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Turning 40 and Recognizing the Person in the Mirror Matters
Episode 5511th July 2023 • Forty Drinks: The Podcast About Turning 40 • Stephanie McLaughlin
00:00:00 00:45:50

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After surviving a challenging childhood, David Richman achieved success as an executive at a Wall Street firm. His personal life, though, was a mess. He was a stressed out, overweight smoker with low self-esteem who spent most of his life trying to please others. While he learned many lessons in his professional life, he never thought to apply them to his personal life. Looking back, he says it’s amazing how much he accomplished in relation to how little awareness he had of himself. When that awareness of himself kicked in David says he was enthralled with the idea that he could actually matter. “Until you believe that you matter, you don't. And, I just didn't know that I mattered.”

Guest Bio

David is an author, public speaker, and endurance athlete whose mission is to form more meaningful human connections through storytelling. His first book, Winning in the Middle of the Pack, discussed how to get more out of ourselves than ever imagined. With Cycle of Lives, David shares stories of people overcoming trauma and delves deeply into their emotional journeys with cancer. He continues to do Ironman triathlons and recently completed a solo 4,700-mile bike ride.

Turning 40 and Recognizing the Person in the Mirror Matters

In this episode of the 40 Drinks Podcast, I had the pleasure of talking to David Richman, a man who transformed from an unhappy overweight smoker to an endurance athlete. David's story is a testament to the power of self-reflection and the will to change. His “forty story” is filled with lessons about self-worth, resilience, and the importance of taking care of yourself.

Here are some of the key highlights from our conversation:

  • David's early life was marked by challenges and obstacles, some self-imposed and others a result of his upbringing. Despite these difficulties, he managed to become an executive at a major Wall Street firm by his early thirties. However, his personal life was a stark contrast to his professional success. He was overweight, a smoker, and in an abusive relationship.
  • A conversation with a friend served as a wake-up call for David. His friend pointed out that David was the problem in his life, not the people or circumstances around him. This prompted David to take a hard, honest look at himself and his choices.
  • David began to question his decisions and his lifestyle. He realized that he had been living his life trying to please others rather than focusing on his own happiness and well-being.
  • David's journey to self-improvement began with a commitment to quit smoking and lose weight. He decided to become an athlete, a goal that seemed far-fetched at the time but would later become a reality.
  • David started his journey towards becoming an athlete by buying a pair of running shoes and gradually increasing his running distance. He later participated in half and full Ironman races, 50-mile runs, 100-mile runs, and a 5,000-mile solo bike ride.
  • Realizing that no one else is watching or judging him was both freeing and empowering.

David's story is a powerful reminder that it's never too late to change your life. His journey from an overweight smoker to an endurance athlete is a testament to the power of self-reflection, determination, and the will to change. 

If you enjoyed this episode, please remember to rate, follow, and review the 40 Drinks Podcast. Your support helps us bring more inspiring stories like David's to our listeners.


The Forty Drinks Podcast is produced and presented by Savoir Faire Marketing/Communication

You might like: David's book, "Winning in the Middle of the Pack," in which David describes how to push forward when nobody's paying attention, when the only person who cares is you, and when you are free to become extraordinary for yourself. 

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Stephanie: Hi David. Welcome to the 40 Drinks Podcast. I'm really pleased to chat with you today. Thanks so much for being here.

David: Thank you Stephanie.

Stephanie: You're not my first Ironman so I'm curious to know what it is about, gosh darn Ironman, that people turn 40 and think, I gotta start doing this, but we'll get there.

David: Sure. Sure. Sure.

Stephanie: Why don't you start by telling me a little bit of background, your formative adult years - like how did you get to where you were in your early to mid thirties? Let's set up the setup.

David: Sure. So early to mid thirties, by then I had kind of overcome a bunch of obstacles in my life, which were some of them self-imposed, some of them left over from my childhood. I was pretty much starting at the end of the line, or a little bit later than everyone else. I didn't really have any guidance or direction from my parents. My parents were nearly 40 years age in difference. When I was born, my mom was 21 and my dad was 59. So there was a big difference. The way I like to to say it is my mom was too young to have kids and didn't really like 'em anyway, and my dad was too old to have kids and really didn't want them anyway. So, my sister and I grew up in a household where it's like you don't ask questions and you're not told very much. So we were kind of behind our peers. I never really kind of dialed into things, but by the time I got to my early thirties, I'd come through a whole lot of problems, a whole lot of issues that I had a lot of difficulty. Some of it life threw at me, some of it I went searching for, but by that time I was an executive at a major Wall Street firm. I used to say that I only pretended to be the smartest guy in the room cause I was the only guy that didn't have a college degree, but I was running a hundred million dollar business for a major Wall Street firm with hundreds of employees and was very successful in work. But in my personal life, um, I was pretty much of a wreck.I was overweight, I was a smoker. I didn't have much self-esteem. I had focused pretty much my whole life on trying to please others, probably left over from my childhood. Um, looking for problems to solve so that I could feel some self worth, maybe looking to try to make other people's problems go away or try to make them be happy cuz that's how I got my gratification was to think that I was, you know, helping others. And then I ended up being in a relationship with someone that was, you know, pretty bad for me. Probably in retrospect, no doubt that it was pretty close to a mirror of my mother. Married an abusive alcoholic that was just unpredictable from day to day. Had four year old twins, and then I just kind of was at the end of my rope. I was overweight, I was a smoker, I was stressed out, I was miserable in everywhere but work. And I just, kind of heard the right words, Stephanie, at the right time, that allowed me to kind of reframe the way I was thinking about myself.

