How To TRANSFORM Your Life At Any Moment: The Alcoholic Lawyer That Became "The Fittest Man On The Planet"!! Rich Roll
嘉宾：Rich
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§01Transcript — part 1
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How much pain are you willing to tolerate before you’re willing to course-correct? A California lawyer turned himself into one of the fittest men on the planet. I graduated top of my class, a world-ranked swimmer. Then I was working as a lawyer. On the outside, it looked like I was doing pretty well. Inside, I was dying. My first escape was through drugs and alcohol. Went to jail, could barely make it up a simple flight of stairs without being winded. That was a harsh dose of reality. I needed to overhaul my life. I needed to do something that was going to be hard and uncomfortable. You can't be a Phoenix if you don't burn in the flames first.
We all want to be this idealized version of ourselves, and yet we still don't do it. We are in a culture that prioritizes comfort and luxury and the impatience that we all have. We overestimate what we can accomplish in a year and completely underestimate what we could do in a decade. We don't have to suffer. We don't have to be in pain. It's our emotional lives that hold us back from accessing that potential. So how do people in that situation take that first step in transformation? What worked for me, after trying many different things, was...
Why should you listen to this episode? All in all, this conversation is fundamentally about transformation. How you transform yourself from where you are now to where you want to be. Rich’s life is the personification of human transformation. This guy has been down and out. He suffered with addiction, failure, and turmoil that most of us will, thankfully, never have to endure. But he says in this episode, and he'll prove to you, that pressure, that discomfort, can and should be your privilege.
If you lean into that, if you understand that pressure is your privilege and discomfort is the pathway to all the good things that you want in your life, then and only then can you reach your potential. One of the things I really got from this conversation is this idea that all of us are much more capable than we believe we are. We have more potential than we allow ourselves to believe.
Also, one of the big things Rich will leave you with in this conversation, which blew my mind if I'm honest, is this idea that addiction is on a spectrum. We tend to think of addiction as, as he says, junkies or people that are ingesting or taking drugs. But if you think about it, we’re all addicted. We’re addicted to distraction, whether that’s our phones, whether it’s pornography, whether it’s food, whether it’s alcohol, as is the case in Rich’s case, or whether it’s our work.
How do we alleviate ourselves of that addiction to distraction? That’s what you’ll find out in this conversation. Most importantly of all, Rich has sat down with 800 of the world’s smartest, wisest, and most successful people. From doing that, he has learned a lot. This is one of the episodes that you honestly should not miss. Enjoy.
Rich, this is a broad question, but it’s intentionally broad. Who are you, and what mission are you on?
Coming out of the gate hot. That’s a very difficult question to answer. I would say that I am a spiritual being having a human experience, endeavoring, attempting to learn and grow in a number of ways. I had an experience in my early to mid-40s where I was able to tap into potential that I didn’t know existed, and I expressed that athletically.
That experience taught me that we’re all capable of so much more than we allow ourselves to believe. It motivated me to go on this journey to grow and expand in other areas of my life because I realized if I had been sitting on this latent potential athletically for so long, there must be other blind spots, and I wanted to explore those.
So my mission has been to grow in the public sphere, learn in the public sphere by having these conversations on my show, and then share that wisdom with other people for the purpose of elevating consciousness and activating positive change in others.
You’ve got millions and millions of people listening to your show all over the world. You’ve interviewed, I think, almost 800 people, right? 750 podcast episodes or something, which is staggering. On an individual level, what is it that you hope to impart, or what impact is it you hope to have on the individuals that listen to your show?
I want everybody listening or tuning into the show to believe to their core that they are capable of more than they may realize. That there is a greater possibility for every single person regardless of circumstances, and there are tools available for accessing that.
I think that’s super important because I think it’s so easy to passively or reactively live our lives. We’re all on some level in a routine, in a rut, and we have blinders on because we’re in a certain social environment where there are unstated dictates about what’s okay and what’s not. We’re all creatures who want to feel a sense of belonging and identity with whatever group that we’re aligned with. I think that comes with very good things—of feeling wanted and needed—but also negative aspects which create blinders to the greater possibilities that are available to us.
Everybody is conditioned in some way or another, and that conditioning starts fairly early. What you’re talking about there, at least in how I heard it, is to try and undo some of that conditioning so we can live more aligned to whatever worthy cause is right for us. When did you start being conditioned, and what was that condition? What was the first context or moment where your conditioning began—the conditioning that led you on the journey that you lived?
I went to a high school that was very achievement-oriented. Grades were very important. Academic achievement in my household was paramount. It was a situation in which no matter what I did, you didn’t quite get the validation that you were seeking, so you’re always chasing it a little bit more, a little bit more.
This was to the point where, unbeknownst to me or on an unconscious level, I needed to escape that paradigm. My first escape was through drugs and alcohol.
And bullying?
Bullying, yeah.
Take me into the mind of that young guy that’s being bullied. What is he thinking? Is he scared going to school? Is he trying to escape who he is? Is he trying to fit in in certain ways? What is he doing, and what is the experience of bullying like for him in detail?
To take myself back, I think I just wanted to feel like I belonged. I always felt "different than," "other than." This sense of not being comfortable in my own skin, like other people had a rulebook for life that I lacked. I just didn't have the social skills or the confidence to be able to make friends or feel like I was part of anything.
And then eventually you cite alcohol and drugs as being the thing that made you feel other than yourself in a good way?
Initially, it made me feel *like* myself. It was like this miracle salve where suddenly all of the unconscious anxiety and sense of difference between myself and others seemed to vanish. That discomfort in my own skin turned into comfort. Like I suddenly felt like, "Oh, maybe this is how everyone else feels all the time."
I discovered this thing where now I feel okay, like I can exhale. I can be around other people without feeling anxious about it. I can look somebody in the eye and have a conversation or flirt with a girl or do all these things that seemed to come naturally to other people but seemed alien to myself. I just remember feeling so at home with that and just wanting to feel like that all the time. It got its claws in me, and that’s how that journey begins for many people who’ve had their version of my experience with alcohol.
Addiction comes in many forms. The role that addiction was playing—the role that alcohol was playing in your life at that stage—can also be substituted for other things, right? Some people have it with food, or with work. From sitting there and interviewing hundreds and hundreds and hundreds of people, what have you learned about the nature of the role that alcohol was playing for you, but also the role that maybe for me, like being a workaholic, or for some people eating is playing? What is it doing for us? Is it like an escape? In your case, it was like the salve that made you feel yourself, but what is that thing?
This is something I’ve spent a lot of time thinking about. As somebody who’s been in recovery since 1998, I’ve been to thousands of AA meetings, I know so many people in recovery, and over the course of 10 years of hosting my podcast, I’ve had so many experts in the realm of addiction, sobriety, and recovery.
I’ve come to believe that this notion of addiction lives on a much broader spectrum than we may realize. When we think of addiction, we think of the junkie or the gutter drunk. But in between that polarity, there’s a whole spectrum of addictive and, I would even weave in, obsessive-compulsive behavior that ranges from continuing to get into the same bad relationship to being unable to put the phone down.
We are seizing moments and opportunities through behavior or substance to distract ourselves from ourselves because we are experiencing discomfort with whatever emotion is coming up. It’s easier to divert to something that will give us a sense of ease and comfort or distraction than to sit with that sense of dis-ease. I think any kind of recurring, repeated behavior pattern that mimics that could be characterized as an addiction. It may be mild, but I think nonetheless, it’s qualitatively the same thing as the person who can’t stop drinking.
It all goes back to this inside job of trying to understand what makes us tick, the nature and origin of those discomforts, what triggers those, and trying to find a way to not only sit with those but confront them and work through them so you can ultimately transcend them and liberate yourself from the behavior or the substance or whatever it may be that is the go-to default thing that you do when you start to feel out of control or nervous or anxious or insecure or perhaps triggered or any number of emotional impulses that might arise.
What is the cost of not learning to be with myself? I’m looking at all these things—phone addiction, I’m definitely addicted to my phone—all of these addictions, I’ve got some of them in various degrees. So what? What’s the cost?
