From Addiction & Rock Bottom to Redemption & Purpose - Rich Roll (4K)

1. 0:00 – 5:33

   When Did Rich Roll Start Sorting His Life Out?

   1. CWChris Williamson0:00

      At what age did you start sorting your life out?

   2. RRRich Roll0:04

      (exhales) That's a good question. I think the moment where I began to really look inward and take stock and inventory of my life, legitimately for the first time, was probably when I was 31 and found myself in a treatment center in rural Oregon. Uh, faced with confronting a decade plus, uh, problem with drugs and alcohol, uh, nowhere to escape, just a bunch of counselors and a bucolic countryside, and 100 days to really start to understand why I had ended up in this place, which certainly was not the plan for my life, I can tell you, uh, and what I was gonna do about it in order to create a new life for myself that would be more in alignment with a truer version of who I was. I didn't know the answer to that question, but that's where that very long journey probably began, consciously.

   3. CWChris Williamson1:24

      It seems to me that a good chunk of your story is a series of reinventions.

   4. RRRich Roll1:32

      Yes. I think that we are all reinventing ourselves all the time. I've said this before, but I think the great delusion that we walk around with is that we are in some kind of perpetual stasis. We are the way we are, the world is the way that it is, this person behaves this way, they're always gonna behave that way. Uh, but the reality is that everything is changing all the time, from the subatomic level all the way to, eh, you know, the vastness of the universe. There is no stasis. Everything is in flux and in, and is in motion. Um, the question is how much are you directing that change versus, uh, reacting to the world around you? Um, and yes, my life has been punctuated by a couple kind of significant Rubicon changes or, or reinventions, uh, to be sure. Um, but I'm always in the process of trying to evaluate where I'm at, where I wanna be, where I wanna head to. Uh, but yeah, I've had a couple sort of, uh, moments in my life that, uh, were sort of s- uh, line in the sand moments for sure.

   5. CWChris Williamson2:44

      Yeah, you have this really famous tweet talking about all of the things you've done successfully and the fact that you didn't do them before a particular age.

   6. RRRich Roll2:52

      Mm-hmm.

   7. CWChris Williamson2:53

      I hadn't started my podcast until... I hadn't run my first endurance race until... I didn't write my first book until... And I think in a, an age where social media allows us to see successes from people very young, um, it gives a good bit of solace to people who, uh, feel like "I'm 40 now. I've missed... I'm in the, I'm on the back nine and I haven't even started swinging the golf club yet."

   8. RRRich Roll3:19

      I know what that feels like. You know, I was that guy. Certainly, you can always reinvent yourself. There's always hope, there's always opportunity. I think now more than ever, with all the tools that are available to people to craft their own career paths, to find ways to support themselves through, uh, pursuits that, that they're curious about or that light them up, I think this is a real golden age in terms of that. Uh, but that didn't exist when I was your age or when I was younger, and I grew up in a very traditional household. Education was paramount, expectations were set very high, and I learned early and often how to play that game of upward mobility. I was an awkward, insecure kid who had difficulty making friends, but at some point I locked in on the sport of swimming, and that's a whole story I'm happy to go into. And what I learned in the swimming pool transferred into the classroom and I became a better student. I had always struggled in school, but by the time I graduated from high school, I was top of my class and got very good at playing the game of getting into all the colleges and going to the right place and getting the right job without ever any self-reflection on what it was that I wanted to do or what excited me or what was unique about me or how I wanted to show up in the world or express myself. Uh, I was just trying to excel, and that path was very narrow at the time. Like, go to this school, get this job, show up early, work late, you know, sort of climb that corporate ladder. Went to law school, was on the partnership track at a law firm, did all of that and had to basically suffer an existential and health crisis e- as a reckoning in order to look inward on myself and reflect upon the, the reasons why I made those decisions, why they were leading me astray, and begin the process of opening the aperture of my vision to, to allow space for something new and different.

2. 5:33 – 17:38

   What People Get Wrong About Turning Their Life Around

   1. CWChris Williamson5:33

      What do you think people get wrong about reinvention? Like, what is it that the people who fail to turn their life around do?

   2. RRRich Roll5:51

      I think people think it's a magic trick. They snap their fingers, they make a decision, and their life is different overnight. I think there's a lack of appreciation of everything that goes into the moment where you change your mind and you do something different, and then all of the work that goes in......to that rebuilding phase and the aftermath of making that decision, that ultimately creates the new life. I think people are impatient. They want results too quickly. They don't appreciate the amount of hard work that goes into actually crafting the life of your desires. And I think, as a result of that, when they don't see results immediately, they burn out and retreat to what's safe and what they know, versus welcoming failure, welcoming uncertainty, getting comfortable with risk, and remaining persistent in their vision to create something more in alignment with their authentic self.

   3. CWChris Williamson6:51

      I think one of the big problems, especially when it comes to reinvention, is, in the Rocky movies, the montage of training is two and a half minutes long. In reality, it can be a decade.

   4. RRRich Roll7:02

      Mm-hmm.

   5. CWChris Williamson7:03

      And I think getting really visceral with what tough times feel like helps people who are going through them to not feel so personally cursed while they're going through them. You're not sure that the difficult thing that you're struggling with at the moment, the, the, uh, breaking of habits of hanging around with people who don't want the best for you, who, uh, you know, uh, getting out of a bad relationship, you maybe want to move and leave home, and your parents don't want you to, whatever it might be, you don't even have the reassurance that there's going to be glory on the other side of this. And it doesn't feel as polished or as triumphant or, uh, even as noble. It just feels, like, confusing and dark and messy and, like, destitute. And, you know, even in portrayals of alcoholism and, and of, of addiction, it's really difficult to capture in popular cinema just how, like, mundanely desperate it is. 'Cause, like, there's not even any glory in the demise, so to speak. And I think that hearing about the challenges that people go through during reinvention helps everybody to feel less incapable of doing it.

   6. RRRich Roll8:31

      Mm-hmm. That's why we love personal stories. We love hearing stories of people who, uh, met a certain fate and figured out how to rebuild their life. Um, I think there, there is something infectious about that, that does give people hope for themselves. But I think you're correct. When you look in the rearview mirror, everything looks like it lined up perfectly to create this situation where I'm sitting across from you right now. But I can tell you, as somebody who has weathered more than a few large personal changes in my life, it is a very confusing, protracted time, and it takes a lot longer than people realize. There's a lot of confusion, there's a lot of self-doubt. There's a lot of judgment from other people. If you're breaking outside of a social expectation or a familial expectation, if you're trying something new, your peers, your friends are gonna look at you a little bit differently. Perhaps they're not gonna be as supportive as you might have expected. So there's a loneliness, I think, that, that, that, um, is part of it as well, and I think with that is this testing process around your level of willingness, around your level of trust in yourself. And it's like being burned in a cauldron. Like you ha- uh, I've said, as I've said many times, like, if you're gonna be a phoenix, you have to burn first. And I don't know if there's an end run around that burning process-

   7. CWChris Williamson10:01

      Yeah.

   8. RRRich Roll10:01

      ...because that is the process that, you know, creates the new version of yourself. It's almost mandatory that one goes through their version of that. So I've been tested financially, emotionally, mentally, physically, um, and I think I'm wired for it as a result of my background, the way I was raised, my experiences in swimming. I feel f- I feel like I'm well-equipped to kind of handle that. But I've been brought to my knees more than once, and I can tell you, in those moments, all you feel is fear and this overpowering impulse to retreat back to what you know. And it is, in those moments, those are the moments of truth that no one sees, uh, where you're at your breaking point, and that's where faith comes in, honestly. You have to believe in yourself. You have to be able to hold that vision, uh, for the better life of your aspirations, and you have to also have an almost transcendent self transcend... You have to have an almost transcendent sense of some other force at play that has your best interest at heart, such that if your heart is true, and you are truly engaged in the process of trying to align your actions with your values, and you have excavated your soul and done the interior work to try to really get honest with yourself, and you're earnest in that regard, I do believe that the universe will, at some point, (laughs) conspire to support you. It's not gonna be on your timeline. It's not gonna be convenient. The results aren't gonna look like you think they're gonna look, um, but I've seen this play out in my life many times and, and in the lives of, of many people that I'm close with.