Stephanie: Well, you've set me up to just, it's a softball, what were the words?

David: Well, I mean, we all have a moment, right? You embarked on this by accident, right? You just had a moment and then all of a sudden you look back and you go, that's the moment of clarity. But you didn't know it going into it. You didn't go looking for that moment.

So it was just one night I was sitting with a buddy of mine and he was listening to me complaining again about my life and people in my life and all the issues and the problems and everything that I had had. And he just, he just looked at me and he said, "man, I'm so sick and tired of hearing you cuz you're the problem. It's not them, it's you". And I went, what? Are you kidding me? You know, like this person, this and this person that, and blah, blah, blah, blah, blah. And he goes, "nah, man. He goes, listen, let me tell you something. Everything in your life is like a wild animal. You see this problem, you see this person, you see this thing and it's this wild, crazy animal. And you go, oh, I know what I'll do. I'll go get it, and I'll take it home and I'll take care of it and I'll feed it and I'll make it warm and I'll treat it nice. And then you go to pet it and it bites you and you wonder, why did it bite you? That's what wild animals do. Why don't you figure out why you keep looking for problems? Why do you keep finding the wrong people? Why don't you look in the mirror and see what your problems are?" And I went, oh, I had no idea.

Stephanie: Oh my God. Was this friend like 22 years older than you and lived on the top of a mountain and was a sage?

David: That's pretty funny cuz I used to call him Socrates cuz he would throw out all thesecrazy little nuggets. And yeah, that one was a real nugget because it just came so stark. Like, I probably heard that before. I probably thought it a thousand times, like what's my problems? But it never really hit me that the guy in the mirror mattered. But in retrospect I realized that, yeah, I lived my whole life thinking that my self worth was in the way that others perceived me. I gotta do this to make the boss happy. I gotta do this to make the mom happy. I gotta do this to be a better father. I gotta do this to be a better partner, whatever it is, but not focusing around who's the guy in the mirror and how does he think about it and how does he feel about it? And so when I went home and did exactly what my buddy told me to do, I looked in the mirror, I probably looked like an idiot. I stood there saying like, who are you? What the hell? What is your deal? And why do you keep finding all of these problems? And why do you keep being in these situations? Why don't you try to change yourself?

Stephanie: Did you literally stand in front of a mirror and talk to yourself out loud?

David: Yeah. I probably looked like a total goof, but yeah, I remember the night exactly. I put my kids to bed. They weren't quite five years old yet, and I remember just walking into the bathroom and leaning in and going, like, seriously? Like, who in the hell are you? And I stood there talking to myself for like an hour and a half.

Stephanie: Wow.

David: Yeah. Because I was kind of intrigued by the fact that I had never really seen myself. I've never really had that discussion with myself. And we think we're so aware that we were thinking, and we are, because we have this inside voice that's going like crazy but we don't ever pay attention to it. We don't put it out there. We don't see the words very often.

Stephanie: Mm-hmm.

David: And so when I'm standing there looking in the mirror going, all right, well you're, this is good and this is bad, but what's your problem here? And why did you make this mistake? And what's your deal? And don't you ever think about things and if you did think about 'em... I just had this open conversation with myself and I was kind of brutally honest and I had a lot of things that I was really proud of and that I admired about myself. I had a lot of things that I was really not happy with and that I did not admire about myself. And I took that assessment. I mean, it wasn't that one conversation and done, but that was certainly the start of it. It was just this idea that if I'm gonna make a change, if I'm gonna care about myself, I gotta start from a point of being honest.

Stephanie: Wow. Do you remember that first night when you were talking in the mirror, if you asked yourself a question, did you hear an answer? Did you get insights as you were talking to yourself or was it truly just a one-sided conversation at that point in time?

David: Oh, no, I had some answers, but I just, put 'em out there, right? I remember one question I said specifically was dude, you live near the beach, you're young, you're successful. You should be an athlete. If you're like in your late thirties, and you don't start now, you're gonna be like this stupid old guy that's trying to be a athlete when they're 70 hunched over trying to learn how to run. That's not gonna work. If you want to be an athlete, if you wanna be athletic, then you better start like now cuz you're so far behind.