Well, time will tell, right? Maybe there isn’t a cost that is so significant that it mandates that you rectify that behavior. Again, it’s a spectrum. So for you, you might be able to engage in a certain behavior without having negative ramifications in your life that are significant enough for you to redress that. For somebody else, it might destroy their life.
But I think developing an awareness around those behaviors and paying attention enough such that if you start to find yourself experiencing negative life ramifications as a result of those behaviors, you’re not in denial over that and you can make a course correction.
And what’s the upside then of just learning to sit with yourself as opposed to reaching for the phone or for the cake or for the beer? What is the upside? I say this because I think I live in a generation that has become so used to distracting ourselves, and the thought of meditating or not having our phone on us is actually a phobia. We haven’t learned to sit with ourselves in silence with our thoughts.
If you can’t sit silently with yourself, with your thoughts, then you are not living an intentional examined life. I think to be addicted to your phone or to be living in that reactive mode where you’re constantly distracting yourself robs you of something that we need as human beings, which is rumination and boredom.
That is the juice of creativity. As a creative person—somebody who does this show and talks to amazing people and is writing a book and is very much in a space where your creativity is really the driver of everything that you do—I would say to you, it is of paramount importance to protect your boredom, to protect your quiet time, to put boundaries around those distractions. Otherwise, you are not going to be doing your best work and you are going to be depriving your audience of the best version of yourself.
The other thing is connection. It’s definitely robbed me of connection.
Well, it’s pernicious in that way because, at least with social media, it gives you the illusion of connection. We’re sitting here together because of social media—you reached out to me, I reached out to you—so it’s not a binary. There are amazing things about it, and my entire career has been built on these digital tools. They’re very important to how I navigate the world.
But at what point does that meter toggle over into the red zone where I’m being used by it, and it’s robbing me of my humanity, and it’s deluding me into this idea that I’m connecting with other people? In the analog world, I’m just at home all the time, and I’m not actually interacting in the real world.
I think one thing we share, Steven, is our show is all about the in-person experience. I tried to do the Zoom thing; I can’t do it. It feels transactional and weird. As much as these tools, which are phenomenal, have given us the ability to connect in a certain way, it’s not true connection. In order to really feel like we’re part of the human race, we’re hardwired to be with people in real-world settings.
When I look at your story, I see multiple chapters and there’s transformation in every chapter. Sometimes for better, sometimes for worse, but it’s always forward. It seems like it was the path that you had to go on. You talked there about the first chapter of your life, which is you're young, there’s bullying, there’s this feeling of inadequacy and isolation. What’s the next chapter?
Awkward, insecure kid, difficulty making friends. But I found solace in the swimming pool. That was really my safe haven, perhaps my first addiction. In lockstep with my improvement in that space came better grades, and I started to perform better athletically.
So by the time I was 18 and graduating high school, I had my pick of going to any college I wanted. I got into Harvard, Princeton, and ended up going to Stanford, which in addition to just being a premier university, also happened to have the number one collegiate swimming program in the country.
Basically, anything I wanted to do was laid out in front of me. I arrived in California for college—I grew up in Washington, D.C., so I traveled 3,000 miles away to go to school—and entered alcohol. That began the slow decline of my ability to express my potential not only as an athlete and as a student but as a human being. It gradually denigrated all of my values and dented my aspirations to the point where I no longer really cared about my trajectory or where I was headed with my life and was solely concerned with rooting out where my next good time would be.
Those were the good times. I would say that initially, alcohol really saved me. It taught me how to be a social person. I enjoyed going to parties, I enjoyed figuring out how to talk to people, and it was really this fuel that transformed me from this navel-gazing, insecure kid into somebody who felt like I could comport myself in a social situation—as long as I was using alcohol.
I’ve taken some of those skills and I’m now able to apply them without alcohol. But very slowly over time, the quality of my life just declined and declined.
I was a functional alcoholic for many years, but I knew very early on that my relationship with alcohol was different from that of my peers because I would be the last person to leave. I was immediately sneaking drinks. I was the one who was throwing up and blacking out when everyone else knew what time it was to go home. I started going out more and more nights every single week.
Fast-forwarding through later years, I was hiding my drinks, sneaking my drinks, hiding the empties, and doing all the dark stuff that one does when they fall prey to this condition. There was nothing really sexy or romantic or rock and roll about it; it was just really sad and pathetic.
To the point where, at the end, I was alone, alienated from my friends, my family didn’t want anything to do with me until I sorted this out. I was on the precipice of—somehow I got through law school—but I was working as a lawyer, and I was on the precipice of getting fired. I was living in a shitty apartment with barely any furniture, sleeping on a mattress on the floor. It was very dark for a very long period of time.
When did you get married? Your first marriage was in 1995?
That would have been ’96, I think. Yeah.
So you had this ill-fated marriage that ended on the honeymoon. That’s a sordid story that would take a very long time to untangle and explain. A marriage that ended *on* the honeymoon?
Ended on the honeymoon. Yeah. Incredibly painful, embarrassing chapter of my life. That marriage took place after I’d gotten the two DUIs, but I was endeavoring to get sober. I think my fiance—not quite my wife because we didn’t sign the marriage certificate, which is a whole other aspect of the story—I think that she realized that I would be problematic as a partner but didn’t have the courage to call the whole thing off and allowed the wedding ceremony to take place even though she didn’t want to be married to me.
It all kind of came to a head on the honeymoon, which is the last time that I saw her. That was really my bottom as an alcoholic, even though I drank for a period of time after that because it was so emotionally devastating and painful. That was really the nadir where I realized that my life had hit the skids in a way that I could have never imagined for myself.
Post that wedding and everything that happened, you returned to drinking again. You relapsed because of the pain of that experience. How long does that last, that period?
It was a long time ago. I think it was about six more months of my life circling the drain before I finally decided that I needed to really take responsibility for my behavior.
At that point, what are the people around you that love you doing and saying?
Friends were slowly stepping backwards from me, distancing themselves from me. My parents were terribly worried and concerned, and they had sought out counsel of their own and started attending Al-Anon. I believe they had seen a therapist as well.
Through that, the advice they got was, "You need to cut ties with this guy. You can't will him into doing what you know is in his best interest; you have to detach." I recall very vividly a conversation that I had with my dad where he's like, "I know what you're doing. It's very clear this path that you're on, and we just can't be part of it anymore. If and when you're ready to make a change or to really entertain sobriety in a real way, we’re here for you. We're your parents and we love you. But until that point, we really don't want to hear from you anymore."
That was a brutal pill to swallow. Incredibly painful, but also catalytic because it snapped me out of whatever denial I was harboring about getting over on people or them not really knowing how I was actually behaving. I think it was an important step in helping me realize just how dire the circumstances were for me at that time.
When your father said that, what did you hear?
I heard, "You're a failure and you are unlovable."
Do you think that was the right thing for him to say?
I think in my case—and I’m only speaking from my perspective in this particular set of circumstances—it was the right thing to do because it effectively moved me in the direction that I needed to be moved in.
They had tried the other way, which is loving me and being supportive and offering up a soft landing pad, and that was not working. I think they needed to do that for themselves, to protect themselves as well. I respect that choice. I’ve been in many situations trying to help people get sober, and it’s a very delicate, difficult thing to do. It’s just really challenging because if somebody’s not ready and they don’t want to get sober, there’s very little that you can do to try to create that epiphany in them.
Willingness is a self-generated response that you can’t instill in somebody externally. Until somebody is really willing to confront their demons, you can’t compel them to do so. That’s why I think sobriety or addiction is so baffling and so painful for the loved ones of people that suffer, who can so clearly see, "You're killing yourself, you need to do this," and yet that person won't make that choice.
It's not just addiction and sobriety in that sense that I was thinking about when I asked that question. I’ve got people in my life that I’ve tried to help in various ways. I’ve got one friend who has struggled with pretty severe addiction, and your natural inclination is to try and jump in there and give them advice and help them and pay for this and sort this out, etc., etc.
But after years and years of it never working, what do you do then? I’m thinking of one particular example of a friend of mine who struggled with addiction, and slowly everybody has just fallen away. The person’s management has fallen away, their friends have fallen away. I wonder sometimes, is that what you have to do? Do you have to basically give them a void, enough space, and stop holding them up in artificially suspending them and let them go to the bottom? Let them go to that rock bottom?