   9. CWChris Williamson11:55

      Yeah, there's a, a cool quote from Naval that says, "Karma doesn't need quantum energy or spiritual woo to be real. Karma is just you repeating your patterns, virtues, and flaws until you finally get what you deserve." And I think that, you know, it doesn't matter how secular you want to get with it, that...... if you continue to stack the deck against yourself, the only way that you end up winning is purely by fluke, and that chance of fluke begins to get increasingly minuscule. And the reverse is true as well. One of the challenges, especially when it comes to reinvention, is you're fighting an uphill battle, it's the most difficult time, and you have the least amount of evidence to have faith in yourself. You've never done this before.

   10. RRRich Roll12:38

       Mm-hmm.

   11. CWChris Williamson12:38

       You've never actually stuck to the diet for seven days. You've never actually been able to go sober or stay loyal to a partner or turn up on time to a job, pick whatever it is. Or take it all the way up to the top. You've never been able to truly have a difficult conversation with somebody, you know, at your business. You've never really been able to sit down with your business partner at this big company that you've built for 15 years and tell them that this isn't working. You've kind of, sort of nudged towards it and blah, blah, blah. Reinvention, I think, happens on really small and really large scales.

   12. RRRich Roll13:12

       Well, it happens small until it happens big. Uh, the reinvention occurs in the micro-actions that you're taking every single day. Uh, the tiny little things that, that perhaps no one even notices that are creating muscle memory around new behaviors that perhaps are very uncomfortable to you, like, "Hey, I'm gonna engage with this person in a different way that I- than I usually do by being more direct or more honest," or, "I'm gonna put down a boundary," or, "I'm gonna say no to this and yes to this." Tiny little things repeated over time is what produces dramatic change. And it's like this curve, you know, it's like this very slow curve until it asymptotes up. And everyone wants to talk about the pivot moment when it goes skyward, but the truth is, the real work is in the drudgery-

   13. CWChris Williamson13:59

       Correct.

   14. RRRich Roll14:00

       ... and the difficult anonymous work of shoveling shit every single day. Um, in sobriety, they say, "Don't leave before the miracle," and I take that as a lesson in- in persistence. Whatever it is that you're- you're pursuing to achieve or- or create or express in the world, I think a lot of people back out before that happens, and I think you're, right now, you're a perfect example of this. You're experiencing this with your show, you're having some large growth at the moment, um, and I think you even shared something about the fact that you've been doing this for a very long time, and most people may have backed out a long time ago, backed out before the miracle occurs, or the growth spurt, or whatever it is. So, for me, it always comes back to perseverance, persistence, uh, high pain tolerance, um, an ability to suffer through discomfort, a welcoming of doing hard things, and, uh, and willingness really, you know? And that's a lesson that I learned in sobriety. Sobriety isn't for people that need it. It's for people that want it. And one of the first things someone will be asked when they enter the- the kind of ecosystem of recovery is, "What are you willing to do? What are you willing to do different? How willing are you? Are you willing to make this your number one priority?" And a lot of people will put words to that, but only time will tell whether those words are followed up by the action that demonstrates the level of willingness that is required to actualize anything of meaning in this world. With respect to Naval's quote, the only pushback I would give to that is this idea that, um, that one is deserving or that one is entitled to anything. You're not entitled to anything. You don't necessarily deserve anything. All you have control over is how you direct your attention and how you comport yourself. What are the actions that you're taking? How you're responding to the world around you? And when you drill that down into the tiniest little things that you're doing every single day and try to repeat that with just rigorous, relentless, um, consistency, that is how you move mountains, that's how you build mountains, that's how you change your life. And that is not something that's gonna trend on Twitter. It's not sexy. There's nothing sexy about it. It fucking sucks, and I wish it wasn't that way. And throughout all of my reinventions and the changes, um, that I've made in my life, I didn't do them willingly. I did them because I was in so much fucking pain that I was boxed into a corner and felt like the only way out was through. In other words, when the pain of my circumstance exceeded the tremendous amount of fear that I was harboring about doing something different, doing something that would change the- the outcomes, because if you're- if you're doing something in a certain way and you're always getting the same outcome, another recovery trope, uh, that's the very defic- definition of addiction, right? Like, until you start doing things differently, you're always gonna get the same result. And yet we're so, um, calcified around who we are and what we're doing and, "This is my identity and this is who I am," that it becomes very difficult to break free of that and to live in a more fluid state where w- where you are in the process of always trying to deconstruct the beliefs that you hold, uh, and- and- and- and really get honest with yourself about the fallacy of the identity that you hold so

3. 17:38 – 28:39

   What Are ‘Lower Companions’ in Recovery?

   1. RRRich Roll17:38

      dear.

   2. CWChris Williamson17:39

      What are lower companions?

   3. RRRich Roll17:41

      Lower companions is another term, uh, from recovery. Uh, as the adage goes, uh, as you pursue your drinking or using career, uh, it starts out fun. Drugs work, right? It's a good time. Drinking is pretty reliable. It's gonna produce a certain kind of effect, right? And alcoholics and drug addicts, um, they don't become addicts because it's dysfunctional on day one. They do it because it's filling a need. It is doing something positive in their life. In my case, it made me...... feel like myself. It was like wrapping myself in a warm blanket, where all my insecurities and my fears would vanish, and I was able to be a social person in social settings, which was something that was very difficult for me my whole life. And it functioned that way for quite some time, until it didn't, and then your life slowly starts to degrade. You start making decisions that you rationalize that aren't in your best interest. It becomes a little lonelier. The chaos factor starts to increase. The, uh, negative repercussions of your behavior start to stack and escalate. Uh, it starts to get uncomfortable. Your higher companions, your good friends, the people that love you who have your best interest at heart start to flee from the hills, and you begin to search out other people who are vibrating at your wavelength who are not gonna give you a hard time for your behavior and are more than happy to do the thing that you want to do, which is just get loaded or get high. So, you find yourself in really compromising, strange, sometimes scary situations with people you would not ordinarily hang out with because you share this one thing, which is you just wanna lose yourself in this substance, or perhaps with people who are addicted to, um, a certain behavior. It could be gambling, it could be... You know, it's like anything. You're gonna find people who are gonna cosign whatever behavior it is, uh, and then as the addiction escalates even more, you start to run through those people, even... They don't wanna hang out-

   4. CWChris Williamson20:02

      Companions get lower and lower and lower.

   5. RRRich Roll20:02

      Yeah, they... Yeah, and you get lower and lower and lower and lower, until there's maybe that one guy. And if not, you're just home alone in a dark room with the shades pulled down, um, and that's how it ended for me, for sure.

   6. CWChris Williamson20:16

      We'll get back to talking to Rich in one minute, but first, I need to tell you about LMNT. LMNT is a tasty electrolyte drink mix with everything that you need and nothing that you don't. It's a healthy alternative to sugary electrolyte drinks. It's got a science-backed electrolyte ratio of sodium, potassium, and magnesium. You might ask, "What do I want with an electrolyte drink?" Well, it'll regulate your appetite, it'll curb cravings, it'll help improve your brain function. Best of all, it tastes phenomenal. First thing in the morning, this orange LMNT salt in water is outstanding. Your adenosine system that caffeine acts on isn't even active for the first 90 minutes of the day, so it's pointless having a morning coffee. Your adrenal system, which is what salt acts on, is active, so this will make you feel more alert, more awake, and improve your hydration. Best of all, they've got a no BS, no questions asked refund policy, so you can buy it, and if you do not like it for any reason, they will give you your money back. That's how confident they are that you'll love it. Head to drinklmnt.com/modernwisdom to get a free sample pack of all eight flavors with your first box. That's drinklmnt.com/modernwisdom. The idea of lower companions, although not, uh, super romantic, I think is really useful, and the first time I'd ever heard of it was from you. And I think that even for the people that don't have a substance addiction, dependency, the idea of, of people who don't have your best interests at heart, who don't make you show up as your better self, the self that you wish that you were more of the time, I think there's something to take from that. And, you know, I met... Across my nightclub promoting career, I met about a million people face-to-face, stood in the front door of nightclubs, right?

