully. Yeah. I mean, he definitely pushed me and was instrumental in helping try to get the best,
Starting point is 00:09:22 you know, version of my book out of it. And I think he succeeded in that. So I'm forever grateful to him. So when I think about your work in a global sense, one of my favorite quotes comes to mind from our esteemed poet, Henry David Thoreau, who once said, the mass of men lead lives of quiet desperation, and what is considered resignation is confirmed desperation. And I feel like a lot, if not the great majority of what you do speaks to that great malaise, what I think is actually kind of an epidemic in our culture these days of people living lives that perhaps they don't even feel like they consciously chose and feeling powerless to change them. Is that a fair
Starting point is 00:10:11 estimation? I like that description. I think I tried to do a lot of my work on discontent, you know, broadly speaking, discontent with life, discontent with work, and probably comes from just my own life of being discontented in different ways and trying to make changes and maybe choosing a different path and seeing what happens there and what opens up. And you've often said that kind of what you speak to is trying to help people live lives of perhaps not nonconformity per se, but living you know a little bit more outside the box so that people can you know connect with their you know higher purpose i guess yeah perhaps i
Starting point is 00:10:53 mean jingoistic sure sure yeah i mean unconventional lives you know living unconventional lives uh you know of their own choosing so obviously it's it's never about telling people you know how to live but maybe providing opportunities and showing people like hey you know if there's something you've always wanted or you had this crazy idea or this dream you're not alone you know there's other people out there who have similar dreams and and you know you can do this and and not only can you do this but you have something to give as well you have have something to contribute. So it's like one part invitation. It's one part, like, you know, come on, come and welcome, like, you know, you're one of us, so to speak. Maybe other people don't understand you, but you know, we do globally speaking, broadly speaking. And then the second part is that is the challenge. It's like, Hey,
Starting point is 00:11:40 you know, if you're, you're listening to this, if you're reading a blog or a book or something, then you're a pretty privileged person, which is great. It means that we all have opportunities that a lot of other people don't have. So what are we going to do with those opportunities? And if we are discontented or if we have that malaise, you know, what is our response to that? Right. Inciting people to action is the trick, right? people to action is, is the trick, right? Like I feel like, and I've said this before, um, but inspiration can come in many forms and sometimes it can be easy. It's easy to, you know, post something on Instagram with some kind of likes, you know, or whatever, but actually trying to,
Starting point is 00:12:20 um, get people to implement the advice and put it to work on a consistent daily basis is a much taller order. Well, of course. And they have to do it themselves. You know, I think they have to obviously understand, okay, here's this option, but I have to be the one to take it. So it's maybe a short-term value versus long-term value or something. So how do you bridge that gap for people? Like, what is your approach in trying to get them, you know, like off the, you know, away from the computer screen and actually into, you know, investing in their life? Maybe it's through telling stories.
Starting point is 00:12:56 Maybe it's through community of showing people, you know, again, you're not alone. Other people that are like you, and maybe your life is not going to be like riches or like Chris's or so-and-so, but look at what this person did. You know, they had this opportunity, they pursued it. Uh, what does that look like for you? Right.
Starting point is 00:13:15 So it's not so much prescriptive step-by-step, you know, here's your 10 step program. Uh, although that can be helpful for some things too, but it's providing examples and maybe helping people think a little bit differently as well, because, you know, obviously most Although that can be helpful for some things too, but it's providing examples and maybe helping people think a little bit differently as well, because, you know, obviously most of us come from this certain mindset of this is the normal order of things, the normal progression of things. And there might be a shortcut to those things, or there might be a totally different way of doing something.
Starting point is 00:13:42 And so I think if you can shine a spotlight on that, then a lot of people are going to be like, yeah, I'm going to do that. I'm going to grab onto that, but it's very much, it's not like about, you know, convincing people or persuading people. To me, it's about all those people who are in the lives of quiet desperation, who are like, yes, I want to make a change. I'm listening to this podcast like all the time. I'm trying to do different stuff, but you know, what do I do? How do I do it? Right. And the way that you've kind of done this in your own work is you infuse your books with your own personal story and for better or worse experience. No, you're saying this is what I did and this is where I went wrong and here's where it worked and all of that. And then kind of compiling, you know, a massive number of case studies and
Starting point is 00:14:25 then curating those to provide, you know, illustrative examples of how other people have done it, uh, all the way from, you know, extreme examples, like, you know, the guy in the, the happiness book about, you know, taking the valve silence and only walking and 20 years or something like that, which are, you you know that's an inaccessible example for a lot of people because they're not going to do it it illustrates a point very well but also people that are that are doing it in ways that i think you know the average person can really relate to and say you know that guy did that like i can i can step in that direction and i think that's empowering right to provide the every man kind of, uh, example of how people are changing in,
Starting point is 00:15:06 in small and sometimes bigger ways. Yeah. You mentioned Rick Horgan. I remember when I was writing that book, the story of the guy who took a vow of silence for 26 years, you know, he says like, you know, take out all these references to that guy. It's like, I want one reference to that guy in the whole book because nobody's going to relate to that. You know, he's like, nobody's going to say like, I want to take a vow of silence, you know, for 20 years or whatever. But even though it was a great story, there was also this guy who ran a marathon. How many marathons?
Starting point is 00:15:32 Did he run like 100 marathons in a year or something? Maybe that was you. No, it wasn't. I remember that guy. Mad Dog? Yeah, Martin Purnell, I think, from Canada. Oh, there was another one. You had two ultra-runner examples in the book.
Starting point is 00:15:43 Yeah, yeah. But yeah, every man examples, um, I think are maybe more interesting in some ways and try to just provide this barrage of case studies, as you said, because I want people to be able to relate to somebody, um, to be able to say, okay, like, uh, you know, if I read this book, like I, maybe I can read a book and like it, but I'm not like the author. I can't do what he did or what she did. Or even if I read this book, like I, maybe I can read a book and like it, but I'm not like the author. I can't do what he did or what she did. Or even if I read this story, you know, biography of somebody else, I'm impressed, but there's this distance, you know, between us. So wherever we can kind of break down the distance and say, okay, well, here's like, you know, I wrote a book, a hundred
Starting point is 00:16:16 dollar startup, which has all these case studies of people who started a business without going into debt, without borrowing money, you know, without going to business school. And it was like so many examples of people who've done this that there's no excuse. You know what I mean? Like it's accessible. At least that's my goal. Yeah. And that book was extremely successful. I think I still see it in airport bookstores. Like that book is still like ubiquitous and everywhere. No, I have to give credit to Rick Horgan again for that too. Thank you. Well, we're going to make this the honorary Rick Horgan podcast. You have to send him a link to this afterwards. Yeah, because one of the things that he said to me early on in the writing process was, you know, I was sort of confounded again that I had this opportunity to write this book.
Starting point is 00:16:56 And because I hadn't, you know, as a sort of athlete memoir, there's also the addiction story and all these other in the sort of, you know, sort of diet manifesto aspect of it. I was kind of walking a tightrope between three different genres and trying to make it all work and trying to figure out how all those puzzle pieces were going to fit. At the same time, from the athletic perspective of the story, I'd never won a big race. You know, I wasn't like a world champion. And at the same time that I was writing my book, Scott Jurek, who's the world's most famous ultra runner, who also happens to be a vegan, was writing his book. And I was thinking, who in their right mind would buy my book when they can buy his book? Like, what can I possibly say that he isn't going to say better? And I realized very early on that the only way that my book was going to work was going to be directly related to the extent to
Starting point is 00:17:44 which I was willing to be vulnerable and very personal about what I was doing. And one of the things that Rick said to me that made all the difference was that it was this distinction between aspiration and inspiration. He's like, Scott Jurek is inspirational. You're aspirational. The average person can see themselves in your story and that's the key here and in a similar sense i i see that in what we just spoke about like the guy who takes the 20-year vow of silence that's perhaps inspirational for certain people right right uh but it's extreme whereas you know what you did or some of the other examples uh you know of of businesses built or you know lives transformed are are aspirational. And I
Starting point is 00:18:27 think that's a qualitative difference. And I think it's important when you're writing in this genre to be bearing that in mind. Yeah. You know, going to every country in the world was actually not that difficult. It was, I mean, it was long. It was a process. I had lots of setbacks, but I liked it because I always knew what to do next. Like I had this linear kind of thing. Yeah, exactly. And I kind of related to that. And it's like in the beginning of when I first started writing about it, had a lot of criticism from people who said, Oh, you're just kind of like checking things off a list. So of course I'm defensive and like, no, no, of course not. You know, but then, um, kind of over time realized
Starting point is 00:19:04 like there's actually value in having a list and, and like being able to see this visual progress as I go along and checking them in my Evernotes. And so I feel in some ways, you know, people are always like, wow, that was such a big thing. I'm like, well, it took 11 years, but I had this really clear outcome. So, I mean, it was just a matter of kind of connecting the dots and following it along the way. I think the creativity was in more in the idea and then in the pursuit of it, um, it was different than maybe some other kinds of goals. So, and also I'd been traveling for a long time before I picked up that, that goal. So it's not like I was, I had some, some sort of, uh, expertise or experience that other people couldn't have for themselves.
Starting point is 00:19:44 some sort of expertise or experience that other people couldn't have for themselves. And that, you know, that quest, which is a word you've, you know, you've sort of used throughout the happiness of pursuit and the importance of having a quest and pursuing a quest. That quest really, in many ways, I think, is the genesis of everything that has followed. Like, you started out as a blogger, like you made this decision, okay, I'm going to, I'm going to, initially it was just 50 countries, right? And then a hundred countries. It wasn't from the outset,
Starting point is 00:20:11 I'm going to do every country. It just kind of organically grew out of that. And this decision to blog about it, but not blog about it from a perspective of a travel blogger, like explaining the places that you were visiting, but more from a perspective of how to do this. Like, this is how I got it done. And here's my, you know, kind of
Starting point is 00:20:30 experience for other people that are interested in following in my footsteps. Um, I'm interested in, you know, we can get into the backstory behind that a little bit more in depth, um i'm interested in in how that um like how how the journey of doing that has has sort of blossomed into you know what you do now like a sort of you know communal enterprise that you've lured over and and i guess what i'm getting at is that a lot of people they set out maybe they have an idea for a huge goal, but they don't want it. They won't even begin until they think they have the entire thing mapped out in their head from beginning to end. And it turns into like a paralysis. And then they never get to it.