Stephanie: Hmm.

David: And then I remember saying to myself, you make a lot of bad decisions cuz maybe you don't think about 'em, right? But boy, you make a lot of bad decisions. Maybe start thinking about your decisions a little bit more. So, yeah, I remember a couple very specific things I said to myself.

Stephanie: Yeah. Yeah. Was being an athlete something that you had been interested in since you were a kid? Like were you an athlete as a kid?

David: Not really, I mean, I was on the swim team, whatever, but I was never like athletic, athletic. First of all, I was a smoker and I was overweight, so I wanted to not smoke and not be overweight. I probably told myself a million times and I heard a million times people say, smoking is bad for you, you shouldn't smoke. But until I faced myself in the mirror and go, why are you a smoker? Literally, what are you doing? Why are you overweight? What's your problem? And I just kind of tied the two together. If you're an athlete, you can't be an overweight smoker, so if you don't want to be an overweight smoker, why don't you try to be an athlete?

Stephanie: Do you know why you were a smoker? Did you ever get internal insight to that?

David: Oh, absolutely. Absolutely. It was out of necessity actually, and then it just became a crutch that I didn't consciously do, it's just, I was that. When I was 18, I left home. I went to go find colleges that I could go to. I got off the freeway, Stephanie in Vegas, and like out of a movie, my car broke down. Followed some guy that worked at a hotel to his house. He fixed my car and I was on my way. And, an hour later my car blew up on the side of the road and it's a long story, but I ended up staying with this family that I met there, and then I got robbed at gunpoint of everything that I had. I bought a car the day after and I ran out of the house, I had nothing but that car and I had 56 cents and most of a carton of Merit 100s in the backseat. And I didn't have anybody to call and nowhere to go and no anything. And I just said, well, oh, well I figured it out. So I literally ate cigarettes for like three or four days cause I didn't have any money and I just became a smoker.

Stephanie: Wow.

David: And then smoking was, you know that thing you do? I worked in the restaurant industry, I worked in hotels, I did anything to make money. And that's what you do, you go on cigarette breaks, you're a smoker. And of course it was cool at some point, but then it wasn't cool and I didn't pay attention to it. Then finally I started paying attention to it, going alright, why, why do you wanna be a smoker? So yes, there was something behind what made me that there was more to it than what made me stop. But that was really what got me started.

Stephanie: How does a guy go from working in hospitality and hotels to running a Wall Street business with no college degree. What's that pathway?

David: Any of your listeners know this, right? If you have a passion to do something, you'll figure out a way to get it done. You just will. Now, sometimes your odds are against you, if you wanna be the greatest guitar player in the world, you could probably become the greatest guitar player in the world. But it doesn't mean that you're gonna be famous or something.

Stephanie: Mm-hmm.

David: The only thing that I felt I was really good at was effort. I could work harder than anybody. Effort. I could work harder than anyone. I could work more hours, I could recover better. You know, I could work 17 hours, take a two hour nap, and work another 14 hours, like no big deal. So how do you go from one to the other? You just work harder. That's the only thing I knew how to do, cuz I had to do it out in a necessity. I didn't have anybody to turn to. No money in the bank, no friends, no family I could call really. I mean a little bit, but not much. And I just figured it out. I just went from one thing to the other, and everything that I did, I just worked twice as hard as everyone and became a manager. Then I said, okay, well I'm going to go do this, and then I worked twice as hard as everyone and became a manager, and then just one thing led to another. I did it outta hard work, basically.

Stephanie: Interesting. So that night when you were in the mirror, what did being an overweight smoker mean to you? What did that represent for you?

David: Well, I know this is kind of deep, and again, it wasn't like in the moment a light shines a bunch of knowledge on you, but I know it sounds silly, but I don't know that I ever seriously took a hard, honest look at myself.

Stephanie: Hmm.

David: And if you take a hard honest look at yourself, you might see yourself for the first time. And I don't know that I knew I was that overweight. I didn't know that I knew I was that healthy, cuz I don't think I ever paid much attention to even noticing the guy in the mirror. Do you know what I'm saying? I know it sounds weird, but look at a horse of blinders on, they can't see anything around 'em. They do that so they can stay focused on here and, and that's what I was doing. I just stayed focused on the problem at hand and I never had developed the skills to understand how to put it all into perspective or to see it a different way. And I never measured myself on what I saw in the mirror. I measured myself on what I thought other people were reflecting back to me. So everything I did was to make them happy or to, to make sure I got their approval or to make sure that they gave me my worth. Does that make sense?

Stephanie: Oh, it does.

David: I wish that I was smart enough to have figured that out earlier in life, or if somebody would've mentored me earlier. All in my twenties and early thirties, I had learned a ton of lessons doing all the crazy things that I had done in business. I was doing things I shouldn't have been doing. Who doesn't go to college and runs a hundred million plus in revenue business for a major Wall Street firm with hundreds of employees, you just don't do that. Right? So I'd learned obviously, a ton of lessons, but it never clicked to try to apply them to myself.