   7. RRRich Roll21:55

      I'm sure you met a lot of alcoholics and drug addicts.

   8. CWChris Williamson21:57

      Correct, yeah.

   9. RRRich Roll21:58

      Yeah.

   10. CWChris Williamson21:58

       And a lot of people that... And, and in that position, 10:00 PM to 1:00 AM outside of a nightclub, it's all the romance and none of the destitution, right?

   11. RRRich Roll22:09

       Mm-hmm.

   12. CWChris Williamson22:09

       Because it's full of energy, they've got their girls on their arm or their, their, their girlfriends are with them, and you see them go in upright and you see them come out horizontal, um-

   13. RRRich Roll22:21

       Who's the guy who comes out last?

   14. CWChris Williamson22:23

       (laughs) Yeah.

   15. RRRich Roll22:24

       I was that guy.

   16. CWChris Williamson22:25

       Yeah. Well, yeah, the idea of lower companions, I just think there's a lot of people that listen to the show, and this is one of the things... Like, if you wanna make me cry by sending me a message, this isn't a request, but the messages that I get that make me weep or tear up the most are ones where people say something like, "Hey, man, like, I'm a, a ice hockey player from rural Canada, and I'm 23 and none of my friends understand me. And when I listen to your show, I feel less alone. Um, I can't talk to any of my friends about, like, what I'm interested in. All that they want to do is keep doing the same thing every weekend." The idea of self-actualization is getting a bag in with the boys on the weekend, right?

   17. RRRich Roll23:10

       Mm-hmm. Yeah.

   18. CWChris Williamson23:11

       And that is, you know, it... It's a even more, in some ways, maybe an even more pernicious type of lower companion, because there's not, there's not even the red flag flying above their head.

   19. RRRich Roll23:31

       Mm-hmm.

   20. CWChris Williamson23:31

       Do you know what I mean?

   21. RRRich Roll23:32

       Yeah, it's not necessarily a bad influence. It's just, uh, at best, neutral, or perhaps somebody who's, um, insidiously but very gradually undermining the quality of that companion's-

   22. CWChris Williamson23:47

       Drip, drip, drip of water.

   23. RRRich Roll23:48

       ... life. Like you, I also get a lot of those types of messages, and it's very meaningful to me. And I think what you're speaking about is super important. Of course there's that adage, "You're the average of the five people you're hanging-"

   24. CWChris Williamson24:01

       Podcasts you listen-

   25. RRRich Roll24:01

       Yeah. (laughs)

   26. CWChris Williamson24:01

       Oh, oh, sorry.

   27. RRRich Roll24:02

       Five-

   28. CWChris Williamson24:02

       The average of the five podcasts you listen to.

   29. RRRich Roll24:03

       Yeah, probably, right? But I think it, it is worthy of examination, this topic, because most people just...... end up in the environment that they're in, and they never try to be in the, in the pilot chair of how they're directing their community. There's a lot of talk about mentors, "I want this person to be my mentor. I want Tony Robbins to be my mentor, or Gary Vee," or, you know, choose your, choose your person. Uh, but the truth is, each and every one of us in our community is surrounded by people that are wiser than us in various ways, people that can help us. And the nature of that community can be crafted and cultivated by you with a little mindful intention. People are good, they wanna help people. I know that I feel good when I'm helping somebody. That is th- my primary purpose as a sober, um, person, is to help other alcoholics to achieve sobriety, and that is the source of, um, my greatest sense of self when I'm in that process. Uh, so I think to the extent that you can engage with the people around you from a place of greater mindfulness and, and exercise some discretion about the people-

   30. CWChris Williamson25:31

       Mm-hmm.
4. 28:39 – 33:54

   The Importance of Having Friends Who Inspire You

   1. CWChris Williamson28:39

      a little while ago saying, "I'm in the very fortunate position where most of my friends are also my role models." And that's not that my role models are my friends, right? It's the other way around. It's that the people that I ha- I'm friends with in the UK, in America, people that are beyond mundanely normal, do things that on a dinnery basis, I look at and I go, "W- that's extraordinary."

   2. RRRich Roll29:12

      Mm-hmm.

   3. CWChris Williamson29:13

      Like, the way that they dealt with a difficult conversation that they had to have, the way that they made a, a, an awkward decision with regards to their business where somebody wasn't fitting and they said it in the, the, the right way early with courage and bravery. Uh, you know, right up to... My housemate had his, uh, uh, a clip from his YouTube channel shared on Rogan a couple of days ago. So, like, he's fired up for that.

   4. RRRich Roll29:35

      Mm-hmm.

   5. CWChris Williamson29:35

      And I'm like, you know, each of these different people, like, extraordinary in some ways and unbelievably normal in many, many more ways. Um, and I understand, you know, if this is... if you're listening to this and it's triggering a little bit of something inside of you going, "Well, must be nice," you know, living in Austin, Texas or Calabasas or whatever and you're surrounded by all these people and, you know, you've got interesting blue ticks knocking on your door asking to be friends. Like, I, I, I do get that, but the bottom line is that you will devolve to the lowest common denominator amongst the friend group that you're in. And if you have the luxury of being able to sit and listen to pontificating podcasts (laughs) for like two hours, you are probably built to take charge of that situation. And I would bet you that there are...... a really non-insignificant number of people that live within three miles of you, who all would love to do the same thing. And yeah, I, I, uh, met about a million people across my nightlife career and had a handful of friends. Um, that's because a lot of the guys that worked with us came and went. They moved on to different careers. Club promo isn't a, typically a long-term career. Um, and I realized that my funnel exposure to conversion friend ratio was off.

   6. RRRich Roll30:58

      Your funnel to conversion friend ratio.

   7. CWChris Williamson31:01

      So think about how wide-

   8. RRRich Roll31:02

      That's such a, that's such like a bro science term. (laughs)

   9. CWChris Williamson31:05

      My... Right. This, welcome-

   10. RRRich Roll31:07

       I'm trying to-

   11. CWChris Williamson31:07

       Welcome to my podcast.

   12. RRRich Roll31:08

       I think I understand what you're saying. Yeah. Okay. (laughs)

   13. CWChris Williamson31:08

       Welcome to my podcast, Rich. Um, the size of people that I was reaching-

   14. RRRich Roll31:12

       Mm-hmm.

   15. CWChris Williamson31:13

       ... compared with the number of friends that I had-

   16. RRRich Roll31:14

       I understood. I understand.

   17. CWChris Williamson31:15

       ... was so-

   18. RRRich Roll31:17

       Yeah.

   19. CWChris Williamson31:17

       ... I couldn't believe it, right?

   20. RRRich Roll31:18

       Mm-hmm.

   21. CWChris Williamson31:18

       And I was like, "Okay, something's up." Like, this is the, I, something is up. And what... It was largely my fault. And the reason that it was my fault was that I was behaving in a way that I thought would make other people like me. And what that meant was the people who did like me, I didn't actually truly like, in large part. And the people who I would have liked saw this person that wasn't any-

   22. RRRich Roll31:52

       You, you, yeah, you become, you're unlikeable to those people.