Starting point is 00:21:19 They never start because they don't have all the answers. Right. And in my experience and from what I gather in your experience, that's not how this stuff works. Like on some level, yes, you want to be prepared and kind of understand what you're getting involved in, but there's a ledge that inevitably you're going to have to jump off of and have some faith and spread your wings and fall where you may. Yeah, I completely agree. I think if you have a small goal, then you can have a strategic plan and everything kind of laid out, you know, exactly what it is. But, you know, if you want to
Starting point is 00:21:51 have a big vision or if you have this discontent that you're trying to respond to, then you're not going to necessarily know. Like once you go down that road, you don't know where you're going to end up necessarily. And, you know, for me, at least it was, it was for the better. Um, but I had, I had, there was no strategy in doing this. There wasn't any business model behind it. Um, I had been to about 70 countries or so when I started writing about it. And before that, it was just my own kind of, kind of thing. Um, and you mentioned like, I'm not a travel writer. Well, I tried to do travel writing and I was pretty bad at it. Like I really was like, uh, I mean, people who do wonderful work, you know, great photography, you know, photo journalism essays, all about these
Starting point is 00:22:30 wonderful experiences they have and, and, you know, cultural, you know, encounters and interactions. And the few times I tried to write like that, I was just, I was just terrible at it. Right. And so for a while I thought the goal was I'm supposed to improve in that. And finally, I just kind of let that go and say, well, I'm going to, I'm going to be myself. I'm going to be vulnerable. As you said, I'm going to write about the process and maybe some people are going to like that. Maybe some people aren't, um, but that's what I can do. So, but you couldn't have known that that was what your voice was. You tried on a few hats. Yeah. Right? Yeah. And so, as somebody who I know loves planning and writes, you know, annual reviews and likes to make lots of lists and create visions for, you know, how the year is going to unfold,
Starting point is 00:23:14 there's a balancing act between doing that and that leap of faith, right? So, where do you find that balance? I guess, you know, you find the balance when you're excited about something, when you're motivated to do something, even if you don't see what's all the way at the end of it. When I thought about that quest, I was excited about it. And I could quickly then move to that level of planning, even if there was some uncertainty to it. The same thing with beginning to, you know, connect with people around the world through
Starting point is 00:23:43 the blog, which is now eight years ago. I didn't necessarily know where it was going. I thought I was going to be a travel writer. It turned out to not be a great one. But I was excited about it. So I think try to kind of respond to, you know, what am I motivated to do? What do I have resistance for? And of course, there's different kinds of resistance.
Starting point is 00:24:01 Sometimes there's resistance to something you have to do, you want to do. But I guess when I look back at all the things that I've attempted and some have succeeded and many have failed, the ones that have succeeded have been when it's, you know, whatever my true self is, when it's something that I, you know, can do somewhat well, but I also like have this belief about, yeah. Right. I mean, the idea of being a travel writer seems to be something that, you know, might've crossed your mind as, well, this is what people want to read as opposed to what I want to say. This is the format, right? Like, here's the format. How can I do this? Right. And, you know, you can replicate.
Starting point is 00:24:36 Try to fit yourself into that box. But yeah, I mean, I don't think the best possible scenario there is that I would have become a decent travel writer. I wasn't going to like reframe that whole narrative or that whole format. And I don't know if we'd be having this conversation now. So fortunately, I did something different. What was the initial drive to visit all these countries? You're laughing because you probably had to answer this question a million times, but I'm interested in, you know, what sparked that and what you were looking to get out of that experience and perhaps in retrospect, you know, how that, how what you actually got out of it may be different.
Starting point is 00:25:18 Well, I smiled because I wanted to not give you a rote answer. I want to respect your listeners, right? I don't want to give you like, oh, well, here's what I've said a hundred times. No, I really want to kind of consider it. I mean, the first part was I loved to travel, just travel by itself, exploration, discovery, probably like many people who are listening. But then for me, where it became something greater was when I connected it to this structure of the quest. And that's when I got really excited because it seemed, it seemed not quite impossible, but whatever is right below that, you know, and it seemed like I, I can do this. It's going to take a lot. Um, there's going to be a lot of costs, you know, time costs, money costs, you know, sacrificing other projects, other things. Um, but I guess
Starting point is 00:26:02 I just couldn't get it out of my head. And that's another thing that I have written about a couple of times. Like if you have this idea and you can't stop thinking about it, there's probably something to it. Like we all have crazy ideas, you know, they go away. We kind of realized like, Oh, I'm not going to do that. But if it stays with you over time, then ultimately I think what led me to say, okay, yes, I'm going to go for it was this fear, healthy or otherwise, of regret. And this fear of looking back and saying, I remember when I had this idea. And I went to a bunch of countries. Why didn't I do that?
Starting point is 00:26:34 Yeah, but I never tried. I never tried to do it. And I have thought about that a lot because there was no guarantee of success, obviously. And if I had failed, that would have been disappointing. But I think it would have been far more disappointing to just have never tried it. Never tried. Right? And how were you supporting yourself during that 10-year of time? I mean, it was a very extended period of time, obviously.
Starting point is 00:26:57 I wasn't traveling, like, nonstop for those 10 years. It was more like 11 years. But, you know, for the first few years, I was an aid worker living in Sierra Leone, Liberia. That's where I got comfortable traveling in different, you know, parts of the world, which aren't always easy. And then I'd always been an entrepreneur. I'd always kind of worked for myself. I did freelance writing, did lots of random online kind of stuff. I did affiliate programs, started these small little businesses. I wrote a lot about that in $100 Startup. So I was never like building this huge scalable business. I didn't have
Starting point is 00:27:29 employees. But for a long time, I did have this lifestyle that kind of allowed me to, you know, take some time off and travel. And that became more and more over time. And then eventually there was a business model that came out of that blog I was writing, but that was also very organic. In the beginning, when you launched the blog, what was the readership right off the bat? Was it like your aunt and your mom? My joke is like, it was five people and one of them was my grandma. And then I found out that my grandma had two email addresses that she had signed up for twice. I was like, damn, it's not just 20%, it's 40%. Thanks, grandma. You can go back and read the very first post on my blog.
Starting point is 00:28:09 I kind of outlined the vision of the blog and it's, it's so funny because I look and read and I'm like, I'm going to like, my goal is like one day I want to have a thousand subscribers, you know, that just seems like, you know, phenomenal and fabulous. Like I would love to have that. I think it's always good to, to go back and look at, like, if you like a podcast, if you like a blog, go back and look at that person's like first few entries, that first episode, it's probably going to be crap, you know? And that's really, that's inspiring to me. That's aspirational to me because you can see how they, how they developed and how they, where they came to crossroads, what choices they made. And,
Starting point is 00:28:42 you know, unless they've actually gone back and cleaned that stuff up, but who has time to do that? Right. How do you think the blogosphere has changed? It seems to me that now, because media is so disintermediated, that the idea of starting a blog now and ultimately trying to create a business out of it is a much taller order than perhaps it was in, you know, 2006 or seven. Sure. I do think it's changed a lot. I think in particular over the past couple of years, maybe I think, uh, I think that model held up for a long time and I think it is still
Starting point is 00:29:17 feasible, but maybe it's not as accessible, at least in the same way. Uh, but you know, media is always evolving. I mean, as you know, very well, lots of people that are being very successful with podcasts now, there'll probably be something else that's coming out. Right. I feel like podcasts in certain ways have sort of succeeded the blog, like it's sort of fit that similar niche. But even that it's not about, you know, like I would say a tiny fraction of the people that listen to this podcast actually go to my website. Sure. You know what I mean? They just get it on their phone from iTunes or what have you. So the idea of having your own website as a destination seems
Starting point is 00:29:56 far less important than it once did. Yeah. I think it's not, it's certainly not critical. It's like, it depends on how you're approaching the conversation. Like, do you have to have it? Absolutely not. Um, but for me, you know, I'm, I'm learning a lot about podcasting, but I was always a writer. That was my format. Uh, for me, writing a book was not a means to an end. I actually wanted to write books. I wanted to write a blog. So I think people, people will still learn in different ways. You know, some people are not auditory learners. Some people actually do want to read, you know, whether on a screen or on a page. So I think to me, what matters and what's relevant is ideas and ideas and community. They don't go out of style. Yeah, hopefully.
Starting point is 00:30:51 so from all these countries that you visited i'm going to ask you the the tropish questions what's my favorite one no not your favorite one i mean you're gonna say it's always the worst question or something like that i haven't i haven't answered but it's not the greatest question the most maybe the most challenging like one of the one one of the countries that that i didn't see come up in, in any of the, you know, sort of articles that I read about you was North Korea. Yeah. North Korea, Yemen, Iraq, Iran. Um, the countries that were actually the most challenging are not those like, you know, half a dozen countries that people think of. Um, there's, there's, there's always a way, or there's almost always a way, you know, to get into any part of the world. Um, if you kind of work on it, um, especially if you
Starting point is 00:31:31 have a U S passport, Canadian passport, British, you know, European union, et cetera. Uh, for me, the challenge, the greatest challenge, uh, were some countries, particularly in Africa that had, you know, visa restrictions and basically just did not want Americans coming, essentially, or any outsiders, any foreigners coming. So those were Mauritania, Eritrea. Saudi Arabia is not the easiest country to go to if you don't have a valid business reason to go. I actually have been.
Starting point is 00:32:00 I'm not nearly as extensively traveled as you, but I have been across Saudi. I've been to three cities in Saudi Arabia. So I have done that. Did you go to Yemen as well? I didn't. I went to Pakistan though. Okay.