There is a logic in that. You don’t want to coddle that person. You certainly don’t want to be codependent in their behavior—in other words, making excuses for them that makes it easier for them to continue down that destructive path.
There is wisdom in just saying, "Hey man, I love you. I’m available when you’re ready to get help. But you’re on your own thing, man, and I just can’t be part of it. So call me when you’re ready, but until then, good luck to you."
Because the addiction elevator is always going down. It’s a progressive disease; it only moves in one direction. The best-case scenario is that person’s life stays the same, but in almost every case, it continues to decline. It will decline to the point where the pain experienced by the person who is the addict or the alcoholic becomes more unbearable than the fear of the change. That is where willingness is born.
Again, it’s not something that you can instill in that person. You could hijack your friend and throw them in the back of a car and drop them off in a rehab, but he might escape from the rehab, or he’ll sit in the back and just bide his time until he or she gets out and they can go back to whatever they’re doing. That’s why this is such a difficult problem to solve. It is an internally generated thing.
The people that I know that have been able to get sober and stay sober are the people that shoulder responsibility for their own sobriety. You can’t get sober for somebody else. "I’m getting sober for my spouse or my kids" or "I’m getting sober because if I don’t, my boss is going to fire me"—those, you might be able to do that for a short period of time, but for the true addict, unless you’re doing it for yourself and you’re making it your number one priority, chances are you’re not going to last over the long haul.
It’s confusing. When you love that person, it puts you in a very treacherous position because if you do create that boundary and that person goes off and something terrible happens, will you feel responsible? Will you feel like you didn’t do enough, or if you had just done this or that, that wouldn’t have happened? That’s a very real predicament to put yourself in.
There’s something quite counterproductive in the sense that when you’re trying to help that person, what often happens is your relationship with them becomes strained. When your relationship becomes strained and you become frustrated with the lack of effectiveness of your support, then arguments start. You might say some things that you regret, further tarnishing that person’s self-esteem, self-worth, or whatever’s triggering them to try and escape themselves through whatever addiction they might have. It actually can make their situation significantly worse and destroy the relationship.
Right, which is why it’s important to interface with that from a place of neutrality. To not get emotionally agitated or activated by it. A good way of recalling that or reinforcing that is to understand that there is the person, your friend, and there is this disease, this addiction. If this person is acting in their disease, that’s not the person. They’re not a bad person; they’re afflicted by something so powerful that they’re unable to override it and be that friend that you remember.
I think when you approach it through that lens, you can have a little bit more compassion for that person rather than take it personally. They’re not acting out of animus towards you; they’re suffering from something that’s so powerful that they’re unable to control it.
Okay, so this was a quote I found about your relation to your opinion of balance. "He finds balance extremely difficult and believes that if something is good, then the more the better. He believes balance is for ordinary people and he wants to be extraordinary. He says this can be a blessing and a curse."
Definitely a blessing and a curse. I am hardwired for extremes. This has been both a superpower and an Achilles' heel. It’s the thing that has fueled me and allowed me to achieve some pretty cool things, but it’s also been the thing that has almost killed me. So it’s that love-hate thing.
But I think behind it, this notion of living a balanced life that we get served up—like, "You need to be balanced and the best way to pursue your life is in a balanced way, everything in balance"—the social conditioning around that idea is so powerful that for years I just felt like a terrible person or less than because I just could never figure out that equation to make everything feel like it was even adequately balanced. Because I feel most alive in those extremes.
That’s part of what addiction is—you’re just searching for those peak experiences in unhealthy ways and also healthy ways through athletics and through creativity and through other avenues. But I always felt guilty about that, like other people seemed to be telling me that I shouldn’t be doing this. And yet, this is where I feel like myself.
Finally, I got to the place where I was like, "Fuck this whole balance thing. This is who I am." And I decided to embrace it. Now, that doesn’t mean that you just blindly pursue these obsessions to the point of self-destruction. What it means for me—again, not giving advice, in my experience—when I allow myself to immerse myself in something that fascinates me, whether it’s an ultra-distance race or writing a book or whatever it is, giving myself permission to really focus on that and take it all the way to the wall is where I do my best work.
But that is only acceptable as long as that pendulum that’s swinging all the way up over here swings back, goes this way, and comes to the center. Because we all have buckets in our life of values that we need to nourish. So a creative project, for example: I’m going to go do that, and that’s fine as long as I come back and my family is nourished, my relationship is nourished, my friendship is nourished. All these other areas that are important to me don’t fall by the wayside for too long.
Balance in the macro but not balance in the micro. So on a day-to-day basis or a week-to-week basis, my life is wildly out of balance. But if you look at it over the course of a year, you telescope out, I think it’s much more in balance than...
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Using that example of the pendulum. In society, we started by glorifying hustle culture, I guess, and being out of balance. And then there was kind of a movement towards "that's toxic." And now I feel like a little bit it's coming back the other way where people are going, "Fuck work-life balance." Balance is such a subjective thing, and work is completely different for everybody.
This is my work. For someone else, their relationship with that work might be tedious; it might be depressing. They might be doing something that really doesn't fill them up. But I think there needs to be nuance in the fact that all work is different. Every individual is clearly different and is wired to find that fulfillment in different ways. So work-life balance in and of itself is a pretty ridiculous concept—to think that there is *a* balance. There really must be, as you kind of described, a subjective balance where there’s a balance for Steve, and as long as I don’t sacrifice social connection, isolation, and all the other things, then I’m balanced. My balance could look much different from yours.
For whom and when, right? If you’re 22 years old and you’ve got this idea for a startup and you’re a coder and you want to code like a maniac, knock yourself out. You have no other responsibilities; you have the time, you have the freedom to do that in that moment. But that 22-year-old, 20 years later, with kids, a mortgage, and whatever—it’s a different time. That person’s in a different place.
These things can't be—they have to be contextualized, right? And yes, if you want to achieve something great, you are going to have to work very hard and you’re going to have to get out of your comfort zone. You may even need to be obsessed. If you’re living an entirely balanced life where you’re home at 5:00 and you’re always at dinner and all that, it’s like you’re making it very difficult to achieve something extraordinary.
That extraordinary thing is going to require an extraordinary commitment, which means in the social construct of balance, you are going to be out of balance. If you’re going to feel uncomfortable with that because you have other priorities in your life, then maybe that’s not for you. Being out of balance to pursue something great, in my opinion, is perfectly fine, again, as long as you allow that pendulum to swing back and those other things in your life that are important are nourished and attended to.
So it’s a very specific thing. It depends on who you are, what stage of life you’re in, what you’re seeking, and having the self-awareness to understand that you can’t be everywhere all the time. You can’t be 100% for all of the things that are important to you in your life on every single day. So it’s about conscious awareness and intentionality about where you’re rowing that boat.
You can only row your boat in one direction. Are you rowing the Steven boat towards Steven today? Are you going to row it towards your girlfriend? Well, you’re going to have to do a lot of rowing in a lot of different directions. Just knowing that you’re making a conscious choice and doing that with that understanding and appreciation, I think is really important.
But all of this is to put the lie to the idea that anybody is living a balanced life on a minute-to-minute, hour-to-hour, day-to-day basis. It’s like a construct that I think makes people feel guilty and bad about themselves because none of us are adhering to that idealized version of a balanced life that we have a mental picture of.
You can’t have it all. You left rehab in September 1998. Earlier when you were talking about transformation, you described someone who goes from being a fairly ordinary person to running a marathon. That was one of the sort of examples you gave of something that intrigues you—like, how did they do that? That's pretty much in many respects what you went on to do upon leaving rehab—is your life slowly moved towards ultra-athletic sports.
Yes and no. I mean, I think the shorthand kind of Google version of my story makes it look like all of this stuff happened in a very compressed period of time. But actually, when I left rehab, which is where I lived for 100 days, and resumed my life in Los Angeles, I spent the next 10 years trying to solve the dilemma of my life that I had self-created. I had to repair my relationships, I had to become trustworthy to other people again, I had to be somebody who was reliable and would show up on time when they said they would—all those sort of normal things that normal people do, I had to rebuild for myself.