   23. CWChris Williamson31:55

       Yes. I'm unlikeable to the people-

   24. RRRich Roll31:56

       Yeah.

   25. CWChris Williamson31:56

       ... that I would like-

   26. RRRich Roll31:57

       Right.

   27. CWChris Williamson31:57

       ... for precisely the reason that I'm playing this persona and role.

   28. RRRich Roll32:00

       Right. Um, water rises to its own level, and you can't transmit something you haven't got, another recovery adage, which basically means-

   29. CWChris Williamson32:10

       What's that? What's that mean?

   30. RRRich Roll32:10

       It basically means, if you're trying to befriend somebody because they have something that you want, um, and you try to pretend that you're at their level, to say whatever it is you think they wanna hear from you, so that they feel comfortable befriending you, it's very, uh, transparent that that is a false and shallow gesture, right? Like, you can't... If you're sitting behind a microphone and you're pontificating about a whole bunch of bullshit, but it's not a result of earned experience in your own life, then it's not gonna have the resonant effect that you think it would have, because you didn't earn it, right? So, in recovery, it means walking your talk, basically. And when you walk your talk, and that talk and that walk is integrated with a value system that is slowly improving your life, then the water in your glass raises, and the level of your companions will raise in lockstep with that. So, I think it's important that if you want to attract a certain caliber of person into your life, then you have to live your life in accordance with the kinds of values that would be attractive to that person. And as somebody who's spoken a lot about dating, like this is the same thing with relationships, right? You're not gonna attract that mate who is living a more aspirational life than you, until you can level up your own life.
5. 33:54 – 46:55

   Aligning Your Life For Authenticity

   1. CWChris Williamson33:54

      from Alex Hormozi that says, "People are attracted to authenticity, but it's hard to define for me. Here's my best attempt. True alignment of what you think, what you say, and what you do. The hardest part is realizing that our thoughts are fucked and that we have to fix them instead of faking the next two."

   2. RRRich Roll34:13

      Mm-hmm.

   3. CWChris Williamson34:14

      What we think, what you say, and what you do. And a lot of the time, you do and say things that you don't think, in an attempt to try and be liked. I know that you had a background in school of bullying, and this is something that I still need to dig into more, but that was like, that was childhood for me-

   4. RRRich Roll34:32

      Yeah.

   5. CWChris Williamson34:32

      ... largely, that was school.

   6. RRRich Roll34:34

      Mm-hmm.

   7. CWChris Williamson34:34

      And, um, like loneliness, like again, there wasn't even any fucking glory or triumph in the, in the loneliness or in the, in the, like, solitary nature. It was very mundane, very vanilla ... sadness.

   8. RRRich Roll34:57

      Yeah.

   9. CWChris Williamson34:58

      Right? And I think what the undertone that that taught me was, fundamentally, the world won't love you unless you can offer it something. Because before, you didn't have anything to offer it and it didn't love you. So now, you need to offer it something, which is why if I look back on the career that I went through in my 20s, every single thing that I did had a shit ton of social, uh, monetary value on the other side of it. So, I became a model before I came to uni. Then I kept working as a commercial model and then moved into editorial. Then I became a club promoter, because people like models, people really like club promoters. You wanna get in VIP? You wanna skip the queue?

   10. RRRich Roll35:37

       Mm-hmm.

   11. CWChris Williamson35:38

       You wanna know where the prettiest girls are? You want a free bottle of champagne? You gotta come through me. Okay. Then I became a DJ. DJ literally makes the crowd have this collective effervescence all together. Then I go on two reality TV shows, right? Two reality TV shows, Blue Tick on Twitter, free charcoal toothpaste, full works. Because maybe if I can accrue sufficient social capital, the world will actually feel, uh, uh, believe that I'm worth something.

   12. RRRich Roll36:06

       And where, and at what point did you have a reckoning with that? Like, where did the bottom fall out on that for you?

   13. CWChris Williamson36:14

       So, I got to this second reality TV show. And what I'd been doing for a long time was playing a persona. Like, my business partner knew who I was truly, and the guys that worked with me knew who I was truly, but largely the public-facing Chris wasn't honest.... about his curiosity, about the person he was. But I was always able to sedate myself with distraction, with-

   14. RRRich Roll36:37

       Mm-hmm.

   15. CWChris Williamson36:39

       ... YouTube and social media and partying and girls and stuff, right? And then I go in this r- TV show, and they take everything away from you. There's no books. There's no f- calls home. There's no internet, no phone, no TV, no nothing. And all that you have to do, for a month, is talk to people who are the hyper-extroverted party people that I thought I was. So, I got delivered what I call a fatal dose of contrast.

   16. RRRich Roll37:08

       Mm-hmm.

   17. CWChris Williamson37:08

       I saw, staring me in the face, inescapable, a team of 13 other people who were the person that I'd been pretending to be for a decade. And I realized that I wasn't that, and I thought, "Okay, I- I literally can't escape this." And it wasn't that, "And the skies opened, and then I realized that my true path was to become a podcaster and talk shit into a microphone."

   18. RRRich Roll37:31

       Yeah.

   19. CWChris Williamson37:31

       Wasn't like that. But it did make me think, "Right, there's something up here." Like, there is an incongruence between the person you say you are and who th- that sort of person actually is. And that really was the beginning of it rolling downhill. But again, even with that, you said it before, like, life needs to be lived forward but only makes sense in reverse.

   20. RRRich Roll37:56

       Mm-hmm.

   21. CWChris Williamson37:59

       And when you're staring into a bunch of unknown, it's, there's no romance. There is no glory medley fucking, like, reel that you've got some cool, like, Jamie Foxx motivational quote over the top of it telling you about where you're gonna go.

   22. RRRich Roll38:16

       No, and you can't put it on a calendar, you know, the end point of this, because you don't even know which direction you're heading. You're flailing before you find any kind of trajectory (laughs) for yourself. And I think it requires, you know, a deep level of commitment to self, and again, faith, to walk a path where you don't know what the- the next brick is gonna look like that's getting laid down in front of you. And I think a lot of people wanna know what the destination is before they take that first step, and that's why they never get out of the gate. Uh, but I think, um, you know, your story makes perfect sense. It- mine is certainly analogous. Um, I was bullied, but it was very vanilla. There's nothing, like, super interesting about that other than it was pretty much a- as you would expect it. But I think as a result of that, my interior experience was to feel like being myself was not safe or okay. I was already insecure. And so, as a survival mechanism, you have to figure out a costume or a mask to wear to avoid the pitfalls of being bullied and just survive and navigate the day. That's certainly what I did. And like you, it showed up in people pleasing. I'm a chronic people pleaser. Only in recent years have I really worked hard to try to deconstruct that. Um, and it's something that- that is also pernicious because, um, the lie you tell yourself is, like, "I'm a nice guy." Like, "I just want everyone to be happy," and so you go out of your way to make everyone else happy. But as a result of that, none of your own needs are getting met- met. You're developing resentment. You're disconnected from who you are.

   23. CWChris Williamson40:03

       It's also, y- y-

   24. RRRich Roll40:04

       I think-

   25. CWChris Williamson40:04

       ... you're not bothered about making them happy. You're just desperate for them to like you.

   26. RRRich Roll40:08

       Yes, that's the fuel underneath the whole thing. And it's an empty fuel because then you get it, it never sates the appetite though.

   27. CWChris Williamson40:15

       There's a quote from Aubrey Marcus where he says, "The persona is incapable of receiving love. It can only receive praise." And what he means by that is if you're playing a role, any of the accolades that you get and any of the care that people give toward you isn't going to hit you existentially. It's like people don't love Russell Crowe. They love Gladiator. People don't love Chris Hemsworth. They love Thor. And this is how you can feel alone in a crowd and hollow in victory. Because if you do a thing without genuinely putting yourself into it, whenever people praise it... And I can promise you, I have tried. I have been there. I have achieved the things that haven't been existentially connected to me.