Starting point is 00:32:11 Yeah, that's good. And then also there's some countries that are just inaccessible. So they don't, it's not like a politically difficult or security concern, but they're in the middle of the South Pacific and very few flights. Nehru is one, one flight a week that brings in like a dozen people. So some of those. You have these great stories and the happiness pursuit about playing,
Starting point is 00:32:33 basically playing roulette with the visa and, you know, flying to New York and getting your passport back, like just in time and all that. Yeah. And sometimes I would show up without a visa. I mean, I did that in Pakistan actually,
Starting point is 00:32:43 which is not something that they're going to let you in. Yeah, I don't actually recommend that to people. But for me, it's not like I was arrogant and I didn't assume. I didn't know if it would work or not. But for me, I wanted to do everything I could because if I did fail, I wanted to look back and say, you know, I tried everything I possibly could. I got on that airplane, even though I didn't know. So when I went to Pakistan, I did have a visa and I had a valid, you know, sort of reason to be there. I was doing a speaking engagement there, but I remember like I'd never been so far, like I didn't have this background
Starting point is 00:33:17 in travel. So for me, this was brand new to go to this part of the world. And it was before I'd been to Saudi Arabia and these other places. And it didn't dawn on me, like I had a layover in Dubai and that was all very exciting. And, but it wasn't until the plane was descending into Karachi and I looked out the window and I had, it just hit me like a ton of bricks. Like, wow, I am like really far away from home and very much out of my element. I was the only Westerner on the plane and, you know, everybody on the plane was kind of looking at me strangely, not aggressively, but just curious, like, what is this guy doing? Like, is he with Blackwater? And then when I got off the plane and I was walking down the hallway towards customs,
Starting point is 00:34:02 I hadn't gotten my bags out or anything. There were two, uh, military dudes with rifles and the whole thing who, who, uh, who looked at me and they said, Mr. Rich, Mr. Rich. And I said, yes. And I mean, they're literally just two guys standing in the middle of a hallway. Like we hadn't gotten to any like gateway or anything like that yet. And they just said, passport, passport. there well at the time i'm thinking this is one of those moments like once i give these guys my passport like who knows what's going to happen like but i don't know that i have a choice right so i gave it to them and then they walked me down the hallway but they stayed very very close to me and i thought that was odd until
Starting point is 00:34:40 later i realized like oh they're like protecting me and then they walked me to the to the far end of the customs there was all like you know you go down to customs there's all the lines like you see everywhere and on the far right was this other desk and they walked me over there and some there was like a discussion slash argument between these guys and some other guy that felt like it was uh out of the movie Argo and just that feeling of like not knowing what's going on and feeling very out of control. I remember like, you know, being, I wasn't scared, but I thought like, Oh, this is what it feels like to be really out of your element. And, you know, I think it's a good lesson. Of course, everything was fine and
Starting point is 00:35:21 all of that, but, you know, a very interesting experience so i guess you know what i'd like to know is in retrospect and now having you know i know you still travel extensively like what were you in doha like a week ago cairo bangkok yeah so you're still continuing this you know love of travel but having put a little bit of time between yourself and the completion of the quest, you know, what is your, you know, how has that colored your perspective of, you know, how we live in America, um, and in general, you know, how you conduct yourself throughout your life, having immersed yourself in so many, you know, basically every culture across the world. Right. You know, in some ways, um, we talked about blogging being different than it was. I feel like the, the world
Starting point is 00:36:10 is even different than it was a few years ago when I was, was doing this more actively because I am still traveling, you know, now, but I'm, I'm not going to Pakistan all the time. I'm not, you know, crossing Saudi Arabia into, into Yemen. Um, I think for me, I mean, some of the lessons sound kind of superficial. I'm trying to think about not to, you know, say them in the usual trite, well, before I, you know, didn't know about the world. And then I went and saw that there were people that were different than me. But in a lot of ways, that is kind of what it comes down to is just an awareness and a respect of, you know, different perspectives and not just in terms of like geopolitical things or religious things but but ways of life and culture and you know body language and and how people communicate and how life is lived and i'm kind of set in my ways you know like i think there's this perception
Starting point is 00:36:57 about me that i'm like this big risk taker and did all this stuff but i actually have a pretty you know kind of standard routine life and those things can be disorienting when you go and, but you have to, as you said, right? And so for me, it was, you know, first of all, the part of the quest, like embracing that discomfort, embracing that disorientation and saying, okay, what can I learn about this? Not just about the world, what are my big lessons of the world, but what, how is this affecting me? As you said, like, what do I carry, you know, with that? And then like, what do I carry, you know, with that? Um, and then like, what's different now, you know, what's different now when I had that focus of going to everywhere, it was great. I love the focus, but now I have, you know, have something different.
Starting point is 00:37:34 Right. But you are in the rare, you know, position of, of having exposed yourself to more cultures than almost anybody walking planet earth and and with that comes a wealth of experience that i would imagine you know allows you to uh you know probably have a little bit more empathy for different people and perhaps might change you know we is we're so centrist in america right you turn on the news like i would imagine if you watch the news that you have a different perspective on the information that's being conveyed than the average American. Yeah. I don't watch the news. I mean, I read the news. Like I read the New York times or the guardian or whatever, but watching news always depresses me, uh, regardless of the network, pretty much kind of, it's just the, the way the story is told the narrative, the filter. And, uh, it's, it's not just that that is wrong, quote unquote,
Starting point is 00:38:27 it's that it's just so limited. Like there is more, there is another story, there is another perspective, you know, for a lot of these things. So maybe just being aware of that and understanding, you know, how the world perceives America, how the world might perceive a foreign traveler, you know, as he's going about doing different things. It was during the height of the Iraq war, the invasion, George Bush presidency, when I was doing a lot of this travel. So that all, that would always, always come up 100% of
Starting point is 00:38:54 the time in any taxi. Whenever I talk to anybody, it's like, you know, what's, what's going on with this? Like I have something to say about your president and, or your country or whatever. And so I had to figure that out. And you never had any issues, uh, getting into a country because you had a stamp on your passport from another country that perhaps is not so friendly to the country you're trying to enter. No, that doesn't actually happen that much. Um, I mean, it's, it's a whole issue of like israel and the arab states or other muslim countries yeah because i've been to lebanon and now i'm thinking well they might not let me into israel if i want to go there no the opposite would be the question but not that not the other way interesting yeah so if you go to a country like that where you maybe not want
Starting point is 00:39:39 to have a stamp in the passport you can just tell them and they won't stamp the passport like they're used to that right basically this is one of your travel hacks. Yeah. But if you're going to, if you want it, you want that stamp. I didn't care about the stamp. No, Rich, I honestly, at the end, I didn't care about stamps at all because, uh, I was actually getting so many stamps. I had to juggle my passport. I already had all the pages added to it. And, uh, you know, it used to be that you could add a whole bunch of different sets of pages to a U S passport. And for a while it was free and then it was a charge. And, uh, I, I had sent mine away three or four times and finally they sent it back rejecting it because it was physically impossible, you know, to like bind more pages into it. So I was actually trying to be conservative
Starting point is 00:40:17 with the stamps. Right, right, right. Well, let's take it back a little bit. I'm interested in your upbringing and your kind of evolution to the present day. You grew up, I guess your dad was in the Air Force, right? Yeah, stepdad. as an adolescent and ended up dropping out of high school. Like, you know, yeah, that's somehow found a way to still get into college though, after dropping out of high school. Yeah. College, college hack. Um, well, I, so I always liked learning. Like I liked, I love to read books, um, love to play video games, which may or may not be learning, but I was, I always liked learning, but I didn't do so well with structure and, um, in high school. And I was a juvenile delinquent and had that whole history. So high school was not good for me. But I wanted to go to college. So I kind of snuck into a junior college or a community college. And there was, there wasn't a whole lot of prerequisites to
Starting point is 00:41:18 registering. And by the time they'd finished, by the time they'd figured out that I actually hadn't graduated, I was already kind of in the process. I had already done well in my first quarter. So, like, we're not going to kick him out. Did you have to go back and get your GRE or anything? No. No? No, I never did because I stuck with that.
Starting point is 00:41:34 And then eventually I transferred to a four-year institution because I was a transfer student. They were just looking at my college records. Right. Right. So, yeah, I kept, I mean, it's funny because I went all the way and got like a master's degree and all this stuff, but without ever having a high school degree. That's fantastic. Right. And so when you graduated from college, was, was the idea that did you know that you wanted to be an author? No, no, no, no, no idea. I mean, I, I graduated really young, which is a whole other story because I took as many credits as I possibly could. Then
Starting point is 00:42:01 I registered at another college and took, so I was taking like 50, you know, credit hours each term and somehow like juggling it all. So I did the whole college experience in about two years. So I was, I was 19 when I graduated. And then it's like, that's amazing. Well, yeah, I don't know if I don't know what I learned because it was all about, you know, maximizing and efficiency. Um, my grades weren't the greatest either, I should say, but, um, I don't know if I had a great idea of what I hope to be at that point. Uh, and I, I had this day job living in Memphis, Tennessee, and I was kind of like schlepping boxes around in the middle of the night. That was the last job I ever had, uh, because I discovered this new website called ebay.com and I started selling things online and realized like, this is, this is pretty good. Like, you know, I'm working in the middle
Starting point is 00:42:51 of the night at the warehouse for like $8 an hour. And I just listed some things on this auction site, which I have no, I don't know how to write HTML. I don't know how to take good photographs. I don't know how to do, you know, a copywriter. Um, but yet I'd made like $15 an hour. Let's do that. You know? So that was your first, like you wet your whistle. That was your first little entrepreneurial venture. Right. And did you, did you ultimately, you were working for FedEx, right? Yeah, exactly. So did you quit FedEx? Yeah. I just never showed, I just never went back basically, which was actually the normal protocol of quitting. Like I don't think anybody ever gave like two weeks notice in that job. Right.
Starting point is 00:43:26 And then you decide to go off on this like sort of service adventure, right? Sierra Leone. Is that? Yeah. Well, I was living on a hospital ship, um, that was kind of deployed in the region, um, docked, you know, partly off the coast of Freetown, Sierra Leone, partly off of Monrovia, Liberia, and a few other countries in that, in that region. What was the impetus for, for, you know, embarking on that chapter?
Starting point is 00:43:50 It was a post 9-11 experience of, you know, being depressed like a lot of other people and asking myself, like, what can I, how can I contribute to the world in some positive way? Because even though I was pretty young, like I was still aware that, that I had it pretty good. Like I had a life of privilege in the sense that, you know, now I no longer had this day job. I wasn't making a ton of money, but you know, I was, I was making like $24,000 a year. And that was, that was a ton of money for me at the time, like 21 years old. And I had freedom, you know, I could, I could choose like what to do with my day and my priorities. I was a musician. I did that, you know, had all this kind of stuff, but I felt like there was more. So I felt that malaise that we talked about in the beginning. I felt that discontent. And
Starting point is 00:44:32 I thought if I want to contribute to a service project, I want like the, I want the most hardcore one. Like if I'm going to go overseas or something like what is the poorest country in the world? So I Googled poorest country in the world. And at the time it was Sierra Leone on the UN Human Development Index. And I knew of this organization that had been working there, and I read the story of a surgeon from California who had been there for something like 18 years at that point. He met his wife there who was another volunteer, and they raised their two children.
Starting point is 00:45:00 And so I felt personally challenged by that story. I was like, okay, if this dude can do all that and essentially give up this very lucrative career back in America, I, I'm probably not going to do it for 18 years. Um, but you know, sign me up. So did two minute, two year commitment and then extended for a third and fourth year. Wow. So you're on the, you're on this hospital boat and treating what kind of patients? Um, so the, the doctors and surgeons and the whole medical team of the ship, they're trying to do procedures that are not normally available in those countries. So there's a lot of prosthetic stuff.
Starting point is 00:45:35 There's a tumor removal, cataract repair, cleft lip and palate, vaginal fistula. So they're trying to kind of correct some pretty serious stuff. Wow. Yeah. It's not primary care. It's not any kind of first aid. It's all more advanced things. Right. And your job was what? Yeah. So my first job was to schlep boxes around once again, which is kind of fun. Back to the boxes. I know. But it was different because I'm actually in this warehouse and managing these supplies,
Starting point is 00:46:04 and I could physically see a connection between what I was doing and people who are being helped, which is very rare. Like with charity, most of the time you write a check, you don't know, or maybe you see a video or something, but you don't realize like your direct impact. So I did that for a few months and then somehow I proved myself capable. capable and through a kind of a strange set of circumstances uh ended up kind of you know moving like way way up the ranks you know from i don't know number 400 out of 400 people to the number two or number three person on the ship and i started working with the host governments that our organization was partnering with so that's why i started traveling in the region i met and worked with the president of liberia, various ministers of health, various other people like that. And I learned a lot, like very quickly. That's amazing. And it was around
Starting point is 00:46:51 that time that you first met Scott Harrison, right? That's right. I knew Scott his very first day in Africa. That's so crazy. Yeah. When he came to the ship, I remember when he arrived and he and I used to hang out a lot in Liberia. We would drive our Land Rovers around. And I remember when he arrived and he and I used to hang out a lot in Liberia. We would drive our Land Rovers around. And I remember before he left, he said, he and I went to lunch and he said, I'm going to start this like this thing, you know. And I have to be totally transparent. I said, well, that's good, Scott. But, you know, like there's probably like 30 water NGOs like right here in Monrovia, Liberia. You know, there's like hundreds of them around the world.