So for 10 years, I immersed myself in the recovery community in Los Angeles and I tried to become that corporate lawyer that I thought that I wanted to be. To be kind of approved of by my parents and by society without really grappling with who I wanted to be. Because I was so caught up and so ashamed of my past and embarrassed of how I had screwed my life up that I wanted to prove to myself and to everyone else that I could be that person that I was at 18 when I had all of these opportunities and choices.
I was blind to kind of the inner journey, despite sobriety—blind to really trying to figure out what made me tick and what I might want to do for myself. That felt like an indulgence. So the ultra stuff came much later. That came—so I got out of rehab at 31; it wasn’t until I was turning 40 that I had another bottom where I had to reckon with my lifestyle choices: with diet and movement, etc. because I’d put on 50 pounds and was just pursuing this corporate life to the point of illness, honestly.
Although I’d been this athlete, I just could barely make it up a simple flight of stairs without being winded, tightness in my chest. Heart disease runs in my family, and I just had a second situation in which I realized I needed to overhaul my life. So there was a whole 10-year period in between those kind of moments of awakening.
That 10-year period is a 10-year period that a lot of people listening to this right now can relate to. Where they found themselves in a professional context or professional endeavor without asking themselves the question of "Who am I and what am I actually interested in?" You might be doing it because your mom wants you to be a doctor, or you have Indian parents and they came over here and they want you to be a lawyer—whatever it might be. I hear that story a lot. What is the question people in that situation should be asking themselves, and how do they take that first step in transformation from becoming the banker that’s in the city with a suit and tie on right now listening to this, to the person that would make them whole and full and love themselves and their life? Is it a question? Is it a retreat they need to go on?
Yeah, it's a great question. I think that question is probably different for everybody. But how about just asking yourself: Who are you? And I mean that in the broadest sense—perhaps the most unanswerable spiritual sense—but I also mean it in the very tangible sense of like: What are you doing? Are you really on the path that you want to be on? Did you choose this path? Are you here because of external pressures or expectations that you didn’t ask for?
I think when you turn inward and start exploring your interior to try to grapple with what is making you tick, what is impulsing the decisions that you’re making—the big decisions and the small decisions—and developing a latticework or an understanding of what those mechanics are sets you on a trajectory to making better decisions for yourself.
So it’s not like, maybe that banker is supposed to be a banker. Maybe he's super happy. That’s fine; I’m not here to tell people they should quit their jobs. I’m just saying that an examined life, meaning that inward glance into understanding why you’re making the decisions that you’re making—historically, the way in which you were raised that might have set you up to make decisions you *think* you’re making for yourself but are actually in reaction to unconscious triggers that are built into you—I think developing an awareness of that is really important in trying to understand that question.
It took me a very long time to untangle that knot. I don’t think it’s a simple process; I think it’s different for everybody. It can come in the form of talking to a therapist or meditation; there is no one modality for that. But I think simply the commitment to try to understand that, I think, is the process of gaining that understanding to help you make more intentional decisions for yourself. Maybe it starts with an easy prompt, like: What did you enjoy doing when you were eight years old that you don’t do anymore? And why don’t you do it anymore? Re-engaging with the childlike nature that is perhaps lost as we grow older and get into the flow of our professional lives.
One of the most important questions I think I would add as well is: How do you feel? We very rarely ask ourselves that, and I think we all have this internal compass which we've been given by life, which is like: How do you feel in this situation? How do you *truly* feel? Not like, how do you feel in the context of: is your mother happy, or is your father happy, or is society impressed by you? But like: How do you actually feel?
I think that sometimes for me has sat apart from the accomplishment. So I could be achieving something great and know that people are impressed and happy, but really, I’m having a fucking shit time internally. Tuning into that voice of "How do I feel?" and tuning out of "How do people feel about me?" has really helped me in those moments where I’ve got to make a big decision to quit. I don’t think people ask themselves that question enough.
Well, they may ask themselves that question, but the answer is flippant, right? It’s like, "I’m good. Cool, I feel good. I slept good last night." No, like: How do you *really* feel? And then continuing to peel back the layers until it gets really uncomfortable, and then you know you’re in the sweet spot, right? That’s where the juice is.
I’ve peeled them back, I’ve raised my awareness, I realize I’m in the wrong place. But I’m 39 years old, and I’ve got kids, I’ve got a house, we live in this part of London so I can get to work quickly. We’ve built our lives around this person I thought I wanted to be, and I’m held in place by my friendship group and my mom lives down... people have that fear. They think: How do I break out of that? How do I shed?
Yeah. Well, first I would say to that person: Congratulations. Like, you created a life for yourself. On some level, even if you want to leave that career path or you’re unfulfilled in that, you still are somebody who is deserving of acknowledgment for building something. And that’s an amazing thing. So it’s not about casting that aside or disrespecting it.
For me, I would say to that person: What is it that gets you excited? Like, what is it that you feel is unnourished in your life? Do you have a creative itch? Is there something calling you, or something again that you used to do as a kid that you really enjoyed and for some reason unbeknownst to you, you don’t do anymore? Maybe it’s music. It could be music or stand-up or—you play football, right?—being on a football team or doing some... just having coffee with your friend or what have you.
Finding a way to build that back into your life in a way that isn’t going to derail your current life. But I think just breathing on that, giving space to the things that bring you joy in the most primal sense. Like the simplest things that just you remember made you happy that you’ve forgotten and recapturing that and finding a way to respect that, protect it, nourish it, and inject it into your life.
I think the more that you tend to that garden, suddenly—oh, a little opportunity over here pops up, or something is telling me I should move this way. These are very subtle energies that you have to be present for in order to notice them when they appear. But I think those are the subtle energies—that’s the—those are the waves you want to be surfing. You can do that while you’re working at the bank. They don’t have to be mutually exclusive.
Over time, maybe you start moving a little over this way. Five years later, your life is unrecognizable. And I think this goes to the impatience that we all have. We all want to be this idealized version of ourselves—happier, fitter, thinner, richer, whatever it is—overnight. We overestimate what we can accomplish in a year, or maybe in a couple years, and completely underestimate what we could do in a decade. We’re not wired to think in decades; it seems too intangible. But if all you do is make tiny little changes to build in habits into your life that bring you joy or fulfillment or happiness or purpose in incremental micro-allotments that don’t disrupt the rest of your life—you do that for 10 years straight, your life is going to be different, and I can promise you that.
Ten years after rehab, you have what you describe as your second rock bottom. You’re a workaholic. You’re trying to appease the perception of people in your life to make them proud, I guess. Just before your 40th birthday, this is when that reckoning in your life takes place. What was that reckoning in your life? What did you realize, and what did you see as the solution to that confrontation?
Yeah. So I had spent the better part of 10 years people-pleasing and doing my best to be successful living somebody else’s life unbeknownst to me. Doing all the right things, checking all the boxes, becoming successful. So if you were on the outside looking in, it looked like I was doing pretty well. Inside, I was dying because my soul, my spirit was unheard and undernourished. Like, I didn’t know how to pay attention to myself or the signals of my soul who were telling me, "I don't think you're that happy doing this," and repressing that year after year after year to the point where I couldn’t do it anymore.
So I was harboring a bit of an existential crisis about how I was living my life, being this lawyer and kind of showing up in the world in a certain way that always felt like a costume that didn't fit me. Meanwhile, although sober from drugs and alcohol, I’d sort of transferred a lot of that addiction energy into food and was eating a terrible fast-food diet, gained a lot of weight, was inactive. Even though I’d been a swimmer in college, I wasn't really moving my body in any meaningful way for a number of years.
This existential crisis that I was having collided with this health scare shortly before I turned 40 where I was going up a flight of stairs after a long day at work and couldn’t even make it all the way up. I had to stop halfway up the flight, winded, out of breath, tightness in my chest, wheezing. You know, thinking, "I swam at Stanford. I was a world-ranked swimmer. I can't—I'm 39 about to turn 40. I feel like shit, I'm fat." And it just broke that spell of denial about how I was living where it became intolerable to continue along that path.