   28. RRRich Roll40:56

       Mm-hmm.

   29. CWChris Williamson40:58

       And I didn't feel satisfied, right? I'd- I'd achieved, in my 20s, pretty much all of the things that society tells a young man that he should take pride and pleasure and- and fulfillment from, right? Like renown and girls and- and money, all this stuff. Not at a... I'm a fucking dan Bilzerian, but like just a- just a- an acceptable normal person amount of that that would put you close to the top of the tree. Didn't fulfill me. It didn't fulfill me. And d- I could have done it for eons, and it still wouldn't have fulfilled me. I love and I'm proud of all of the things I did in terms of the business. But that's not, that- that's not what society told me. It wasn't about... I was never told, "You are going to adore working until 3:00 in the morning with your business partner trying to get this copywriting exactly right so that you can do a thing that's- that's cool in your business." What they said was, "You should leave at 1:00 AM and go to the cool after-party 'cause that's where people are gonna see you," and that's... And it- that wasn't the case. And I, it was really, really tough. I'm glad, you know, thinking about the time when you were that age and my age now, had it not have been for influences that- that I did get access to on YouTube and podcasts and stuff like that, I don't know where I would've been given a different frame. I don't know how I would have been ripped out of it.

   30. RRRich Roll42:18

       So, that hole that you were trying to fill, what does that look like now?
6. 46:55 – 58:53

   The Tension Between Striving for Success & Feeling Sufficient

   1. CWChris Williamson46:55

      adaptation, like imposter adaptation. I'm gonna read you this. "One of the most common tensions I talk about at the moment is between a desire for success and a desire to feel like we're enough. Success is a strange thing. Presumably we want success because we think a more successful life will bring us more happiness, meaning, and fulfillment. Here's the problem. We sacrifice the thing we want, happiness, for the thing which is supposed to get it, success. Failure can make you miserable, but I'm not sure success will make you happy. One of the most common dynamics I see amongst high performers is this. Parents want their child to do well. Parents encourage their child to do well by praising when they succeed and criticizing when they fail. The child learns that praise and admiration is contingent on succeeding. That lesson metastasizes through early adulthood into, 'I am only worthy of love, acceptance, and belonging if I succeed.' Now powered by an internal feeling of sufficiency, this person is driven to achieve many things. They're prepared to outwork, outhustle, and outsuffer everybody else because they're not just running toward a life they want, they're running away from a life that they fear. Success and progress ameliorates the feelings of insufficiency. Therefore, success and progress become prioritized above everything else."

   2. RRRich Roll48:06

      That sums it up. Uh, I'm certainly, uh, somebody who would fall into that category. Um, I've pursued success in a variety of areas as an athlete, then as a lawyer, that was a disaster-

   3. CWChris Williamson48:27

      (laughs)

   4. RRRich Roll48:27

      ... um, then again as an athlete, now as a podcaster.

   5. CWChris Williamson48:30

      (laughs)

   6. RRRich Roll48:30

      It's, it's funny, you know, I, I, I went through like a seven-year financial dismantlement. Like, we almost had our house repossessed, I had our cars repossessed, I couldn't pay for the garbage bins. Like, it was bad. And I think with that was a tremendous amount of emascul- emasculation, um-

   7. CWChris Williamson48:48

      Protector. Provider.

   8. RRRich Roll48:49

      Yeah. And a huge, um, resurgence of all the insecurities and fears that I harbored as a- as a- as a child, and I became utterly convinced that I was incapable of success, at least financial success.

   9. CWChris Williamson49:03

      Hmm.

   10. RRRich Roll49:03

       I just- I just didn't believe that it was possible for me. When I was a drunk, I could never pay my bills, I ruined my credit. Then I get sober and I can't figure out this career thing, and I was as broke as ever, and then I'm trying to-

   11. CWChris Williamson49:17

       Not even drunk this time.

   12. RRRich Roll49:18

       ... I'm trying to- I'm not even drinking and I can't figure it out. And then I'm like, "Oh, I'm gonna go be an ultra-athlete when I have little kids and a mortgage." There's no career path in that. And I just thought, "Maybe I'm insane."

   13. CWChris Williamson49:30

       (laughs)

   14. RRRich Roll49:30

       Like, I- I honestly thought... Like, I found- I would find myself, you know, at times on a weekday afternoon at the park with my small children, pushing them on the swings, and having this dual- this tension between these two ideas. On the one hand, recognizing that by leaving the comforts of the partnership track on a- at a big law firm, I had the privilege of being able to spend time with my young children in the middle of a weekday afternoon at this park, where there's a bunch of moms and I'm the only guy, while also believing at the same time that I was an utter failure-

   15. CWChris Williamson50:17

       Yeah.

   16. RRRich Roll50:17

       ... because I didn't know what I was doing with my life. I didn't have a sense of what I should do or shouldn't do, and really starting to believe that nothing was ever gonna happen for me.

   17. CWChris Williamson50:27

       So, this is one of the problems that I have with the modern move of asceticism, right? Of- of recanting, uh, worldly success, because I believe that inbuilt in almost all humans is a requirement for the world to validate them genuinely through actual achievement. And this is another Naval quote where he says, "It is far easier to achieve our material desires than to renounce them." And the difference is, had you have had the material success now, then how much more present would you have been with your children, pushing them on the swing?

   18. RRRich Roll51:14

       Well, had I had material success earlier, I wouldn't have grown and evolved mentally, emotionally, spiritually, and physically in the way-

   19. CWChris Williamson51:24

       'Cause of the phoenix and the flame stuff.

   20. RRRich Roll51:26

       ... that I have. Yeah. I had to endure that process to be worthy of the growth curve that I've been on. And frankly, you know, the- the success that I have now is- is embarrassing because I never would have thought it possible. Uh, so my relationship with success now is- is very different than it would have been had I- had I achieved it earlier or- or easier, I guess.

   21. CWChris Williamson51:51

       In other news, this episode is brought to you by Levels. One of the single biggest predictors of how long you're going to live and how good you will feel whilst living is your metabolic health. The single best way to understand how your daily decisions are impacting your longevity and your vitality is by tracking your glucose. This is why I wear a continuous glucose monitor from Levels. It allows me to understand in real time whether the foods that I'm eating are having a positive or a negative impact on my health. The Levels app interprets your glucose data and provides a simple score after you eat a meal so that you can see how different foods impact your health, and develop a diet which is custom and personalized perfect for your body. The main realization that I had was eating cereal at any time of the day spikes my glucose through the roof, but if I took a walk for about 15 minutes, I could bring that back down. I would have never realized this if I hadn't been wearing a continuous glucose monitor. Right now, Levels has a special offer for my listeners by going to the link in the description below or heading to levels.link/modernwisdom. That's levels.link/modernwisdom. I've heard you say, "I still find myself with this sense that success has to be earned, and the only way to earn it is to inflict pain on yourself. And if you're not in pain, you didn't try hard enough, and it would have been better if you'd suffered more. And I think that's a lie, and I want to find out if it's a lie or if it's true." That resonated with me so much. Tell me what you meant by that.

   22. RRRich Roll53:24

       I don't think that I'm particularly gifted in any kind of traditional way. I don't think I'm that much smarter than anyone else. I don't think that I'm, uh, a super talented athlete. Uh, but if I do- if I had to identify a talent, it would be a capacity to suffer, a willingness to do hard shit, uh, and a very high pain tolerance. And I learned this as a young swimmer entering into, uh, the kind of club ecosystem of- of swimming in the Northeast where I lived, and realizing quickly as a 13-year-old that I was not the most talented swimmer, that there were a lot of young gifted swimmers who were much better than me. But I also realized very quickly that there was an equation between work and results, and that equation was pure arithmetic for me. And the more I worked, the narrower that gap, that talent deficit gap, became, to the point where as a senior in high school, I was one of the best swimmers in the United States, getting recruited everywhere, and was able to match all of those peers that previously I thought were much more talented than me. So, the message that got inculcated in my mind was, talent doesn't matter-... "You have the ability to outwork everyone in the room. That is your gift, and your job is to double down on that in all areas of your life, and this is what is going to create a trajectory for you." And the truth is, it worked. It worked in the pool, it worked in the classroom, and I was able to achieve some pretty amazing things as a young person.