Starting point is 00:47:26 Like, it's good that you're going to, you know, do something with it, but I had no idea, you know, no idea. I mean, that it was, it would become, you know, charity water. It's so crazy. Yeah. I mean, for the listener, Scott Harrison is the founder of a wildly successful charity called Charity Water. And he initially moved to Africa as sort of a self-imposed purgatory
Starting point is 00:47:47 to atone for his many years of being a debaucherous nightclub promoter in New York City and had this sort of epiphany, much like your own, I would imagine, where he decided that, you know, he really wanted to change his life and to create, you know, to sort of contribute and create meaning and charity water was born out of that and it really has redefined uh giving across the world and created new parameters for what charities can be and do and it's it's very inspirational what he's done and the success is extraordinary i love how you describe it like that i love how you say it's like not only was it is an amazing charity which of course it is doing all this great work in
Starting point is 00:48:26 Ethiopia in particular, but elsewhere. Uh, but also it has changed the model of charity. And I think that's, uh, just a huge testament to what he's done through transparency, you know, sort of this souring, uh, that I think a lot of people have about giving because we feel disconnected from where our dollars go. And he created a model whereby you're incredibly connected to where your dollars go. Every 100% of every dollar donated to Charity Water actually ends up doing what, you know, the giver would like it to do. And I think what do they, they, they raise capital just for operating. Yeah, exactly. They separate their, separate their programming and operating expenses, which is also kind of a groundbreaking thing when they did it right and it was very difficult for him to create that and everybody told him that it couldn't be done yeah and he had to hustle
Starting point is 00:49:11 quite a bit uh i mean in those beginning years i do remember you know that because he was so persuaded by that model of like all the money that's raised is going to the field it's going to programming but then obviously you have to pay for he in New York City, and he wants to hire more people. And he had to hustle quite a bit for those operations, but I think it was obviously well worth it for many ways. And then you ended up donating the proceeds from the $100 startup to Charity Water, is that correct? The first book I did, The Art of Nonconformity. The Art of Nonconformity. And then Scott actually came and spoke at World Domination Summit, which is an event that I
Starting point is 00:49:48 produce here in Portland. And I think he was there for year number two. And he did a big challenge with the audience asking everybody to stand up and give up their birthday, which was a big thing they were really pushing at the time. And the audience responded very well. And I think we raised a couple of hundred thousand dollars or something. And that made me happy. That's fantastic. I felt that was my repentance for like not believing in him in the beginning. You know, it's not like I didn't believe in him. I just had no idea of the scale.
Starting point is 00:50:12 Like I'm sure I thought he was going to have like a small little organization. So, but obviously I was wrong. And the birthday campaign was massive, right? Basically getting people to, instead of get, get, you know, getting gifts for your birthday to donate the dollar amount of the age that the person is turning. And people have created viral videos out of that, and it's been wildly successful. It's very inspirational. Fantastic.
Starting point is 00:50:35 And I assume you guys have stayed close ever since then. It's just crazy that both of your lives have taken on this wild trajectory that began in, that, that began in a small African country. Yeah. Back in those land rivers. Right. So, uh, so what, you know, what drew you to return from that adventure on the hospital boat? Yeah. So I was there four years. Um, first two years, absolutely loved it was completely immersed. I felt like I gave 101% or whatever. Um, and year three and year four, I don't want to suggest that I wasn't working hard because I was, and I did like it, but I didn't love it as much. And I felt like that was not the kind of environment to be in unless you were like fully, fully committed. And I had kind of seen like with the exception of
Starting point is 00:51:22 the surgeon I mentioned, who'd been there for 20 years, seeing people that kind of stayed on and on, maybe get a little cynical, maybe get a little bit demotivated or de-energized in some way and like losing their, their passion for it. And I didn't, I guess I just didn't want that. Right. Coming a little jaded. Yeah. A little bit. And I was like, this is a wonderful experience. I'm so glad I've had a chance to be part of it. I feel like my life has changed, you know, because of it. I always tried to correct people when they would say like, oh, you know, such a wonderful thing that you're doing. I'm like, well, hopefully other people are helped through it. But, you know, if nothing else, I am like my life is permanently changed because of this. But then I was excited about doing other stuff. I wanted to travel in other regions.
Starting point is 00:52:04 stuff. I wanted to travel in other regions. I had this inkling of being a writer and sharing some ideas with the world. And I knew to kind of move to something else, I'd have to be off that environment. This notion of contributing to the betterment of society, you know, being of service through your work is a theme of everything that you do. And kind of infuses, uh, you know, all of the work that you do. And, you know, one of the things that you always say is, you know, you can be successful and contribute to a better world at the same time that these are not mutually exclusive principles. Um, and you've remained true to this idea of contribution as an integral aspect of the work that you create and how do you so how do you maintain that and how do you help other people like access that for themselves i think contribution is essential to well-being i think contribution is it's it's part of the human condition it's uh
Starting point is 00:53:02 you know as we kind of give, we ourselves benefit. So I use this phrase, selfish generosity, like, let's be clear, like, it's great to give, but you're going to, you're going to receive something about it, about it, you know, through it too. And I think, you know, you mentioned you can be successful and still contribute. Um, I almost wonder like, how can you really be successful without contributing? Because obviously people can be financially successful or whatever that kind of definition of success. But I do believe that, that most of them are probably going to feel that something's missing without that element of contribution. I think that is, that's kind of the missing link and different times in my life I've struggled with depression
Starting point is 00:53:38 or anxiety, still haven't got that all figured out. But, you know, I have noticed when I go into these periods, you know, getting back to contribution and getting back to service helps me at least. Yeah. You know, so I don't know. It's a fundamental principle in addiction recovery. You know, service is absolutely, you know, non-negotiable. But one of the adages or sort of, you know, aspects of staying sober and sort of heightening your sobriety is getting out of yourself by giving. Right. So if you're depressed or you're not feeling yourself or you're not feeling good or you're have a lot of anxiety or you're in the throes of self-obsession, which is something that I like to do. Sure. Same. Same. Totally.
Starting point is 00:54:21 The ultimate the ultimate way out of that is to avail yourself to somebody else, right? Just pick up the phone and call somebody who perhaps is less fortunate than you. It doesn't have to be some grand gesture. It can be a simple thing, but just to get out of your own self and invest yourself in somebody else in the most simplistic way is always a way for me to change my mindset and my mood and anchor me in what's most important. Um, and I, that's a different, you know, a different example of, of what you just said. Um, but in, in thinking about service, you know, culturally, we live in a very kind of binary dualistic society where it's like, you know, you're getting,
Starting point is 00:55:02 or you're giving and those don't overlap. And, and, you know, being somebody who's in this world of startups and entrepreneurship and, you know, building businesses, it's all about the hustle and, you know, you got to get yours and, you know, who's working the hardest and all of that. And that is, can be interpreted at being at odds with service, because if you're giving then you're not getting right yeah i mean it's how is that reconciled for you like you know it's kind of a trap to think that way i mean i can see how you have how you know people do obviously and and i mean let's be clear i can look at my life and say like what was that phrase you used about the
Starting point is 00:55:39 throes of self-obsession or something like that you know i have that whatever that is uh too and i can i can see lots of times where i get off course and, and kind of just neglected that whole area. But I think whenever I do, it's like, there's a signal. It's like, something's wrong here. Uh, and I'm actually probably not going to be actually successful in whatever else, you know, my career goals are, uh, because I have the wrong motivation or something. So I don't know. I think maybe just awareness of that awareness, um, that there is this principle, this guiding principle, um, that, you know, should be with us like throughout our lives and it can take on many different forms. There's lots of different ways to
Starting point is 00:56:14 contribute. You know, if you're, you're super busy, if you're working 80 hours a week for some project or something, maybe you can't, you know, volunteer 20 hours a week at whatever the local charity is, but there's probably something, you know, volunteer 20 hours a week at whatever the local charity is, but there's probably something. You know, there's always something. You can, like you said, you pick up the phone, you call somebody, right? Yeah, there is a bizarre, spiritual, mystical, universal equation at play here that I can't, you know, begin to understand, but I know it to be true. And that is, you know, when you are in the mindset and the activity of giving, that you are always repaid, you know, twofold, tenfold, whatever it is.
Starting point is 00:56:47 But never once in my life experience have I ever suffered as a result of giving. You know what I mean? So, it's about broadening your perspective about how these, you know, rules, for lack of a better word, you know, function in our society. And again, it's not about dogma or any kind of religious, specific religious perspective per se, but just understanding that that is almost the fundamental law of how the universe operates, you know, should be a guiding light and a North Star for people. I mean, it's changed my life tremendously just practicing that.
Starting point is 00:57:24 Right. And so, I guess... And I'm not always so good at it. Yeah, I know. I think it's... I'm saying, I'm saying, of course, I think it's changed my life tremendously just practicing that. Right. And I'm not always so good at it. Yeah, I know. I think it's the same. Of course. I think it's, you know, part of what I've tried to do with Art of Nonconformity is to show that, yeah, it's not binary. As you just said, you know, contribution is necessary. But it's also okay to follow your own dream. And it's also okay to, you know, if you got this crazy thing you want to do,
Starting point is 00:57:45 like go and do it. And the, the service connection, I think this is important. It doesn't necessarily have to connect directly to everything else. And I think in our culture, one thing we also have is like, if somebody is doing something kind of wild and crazy, uh, then there's a, there has to be a reason for it. You know, like I wrote in the book about this young guy who walked across America and he had this vision of like, I'm going to leave Maine and walk to San Francisco. So a few months later, he did that. And I loved what he said. People would always ask him, like, are you raising money for cancer research? Are you like, whatever? And he's like, I'm just doing this for myself.
Starting point is 00:58:20 You know, it's something I feel like I have to do. And I think there's a purity in that. I think like he's a better person now because of that experience. And, you know, it's something I feel like I have to do. I think there's a purity in that. I think that he's a better person now because of that experience. And, you know, he's going to contribute so much more in his life along the way. So I always want to challenge people like there's a dream, you should follow it. And how is that connected eventually to other people? But it doesn't have to be directly. Right. Yeah.
Starting point is 00:58:39 He seemed like a very almost sheepish about even talking about what he was doing like almost embarrassed yeah even let anyone know that he was doing it but obviously that you know the collective wisdom of having had that experience you know the bear attack and whatever else along the way uh is going to allow him to be able to contribute more fully the rest of his life. And that's a beautiful thing. You know, along the lines of, you know, the hustle that comes with entrepreneurship and the hashtags and all of that, there's also this idea that gets thrown a lot, around a lot and very cavalierly of chasing your passion.
Starting point is 00:59:21 You know, we should all have a passion. And you should live your life passionately and for those that are already passionate they don't need to hear that right for the people that are having difficulty accessing something they're passionate about i would imagine that that makes them feel lousy about themselves yeah you know can be depressing to think something's wrong with them because they don't know that message. Yeah, for sure. So how do you, you know, navigate that? And, you know, linguistically and kind of intellectually. Yeah.