It was very much like the day that I decided to go to rehab. Back to willingness: suddenly out of the blue, I was blessed with this realization not only that I needed to change my lifestyle habits but that I had the willingness to actually take action on that. Because the decision that I had made 10 years prior when I went to rehab had been so transformational—I could have woken up that day and made a different decision. What would my life look like? I had this palpable sense that once again, this was just such a moment where if I could make a decision like I had 10 years ago, maybe I could change the trajectory of my life.
I know that these moments are fleeting and they require immediate action or they pass, right? You could say, "Maybe I should eat better or go to the gym once in a while. I’m tired of feeling like shit." That’s so vague; I knew that that wasn’t going to work for me and I needed to do something immediate that was also difficult that would mimic the experience of going into a treatment center for drugs and alcohol. I needed to have a structured situation that would snap me out of my comfort zone and create a new trajectory upon which I could build something different.
I think about this a lot in businesses and organizations. They almost need to "stage a crisis," I call it, to make change happen. Because when you're in an organization and there's maybe thousands of people and let's say it's AI or an innovation comes along, people will go, "Yeah, that's a problem, but you know, it's fine." And then they'll kind of carry on keeping on.
The organization almost needs to stage a crisis—get everyone in a room and say "We're changing today" and really terrify their team about the prospect of not changing. It's almost like staging a rock bottom, because it will be the "frog in the frying pan." It will slowly creep upon you if you don't at some point, as I call it, stage a crisis.
To really get clear on where this is heading and where we’re sleepwalking ourselves into, whether it’s with our health, our relationships—I actually had this conversation with a friend of mine in his relationship because he's now in a sexless relationship and he's really unhappy, but he's not saying anything about it. He's kind of bringing it up sort of quietly once in a while, and his unhappiness in the relationship and resentment is coming out in other ways—like arguments and fighting—where he needs to stop and stage a crisis. Like, not allow it to be brushed under the carpet anymore and sit down and say, "Listen, if we can't solve this, I have to leave this relationship. I want to solve it with you, but it's a dealbreaker for me." You see what I mean?
Yeah, I get what you're saying. Basically, short of sleepwalking yourself towards the cliff’s edge, staging an intervention on your life by concocting a crisis that’s going to compel you to confront the elephant in the room that is the thing that is holding you back—that's obvious to everyone else and yet you’re refusing to look at it.
Yeah, because we, as you said earlier, we want to avoid discomfort. So if we can just sweep discomfort under the carpet and procrastinate it into tomorrow, we do. We do that in business; we do it in our own lives. So how do we maximize the discomfort today by presenting what the future will look like if we don’t take action right now? And there is often a point of no return in relationships and in business, for sure.
Yeah. I think that’s a very pragmatic, actionable way to look at it. Perhaps a more mystical way to approach this is to say that when you are living your life out of alignment with your best self, the universe comes knocking, and it knocks gently. Like, maybe you’re out telling lies or whatever it is; you’re just not living your life in integrity, in alignment with your own values.
We all do this, right? We’re not all living perfect lives. And so when you do that, there’ll be nudges. Those nudges will be very graceful at first, and if you ignore them, a little bit louder. "Yeah, that's fine. I can deal with that." The knocks start to get more intense, more intense, more intense. And then you get two DUIs in six months and you’re in jail, or your partner leaves you, or whatever it is, right?
How much pain are you willing to tolerate? How loud does the knock have to be before you’re willing to course-correct? Change is very difficult; we don’t want to make change. If change were easy or it were a logical thing—like "Here's the answer, do this"—and if everybody just did it, there would be no self-help industry. There wouldn’t need to be any books. You just tell somebody what to do and they do it. So why don’t they do it?
We don’t like to be out of our comfort zone. We have a certain way that we live our life, and until that is so disruptive, we’re going to continue on that path. So the question becomes: How much pain do you have to be in before you’re willing to walk through the fear of the unknown that the change presents? How loud does the knock have to be? How low does the elevator have to drop? I think that answer is different for everybody. But the amazing and confusing thing about it is that the possibility of change exists in all moments. We can make that choice at any time. We don't have to suffer. We don't have to be in pain. And yet, we still don't do it.
Unlocking that mystery—yeah, I mean, well, there’s your book; you can answer that question. Well, I've been playing around with this idea in my book. There was a chapter I was going to write about time. I wanted to write something about time and time management. So I thought the best place to start is talking about death, because that kind of puts time in context. It’s finite.
So I started writing about that. If you’re 35 years old, you’ve got 17,000 days left. I’m trying to find all these ways where people can visualize because of what you said—people can’t think of decades. We can't think of finality; we can't think of infinity. We can't think of long periods of time. I also at some level don't believe we know we're going to die. We don't live our lives accordingly. We think it happens to other people. Deep down, we’re like, "Somehow I’m going to sidestep this thing, it’s not actually going to happen."
And you see that in our decisions—the things we pour our attention into. Clearly, we don't think we're on a clock, a clock we can't see. So that’s how I started the chapter. Then I went into time and I was like, okay, time management techniques. I was thinking about my own time management techniques. I then was like, "I’ll Google it, ChatGPT." Went on ChatGPT: talk to me about time management techniques. There’s so many. And I thought to myself, the reason why there’s so many is the same reason there are so many fad diets: because none of them work unless you have discipline.
So people just keep making new ones and they keep selling because none of them work without this thing called discipline. So what causes discipline? Then I arrived at this discipline equation in my head where I kind of believe—I’m going to say this in a super vague, broad way—when your perception of how meaningful the goal is, plus the enjoyment and psychological engagement you get from the pursuit towards the goal...
So for me, I really want to be a DJ. I’ve played around with the idea for a long time. I finally made the decision I wanted to do it. Why do I want to do it? Absolutely love music, love the thrill and how energized I am from performance, plus the psychological engagement and enjoyment I get from the pursuit—it's like meditation, DJing and the practice of it. So I go upstairs into my kitchen, I spend hours listening to my favorite music and merging it with other songs I love for hours, forgetting about the whole world—minus the perceived psychological cost of the pursuit.
What does it cost me to pursue DJing? And I think that is roughly my discipline equation. So if you think about these three elements—how bad you want it, how enjoyable it is, what does it cost—you can kind of think of why people might or might not change. It somewhat fits into what you said about when the pain of staying the same becomes greater than the pain of making a change, then people make the change. When they really, really want it and it's more enjoyable than it is painful to go in that direction, behavior changes.
Right. Well, I would take it one step further, but first let me say this. I would say that you’re already a DJ. You’re making an assumption around what it means to be a DJ or to pursue DJing—that comes with a lot of baggage. It means success, maybe you’re envisioning a big crowd of people who are listening to your music. But the fact that it brings you joy and you found a way to carve time out to nourish that—it doesn’t matter how far it goes or doesn’t go as long as you are kind of cultivating that out of that purity of spirit, because it nourishes your life.
That’s what I mean when I was talking about the banker, right? Just DJ at your kitchen table; it doesn’t have to be any more than that. If you’re finding so much joy in it, then you can recalibrate that equation about how much energy, resources, and time you’re going to invest in it. But right now, if it fits into your life and it’s making your life better, then the question would be: Does it need to be more than that? Do you need it to be attached to some external validation or monetary reward or recognition in order for you to believe that you actually *are* a DJ? Not saying there's an answer to that question, but it's something to think about.
The reason I gave the DJing example is because it was something I was able to stick at, I was able to essentially change. And my health was the same thing. It fits into that discipline equation of: at some point in my life, I saw this pandemic happen, I saw the fragility of this thing called health that in my young 25 years I’d never even knew was there. I never even knew I *had* health because mine had fortunately always been well.
Upon seeing the pandemic play out and hearing the doctors and scientists say that your current health—obesity is linked to your chances of having worse effects of this disease—that was enough for me to put me in the gym for the next three years. I haven't missed more than two days, pretty much, in a week for the last three years. That was my behavior change. Before then, I was the guy with the fast food.
Right. So that was the moment. That was the line-in-the-sand moment. That piece of information created willingness in you.
Which is the first part of that equation, which is the "Why." Like, why do I care about my health? It added so much weight to me caring about my health.