   23. CWChris Williamson55:19

       Outsized results beyond your talent level.

   24. RRRich Roll55:21

       Yeah, I was world-ranked in the 200-meter butterfly. I went on to Stanfor- I said no to Harvard University, and went to Stanford, where I was a member of, uh, a two-time NCAA championship squad, where every single day I trained with world-record holders, American record holders, NCAA champions, and Olympic gold medalists. These were my athletic heroes. And by sheer force of will, I told myself I was able to manifest a situation in which now I was a member of a team in which I got to spend five hours a day, every single day, with the greatest swimmers in the sport. What does that do to a young mind? It tells it, "You're capable of anything, but the only way th- you're gonna get there is by suffering. Suffering is your success equation." And I would do things in the pool in high school that my coaches, to this day, still talk about. They're like, "Remember when you did this set in 1984? Like, 40 times 200 fly on..." You know, like, I would do insane sets that no one else would do, because I knew no one else would do them, and I picked the hardest th- the event that creates the most suffering because that was the easiest to distinguish myself in.

   25. CWChris Williamson56:37

       (laughs)

   26. RRRich Roll56:38

       And that was a success equation. And so I've carried that my entire life. And to this day, as somebody who doesn't believe they're particularly talented, it's all the more important that I outwork everyone in the room. And I believe that in many ways, I've done that, and I kinda continue to do it. I've done it with the podcast, I've done it with books that I've written. If I don't suffer, if I'm not completely depleted at the end of a project, and I turn it in, whether it's a book or whatever creative thing that I'm working on, then it's not good enough. You have to bleed in order for it to be the highest expression of what you're capable of. And the truth is, through a lot of therapy (laughs) and a lot of work, I have realized that that is in fact a lie. Now, untangling that knot and trying to create new neural pathways is extremely uncomfortable. What does it feel like if you sit down and you write something and you do it from a place of, of ease and presence and awareness, and you turn it in, and it didn't cause you to suffer, and you didn't experience pain? I'm instantly going to feel like, "Well, that's shit. I didn't work hard enough for it. I didn't earn it. Give me that back, and let me rewrite it-"

   27. CWChris Williamson57:53

       In blood.

   28. RRRich Roll57:53

       "... until 4:00 in the morning." You know? And I've done this many, many times, and then I'll look at it with clear eyes the next day and, and realize, "You made it worse."

   29. CWChris Williamson58:01

       First draft was better.

   30. RRRich Roll58:02

       Yeah. "You made it worse." It's a hard pill to swallow. It's been a very difficult lesson for me to learn. It's certainly not something that I've mastered. But I have created systems in my life that make that process of ease, um, more accessible and, and conducive in my daily schedule, to try to disabuse me of these old patterns that, that are reliable, but ultimately, uh, are short-term strategies because they lead to exhaustion and burnout and disaffectation and all of these things that are at cross-purposes with the goal of having any kind of longevity or continual growth in what- whatever it is that you're trying to do.

7. 58:53 – 1:09:25

   Rich’s Systems for Success

   1. RRRich Roll58:53

   2. CWChris Williamson58:53

      What are the systems?

   3. RRRich Roll58:55

      I surround myself with a team of very talented people. So for a long time, I did my podcast, which I've been doing 11 years, almost 11 years at this point. For many years, I did almost every single aspect of it myself. My stepson Tyler would edit it, but other than that, I handled everything about it. And I was very resistant to letting go of any aspect of it and letting (laughs) in- you're laughing-

   4. CWChris Williamson59:20

      I can see-

   5. RRRich Roll59:20

      ... letting anybody come in to help me.

   6. CWChris Williamson59:21

      ... I can see some of my team-

   7. RRRich Roll59:23

      Now-

   8. CWChris Williamson59:23

      ... over your shoulder-

   9. RRRich Roll59:23

      Well, you have an amazing team here, right?

   10. CWChris Williamson59:25

       ... nodding at me. (laughs)

   11. RRRich Roll59:26

       Uh...

   12. CWChris Williamson59:26

       Yeah, but they know that they have to rip-

   13. RRRich Roll59:28

       I would rather-

   14. CWChris Williamson59:28

       ... rip tasks out of my hand-

   15. RRRich Roll59:30

       I would rather-

   16. CWChris Williamson59:30

       ... fuckin' nail by nail.

   17. RRRich Roll59:33

       I would rather forgo, uh, nights of sleep-

   18. CWChris Williamson59:37

       Correct.

   19. RRRich Roll59:38

       ... than let any, invite anyone else in, because you know what? I'm the only one who knows how to do it, I'm the only one who can get it the way that I want it to be, I'm the only one who's qualified to make it as good as I know it can be, and I'm the only one who's gonna care enough to go that extra mile to make it great, right? And the reason why you're (laughs) y- y- I know you're connecting with me-

   20. CWChris Williamson59:59

       I'm still grinning. I'm-

   21. RRRich Roll1:00:00

       But the reason why-

   22. CWChris Williamson1:00:02

       (laughs)

   23. RRRich Roll1:00:02

       ... that is so romantic and powerful is that there is some truth in it, because no one is gonna care about modern wisdom as much as you. It doesn't matter how much you pay people or how m- how talented the people are that, that are around you. So you're faced with a choice. Either you loosen the reins, you let people in, you find people who are better at their respective skillsets than you are, you train them, you empower them, and you get out of the way, and then you are freed up to do the work that only you can do, which is to prepare for and conduct the conversations to the best of your ability. Everything else can be handled by someone else. In my case, I did the show for years before... I, I was kicking and dragging in order to let go. But as a result of going through that process, I now am able to focus on those things that are most important. And as to the freedom point, um...... the systems that I have in place create the added time for the head space required to contribute to the creative work that only I can do. And I create rules for myself, like, "You have to stop after two hours." Or, "You're not allowed to, you know, edit while you're writing." Or, you know, "You have to put this away and not look at it for a week." Like, I have to create stopgaps.

   24. CWChris Williamson1:01:38

       Like a crazy person.

   25. RRRich Roll1:01:39

       Yeah. Exactly.

   26. CWChris Williamson1:01:40

       (laughs)

   27. RRRich Roll1:01:40

       Because I am a fucking crazy person.

   28. CWChris Williamson1:01:41

       A crazy person, yeah.

   29. RRRich Roll1:01:42

       Chris, I don't know if you know, but I have spent quite a bit of time in a mental institution, so...

   30. CWChris Williamson1:01:47

       (laughs) Okay. So-
8. 1:09:25 – 1:16:31

   Rich’s Thoughts on Will Goodge

   1. CWChris Williamson1:09:25

      to endurance racing. Mutual friend of ours, Will Googe, recently ran across America.

   2. RRRich Roll1:09:32

      Yeah.

   3. CWChris Williamson1:09:33

      What do you make of Will Googe?

   4. RRRich Roll1:09:34

      I love Will Googe. I think he's great. I think he is an interesting and compelling breath of fresh air into the ultra running community. Um, just by way of background, I have some experience in ultra endurance events. I've done a bunch of hard races over the years. Um, so I have, uh, a connection to that community. I know a lot of people in that community. I have a lot of friends in that community. Um, Will's BFF in, in ultra running is our mutual friend, Robbie Balenger, who ran across the United States, has done a lot of hard things, set the record, the f- the, uh, FKT for the Cent- how many laps of the Cent- how many miles you can run around the loop in Central Park in one day. Like, he's done a lot of-

   5. CWChris Williamson1:10:21

      Hmm.