Starting point is 00:59:52 So linguistically, I guess I try to be careful about some of these terms and some of these phrases just because they have kind of taken on a different meaning. And there's nothing wrong with the word passion. I mean, it's good to be excited about something and to believe in it and to pursue it, you know, with all your heart. But because of this phenomenon that you've just discussed about how like we feel there's something wrong with us. If we don't know, like, here's my thing, I'm going to run ultra marathons. I'm going to go to every country in the world. Um, I think I talk about experiences, you know, uh, it's not about follow your passion, but can you follow different life experiences? Can you follow your skill? What are you good at? What do you like
Starting point is 01:00:29 to do? Um, what did you like to do when you were 10 years old? You know, are you still doing some of those things? Is that something that you want to get back to just kind of helping people explore? And I think it's through the exploration that the broader thing comes out. At least it was for me. Yeah. It's not about some lightning bolt moment where you're darting out of bed and you're like, you know, suddenly you're converted into Tony Robbins or anything like that. You're like a trampoline by your bed. So I did this event once where I've never actually met Tony Robbins, but I did this event once where he was also speaking and there was like a trampoline in the green room. Like that's what Tony requires.
Starting point is 01:01:04 Like it's part of his rider. He has to have a trampoline. And I was like, wowoline in the green room like that's what tony requires like it's part of his rider he has to have a trampoline and i was like wow i need to start getting that myself yeah and unless you're you're sort of walking in his footsteps or behaving the way that he does that you're not living passionately right right you know what i mean well it's also an extreme you know extrovert expression of that right and so you may you may be just a quieter person or you more more focused on your inner world or you know more introspective and that's also okay this distinction between passion and purpose you know, Ryan Holiday speaks to this quite eloquently. Like, he sort of refers to passion as, like, the flame that burns out quickly, you know,
Starting point is 01:01:54 and might lead you to make, you know, sort of impetuous decisions or, you know, act spontaneously against your interest or flame out, as opposed to kind of the slow burn of of living purposefully um and linguistically like at the very least that seems to make more sense to me and i i think the idea of trying to connect with purpose might be more accessible for for you know certain people than the idea of like finding your passion yeah i mean i like it but i also think like finding your purpose also feels a little bit overwhelming or intimidating to some people. Like what is my purpose? What's the meaning of life? You know? Oh, Rich has got to figure it out, but I don't know. I don't, you know, right. So yeah, it's true. It's true. And it almost
Starting point is 01:02:37 sounds heavier actually. It sounds heavier because like passionate, you could just, I'm passionate about whatever, you know, the thing is in front of me, but purpose, like that's defining. That's like, uh, you know, can my purpose change over time? Is it, do I have it for life? Like, you know, I understand what you mean. Yeah. It's a very good point. I mean, all I could, all I know is my own experience. Right. Right. Like, and my experience is that I wasn't struck with a sense of purpose, you know, overnight. And I don't know that I ever, you know, sort of consciously embrace some idea of passion. I slowly navigated towards investing myself in things that I enjoyed doing.
Starting point is 01:03:13 And I trusted and had faith that my instincts were leading me in a positive direction without knowing where it was leading and certainly having no idea that it would ultimately translate into some kind of business or anything like that. It had nothing to do with that. And, you know, I'm not somebody who creates vision boards or creates five-year plans or anything like that. It was about sort of on a day-to-day basis, really just trying to pay more attention to myself and listen to that, like have the confidence to be able to trust that that was a good choice for me when perhaps external evidence might suggest otherwise. And I think- Or commentary might suggest otherwise, right?
Starting point is 01:03:58 Of course, friends and family, like your external environment, you know, not smiling, you know, upon that in the way that maybe you were internally. And I think the only way I was able to do that was because I had spent 10 years doing internal work, you know, to try to get myself right with myself, like really, you know, uh, doing the inside job in a very profound way to connect with myself in a way that I could be the healthiest version of myself mentally, emotionally, and spiritually. And I think that's what gets lost in this conversation about, you know, living purposefully or living passionately or, you know, finding your dream job or any of these kinds of things i my my personal opinion is that in order to really do that properly uh you have to commit to that that sort of journey of self-understanding and self-knowledge and that's not very sexy and
Starting point is 01:05:00 it's not really necessarily bloggable and it's not going to show up on instagram right and it's not really necessarily bloggable and it's not going to show up on instagram right and it's messy and it's scary too and it's different for different people and it looks different for different people and there's no no one way of doing it uh you know mine was motivated out of pain and and crisis but i don't necessarily believe that you have to suffer in order to do that work. But I think in order to really be able to trust those instincts, you have to do that. Because otherwise, if you have some goal, like I want to run an ultra marathon or I want to do whatever it is, it doesn't matter what it is. If you're not right with yourself, then that instinct can very easily lead you astray because you don't really understand why it is that you have that impulse yeah my question for you was going to be how do you because you were talking
Starting point is 01:05:52 about how you had to learn to trust yourself and so how do you learn to do that but you basically answered it by saying well i spent 10 years you know on inner work i spent 10 years before all the other stuff so yeah i mean i also spent 10 years before all the other stuff. So, yeah, I mean, I also spent 10 years before that making decisions that ultimately got me locked up in a mental institution. You know what I mean? So you had a lot of experience and all of these ideas that I thought were great at the time that, that ultimately were destroying my life. So, so there was a long period of time where I felt like I couldn't trust my instincts. Like, how do I know that the decisions that I'm making for myself are leading me in the right direction? I have a wealth of experience that says that, you know, my decision maker, my picker is broken.
Starting point is 01:06:34 And in order to really be able to trust myself again, I need to fix that. So, it was compelled by, like I said before, a crisis. But, you know, most people, you know, don't have to sort of go through extreme examples of that. But I think to the extent that you can hone that antenna and really know, like when that impulse arises in you, that that's a good idea for you, um, is, is, is priceless, but, but the cost is, is that work, right? Yeah. This is also something that I'm learning about myself you know it's kind of new to me in a lot of ways i know that you're going through you know a fair amount at the moment you know i know that you recently suffered the loss of your brother and that's that's led you in kind of this direction too so i was interested in kind
Starting point is 01:07:20 of knowing where you're at with all of that at the moment? Yeah, well, it's a process. It's a journey. And for people who are listening, my brother died maybe just a little bit more than a year ago now. And the circumstances of that death were not good. He was 31 years old and he made a choice to end his life. And so it was something that for all of us, um, you know, family, friends, uh, it was a complete shock, like never saw it coming whatsoever. Um, and so in, you know, kind of examining, not just examining that, but like, where do we go from, from here? And how, what does that, what does that entail for, for my life, both in retrospect and in present tense and in future? And I realized that I was lacking a lot of skills, essentially, a lot of these kind of emotional skills that you talk about and the ability to trust yourself and to know that you're on the right path, whatever that is. And as for where I am in the process, I'm still kind of working through it.
Starting point is 01:08:24 I went to therapy, which I hadn't done before. I actually started some medication for depression and anxiety, which I'd always been kind of, you know, I don't know if morally opposed, but just kind of personally not excited about. But it finally came to a point where basically I was like, I need a baseline, essentially. to a point where basically I was like, I need a baseline essentially. And so I've been doing that for maybe about six months now. And it was interesting when I began that process because I had a new book come out and I went on tour to promote the book and the tour was really good. Like I felt like I was giving a good stump speech and connecting well with people. And so like the career thing is happening and that was, that was all positive.
Starting point is 01:09:06 But at the same time I'm like dealing with all this kind of emotional stuff and it's not like either one was inauthentic. They were both true in my life. And so now book tour is over working on some new stuff. But I don't think I could say that I have learned, you know, the same kind of lessons that you've learned. I think I'm still kind of figuring it out. And in some ways I'm a slow learner, which is very frustrating because, you know, throughout all the random stuff that we talked about, about selling
Starting point is 01:09:33 things on eBay and like getting visas for, for countries, like I'm pretty good at that stuff. I'm pretty good at figuring out these processes and, you know, decoding and deciphering. Um, but it doesn't always kind of work the same way when you're thinking about these kind of things. It definitely is a different, yeah, it's a different animal. The five-step thing doesn't always apply. Right. So what has come up, though? What have you confronted that maybe you didn't understand about yourself prior to this experience?
Starting point is 01:10:01 Well, I mean, I used the word regret before. I do feel like a deep sense of regret for, not that I'm responsible, of course, for what happened, but, you know, I do feel like a lot of regret about not spending more time with him. And so I tried to learn the lessons from his life and one central value of his life was kindness. And he was extremely kind, you know, to everybody. And now it's kind of like, we look back and we realize like he actually wasn't very kind to himself. Um, but he was like very kind to all of his friends and family, never forgot a birthday, you know, planned ahead for those kinds of things.
Starting point is 01:10:41 Like he would put his, he would put people's birthday on his phone, like three days before their actual birthday so that he would remember, you know, it's like set reminders to get something for him. So, uh, you know, long story short, um, for all that we've talked about contribution and service, I felt like a lot of ways, um, I was kind of off kilter with that. And maybe I had contribution in the sense that I'm giving, you know, X percent of my dollars or something to charityity Water. Great. You know, I believe in the work that I do. I think that a lot of it does help people, but still like these things will pass away, right? These things will go, you know, what, what remains, what is essential. And I felt that there was some kind of gap there. And so I'm trying to fix the gap. That's one thing. Was he in the service? He was, yeah, it was a veteran, a veteran of Iraq and Afghanistan army veteran. And then he was an NCIS special
Starting point is 01:11:30 agent when he passed away. Wow. So I would imagine, you know, post-traumatic stress is something that we think so. I mean, like, you know, we're obviously like diagnosing from a distance and we're not qualified to do that. And unfortunately, in those kind of careers, you know, if you are struggling with some kind of mental health issue, it's actually very difficult to get to get help. You know, I mean, he's he's in law enforcement. You know, he's essentially like an investigator for the government. And if you report that you're struggling with depression, you very well could lose your job or be reassigned or something like it's actually a real thing. So obviously was going through some stuff that we didn't know about. Yeah. I'm sorry to hear that.
Starting point is 01:12:14 But like everything, you know, it's an opportunity for self exploration with you. I would imagine it sounds like you're taking advantage of that. There's no other choice yeah you know like the choice is you kind of like wallow and remain stuck uh or never go anywhere with it um or you do something with it right now it's not like there's not the choice you want to make like you would love to go back and make a different choice to change the whole situation yeah but since that's not possible what what are the options available right so well there's a there is a gift in there i think you know for yourself to you know explore and and ultimately discover but i'm i would imagine that that would have been it was it must have been very difficult for you to get up and you
Starting point is 01:13:01 know sort of sling your book and you you know, like talk about your book and have people projecting onto you this idea of who they think you are as this, you know, sort of person who has lots of answers to life's questions, whether it's entrepreneurship or self-discovery while you're simultaneously dealing with this very personal and private pain. Well, I tried to be honest about it. I tried to be, you know, relatively transparent in terms of like I wrote about on my blog. And so people who, people who like want to know can know and people who, you know, might not care, might not be important in their life, they don't have to. And so for me, it's not false, you know,
Starting point is 01:13:41 to talk about career development and help people with their side hustle to help people, you know, make these career decisions. Like I'm actually like somewhat good at that having gone through a lot of different experiences and all the research I've done. So for me, it was actually kind of good to focus on that, but yes, it's also like simultaneously in the back, you know, of my mind, the other thing. And I, like I did the 30 city tour and, you know, my mind, the other thing, and I, like I did the 30 city tour and, you know, like I never got like emotional during my talks or anything, but like right before I would go out, um, every night I did kind of, you know, think back about Ken and just kind of like dedicate the night to him in my mind. Um, and then I never said anything about that. I just went out and did my, did my talk. So that kind of worked for me. Yeah. It's's a, I appreciate your, your honesty on that.