Stephanie: How does one take a hard, honest look at themselves? How do you get past the lying to yourself and the talking yourself up and rounding off the hard edges and justifying the things that you're seeing? Cuz we can all justify ourselves into anything. How did you get beyond that to honesty?

David: It's really a great question because I feel totally fortunate that I was that unaware, that I was that dumb about myself, that I was that not schooled on the fact that you should worry about yourself first and then you can help everyone else. That concept was absolutely 100% foreign to me, and I guess I'm kind of grateful for it because when it hit me, Stephanie, it hit me like a ton of bricks.

Stephanie: Yeah.

David: And you know, I've said to my kids many times over, the most important person in the world, by far, is you. By far. You're living your life. Everybody else is living theirs. You gotta focus on you. And nobody ever told me to do that. So here I am, fast forward to my mid to late thirties, I accomplished a ton of stuff, I had learned a million lessons, I had led people through crazy things. It was really amazing what I accomplished in relation to the fact of how little awareness I had of myself.

Stephanie: Mm

David: So I'm kind of glad that I had that little awareness because when it came crashing down, I was like, oh my God, I've got this like vast amount of knowledge and now I have some awareness that I gotta fix the dude in the mirror. It was just so foreign to me. So it became really, I'm not gonna say addictive, but I was enthralled with the idea that I could actually matter.

Stephanie: Oh, that's an interesting statement.

David: Yeah. Because if you're overweight and not paying attention to it, you obviously don't care about yourself. If you're smoking and you have young kids, you don't care about yourself. If you're an abusive relationship, you don't care about yourself. If you constantly beat yourself up saying you don't belong in that room with everyone else, you don't care about yourself. I could give you a hundred other examples that I think I could relate to, that I know tons of people in my life could relate to this. Until you believe that you matter, you don't. And, I just didn't know that I mattered. Does that make sense?

Stephanie: Yeah, and it does. It's a little breathtaking actually. It's interesting the way you describe it. The fact that you had so little understanding that you mattered actually worked in your benefit because when you did decide to look at yourself, you hadn't built up all the stories, all the justifications, all the excuses, or the reasons, cuz you had never even looked that direction before.

David: Ever. I wrote this book called Winning in the Middle of the Pack, and it's this idea that at the front of the pack, like if you go to LA Marathon and all of a sudden they announce that Matthew McConaughey and Oprah Winfrey are running it, then everybody's watching them, right. Where are they gonna finish? And certainly everybody's watching like the person struggling to just make it before the cutoff. Everybody wants to see who finishes first, who finishes last, like the major celebrity. But everybody else, nobody cares, nobody's watching.

Stephanie: Mm-hmm.

David: And it was such a wonderful idea. It's like, well wait a second. If nobody's watching, nobody cares. Why am I doing it? Oh, I'm doing it for me. What the hell is that? Nobody cares and nobody's watching. Cuz I'm always thinking people are watching. They're not. But that's the way I thought, right? Everybody's judging me, everybody's watching me. I gotta do this because then they'll think better of me or whatever. Meanwhile, when you realize nobody's watching, nobody cares, how freeing is it cuz you do it for yourself.

Stephanie: Right. Wow. All right, let's back up a minute.

You have the night of the soul with yourself in the mirror, and you talk to yourself about being overweight, about smoking. What were the first couple of steps you took after that?

David: Well, so at the same time, my sister was diagnosed with terminal cancer.

Stephanie: Oh.

David: And here I was within this like week, maybe two weeks period, where I got myself out of that bad relationship, or at least to safety with me and my kids, and I started to look in the mirror and go, wow, the guy that's there matters. And then at the same time, my sister was diagnosed with cancer and one of my kids, my little daughter, I had twins at the time, they weren't quite five, she goes, Daddy, so I understand that cancer will kill June and smoking causes cancer, so why don't you stop smoking? You know, I would say it's probably one of the smartest things she's ever said and she wasn't even five yet. Right, So, I mean, you know, sometimes kids say that the smartest things. And I went, Hmm. You know, okay, I'll make you a deal, you quit sucking your thumb and I'll quit smoking.

Stephanie: She got the easy end of that deal.

David: She got the easy end of it. So it was just at that time, and so here I was seeing this open road of possibilities, like, wow, I could care about myself. Let's go find out who I am. And I thought, wow, this is great. And at the same time, June was gonna be on a very short road, you know? And so that dichotomy was really fascinating to experience.

Stephanie: So who did you start finding on that wide open road?