But discipline is easy when you have that "Why" answered, right? If it were just that easy, I think that more people would be able to make positive changes in their life. But I think where it gets more complicated is when we understand beneath the surface that it’s our emotional lives that are truly the things that hold us back from accessing that potential.
You can be incredibly disciplined, but if you think you’re a piece of shit or you don’t deserve good things in your life, or you’re being impulsed by some trauma that happened to you—you were abused as a young person—that’s going to show up in your life as a barrier or an impediment from you doing the thing that you know you need to do to become the person that you could potentially become. So the head—discipline—can drive us so far, but if we don’t sort out the heart and what is making the heart beat, what is making us move in one direction versus another, and untangling or detaching or transcending the emotional baggage that is the true impediment to our growth, discipline is only going to take you so far.
You became an ultra-endurance sport athlete from that point of where you couldn't walk up the stairs without losing your breath. What was that transformation?
After that moment, I decided to take responsibility for my well-being, and thus began a pretty long and inelegant and nonlinear process of, first, trying to figure out how to eat in a way that would allow me to feel good in my body.
That began with a seven-day juice detox cleanse. Not because I felt like I needed to detox anything, but I needed to recreate the experience of detoxing off alcohol that I had in rehab. I needed to do something that was going to be hard and uncomfortable, and not eating and just drinking juice seemed like a good way to accomplish that. I’d never gone a day without eating food before. That was an experience where I was incredibly uncomfortable and I felt horrible for a couple days, but on the seventh day, I felt amazing.
I couldn’t believe that only drinking juices for seven days could result on day seven in this boost of vitality and mental acuity that I hadn’t experienced in a long time as somebody who was eating cheeseburgers every day. That made me want to figure out a way to feel like that all the time. I ended up trying a bunch of different diets, and what worked for me ultimately, after trying many different things, was going entirely plant-based.
I’m not here to tell everyone that that’s what they should do, but that’s what agreed with me, and that’s the way I’ve been eating for the last 16 years. This approach to nutrition restored my vitality and gave me a renewed sense of energy, so much so that I had difficulty sitting still and finally wanted to move again. I pulled out an old pair of running shoes from the closet and just started moving my feet again, and I went back to the pool for the first time in a very long time.
I was just connecting, frankly, with these things that brought me joy as a young person. I was a swimmer, and I hadn’t done it in a long time, and I’d forgotten what it feels like to jump into a swimming pool on a sunny day and feel the water and connect with my breath and move my legs on a trail at dawn. I really loved it, and I felt like that was a journey towards answering these questions that I was having on the existential front about what I was going to do with my life. Because I had a lot of confusion at that time, and just the mental space of being alone with my breath in the pool or on a trail running was very healing for me.
I had no aspirations of becoming a competitive athlete with it; I just wanted to feel good. I wanted to lose this gut, frankly, for vanity reasons; I didn’t like how I looked in the mirror. And the weight came off really quickly, and I felt like I was making incredible progress athletically week after week after week.
And then one day I went out, like maybe six months into this experience, and I was just going to run for like an hour. I had one of those days—you’re an athlete, you know those days where you just feel like you just are bulletproof and you can go, go, go. I just kept running and ended up running the better part of a marathon that day—like 24 miles. I’d never done anything like that before. Despite having been a swimmer, I’d never been a runner.
That was a real watershed moment where I thought, "Wow, I feel really good. I didn't know that you could feel this good, certainly not at age 40." And that got me thinking about potential. I had never really realized my potential as an athlete in college because alcohol really destroyed my swimming career. So there was a sense of unfinished business there, but I just wanted to see what I was capable of.
That set me on this journey to find experiences where I could tap into that. That's where I discovered this whole world of ultra-endurance and these crazy races, and I became fascinated with that and ended up competing in this race called Ultraman, which is a three-day double Ironman race. That’s the race that I ended up distinguishing myself in.
Really the instigating point in that was reading an article where David Goggins had done that race back in 2006, I think. It was the story of how he got through that race that really inspired me. Because he wasn’t the traditional endurance athlete triathlete, I was able to convince myself that if he could do it, that maybe I could. That set in motion me training for this race and competing in it a couple times.
I've had two guests come here and tell me that we’re in a "comfort crisis." What they mean by that is they say that we’re kind of optimizing our way away from comfort in every sense of the word. We live in these room-temperature rooms where we can go on a piece of glass and get someone to bring us our food in a metal car right to our doorstep. In fact, discomfort and pressure is where our growth, our health, and all of these things—our fulfillment in many cases—comes from. Doing an ultra-endurance race is for me, you know, the epitome of pressure and discomfort and sitting with that and accepting it. Do you believe that more of us should be making ourselves uncomfortable in that context more often and that there's tremendous value in that?
100%. You don’t grow unless you go out of your comfort zone, and that’s in every facet of your life. If you want to become smarter, you have to read books or go to school; that’s not always comfortable. There’s a million different varieties of this, but yes, we are in a culture that prioritizes comfort and luxury and it’s all about making our lives easier.
Ironically, what makes us happy is putting ourselves in difficult situations—not so difficult that they capsize our lives, but difficult enough that we’re testing ourselves. We’re grappling with obstacles and we’re overcoming them. On the other side, we feel a boost in self-esteem. We feel more ourselves, we feel more alive. We experience growth and connection with self and connection with other people.
This is the stuff of life, and yet it is not the way that society is constructed. We have to go out of our way now; we have to seek these—it used to be this was everyday life just to survive, right? And now we actually have to pay money and travel to places to have these experiences.
What’s so amazing is that when I started doing these ultra races, they’re all very kind of low-key, under the radar; there’s not a lot of media attention on them. It’s a subculture that has been around for a while. But in the last decade, we’ve seen an explosion in interest in doing 100-mile races. There’s lottery now to get into a race where you have to run 100 miles! Like if you had told somebody in 1800 that this was going to be the case, they would think you were insane, right? So what does that say? It tells us that we feel nourished by doing hard things. We are extracting value from those experiences that we don't get in the mundanity of our everyday lives.
Yes, we have to consciously extract ourselves from the comforts of our environments and put ourselves in those positions. But the good news is there’s lots of those things right now. It’s insane how many marathons—the London Marathon was the other—like how many thousands of people ran it? And then there’s the Spartan Race and there’s just a million of these things now that didn’t use to exist because the human spirit needs it, it demands it. We have too long deprived ourselves of these types of scenarios. That doesn’t mean that you want to be unsafe or put yourself in peril, but I just don’t see any other way or any other path towards becoming the better version of yourself without placing yourself in scenarios in which you’re tested. Because succeed or fail, you have an experience that’s going to teach you more about who you are, what your limitations are, and what your capabilities are.
The popularity of these endurance races and even things like ice plunge pools and stuff... all these things that make us feel really uncomfortable. Again, it reminds me of what I said earlier because there’s been a real rise in sort of social media and the digital screens and all these things. Now people are looking for places for community—so bowling alleys and in-real-life events have increased. In the same way, because we’ve optimized our lives to be more comfortable and easy, now there’s a booming industry around things that make us feel uncomfortable. You said, "I didn’t get into ultra-endurance sports to win races, beat others, or stand atop a podium. I got into it because it’s the perfect template for self-discovery." What did you discover about yourself? And also, I think it’s probably important to say to people: You’re really, really good at this ultra-endurance stuff. We haven’t quite gone through your CV yet, but I mean, I’ve got a list of accolades that you’ve achieved, and you’re one of the best at this. So I think that’s worth saying before we proceed.
Yeah, thank you for that. I mean, I think I’ve learned so much. The amazing thing about endurance athletics is you have to spend a lot of time with an elevated heart rate that’s not so uncomfortable that you can’t perpetuate it for hours and hours and hours, but is just uncomfortable enough where you’re sitting in that discomfort and you have to develop a tolerance for that.
So what it does is it teaches you how to suffer, how to manage pain, but also how to be with yourself. When I was training for these races, I would go out like all day alone, and it’s just you, your breath, and your mind. At that time, I really was trying to figure out—I can’t be this lawyer anymore; like, what am I going to do? All I know is I really like doing this; this is not a career path. This is not—I’m not going to support four kids doing this thing that I love.