Starting point is 01:14:27 You know, I, um, I noticed that, you know, one of the things I mentioned to you before the podcast, you know, when we were kind of talking about like, well, what can we talk about? That would be interesting. One of the things that's been on my mind that I I'd love to get your perspective on is kind of the state of the health, the, the self-help industry on my mind that I'd love to get your perspective on is kind of the state of the self-help industry. You know what I mean? And this proliferation of self-help gurus, for lack of a better word, who, you know, I think there's a lot of well-intentioned people and there's a lot of people doing amazing work.
Starting point is 01:15:00 And this is not a slight on anybody, but just a general observation of perhaps a lack of authenticity and you know of people trying to hold themselves out as as maybe a little bit more than they are as having answers to everything and and just kind of paying attention to how this is going on on the internet causes me some concern you know and i'm interested in yeah i mean there's a lot of a lot of different ways to to go from there i feel like you know self-help is one thing self-help gurus the self-help industry is kind of another thing and um i don't know i tend to gravitate more toward voices like our mutual friend jonathan fields know, he is a great example to me of someone who, you know, is in personal development, quote unquote, self-help. Um, but yet is kind of, you know, the opposite of being that guru telling you what to do or kind of
Starting point is 01:15:57 uplifting himself. Um, he's very much about uplifting others. And so he's someone that I've learned, learned from for many years and kind of noticed that like when I'm, when I'm, at least for my work, like if I'm helping, like for me, the goal is, is genuine empowerment and affirmation. And I think there's value in that, like helping people understand their self-worth, helping people understand their potential and not just understand it, but then actually do something about it, taking the action that we touched on briefly earlier. That to me is the value. Whenever it has shifted to become like this personality based thing, then that feels a little bit less comfortable, you know? And so I just kind of, for me personally, I will deflect a lot of
Starting point is 01:16:40 that stuff. And if people have a question about, you know, how to ask for a promotion at work, um, or how to start their little side business while they have their day job. Great. I can tell you exactly how to do that. Um, if people start asking me some like really big questions about life that I don't have that I don't have, I'm just going to say that I'm like, I don't know, dude, I don't know. I get emails. No, I mean, but that I dare you say you don't know. It's probably disappointing to people, but I'm like, what am I supposed to say? I don't have the answer. Like I'm like, I affirm your supposed to say? I don't have the answer. Like, I affirm your question.
Starting point is 01:17:07 Like, I understand that you're seeking. Me too. You know, let me know when you figure it out. So, I don't know. I think self-help is this complicated thing because it's like passion. Like, we can be very cynical of it, and we should in lots of ways. At the same time, like, we can probably all think of people in our lives who have helped us in different ways, who've kind of led us along a path and, you know, kind of pointed the way towards something. And without that resource, whether that's like counsel or mentorship or a book or something like without that, we wouldn't have been that far along.
Starting point is 01:17:37 Right. Right. Yeah, I think it's I think that was a great answer. Thank you for that. And by the way, I absolutely love Jonathan Fields. I did a podcast with him that's not going to go up until October, but he's one of my favorite people. I just think he's fantastic.
Starting point is 01:17:53 And I think it's the distinction between, well, I guess, I think it's about authenticity, you know, and I think it's about transparency. i think it's about authenticity you know and i think it's about transparency and i think as as people become more savvy uh consumers of the internet what you see is a much more finely attuned radar for bs you know what i mean which i think is a great thing that's good you know and the quality i think the quality also bs first of all and then quality second maybe yeah raises people's work because everybody's got a thing a lot of noise out there yeah but it's it is disturbing to me when i when i can clearly identify from you know a mile away when somebody's you know through their language i can tell this is like some kind of crazy sales pitch for some you know product that probably isn't so great.
Starting point is 01:18:46 And I see it working and profiting and it, it upsets me. That's when it's scary when it's working. When you see it not working, it's like, well, people are, people are smart. They're using that radar. Right. It's interesting. But I'm, I'm hopeful that the internet is self-selecting, you know, that, that, that this economy, you know, online will, that the internet is self-selecting you know that that this economy you know online will over time that the quality will raise to the top and you know i think that you're you're a great and shining example of you know putting out phenomenal content at like an alarming rate like i don't know how you create so much so consistently i know you write at least a thousand words a day but your output is pretty tremendous.
Starting point is 01:19:32 I've had some slow periods, but thank you. But it's, it's like, it's all very, um, useful advice, you know? Well, hopefully that's the goal. If it's not, if it's not useful, if it's not helpful, then, then it is kind of BS, right? So I guess, and I think everybody has a certain amount of BS in their life and their writing. So I guess I want the BS quotient to be very low. Well, I think you're succeeding in that. So are you still doing a thousand words a day? Is that still a practice that you maintain? It is a practice. It's like a gratitude practice or something in which I try to be consistent with it.
Starting point is 01:19:59 But I also kind of get off track. So it's my goal. I would say I'm probably at about five days a week, five out of seven. And is that how much of that gets published? It depends, you know, when I'm writing a book, I mean, obviously, you know, a lot about writing books as well, probably write two to three times, you know, more than what's actually used in the manuscript. Right. Online might have a lower standard, right? Because it's online. So, and when you're writing a book, how do you balance writing for the blog versus writing for the book the blog
Starting point is 01:20:29 suffers pretty much one of them i mean it's it's nice of you to say that i'm prolific but uh you know things will always suffer you can't do you know everything you want right so you know what i mean right despite the pressure on you to be constantly uploading. I mean, one of the things that I appreciated that I heard you say was when you were traveling, you initially felt this pressure to be photographing everything and to be sharing this and to kind of have that level of transparency to be this, you know, sort of social media presence with what you were doing. And then ultimately coming to a place of saying, this is not for me i don't have to share every aspect of my life and alleviating yourself of that pressure because there is that
Starting point is 01:21:10 kind of thing of that takes you out of the moment of the experience like if you're not sharing it it's not happening yeah and the illusion of that yeah i think my social media in general is something that i actually don't do a really good job at and And at least at this point in my life, I'm okay with that. At this point in my life, because in other seasons, I've been like, oh, I really need to get on my game with this. I need to have my calendar for all this different stuff. And speaking of authentic, that to me feels inauthentic. I know people who do that very authentically. But for me, it didn't feel good.
Starting point is 01:21:42 And I thought, ultimately, if I'm going to change the world or my small little part of the world, um, for me, I should be writing, I should be thinking about ideas. And then if I'm actually doing something of value, hopefully other people are going to share it. Right. As opposed to this grand strategy of here's like the X number of Instagram posts or whatever a day. Yeah. And I think that speaks to balance too, right? Like, and you have some interesting ideas about balance. I've been thinking a lot about balance lately, but you know, how do you perceive balance in your own life? small distinction or something, but balance just, um, balance to me is kind of, I think of life work balance, which leads me to like some corporate, you know, corporate speak, corporate benefit. Like we're a corporation, we're taking your life away from you, but we want you to feel good about it because there's free yogurt, you know, in the fridge or something. So therefore life work balance. Um, so I, I have been for better or worse, very focused on like what I've been trying to make or create.
Starting point is 01:22:46 And I like that. I enjoy it. Um, but I don't know if I have a lot of balance, whatever that is, I guess I feel okay right now. I mean, I'm all right. And the time, the time that I was like, just speaking of depression and anxiety, I don't know if that was a reflection of lack of balance. Like maybe it was, maybe I would have, if I went out for like more walks along in the woods or something. Um, but I don't know. Not sure. Well,
Starting point is 01:23:12 I feel like there's a cultural pressure to live a balanced life and eat a balanced diet. This is the key to being a happy, successful person. Uh, and, and that is at odds with basically every example of every human being that's achieved something extraordinary. Because those achievements are birthed out of, you know, being out of balance, for lack of a better word.
Starting point is 01:23:36 And maybe it goes back to linguistics. Maybe that's the wrong word for it, you know. And I struggle with this because if I'm writing a book or I'm training for Ultraman or, you know, my life by very, by its very definition has to be out of balance, at least for a period of time. I can imagine it's a very balanced thing to run an ultra, you know, I did a couple marathons and that was unbalanced for me. So, I mean, it's, it's, it's not a sustainable equation for your life. It is for some people, but not for me as a father with four kids and other things that I'm doing. But I look at it more like a pendulum swinging, you know, and I'll allow that pendulum to swing way to one side as long as it's going to come back, you know.
Starting point is 01:24:18 And so, in the macro, you know, over the course of a year, my life will look in balance. But on a day-to-day basis, like, I'm not a multitasker. I like to go deep into something and that's how I get the results that I'm seeking. But that does require, you know, sort of being slightly obsessive, not to the point of, you know, harming myself or being sort of, uh, self-damaging or any of that, but, but giving myself permission to do that, I think has been important to me. And I think that I'm a better servant as a result of it, but I don't know that I'm doing it the right way. What seems to be working, right?
Starting point is 01:24:58 I don't know. Not just, I mean, obviously successfully, quote unquote, but also you seem happy. I think there's value in being, you know, obsessed is also this word that people can, you know, but also you seem happy. I think there's value in being, you know, obsessed is also this word that people can, you know, it seems very negative, but I think there's a lot of value in being like, here's this thing, I'm going to go after it. You know, whatever this thing is, I'm going to, I am going to devote a lot of my life to it because I believe in it. Right. Oh, that guy's obsessed. Right. Like, and there's a negative connotation associated with that. But you could say he's passionate yeah like now you're
Starting point is 01:25:25 like he's found his purpose you know he's found his purpose you can't say he's obsessive you know so what's the difference is it kind of like this whole thing about pornography you know it when you see it right well i think obsession uh connotes like a level of myopia maybe where you're discounting other aspects of your life i don't know or maybe what you're doing actually is not going to lead to the results that you and you think it will right perhaps right right it's a self-destructive passion right or ultimately maybe right like when you come to the end of it you'll actually look back and say why the hell was i doing that that would be obsessive in a negative way right whereas if you come to the end of something
Starting point is 01:26:03 you're like man that was really hard that ultra whatever it was uh you know at this point i wanted to quit at this point i had this physical problem at this point i had this emotional problem but here i am i'm so glad i did it you know that seems to me like passion or a good obsession or whatever you want to call it i think it goes back to self-understanding as well you know like i'm i'm an alcoholic you know like i just can't help it but i'm magnetized, you know, and this is how I'm hardwired. And I can deny that and try to repress that, or I can try to harness that and put it into, you know, a positive direction for my life. And, you know, I, I contrast that with someone like Ryan Holiday, who seems to me to be an incredibly balanced person.