   6. RRRich Roll1:10:22

      ... crazy, wild stuff. And those guys couldn't be more different, uh, and yet are the closest of friends. Train together, race together. They crew each other's endeavors, and it's a really beautiful friendship that I, I've been pr- sort of privy to, to witnessing and observing. Um, I know Robbie a lot longer than I know Will, uh, but I followed Will... It was Robbie who introduced me to Will, originally. Uh, so I started following Will online. And, uh, I just found him to be so unique as, uh, a figure in this strange little subculture of ultra running, because that is a culture that historically has been populated with, you know, guys that, uh, you know, live in the van down by the river, know how to grow a nice beard. Um, it's a granola crowd. It's a very gr-

   7. CWChris Williamson1:11:17

      (laughs)

   8. RRRich Roll1:11:17

      It's a very, it's a very... In a beautiful way, it's a grassroots community, uh, that has, um, that has, uh, you know, participated in and helped grow a sport where typically there's no media coverage, there's no prize money. Nobody's doing this for glory or media attention. You pitch a tent at the starting line the night before. You wake up, you do your 100 miles, and you go home, and, and nobody else in the world knows what you did except for you. And there's something really pure and, and amazing about that. And, and, and, uh, and that's sort of woven into the fabric of what this sport is about. Here comes Will Googe, male model, six-pack abs, looks a lot more like a rugby player than an ultra runner. He's got, you know, the shaved torso, and the, uh, skincare routine that he's happy to share with you. He's walking the catwalks. He loves a nice bathrobe and a five-star hotel and tea service. Uh, he enjoys the finer things in life.

   9. CWChris Williamson1:12:19

      Good British gentleman.

   10. RRRich Roll1:12:20

       At the same... Yes. At the same time, he's an absolute beast when it comes to ultra running. Uh, fueled by a desire to make peace with the early passing of his mother, who, who died of cancer, and to raise money and awareness around cancer research, he begins participating in these ultra runs. Uh, mostly, I think... He started doing some marathons, and he did the, the John O'Groots run. He did a couple hard things, but then created some self-styled adventures for himself. Ran around Lake Como, and this past summer, ran across the United States. No small feat. 3,000 miles. Robbie was there every single day supporting him. Uh, Reece Robinson, uh, was the guy who created the weekly vlog on the Audacious report, which is a YouTube channel that they have. Reece used to work for me. He lived at my house. He created videos for me. So I know these guys really well, and it was super fun to watch Will-... throw down, day after day, 52 miles, 54 miles, 56 miles, and do it with a smile and a certain flair and a passion for fashion. This guy looks good. And as hard as that was, there's something inside me that was thinking, "He may... He's kinda making it look easy." And this, in turn, ruffled some feathers out in the ultra running community-

   11. CWChris Williamson1:13:52

       I fucking love this.

   12. RRRich Roll1:13:52

       ... uh, that, that-

   13. CWChris Williamson1:13:53

       I, I want to know about these feathers.

   14. RRRich Roll1:13:55

       Yeah, well, that, y- you know, there's a certain idea of, of, of what an ultra runner looks like, how they're supposed to be, and Will is in- Will is very different from that, and I think people don't like different. And so there was a, a sort of, "Who is this guy and what is he doing?" Um, and then on message boards, people started, uh, taking shots at him, and there was a little, uh, movement about whether or not he was actually doing this legitimately.

   15. CWChris Williamson1:14:25

       Okay, so skepticism around the actual achievement.

   16. RRRich Roll1:14:26

       A lot of skepticism, yeah.

   17. CWChris Williamson1:14:28

       Yeah.

   18. RRRich Roll1:14:28

       So much so that one guy flew from the United Kingdom and showed up. They were, I don't know where they were, in the middle of the Navajo Nation or something like that, convinced that Will was cheating and that he was there to root him out. It's a story that Will shares on my podcast. I don't know when this is going up, and I'm not sure when my conversation with Will is going up, but, um... And Will had to kind of weather that on top of the difficulty of just actually competing this very difficult task. Uh, and so... Which he did, and he did it again with flair.

   19. CWChris Williamson1:15:03

       Do you have a-

   20. RRRich Roll1:15:04

       Uh-

   21. CWChris Williamson1:15:04

       I think it's a British record perhaps. It's not a world record, but I think it might be.

   22. RRRich Roll1:15:06

       I don't even, I don't remember offhand. I could have looked that up.

   23. CWChris Williamson1:15:09

       Yep.

   24. RRRich Roll1:15:10

       Um, I think that was part of what ruffled feathers, that he was gonna be the fastest British guy, but there was this other guy. It, it's like, who cares? Like, Will doesn't even care.

   25. CWChris Williamson1:15:18

       Yep.

   26. RRRich Roll1:15:19

       You know, he just wanted to go do this hard thing and raise money and, um, experience it with his friends. And you can watch the weekly vlog on The Audacious Report and see how it all went down. But I respect Will for his conviction and his sense of self to just be who he is, unapologetically.

   27. CWChris Williamson1:15:41

       Do you know who he reminds me of? Ross Edgley.

   28. RRRich Roll1:15:44

       A little bit. Uh, I love Ross, yeah, yeah.

   29. CWChris Williamson1:15:47

       Ross is great. My, my, not so much in the way he looks or the way he dresses. Ross is, like, permanently in athleisure.

   30. RRRich Roll1:15:53

       Ross is sil- Ross is a lot sillier.
9. 1:16:31 – 1:21:00

   Does the Endurance Community Like Ross Edgley?

   1. CWChris Williamson1:16:31

      the endurance community's response to Ross been? 'Cause he did, he sw- for the people who don't know, Ross swam for about 200 days, six hours on, six hours off, without stopping.

   2. RRRich Roll1:16:45

      Right, all the way-

   3. CWChris Williamson1:16:45

      Around the UK.

   4. RRRich Roll1:16:46

      ... he circumnavigated the UK.

   5. CWChris Williamson1:16:47

      The first man to ever swim around the UK.

   6. RRRich Roll1:16:49

      Yeah.

   7. CWChris Williamson1:16:49

      He has recently tried twice, unsuccessfully, in combination with Gymshark, to complete the longest ever single-duration swim. Uh, first time in Loch Ness, too cold. Second time in Italy, too hot.

   8. RRRich Roll1:17:04

      Yeah.

   9. CWChris Williamson1:17:04

      Uh, th- this African heatwave comes in and the water temperature's 32 degrees, and the air temperature's 40 degrees. It's u- uh, it's unbearable. Anyway, what was the endurance community's response to this guy who trains Chris Hemsworth, looks like a bodybuilder crossed with a salty old sea dog, but is a, always laughing?

   10. RRRich Roll1:17:26

       I didn't see any, any, uh, negative stuff about him, but I wasn't looking for it either. I don't know.

   11. CWChris Williamson1:17:32

       That surprises me.

   12. RRRich Roll1:17:33

       Yeah, I mean, he's a, he's a very affable guy. Um, people, especially in open water swimming, can get very particular about rules and how these things are conducted. There's a whole controversy around, uh, Diana Nyad when she, uh, did her Cuba swim to Florida. Some people say she broke the rules, it shouldn't count, et cetera. So there's, there's some persnickety kind of, you know, attitude around these types of things. I don't have a sense of negative blowback on Ross. Um, maybe there is, maybe there isn't. But I think, to your point of the similarities between Will and Ross, like, Ross doesn't look like an endurance athlete either. He's built like a tank. And yes, he trained, uh, Chris Hemsworth for Thor. He's just an absolute unit, this guy, which is not the kind of, uh, uh, physique that you wanna have for long distance open water swimming. And I've told him, I'm like, "Why are you putting on all this bulk? You're making this harder for yourself. If you lost 20 pounds of muscle, your shoulders wouldn't get tight. You'd lose a little bit of power in your stroke. But when you're going for, uh, ultra endurance, that's not important. What's important is efficiency and your ability to conserve energy." But he is who he is, and, uh, I, I love him to death. I just think he's a delight to watch, and I'm always cheering for him.