But it is bringing so much value to me that I just know I want to keep doing it and I’m going to pay attention and pull whatever threads show up. What I learned through this journey of training—most importantly the training; the races are just a demonstration of what you put into getting to that point—was on a surface level, as an athlete, I had a lot more to say than I ever believed that I could. I was able to do things I never would have thought possible and do it in my 40s, which is an age where people think you’re way past your prime.
So that was huge. Like I said earlier, that opened up the possibility of tapping into potential in other areas of my life. But I also learned that when you cultivate and nourish that thing that is bringing you joy and you pay attention to the subtle voices that are telling you "This feels right," when you commit to that completely, that will set you on a journey that will lead you to a place you can’t possibly imagine.
When I put on the running shoes for the first time and just thought, "I love doing this," could I have imagined that I’d be sitting across from you right now having a conversation? It’s ridiculous; it’s preposterous. So what I learned was the power of connecting with the heart. As somebody like yourself who lives in their mind and prides themselves on their intellect and their analytical abilities, understanding the limitations of that and finding a way to really pay attention to those kind of more ephemeral, ethereal messages that one will receive when you’re really quiet, you’re really honest with yourself, and you’re committed to taking actions that are in alignment with that in a way that maybe you never prioritized before. That has been a path that I’ve blazed for many years at this point that has caused suffering and hardship but also beautiful creative offerings and a life that I could have never imagined for myself.
Metaphorically, it sounds like you almost ran away from your career in law.
Yeah, I guess so. I guess so. The law and me... I don't like conflict. I don't know how I became a lawyer in the first place. I could will myself to *be* the lawyer that I was, but it never felt right to me, and I knew that I wasn’t in the right situation for myself. It took me a really long time to walk away; I probably walked away from it over a very extended period of time. It wasn’t a very dramatic split.
I was trying to figure out from the point of when you start doing the ultra-endurance racing to the point where you get into financial hardship, 45 years old, you launch your Rich Roll podcast. You've got this law job, you start ultra racing, there's financial hardship. Is that because you quit the law job, or is that because...
Because I was a bad lawyer. Okay, here’s what happened. So I did exit the big law firm thing, but I continued to practice law as a solo practitioner and then in a couple different incarnations of partnerships with a couple people. But as I got more and more immersed in the ultra world, my enthusiasm and interest in my law practice continued to dwindle. I was my own boss at that point, practicing law, so not a lot of new clients coming in.
I was still doing it, making just enough money to get by, but wasn’t doing great because I just wasn’t into it. But I held onto it for a very long time. When you’re holding onto it, it’s hard to get into the new thing until you’re really willing to let go of the other thing. But making that transition was very challenging even after *Finding Ultra* came out. I completely severed my ties with the law at that point, but the phone wasn’t really ringing that much and there wasn’t a lot of opportunities coming my way.
It took a lot of patience and faith. I did the podcast for years before we were able to monetize it or do any kind of ads or anything like that; I just did it as like a fun hobby or project.
What was it like for Julie during that period between 2008 and 2015? Things are really tough financially. You almost lost your house, couldn’t pay a lot of your bills, had your cars repossessed.
Yeah, it was very difficult. She was really the strength in that equation because there were multiple occasions where I couldn’t take it anymore and I thought, "This is ridiculous. I need to go back and get a law job. What kind of head of household or man of the house am I if I can’t even pay the bills and I’m chasing this fool’s errand in this direction of trying to do these creative projects or be this athlete? Who the hell do you think you are?"
Julie was the one who was like, "No. We've come too far for you to move backwards. The answers that you are seeking and the solutions to the problems we face are only going to be found by continuing to blaze the path that you've established for yourself."
She had a conviction and a belief and an ability to see the more actualized version of myself that I couldn't at that time. Without her strength, her faith, her conviction, I definitely would have abandoned the path. But she was in all the way. She would say, "These things are just things. You're definitely on a path that you should be on; I can see that and I want that for you. If we lose the house, we lose the house. Cars are cars. This stuff comes and goes, but we're together and we're going to walk this path. This is what we're here to do."
Which is a fucking amazing thing for a partner to say to you. To have that kind of belief in you is such a gift. So I just can’t emphasize enough how powerful she has been in this whole thing.
Of all the things you’ve accomplished in your life, of all the things you’ve done, what does she mean to you?
I mean, she's... she is my partner in all things. She's my North Star. She's my spiritual counsel. She's my mirror. Yeah. And we’re normal people with kids who bicker and argue and have the same kind of issues everyone else does. But she’s a really special person. Really special.
It's really something when someone can see the potential in you in a way that maybe you can't see it at that moment in time, or maybe you don't quite believe it.
It is such a gift. They say the greatest gift you can give somebody is your attention. But if you have somebody in your life who believes in you so thoroughly that they can see past whatever situation you’re in or whatever faults you have or things that trip you up, and holds a vision for that better version of you—and not only holds it for you, says, "I believe in you"... they’re not telling you what to do or how to do it, they’re saying, "I believe in you and I trust you to find your way towards that person, and I am holding that for you in my daily consciousness, in my sleep, in my thoughts, in my prayers." That’s a very powerful energy.
It's a curious idea that someone else can manifest your life for you in a kind of inadvertent way. I've experienced that as well—there’s been moments in my life where my partner has said something to me, I’ve heard what she said, I didn’t believe necessarily myself, but because *she* believed that I could do that, maybe it *did* change something in me. Maybe it did make me go, "I trust her, and she’s smart and she’s usually right, and she’s telling me that I can do this thing, so maybe it *is* possible." I can remember so many conversations over 15 years where someone said something to me about what my future will look like, and because I trusted them, I think it helped that future become a reality.
Sure. I mean, just imagine the young person who has the opportunity to be with a certain teacher and that teacher says, "You can do this. Like, you're good at this." There’s countless stories of people who win Oscars and get up and thank their whoever who said, "You should keep doing that thing." Those are really powerful gifts that we can give to other people.
"He believes that if you follow your true path, the universe will support you." Quote I read about you as well.
Yeah, I do believe that. That's been my life experience. I’ve seen that manifest in many people that I know over the years—a lot of people in recovery. That doesn’t mean that it’s easy or convenient or on your timetable. I would say that the path that I’ve pursued has been the hardest path I could have imagined. It’s the most meaningful and fulfilling, but it didn’t happen overnight. It happened over the course of more than a decade, and it required a lot of conviction and faith and patience and pain.
We had to lose a lot. But there’s that adage, like: You can't be a Phoenix if you don't burn in the flames first, right? And I feel like we had to burn in the flames or burn off the residue of whatever in order to be reborn to do something different. I think when you have run that type of gauntlet and you emerge on the other side of it, what you have to share with other people is all the more poignant because it’s your own lived experience and it’s authentic and real.
So many chapters in your life, Rich. So many of them. We’ve been through pretty much all of them so far, and we arrive now at today. Now, if I was to ask Julie what the next chapter looks like, or you... I know, it’s funny because when people ask me this, my instinctive answer is "I don’t know, but I’m going to do my best at what I’m doing now." But if you were to try, if you think back to your mission—the mission you described at the start of this conversation—what do you think the next chapter is for you?
That's a great question. I think for me, the challenge and the opportunity comes from learning how to let go of striving and step into a place of *allowing*. Rather than being this animal of self-will who’s pursuing and achieving and pushing and really kind of in their ambition to manifest something for financial security, for legacy, whatever it is—to ease off that gas pedal and just be in a place of ease with everything where it doesn’t have to be hard.
What would it feel like if you didn’t push, but you still did the thing? Would you still be you? Would you feel like you left something on the table because you didn’t suffer to create the thing that you share with the world? I think that is so hard for me, and I imagine might be a difficult thing for you to digest for yourself, right? Because we both know if I go out and I push really hard, I can do something and I can make it great, and I’m pretty sure what the result of that is going to be.
But what if you created out of a sense of joy and you didn’t have to exhaust yourself in doing it? You could enjoy your friends and your family and live a rich life without the stress that you place upon yourself, or the pressure, or the people-pleasing, or the need for any kind of external validation. So that’s the mountain that I’m trying to climb right now, and I would say that I’m not doing it very well.