David: The very first thing that I did, Stephanie, was go get a pair of shoes cuz I figure if you're a smoker and you're overweight, you can't run. So if you run, you can't be a overweight smoker. Then I couldn't run even literally down the block. It just wasn't gonna happen. So a week later I said, okay, well, I'll try again. And I ran two minutes, and then I ran a mile, and then I ran two miles, and then I did a 5k, and then I did the 10 K. And I just started down the path. And what really empowered me was a couple of months after I quit smoking, I heard about this thing called on Ironman. But you can start out doing a half an Ironman, which is a 1.2 mile swim, 56 mile bike ride and a half marathon. And I thought, oh my God, those are athletes. Man, if I ever could do something like that, I'd be an athlete, right? That's what I wanted to be. Just a few months ago. I said, why don't you try to be an athlete? So I drive up to the race. And it's one of these wave starts. So I get there the night before, wake up in the morning and I go to the start line and I see the few waves that are in front of me and I go, oh my God. Everyone is like a Greek god or goddess. There's not an ounce of fat between any of 'em. And I'm like, oh my God. Like these are athletes. And then that inner voice came in that went like, you're just a fat smoker. You don't belong here. And people are walking around and they're looking all smooth and I'm like, oh my God, what the hell? I don't belong here. Everybody's gonna look at me and go, what the hell are you doing here? This is for athletes. And I believed it. That's the discussion that was going on in my head. Then the gun gun goes off, Stephanie, and the racers take off in the water, and of course a bunch of 'em are really good athletes. And they go, and then I look to the back and I go, oh my gosh, look, there's a guy flopping around on his back and there's another one scared to jump in the water, and there's another one's like swimming circles. And I'm like, well, they don't care. Why do you, why do you care? That was really empowering me to think nobody's watching, nobody cares. So the only thing that matters is me.

Stephanie: Hmm.

David: That's the only thing that matters, which is really, really empowering. So that was pretty much the start of it.

Stephanie: Did you finish that race?

David: I did! Fortunately, I've finished almost every race I've ever done. After that half Ironman, I did a full Ironman in November. Since then, I've done nearly 20 of 'em. I've done like 50 mile runs. A hundred mile runs. I did a 5,000 mile solo bike ride. I've done some really ridiculous endurance athletic events. A couple times I've had to quit, but very, very rarely. You just kind of figure out a way. I brought that lesson. Right. Work harder. Figure it out. You gotta get to the finish line cuz you know. You, you just, you just gotta do that. And I brought that to sport too, I'm not gonna win the race, but I certainly have to finish.

Stephanie: Yeah.

Do you get to call yourself an athlete now?

David: My bio says endurance athlete. I'd say I'm extremely athletic. I don't know if I'm an athlete. You know, I just did a half Ironman, two weekends ago, and somebody goes, oh my God, what time does the race start? I go, I don't know what time the race starts, I'm participating, I'm not racing. So, yeah, but I'm still, I'm athletic. I'm not, an athlete, I don't know about that.

Stephanie: How is it that one could complete more than 50 triathlons, 15 Ironman, 25 24 hour runs, 5,000 mile bike rides, and not be an athlete?

David: Well, like I said, I think I'm athletic. I'm not trying to degrade myself. Doing these kind of events is more of a mental and emotional journey for me than a physical one. Yes, it's physically difficult, but what I like about it is to see who I am and who I can be. And when you are faced with adversity, especially adversity that you bring on yourself, then you get to see what you're made of. How many people have started a diet and stopped? How many people have started a project and stopped? How many people have done something and life gets in the way and you go, no, it's just too tough. I don't have the time, whatever. And you stop.

Stephanie: Mm-hmm.

So when you bring something onto yourself, to be able to see it to fruition is a mental and emotional challenge at times, because you got lives to lead. But if you set a goal and you want to achieve it, and you're willing to do whatever it takes to get there. That's definitely more of a emotional thing and a mental thing. It just happened to be in the physical realm that I was doing it, but it's just as difficult to finish a book. Or finish a, I do mosaic artwork, a mosaic artwork, or to host a party or whatever you're doing, if you do it right and you do it to the finish, it's not really about that. It's about the mental, emotional, psychological struggles and benefits that you get from it. So I always looked at doing endurance events as good for my mind. It always let me solve problems. Interesting. So, is it all right if I challenge you a little bit,

David: Challenge. Go for it.

Stephanie: and I'm not even sure this is fully formed yet, but there's something about the way that you are describing this that I'm reacting to a little bit. When you talk aboutif you don't finish something. Finishing something versus not finishing something. I know that there have been periods in my life where, certainly in my romantic relationships, um, I have stayed too long. I have tried too hard. I have put in too much effort, all of those things and that was a pattern for a long time. And I remember one day sort of, you know, as I was on my personal growth pathway, I remember getting sort of a download of information. I was sitting in my convertible on a bright sunny day, pulling out of a parking lot, and all of a sudden just before I pulled out onto the street, I had this like flash in my head that said, you don't know how to quit.