Starting point is 01:26:45 Like he can wake up and he sets aside certain hours every day where he writes and then he stops writing and he goes home and he's with his wife and he takes care of his goats. And it's all very functional. And he runs like an hour a day, too, it seems like. It's all, you know, it all goes very well for him. But I just I function differently. You know, like, you know, when I'm writing a book, I do have to kind of go into a little bit of a cave to do that. And that means, you know, long writing streaks late into the night and then days of pulling my hair out because I can't write anything and the like, you know, so it's not a function of just, oh, between, you know, 11 and four is when I, it just,
Starting point is 01:27:22 it doesn't work for me. I've tried to do that. So how does that work for you? I also don't have a time-based schedule for me. It's much more about like deliverables outcome. What am I trying to, you know, accomplish? And then how do I adjust, you know, to make, what are my peak periods? Um, not just of the day, but of the season. Like my, my book writing season is different than, you know, business building season or tour season, like my, my book writing season is different than, you know, business building season or tour season, you know? Um, so I don't know if I have like a hack or something
Starting point is 01:27:53 for that. I just, I, I do know I have learned, uh, for all that I have yet to learn about myself, uh, and all the other emotional like areas that we touched on. Uh, I feel like I know myself pretty well in terms of how I can do, how I do my best work. And so maybe one thing is I do try to kind of siphon myself off and like, I'm enjoying this conversation very much, but I try to actually limit like the number of phone calls or meetings I have during the day because I am pretty introverted. And so I know that if I have a lot of conversations, it's actually going to take my energy away. I'm not going to be able to do that thousand words or whatever. Right.
Starting point is 01:28:27 So I tend to say no to a lot of stuff. Maybe that's a long kind of rambling answer to say I tend to say no to a lot of things. And I think someone of your stature and the position that you hold, like you're in a place where I'm sure you have to say no a lot. Right. To opportunities that probably sound interesting and cool. Yeah. And that's no interesting and cool. Yeah. And that's no fun. Actually, I would say life, it would be cool to do all of them.
Starting point is 01:28:48 But I would say in the first like three years of my blog, even after it was like full time, I made it a business. I still actually had a very like say yes perspective. And I was kind of counter to that whole thing about should always be selective and have this filter and say no. And it's interesting because like a lot of the great opportunities, you know, things that have happened since then have been because I said yes to things. But then maybe it's like as your life seasons go on or something, as you kind of figure out a little bit more about
Starting point is 01:29:14 what you're really good at, then you have a higher filter. So now I do, I do say no to stuff. Right. And as you continue to grow, those opportunities are only going to increase in volume, right? And ultimately taking advantage of those means less time writing the next book. So you're undermining, you know, ultimately what you're trying to achieve. Right. But you cranked out four books in a pretty short period of time. Like the first one came out in 2006, 2009, 2009. Okay. So four books and that's, that's a pretty good pace i was i was late on one of them though we talked about rick at the beginning i was late on uh my delivery shame on you well i felt bad about it i actually felt really guilty uh-huh i took it seriously and
Starting point is 01:29:54 then i failed so no one asked herman melville if he turned in moby dick on time well i can maybe you don't know maybe i don't know well probably, I don't know. Well, probably his editor did. Right. So, so punctuality important. Sure. Well, you know, if you, if you're like, I'm going to do this. By the way, I was on time on my books. Great. See, I'm sure you were.
Starting point is 01:30:17 Well, you know how publishing works. It's like, it's different if you're self-publishing and that's, that's great too for lots of things. But if you're working with a traditional publisher, it's not just about you. Like you're the author, right? Like you are the bottleneck, but there's lots of other people too, for lots of things. But if you're working with a traditional publisher, it's not just about you. Like you're the author, right? Like you are the bottleneck, but there's lots of other people that are involved in the process. And if you kind of let down the team, then yes, in the end it will be okay, but they're going to have to scramble to pick up after you. So I don't like that. They might be a little less enthusiastic about helping you out next time.
Starting point is 01:30:41 Sure. As somebody who kind of embodies this, you know, alter Chewian, James alter Chewian, choose yourself ethos. Why have you not self-published? Well, I do self-publish every day.
Starting point is 01:30:55 Right. But, but like a book. Well, I have self-published, like I've written a couple of manifestos. I wrote one called a brief guide to real domination. That's how I got started way back.
Starting point is 01:31:03 And I put that on myself. So I think there are different avenues for different projects. That's probably the short answer. And then I would also go back and say, well, I've always liked books. And yes, I know books can mean different things, but for me growing up, books were like a print book that came from a bookstore. And I still find a lot of value in that. And when I go out on book tour, I meet a lot of people who go to bookstores and don't necessarily know me online. They don't necessarily read blogs or even listen to podcasts, although of course that's changing, but I guess I still believe in that medium. Yeah, it's interesting times. I mean, there's no denying that self publishing is now a very real thing and
Starting point is 01:31:45 that's very exciting and I think it's fantastic. And yet there still is something about, you know, having that book published. Yeah. I think it's good. I remember like eight years ago when I was first talking with David, my literary agent, who I'm still working with now all these years later. And at the time I asked him that I was like but David like is publishing going away you know like and he said basically everybody he talks to always asks that question every author and he's like you know publishers are still buying books you know for some reason the cycle you know still continues to work um and so you know eight years later still writing books you know still happy about it I want to shift the conversation a little bit to community.
Starting point is 01:32:42 One of the things that I so respect about what you do is you have built this unbelievably passionate and engaged community of people through the books and the blog, of course, but also through the World Domination Summit, which is like this amazing event that you've been. How many years have you been doing it now? We just finished year six. Six years. And you get, how many people come to this thing? It depends. Yeah. Lots of people.
Starting point is 01:32:52 Lots of people. And this community of people that you have taken care of and that you cater to and have become deeply connected to is really kind of an amazing accomplishment and achievement, perhaps, you know, more impactful than any of the other things that you've done. And, you know, it's led me to do a lot of thinking about how I can cultivate community better in the work that I do. You know, you've created some amazing examples that have been very instructive to me. And I'm thinking, you know, I'm trying to, I'm playing with ideas about how I can do better in that regard. Because I think there's an opportunity for me there that I have yet to really step into.
Starting point is 01:33:34 And so I'm interested in the evolution of this community that you've built and kind of your perspective on that. Yeah. I like what you said about how, you know how your perception is that it's probably more impactful than anything else. And I would agree. And I would hope that that's the case. Because as I said, your book is going to go away, your blog is going to go away. But if you legitimately make an impact on people, that's good. Evolution, I would say like right in the beginning, started writing the blog, didn't know who was out there. There was grandma reading, and then tried to be a travel writer. It didn't work out so well. But probably within the first six months, a lot of people did start subscribing, reading, engaging. And I was like, who are these people? And so right from the beginning, every time someone subscribed, I would write to each
Starting point is 01:34:19 person. And I did that. I did that for three years. And there'd probably be between 50 and 100 people a day that would be subscribing. And so I'm not I did that for three years and there'll probably be between 50 and a hundred people a day that would be subscribing. And so I'm not like writing a long thing. I mean, there's some copying pasting, you know, involved, but it is just kind of like, Hey Rich, I saw you subscribe, you know, Hey, thanks a lot. It's not automated. Like it's not like a thing that happens. Like I'm actually, you know, doing it, um, myself and a lot, and lots of people would write back. And so I, it's not like I had these extensive conversations with every subscriber of the blog, but I had a lot of conversations and began to learn a little bit more.
Starting point is 01:34:53 And then I started doing meetups. I did one in New York City with Jonathan Fields. And, you know, it was like for me at the time, it felt like a very large number of people who came. It was like 50 people. And I had never done anything like that before. And I went away and I was like, I was just blown away. I was like, I had these conversations with people. I heard what they were doing and they were traveling and starting businesses and like they were pursuing their own alternative lifestyle, whatever that was for them. And I got so excited about it. It shifted my whole focus, shifted my
Starting point is 01:35:21 whole like, you know, what am I doing for people when i then when i thought about what i'm writing i thought about those people i thought back to that conversation you know i had with somebody and thought how is this relevant to them not just like these faceless you know nameless people out there in the ethernet or whatever but so and then i did more meetups found them very engaging like very draining for me as an introvert, but actually still very like positive. And then we started WDS in 2011, which was, uh, kind of an outgrowth of my first book tour where I went to all 50 States. That was also great. You know, lots of small groups, different places and big groups, but mostly small groups. And, um, you know, that first time we did that, that event, um, we just felt it was very special.
Starting point is 01:36:06 And the team that I worked with, like we had no idea how to produce events. Everything's been a learning curve, but we, you know, came back the next year and did it again. And then we've been doing it ever since then. So it's something that I take a lot of joy in. Yeah, it's a beautiful thing. You know, I think that I'm in this place right now where I'm starting to connect the dots a little bit with respect to the work that I do and the impact that it's having on people. And I think I've kind of sort of brushed it off or said, oh, whatever, you know, people listen to podcasts but you know like i'm i'm i'm hearing from people with increased regularity about you know changes that they've made in their life and i just get amazing emails of you know people who have who just tell me incredibly detailed you know stories about very private stuff and i really want to be motivating it's incredibly motivating
Starting point is 01:37:03 it's it's emotional it's very touching you know and even on the walk over here i walked across town to come to see you stopped on the street a couple times listen to the podcast like that just like my head explodes you know yeah so what to do with that you know like how can i how can i better serve these people who who really want to be part of this community? My wife and I started doing these retreats, but they're small and they're expensive. So how can I create a more populist, inviting scenario for everybody else? And I don't have the answer to that yet, but it's just something that's on my mind right now. And the model that you've created and what you've accomplished with that i think is really something special and cool well i love the awareness that
Starting point is 01:37:48 you have of that of you know you have this awareness that you have this desire and you have a curiosity about how to figure it out i think that can only lead to to really good things and and you know a lot of people have have done community a lot better than than i have one one thing that i am just now starting to do that other people have done much better is local community groups in different cities. So I wonder if that could be something that's worth exploring because obviously like that is populist and it is open and it is accessible, you know, to people. And it's self-sustaining without your personality having to be involved, right? How do you transcend, you know, if you do it right. Yeah. Like that's the idea. Like I don't want it to be
Starting point is 01:38:24 about me. I want it to be about the ideas yeah you know and i want other people to take ownership of that outside of my you know my personal involvement so i think it's a good question to ask yeah so what should i be doing i don't know i mean this awareness curiosity where does it lead how can you gather people together i think there's a lot of value in being a connector um and you know i'd be the first to say that of wds and all the meetups i've done the book tour stuff um focusing it on like how can it not just be like one to many but like everybody's speaking to each other and and providing platforms especially for people who are maybe sensitive or quiet or they wouldn't necessarily be the ones to speak up, but they have something to say. It's really interesting. Anything you can do to pull that out is good. Um, then a lot of it happens on its own. And that's
Starting point is 01:39:12 the beautiful thing about it is you can look back and say like, well, maybe I was a little bit of a catalyst here or something, or maybe I was an amplifier at parts of it, but really it's its own kind of thing. And that to me is, is, is really beautiful. Like when I hear those stories of people who've connected, uh, with my work in some way, like I'm just like, how can I do that more? How can I do that more? How can I bring these people, you know, something of value? Yeah. Very cool. What was the first, you know, initial spark or idea to put on the summit? Uh, when I did those small little meetups, I thought this is pretty cool. What would it be like to bring people together, not just from one city, but from like all over
Starting point is 01:39:51 the world. And that was, that was the spark. And I actually hadn't been to a lot of conferences. I hadn't been to, you know, I didn't really have a model that I was starting with. And I kind of went out to all my friends, Jonathan and other people, and I was like, hey, come in, let's do this, right? And it's kind of funny because we were all coming up at the same time and they also, like everything was new to them too.