Why do you want to climb that mountain, though? That’s the mission.
Because I think that there’s a lot of wisdom in being more in flow as opposed to willfulness. I think that there’s a peace and a happiness to be found there that I’m probably missing in my life right now. And because it’s new territory to be explored. I know what it’s like to do this other thing, and it’s exhausting and it’s not sustainable. I believe that there is a better way over here.
So am I in enough pain with this where I’m willing to entertain the possibility of trying something different, or am I holding on too hard to this old modality and unwilling to embrace the possibility that the result and the fullness of life could be better by this different way of approaching things?
Has there been personal symptoms that have encouraged you to seek out another way of being?
Sure. Yeah. I have tiptoed up to burnout a couple times with the podcast, and that’s been ameliorated by now having a staff of really talented people to help me. Because I was a control freak perfectionist who tried to do everything myself for too long to the point of it just being completely unsustainable. To now having people that I empower to do a lot of the work that I used to do and who now do it very well, which has freed up my time.
And 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 suffered more. I think that’s a lie, and I want to find out if it’s a lie or if it’s true.
Thinking back through endurance racing, it seems to be that it might be true. You achieve that through pain.
Sure. Discomfort seems to be the first hurdle to all the good places we want to go. But actually, that’s very comfortable for me. The *real* discomfort is to see what it would be like without the suffering. That’s harder to do. Yeah, it’s harder to do for me and you.
I often ask my guests: Are you driven or are you being dragged? Saying you’re driven is a nice way to frame yourself—that’s like an intentional person. But so often we’re actually being dragged by the insecurity, the shame, that desire to be enough. We’re like strapped to the end of the lorry and it’s flying down the highway, but we think we’re in the driving seat.
I think in so many facets of my life right now, I know I'm—well, I suspect I'm being dragged, but I think I'm being driven and I'm portraying an image of it. Even the podcast, you know. Do I have to be so neurotic and obsessed with every thing and every detail? You said it before we started—you’re very obsessed about the detail. The fact that when we do the podcast in L.A., we have every book is the same in the same order.
§02Transcript — part 2
You know that's insane. I mean, it's a great story, it's very entertaining, but it's fucking bananas, dude.
But for me, it's—I’m probably going to try and justify it here—but for me, it’s about... I know that the small stuff is the stuff that most people don’t think about, so it’s my place, it’s where we find the opportunity. But generally, of course, I think about all the things I do, all the businesses, all the details, to the point of some level of suffering. There’s definitely a cost to my personal relationships when at Sunday, when I’m on a date with my partner, I get a message and something’s not quite right and then I lose 30 minutes in despair, like silent despair to myself in my head; I just leave the dinner table. That’s not a great way to live.
Right. I relate to that deeply. So I’m right with you in lockstep with that. But what if you were to say: "It's okay. It's okay."
But then everything, the whole house of cards caves on top of itself and all the good things in your life could disappear. That's what I think!
I know! And I’ll say, well, all our ancestors, they built these skyscrapers and this AI stuff and these cameras that we're using, so we're innately meant to struggle forward. That's hardwired into us. It's why I'm here. My ancestors struggled forward, they built buildings and civilizations, and they left that in my genetic code as a little message saying: "You too shall struggle forward, Steven. You too shall be wired to climb upwards."
Do you feel that to enjoy your life is an indulgence that’s fine for other people, but you’re on a mission, so you can have a different relationship with those aspects of life that other people find important?
I think so. Yeah. Is that bullshit? Do you think I'm bullshitting?
No, I’m just seeing if you see the world the way that I do. You know what I mean? But what are you, 30? How old are you?
I just turned 30, yeah.
Yeah, so I'm 56, dude. You know, so check in with me in 26 years.
What advice could you give me? If we've got the same mindset.
Look, I think it’s great that I’m all about the details, and I just want to say for the record, I shared it with your team earlier: I think that what you have built here is extraordinary. I have so much respect for not only the show, the way you comport yourself, the way that you are curious about the people that you talk to, and the fact that you’ve built this incredible audience in such a short period of time and the integrity and the quality is fantastic.
A lot of that is because you *are* attuned to the details. I see that in you, and I think there’s something beautiful and wonderful about that. The trick is to not allow it to become toxic to the point where it starts to denigrate the quality of your life. So can you toggle it such that you’re still pursuing what’s important to you in a way that’s sustainable? Because you want to be doing this for a long period of time, right?
So after five or six years or 10 years, what is your relationship to this thing going to be? If it’s not sustainable now where you feel drained at the end of the week rather than energized, then maybe you’re a brilliant business person—look at the model and figure out how you can tweak it so that you can stay in love with the process. I think for me, it’s all about enjoying it for what it is and detaching from all the externalities.
If I start looking on Spotify or Apple at the ranking, all that kind of stuff, I know that I’m in a dark place, right? I shouldn’t be comparing myself to other people; I should just be present for the experience of having these conversations and trying to deliver value to the people who are taking time out of their day to listen. That’s it. Doesn’t have to be any more than that. When I get caught up in that other stuff is when I start to make decisions that begin to become out of alignment with the mission.
Thank you. Thank you for that advice. And thank you for such a rich, wonderful conversation. I think especially that closing piece of advice is something that will resonate with everybody. I've thought a lot actually starting out my career as an insecure young man that wanted to make millions and thinking that life was this kind of sprint where you can—everything else can wait, including relationships, social connection, romantic relationships, family, while I get this thing. Getting the thing and realizing that the thing just moves forward off into the distance like a mirage.
Then I’ve read Simon Sinek’s book about infinite games and thinking, okay, how would I design every system in my life so that I could run those systems for 40 or 50 years in a sustainable way? This is one of them. This podcast is one of the systems where I need to continue to remind myself that I need to design it in a way that is sustainable for 40 years of my life, including the period where I have seven kids and a mortgage and a wife that needs me to be there, and also not just for me but for all the people that work here as well. Everyone can relate to that, especially people that are being "dragged" in some way.
Beautiful.
We have a closing tradition on this podcast where the last guest leaves a question for the next guest, not knowing who they are leaving the question for. The question for you is: You get a 60-second phone call with a previous version of yourself. What do you say? You then get to pass the phone to someone who is in your life at that moment, and you get 60 seconds to speak to them too. What do you say?
I think I would call up the 18-year-old version of myself and tell him that it’s okay to be who you are. That you don’t have to live up to anybody’s expectations. That you don’t need to earn love. And the best gift that you could give to yourself would be to find out what you love, to discover the animating force within you, and above all to nurture that. To mute out all the noise of the external world, the social and familial pressures, and to just find a way to be comfortable with who you are. Because who you are is 100% fine, and you don’t need to be anyone else in order to be accepted or loved.
The corollary to that would be to not get caught up in trying to make decisions about the rest of your life or your career path at such a young age, but to instead explore and invest in as many experiences as you possibly can. To live lean and to be adventurous.
And then I would say: Put your mother on the phone. And I would tell her, "I know you love your son, but you've got to leave him alone and let him be him."
Why would you say that?
How many hours do you have? I understand. Rich, thank you so much for an incredibly life-changing conversation in many ways, but for your honesty and your vulnerability and for all the work you do because it's people like you that pave the way for what I do here, and we're big fans of yours. That’s why I reached out to you and wanted to have you on the show. I’m so privileged and honored that you said yes.
I freaked out a little bit when you responded because I’ve spent a lot of time watching a lot of your episodes. I love the way you do what you do; the integrity in which you do it shines through. Everything you said to me today about authenticity and being more aligned with yourself now makes perfect sense. It makes sense as to why what I’ve seen from your content and the way you’ve lived and the man that I’ve met today—I see the alignment. So thank you for the inspiration and thank you for the kindness and generosity today.
I really appreciate that, Steven. That means a lot. I have crazy respect for your mission and what you guys are doing here, and I've loved watching your trajectory. It was a real honor to come and talk to you today. And man, you're good. You're *really* good at this, man. You were like—I was like, "Wow, what did we talk about?"
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