   13. CWChris Williamson1:18:58

       Yeah, I, uh, I've really enjoyed watching Ross. His book, uh, The Art of Resilience-

   14. RRRich Roll1:19:03

       Mm-hmm.

   15. CWChris Williamson1:19:04

       For anybody that's going through a bit of a tough time, if you've read or listened to The Obstacle Is The Way, enjoyed it, and thought, "I want more," like, a spiritual successor to that book is The Art of Resilience-

   16. RRRich Roll1:19:17

       Mm-hmm.

   17. CWChris Williamson1:19:18

       ... from Ross, so stoic sports science, I think he called it.

   18. RRRich Roll1:19:20

       Yeah, yeah.

   19. CWChris Williamson1:19:21

       Um, and it's this sort of semi-autobiographical...... diary of his swim around the UK, where he applies both stoic philosophy lessons and sports science to the narrative. Fucking awesome.

   20. RRRich Roll1:19:34

       And he's a great writer. He-

   21. CWChris Williamson1:19:36

       He's an awesome writer.

   22. RRRich Roll1:19:36

       ... was a contributor to GQ. Like, he's been writing for a long time. I think he has a sports science degree. Um, and he's done a lot of crazy stuff. Like, he did a-

   23. CWChris Williamson1:19:46

       Log swim?

   24. RRRich Roll1:19:46

       ... triathlon, like Karon. Yeah, log swim. He pulled a car, you know. Like, he's done a lot of kind of Jack LaLanne type stunts over the years.

   25. CWChris Williamson1:19:54

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10. 1:21:00 – 1:46:57

    Keeping Up with the Pressure of Consistency

    1. CWChris Williamson1:21:00

       "The prize doesn't go to the fastest guy. It goes to the guy who slows down the least." That pressure of potential and pressure of consistency, to me, in all areas of life. You know, you were specifically not talking about racing. You were talking about this, uh, on-off, uh, burn and coast workload thing-

    2. RRRich Roll1:21:27

       Mm-hmm.

    3. CWChris Williamson1:21:27

       ... i- i- in professional life. How do you deal with that? When you've got this engine inside of you, "I want to work, I- I- I care about the work that I do. I care about the things that I do. I want to serve," all the rest of it. How have you learned to switch yourself off and what's the journey been like to releasing that right foot from the accelerator pedal?

    4. RRRich Roll1:21:50

       Yeah. It's- it's- it's been an interesting lesson, uh, that I have reluctantly embraced, I guess I would say.

    5. CWChris Williamson1:22:00

       (laughs)

    6. RRRich Roll1:22:01

       Um, but you can't serve to your maximum effect if you're not also serving yourself. So, you have to tend to the vessel if you wanna be a vessel of good in the world. And when you're a workaholic or you're someone who's prone to suffering and feels like your self-worth is tied up in going the extra mile, being in that place of letting go and allowing yourself to take time and step back is the most counterintuitive thing that you can possibly do. Again, that's the discipline. But the truth is, to the point of that quote, "The prize doesn't go to the fastest. It goes to the person who slows down the least." That was originally said to me by my coach, my endurance coach. In ultra-endurance, there's nothing about it that's fast. You could go out and run a mile right now faster than any of these ultra-runners. But if you were to run a 10-minute mile, which is easy for most fit people, uh, 130 times over, then you would crush the Badwater and probably break the record. So, it's not about fast. It's about the ability to persist. And your ability to persist is correlated with your capacity to conserve. You have to be able to mete out your energy in small bits in order to go the full distance. I'm somebody who's always thinking about the long-term. I'm not somebody who's trying to create a viral hit or make a big splash tomorrow. I just do my daily work every single day. And I trust that as I continue to get better at what I do, that I hone my craft, and that my focus is squarely placed on the things that are most important, that the success will come eventually and as a result of that, as opposed to engineering success in some kind of fast track way. I think that's misguided. It may be effective in the short term, but what are you doing 10 years later? And I wanna be somebody who can continue to do this thing that you and I both do for as long as possible. I've been doing it 11 years. As you know, it's taxing. It's a lot. I don't think it's as- as, uh, easy as people think. I think there's so much work, more work that goes into it than people realize. And in order to run that marathon, you have to take breaks. And it's scary to take breaks. Because if you're not doing, then who are you? The world is passing you by. You're gonna miss out. All this, uh, forward momentum suddenly gets arrested. But I have learned that taking that time ultimately becomes a growth accelerator, because that time is necessary to not only recharge your battery, but also to develop clarity around the how, what, and why of what the fuck you're doing. So about four years ago-... uh, I decided to take a month off sabbatical.

    7. CWChris Williamson1:25:34

       Terrifying.

    8. RRRich Roll1:25:35

       I went to Australia for an entire month. And yeah, it was terrifying.

    9. CWChris Williamson1:25:40

       Terrifying.

    10. RRRich Roll1:25:40

        I mean, it was great too. I was in Australia, what's not to love? Uh, but to not open the laptop, to not edit the blog post, to not engage in any of that, was perhaps the most uncomfortable I'd ever been. And it's not a switch that can just get switched off, and it's not something that, um, gets easier even a week later. Like, you really do need a lot of time. Like, I needed that entire month. Like, it wasn't even actually until the last week where I started to feel a little bit more grounded.

    11. CWChris Williamson1:26:17

        What did you do?

    12. RRRich Roll1:26:19

        Uh, I kept it really simple. I mean, I have friends. I was in Sydney that year. I've gone, I've gone to Australia twice, so I've done this every year. I've gone to Hawaii twice. In all those places I have lots of friends, lots of opportunity to do fun stuff and see lots of people, and blah, blah, blah. But I really treat it like a retreat. And so I live those days quite monastically. I do what I enjoy. I'm in a tropical location, I get up, I make my morning smoothie, and then I go out and I train. I ride my bike for four hours, I go to the ocean and swim, um, I, I push myself physically. And then I come back, I eat, I would, I go to the beach, I read, watch a movie, go to bed at 8:00. And, and try actually not to talk to anybody and to not be online. Um, if there's any output at all, it's just in journaling, with intention, and those pages ultimately creating the foundation for an idea or something later. But besides that, no work.

    13. CWChris Williamson1:27:32

        What have you learned about your direction or your goals or yourself through these manuaries?

    14. RRRich Roll1:27:44

        One, a very tactical level, I've learned to trust my team and that I can let go. So that in and of itself that you can take a step back and the whole castle doesn't cave in on itself and the world continues to spin and the work gets done, um, is incredibly comforting and empowering, um, 'cause it taught me that I can step away and it's not gonna be a disaster. Uh, I don't think that you can have the level of clarity on who you are and what you're doing when you're in the machinations of the creative process. There's a myopia. Like, you're, what, you're doing six interviews in four days or something like that? And then, I mean, you're on a hustle grind, right? When you're on the hustle and you're on the grind, there's a, a sort of euphoric feeling that comes with that and a sense of pride and, and accomplishment that are, that's all good, but you're not seeing the forest for the trees because you're staring at the leaves on one particular tree. Uh, and so in order to have that perspective, you have to stop. And if you don't, you're robbing yourself of the greater opportunity that's right in front of you because you've created your own treadmill for yourself. And it becomes very easy, especially if you're getting success, to just keep doing that thing. But sometimes you have to pattern interrupt in order to identify the greater opportunity or the orthogonal, uh, opportunity that you can't see when you- you're in the midst of the grind.

Episode duration: 1:54:10