Starting point is 01:40:16 So it kind of felt normal or organic. And I just really enjoyed the process. And I still do. I still enjoy the process of like curating and planning and enjoyed the process. And I still do. I still enjoy the process of curating and planning and all the logistics. And it reminds me of working in Africa on the hospital ship, of coordinating things. And it reminds me a little bit of pulling the boxes from FedEx, except I'm actually helping people.
Starting point is 01:40:37 Or trying to get visas so you could travel. Right. But for a much better cause, right? Because me traveling on my own, that's great. But that's for me. Whereas, you know, putting together like community groups, that's for them. Right. So we touched earlier a little bit on this idea of having a quest and the importance of having a quest in your life.
Starting point is 01:41:01 So you've had a couple quests in your own life. But what is the current quest? What is the, you know, 2016, you know, vision board for Chris look like? Right now I have a focus. I don't have a quest and that focus. Uh, well, personally, the focus is like this internal work that we've been talking about, um, and continuing that process and seeing what I can learn and how I need to apply that in my life. Um, but otherwise the focus is community, what we've just been talking about. And I don't have like a little metric that goes with it. Um, I don't have like a, you know, I will have accomplished this goal when X occurs. Um,
Starting point is 01:41:40 but after I finished like the every country quest, I knew I wasn't going to do another big travel quest. Like I want travel to always be part of my life for sure. But you know, at one of my events, uh, somebody like raised their hand and said, Oh, I know what you should do next. You should go back to every country, uh, in the world, but in reverse order. I was like, that sounds terrible. I was like, you can do that, dude. You know, thanks for volunteering. Let me know how that goes. Um, so I didn't want something like that. And I wanted to shift to like, okay, that was then where does this bring me? Where are we going? Great power, great responsibility. Like I do feel very fortunate that I've been able to do all this stuff. So
Starting point is 01:42:17 how can I truly contribute? You know, so that's what i'm trying to figure out so that sounds a little bit more amorphous than perhaps your guiding arrows in the past yes which is frustrating you're so you're in the contemplative phase it sounds i guess so yeah i guess so like i said i would love it if i could connect it in a way that was similar to what i did, that linear progress of like checking things off. But I don't know if it's going to work that way because, you know, it's, it's not like there's a, it's not like you're going to reach the limit of people or whatever. It's not like I could say, I'm going to have a, I'm going to do a community group or a meetup in X number of cities, but there's always more cities or there's always more, you know, so I don't know. And that's not necessarily the
Starting point is 01:43:04 outcome either. So the goal is to strengthen community right and it's okay to like you have comfort in in in in that sort of lack of complete understanding of what that's going to translate into right like the ability to having more comfort to be patient i'm starting to have more comfort that's what i'm learning okay you can't control all my circumstances as i have learned um so i'm starting to have more comfort so for people that are uh out in the world in the podcast of sphere or whatever you would call it who who are you know stuck in that cubicle or are starting to question perhaps like the trajectory of their professional career or are searching for that thing that's
Starting point is 01:43:46 going to infuse their life with purpose, what's the first step? Accept the discomfort. Accept the discontent. Don't try to fight it. Don't try to ignore it. Make your peace with it because it's going to be what leads you into something better. And maybe a second step is what is that for you? What does that look like? You know, if you, you feel like you're stuck in that cubicle, what would life be like if you weren't stuck in that cubicle? If you're stuck in some other thing, like what, what is it that you want? And maybe you don't have like all the answers, as I said, but you have something. And then to me, it's about execution, implementation, how to go from one to the other.
Starting point is 01:44:30 But the first and foremost is, you know, do not try to just fight that discontent because it's going to be your friend, I think. Yeah. I think there are very few people who are going to have all the answers. You know, in your own case, you started selling things on eBay. That was not your passion. That was not my purpose. But that was a tiny step that infused your life with a little bit of freedom and a little bit of self-governance that you didn't have prior to that. You know, in my own case, it was, you know, riding my bike in the middle of the work day and not telling anybody you know that's not a
Starting point is 01:45:06 good business plan for anything you know but it was a tiny step that i took that that gave me a little sovereignty over my time in my life that that ultimately was a step that led to another step and you know i couldn't see past that two-hour bike ride at the time. But, you know, fundamentally it was a, it was a, it was something that I did almost symbolically to say like, I'm going to, I'm going to step outside the norm a little bit here and give myself permission to do that. Um, and I think that that's really important, uh, to provide people with the, like a, a sense that it's safe to express yourself in that way right like one of the things you always talk about is like freeing yourself from the peanut gallery of social
Starting point is 01:45:52 expectations like can you get to a place where you don't care what other people say and that's a very tough yeah i was gonna say it's hard a lot of people it's not like myself included it's not like today you care and tomorrow you don't. My whole life was premised upon, you know, making sure that everything I was doing would be socially approved. Most people's lives are. But I think as you, you know, as you find more of that authentic self, I mean, ultimately I think more people will approve probably because you're going to be helping more people. But if some people don't, well, you still have to do it. You still, you don't want to be stuck in that place wherever you are stuck in. Who were some of the mentors that you look to during that time or perhaps still look to for a lifeline? They aren't celebrities. They aren't like other authors, other bloggers,
Starting point is 01:46:42 public figures. They're more like people who have impacted my life in a personal way. The surgeon from California, Gary Parker, his family, Scott Harrison. I mean, he is kind of a celebrity, but it's more like personal friends. And I would say like people in my community who have these stories of intersection, they are very inspiring to me. I don't really go to people for advice. I might go to people for some specific technical advice, but I'm kind of busy with what I'm already doing.
Starting point is 01:47:20 But when you were kind of in your emergent phase? I read a lot of books. What were some of the books? I read a great book called Wishcraft by Barbara Sher. It's a wonderful book about finding your purpose in very practical terms. That was great. I read a good book called Mountains Beyond Mountains by Tracy Kidder about Dr. Paul Farmer, who did all this work in Haiti. Um, some practical books I read getting things done by David Allen. It's like still affects my life in terms of how I like organize my tasks and projects. I tried to just, you know, read broadly, learn broadly, different fields, different topics. It's
Starting point is 01:47:59 one thing I feel like I don't do very well anymore. I don't feel like I learned broadly. I'm so focused on what I'm doing. But what do is is learning in and of itself right especially when you're canvassing all these people and collecting all these case studies right you're learning yeah no i'm learning for sure i just feel like i'm learning in a more focused manner and maybe that's okay but i do sometimes long for the days of when i was like in this emergent phase, as you called it. And I'd have like, you know, 10 books, you know, next to me and the topics were all like totally different. I think you're in an emergent phase in a different way. Maybe. Are you working on a book right now? I am actually. Yeah. Can you talk about that or no? It's a top secret. It's not a top
Starting point is 01:48:41 secret. Um, I'm one of the concepts that people really responded to the most and born for this is this notion of having a side hustle, having something that they do apart from their day job. And I've noticed that this resonates with a lot of people, even people who don't want to quit their jobs. They don't want to be entrepreneurs. A lot of people who love their job but would also love to have another source of income. And I have seen like how disproportionately happy it can make people when they have another paycheck, even if it's a small amount of money, they have more confidence and more security. They're like, I did this, you know, I have my day job, but I made this other thing. So, I mean, I've done that in different ways, but never had a whole project focused on that. So the new book is going to be about helping people with a side hustle.
Starting point is 01:49:28 I like that. You know, I feel like with the advent of, you know, startup culture and the sort of ascendancy of the entrepreneur as rock star, it's almost like if you're not an entrepreneur, there's something wrong with you. Right. There's pressure to be, you know, you have to be an entrepreneur and a self-made man. And, you know, not everybody is hardwired for that and not everybody wants to do that. But the idea that you could recapture a little autonomy in your life by, you know, monetizing a side project and creating some side income and, you know, perhaps enhancing your personal fulfillment through that, I think is really cool. Yeah. So that's what I'm working on. Good, man. Thanks. Well, I really, uh, I really appreciate you, man. It was, uh, this, that was a great conversation.
Starting point is 01:50:14 Thank you for being open and vulnerable. And, uh, your work is, uh, exceptional. All of your books have been, you know, uh, very, uh, instructive to me. And, uh, I hope that you keep doing it. Keep cranking out these books. You're raising the bar. I'm still trying to figure out what my next book is going to be. Uh, I'm feeling the pressure on that, but, uh, thank you for your time. Thank you so much. Beautiful. Big honor. Thank you. So, uh, if people want to connect with you, uh, obviously the best place I would imagine is the blog. Chris Gillibow. It's Chris Gillibow on all social media.
Starting point is 01:50:49 And no one could ever spell my name. But if you just type in something close to it in Google, you'll get to it. But your Instagram is like 193 countries. 193 countries. Yeah, exactly. And everything else is through the blog. And best place to buy the books. Wherever people buy books.
Starting point is 01:51:05 Bookstore, Amazon, whatever. else is through the blog and best place to buy the books wherever people buy books yeah bookstore amazon whatever i would suggest uh beyond the books the first place to to really dive into chris's work is through one of your several manifestos how many do you have now like four oh just three five three of them uh-huh and they're easily sure they're all free on my website right they're great so thanks a lot, man. Thank you. Peace. Peace. Peace. Yeah, dude, we did it. What'd you guys think?
Starting point is 01:51:34 I was really touched and moved by Chris's honesty, his rawness, his realness. And I hope you guys got a lot out of that as well. As always, please make a note of checking out the show notes at the episode page for this episode i got tons of links and uh resources to help you guys learn more about chris and what he's up to and what he's done in the past and all that good stuff so tap into that and take your podcast edification beyond the earbuds why don't you uh we got great plant power plant-based schwag at richroll.com. Signed copies of
Starting point is 01:52:08 Finding Ultra. Signed copies of the Plant Power Way. We got cool Plant Power t-shirts. We got tech tees for working out, for going to the gym, for running, all kinds of other cool sweet schwag and merch. I want to thank everybody who helped put on the show today. Jason Camiolo for audio engineering and production. Sean Patterson for graphics.
Starting point is 01:52:24 Chris Swan for production assistance and a. Sean Patterson for graphics. Chris Swan for production assistance and a lot of help compiling the amazing show notes and theme music by Annalema, as always. Thanks for all the support,
Starting point is 01:52:32 you guys. I love it and I will see you guys soon. Peace. Plants. Thank you.

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