David: Mm-hmm.

Stephanie: And it was like, oh, that was actually the solution to a number of my problems was that I was going to finish them no matter what. I was gonna be the one who put in all the effort and all the endurance and all of those things to reach what end goal, I don't know.

So I'm listening to you talk about the endurance, athletic events and the counterbalance being, if you start something and you don't finish and you start something and you don't finish, and I'm thinking to myself, well, actually in some cases, can't not finishing be the healthy part. So I'm, I'm curious to hear your thoughts on that.

David: No, absolutely. I totally agree with you. Know when to quit is a great lesson to learn, and know when not to quit is a great lesson to learn. I did a 4,700 mile bike ride and what I've learned, one of the things, I learned a million things on that ride, but one of the things I learned was how uncanny it was that when I had to figure out a way to get from point A to point B without help, that I could do it. And how uncanny it was that when I get to point A to point B and I needed help, man, I really needed the help. Right? There were a couple of times where I really needed help and there were a couple times where I really needed help, but I didn't have any, so I figured it out that I didn't need it. And I think that, that both knowing when not to quit and knowing when to quit are equally as important. It was a skill that I needed to learn, to say it was okay to quit. Know when to quit. That's an important skill to learn, and I like you, I in relationships, in bad decisions, I was so stubborn about having to be right or so stubborn about having to fix the issue or so stubborn about needing to be the one to see it to the end, that It was the wrong path. You gotta know when to quit. And I love that lesson.I've probably preached it a hundred times before I understood it for myself.

Stephanie: So tell me about some things that you have tried or even committed to and then quit or stopped or put aside for reasons X, Y, or Z.

David: I could tell you the very first long race that I quit was a stark lesson in being more aware and being conscious of your decisions and not being like, it's okay to get in over your head, but don't be that far over you. I mean, I learned a hundred lessons that day, but I signed up for a hundred mile run. I'd never run a hundred miles,

Stephanie: How far was longest you had run before?

David: At that point, 50 miles was the longest I'd ever run. So I decided a hundred's, only twice as hard. It's way more than twice as hard.

And it was in the hills and in Northern California and Tahoe, very hilly, changes in temperature and the whole thing. And being that I was not aware or experienced or very smart, about 15 miles in, as everybody is taking their shoes off to run through a creek, I'm looking around going, what are these idiots doing man? It's just a little bit of water. And I ran through the creek. And about mile 20, I realized, oh, you mean you're not supposed to run with wet shoes and socks that are wet, that fold over and cause blisters? Ah, got you. So I get to the aid station at mile 21. I'll never forget, I have a friend that will not eat jelly beans right now for the rest of his life cuz of this story. But I pull my shoe and sock off and the doctor comes over and he looks at me and he hands me a pair of scissors out of his jacket. And he goes, you cut that jelly bean off. I'm not touching it. A piece of skin the size of a jelly bean that come outta my toe. It was gross. It was absolutely disgusting. So I wrapped it up and I kept running and I got to mile 50 and I'm like, ah, this is the greatest thing in the world. And then I took off for the second loop, and about four miles in, that's when the missing jelly bean started to hurt and it hurt to the level that I can't even explain. All I could tell you is this: if anybody's ever gone for a run, scratch that. If anybody's ever gone for a walk, if you ever walked at a casual pace, you're walking about 20 minutes a mile. It took me four hours to go three miles.

Stephanie: Oh wow.

David: Four hours to go three miles in the middle of the night. I was crawling and crying the entire time. My little toe hurt so much, it brought me to my knees. And I crawled, stop, walk, crawl backwards, cry, you name it. Took me four hours to go three miles to the next aid station and I had to quit. And I was as miserable as you could ever imagine. And I said, well, okay, either you're a failure or you're gonna go home and figure out what the hell you could learn from this. And quitting was the right thing to do cuz I learned a hundred valuable lessons. I got a million stories like that.

Stephanie: Yeah. Yeah, I just wanna be thoughtful of people listening to this who might bein their own phase the before phase. Right. I just wanna make sure that we're clear that commitment is one thing and pursuing a goal is one thing, but there has to be balance or reasonableness there around if something turns out that it's not right for you, that it's okay to choose another path.

David: It absolutely is. And I wanna be really clear about this, Stephanie, I did not do this stuff to punish myself. I did it as a way to learn. The very first endurance athletic event I did that was of any note was a 85 mile roller blade race in Georgia. Who would ever do something stupid like that, right? Especially someone that's not an athlete. Again, these things sound trite, but they were just moments of inspiration and enlightenment for me.

I remember going as hard as I could and as far as I could in this race and about 35 miles in, I was a hundred percent spent, was done. I had no energy. I was dehydrated. I had no business being in this. I had no idea what the hell I was doing. And I remember standing parallel to the mountain cuz I would slide down if I wasn't, I was parallel to the mountain. I'm leaned over and I'm sweating crazy on the ground and I look back and there's the van that's gonna pick you up if you're too slow, and take you to the finish line. I said, okay, you got two options, dude. one is you gave it everything you got, now you know your limits and it's okay. You go back, let the van pick you up and take it to the finish line.

And then I go, okay, what's the other option? The other option is if you just figure out a way to take one step forward, you're gonna learn something new about yourself cuz you you're past any limit you've ever experienced in your life. And how cool is it to learn something? Like, wow, what am I made of? Or what could I do or what could I learn? And it just became like this, like really wonderful thought. So I took a step and then another, and then another and another, and then I went an hour and two hours and yeah, I stopped and I helped my myself, whatever. But I eventually got to the finish line and it was shocking. I didn't think I was proud of myself for getting there, I just said to myself, I just spent like the last five hours learning something new about myself. How cool is that? So it wasn't the pushing yourself beyond your boundaries. It wasn't the putting yourself in physical danger. I wouldn't do those kind of things, but I felt like I was learning. I was finding out who I was, what I was made of.

Stephanie: And what about that was appealing to you?

David: Because like we said earlier, I'd never focused on, I never cared about what I thought about myself.

Stephanie: Mm-hmm.

David: I didn't even know who I was.

Stephanie: And what have you learned about yourself? You've said I learned a hundred lessons through these processes. How about give me some of the first ones you learned as you started this endeavor.

David: Yeah. So first of all, know one to quit when know when not to quit. And then I thought about setting high enough goals, right? In business, if you tell someone hey, go out and accomplish X, if they're super capable, they're gonna accomplish X. And if you would've said to 'em, accomplish two x, if they're super capable, they would've accomplished two x. In business, we know that, right? Set a goal, people are likely gonna achieve it, the best people. Set a goal twice as high, the best people are still likely gonna achieve that. And so I applied that to myself going, maybe you're not setting your goals high enough. So I've learned how to set high enough goals. Like what's a stretch goal? Double it and figure out a way to get there. I like that idea because I don't think we set high enough goals for ourselves, and that's a big thing that I learned. Knowing when to ask for help.

Another goal I learned. So a guy who needs to fix everything and be the guy that's in control, and I don't wanna let anybody else down it, it's hard for me to accept help. And I learned that if you actually have people that care about you, accepting their help is an empowering thing. It's a strong thing. It's a good thing. You're allowing people to help you. Imagine that. It doesn't mean that you're weak. It doesn't mean that you're not capable. It doesn't mean that you're not in the position of power or whatever else, the million things are that guys especially don't want to ask for help or look weak.

Stephanie: Right.

David: It's like really you're offering authentic help and how dare I turn it down? What makes me so special that that I can't accept your help, but I can do everything for you. It's still a lesson I'm learning today, but that's a big lesson. I could go on and on. There's tons of those lessons.

Stephanie: Tell me about the impact of your endeavors on your family, on your wife, on your kids.

David: Yeah. Wow. That's a real big question that to deal with. My twins are grown now. They're nearly 25 years old. They're wonderful people. They're great kids. I think I've taught 'em some lessons. I think one of the things I taught 'em is to care about themselves first. You know, that whole silly, put your mask on first and, and then put it on others. I know it sounds silly, but it does make sense. I mean, if you're not happy, how are you gonna make anybody around you happy?

Stephanie: Mm-hmm.

David: If you're not working on yourself, then how can you help other people? You just can't be a hypocrite. You gotta put yourself first. So I think I've done that with them. With my wife, I've been very, very fortunate because she came around at a time when I was willing to question myself the way I did in front of that mirror that day. So every relationship that I was in, Stephanie was somebody that needed fixing.

Stephanie: And I wannaback up to that. So you were married to the mother of your twins

David: The twins,

Stephanie: and then as part of this process, you actually left that marriage, is that correct?

David: Yeah, I had to, it was just getting too dangerous for us, you know? It's just, it was too volatile situation. It was not gonna be good. So, yeah, it was a hard decision. But we jointly raised our kids up until the time when they said, Hey, can we just be with you the whole time? Cause I wanted to have them take a hand in that decision.

Stephanie: Mm-hmm.

David: But, yeah, we were on our own since they were five. And every relationship before that and every relationship after that, I still hadn't learned everything I needed to learn, right? One of the things I didn't learn was that, you know what, I don't need to find problems. That finding a wild animal and having to bite you thing, it took a long time for that to hit.

And I met my wife, we've been married now for six or seven years, and I met her and we had the worst date possible. The worst ever. I remember trying to give her a kiss goodnight, and it was the worst kiss in the world. I'm driving home and I'm like, well, dude, wait a second. She's successful. She's funny. She's pretty, she's smart. She seems super capable. I don't see any problems there. What is your deal? If that's what you want, what is your problem? So I called her up, she laughs about it, now I call her up and I go, "Hey listen, that was probably the worst kiss in the history of humankind. I do not kiss that bad. I need another date cuz I gotta show you that I am not a terrible kisser." She goes, that was a pretty awful kiss. And I'm like, oh, I know, but just let me explain to you what's going on. I kind of gave her a little, a little snapshot of that and so I, you asked me how, what's the effect been? Well, she wouldn't be in my life if I wasn't willing to accept the fact that I don't need to fix the person I'm with.

Stephanie: Mm-hmm.

David: I don't need to create the problem and then figure out a way to make the problem go away, you know?

Stephanie: Yeah.

David: Like, oh wait, she doesn't need me. That's, that's kind of cool. Isn't that what you want? Somebody that doesn't need you? So she came along for me at the right time and I'm very fortunate.

Stephanie: That's wonderful. David, I have so enjoyed speaking with you. Let me ask you one more question before we go.

David: Yeah.

Stephanie: If there's someone out there who's listening to this, who is feeling the same way or similar to how you were feeling in your late thirties, whether they're overweight or a smoker or in a terrible personal relationship, what kind of advice would you give to that person on how to find their way to the other side.

David: You know, it's great and I don't know that I would've taken this advice because sometimes people tell you stuff and you're like, great, put it on a yellow sticky and put it on the wall and, oh, so make me feel better, whatever. And I don't know if this resonates with anybody else, but it, it resonated with me that in retrospect and collectively what I've learned is one, I actually really did have that honest discussion with myself in the mirror. And I've had that discussion a hundred times since probably. One is have the honest discussion with yourself. Are you who you want to be? Are you living your best life? Are you authentic? Are you doing the activities that matter to you based on the things that you say matter to you? Like no judgment. if you don't want to be an athlete, then don't be an athlete. But don't go around talking to everybody about how you're gonna go to the gym every day. that's not authentic. So I think one is have an open, honest discussion with yourself. What's good about you? What's not, who are you? Who do you want to be? Number two, and sorry if this sounds prescriptive and a little canned, but it's not, I'm telling you its greatest feeling in the world is just forgive yourself. Just let it go, man. Stephanie, when you were having bad relationship after, bad relationship after bad, you didn't know until one day you went, the hell am I doing? Like you knew. And if you can, to the extent that you can, just forgive yourself. Just free your mind, let it go. You didn't know until then.

Stephanie: Right.

David: Why are you gonna beat yourself up? Okay, I'm never gonna run in the Olympics, but guess what? I can go run a hundred miles. Okay? Just forgive yourself. I didn't start when I was 22. I started when I was 38. All right? Just forgive yourself, let it go. Free your mind. And then the, the third thing, which is what drew me to you is I love how after all the things you've been through the number one quality you have is optimism. And for me, optimism is I kind of still believe that my next best day is ahead of me. My next best step, I'm gonna learn something. I'm optimistic that if I get it wrong, I'm gonna do better and get it right. So it's like honesty, free your mind, and then just bring optimism to everything that you do. And either you'reoptimistically,you're gonna get it done or you're gonna learn something.

Stephanie: Yeah.

You talk about the optimism. I've just today have had a little bit of a challenging day at work and a little bit of a setback with a client. And so I am doing two things right now. I am processing the disappointment and I am also understanding and giving space for the fact that I've just made room for something better. And right now, of course, disappointment is probably winning out and frustration because that's what happens when you have a setback. But even to have had that setback and immediately know that something better is gonna come and fill that space. I know that over the next couple of days and that's the one that will become primary. The frustration will process. We'll put it behind us. And that optimism for, all right, what's next and what's gonna fill that space. And I bet it's gonna be even better.

David: Yeah, and I just think you could be a realist still. You could be disappointed and you could wonder what the hell am I gonna do to fill that void or whatever. But then you go figure it out because you're going, you know what, I got no other choice. I'm either gonna try hard and it's gonna happen, or I'm gonna try hard, and it's not gonna happen. But by not trying, it's definitely not gonna happen.

Stephanie: Right, right.

David: I'm definitely a realist and we all have bad things that happen and I don't smile at every crappy thing that happens, but, you know, eventually I just go, yeah, I got two choices. I could either look behind me or I could look ahead of me and I just choose to look ahead of me.

Stephanie: That's great advice. Very thoughtful advice. I appreciate you sharing that with me and with everybody who's listening.

David, thanks so much for joining me today. I appreciate you being so generous with your story and sharing so much with us.

David: Oh, thanks for having me. Totally enjoyed being on your show, Stephanie, and I'm gonna count how long it takes me to get to 40 drinks.

Stephanie: Don't do it in one sitting. We're too old for that.

David: Yes. Too old, but I'm too, I'm too weak for that.

Stephanie: I, when I say too old, I mean, I don't know that our systems would handle it anymore. Right. That's, that's the kind of thing you leave for your twenties.




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