Failures Podcast

You’re Winning… So Why Do You Feel Broken?

Failures Media Episode 38

Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.

0:00 | 1:00:49

What happens when a man does everything right, builds a good life, and still feels like something is broken underneath it all?

In this episode of Failures Podcast, we break down the mindset of the broken overachiever — the ambitious man who looks successful on the outside but still wrestles with imposter syndrome, anxiety, old trauma, and the constant feeling that he has to prove himself.

We talk about the hidden cost of overachievement, how childhood survival mode can turn into adult success patterns, and why so many driven men still feel empty even after they get the job, the money, the recognition, or the title.

Rich opens up about how one moment of criticism triggered deep feelings of self-doubt, despite years of professional success. Justin reflects on how validation, ego, and the pressure to “make it” can quietly turn success into its own prison.

This episode is for the man who:

looks composed on the outside but feels pressure internally
keeps achieving but never feels satisfied
struggles to enjoy wins before chasing the next goal
wonders if ambition is coming from purpose… or pain

We get into imposter syndrome, toxic hustle culture, identity, ego, trauma, validation, and the difference between external success and internal peace.

If you’ve ever felt like you built a life that looks good on paper but still doesn’t feel right inside, this episode is for you.

Failures: The Podcast  2025
We're not gods. We're not gurus.
Just two men in our 30s sharing what we’ve learned the hard way—so you don’t have to.

🎙️ New episodes every week
📲 Follow @FailuresMedia on all platforms
 🧠 Join the movement: https://failuresmedia.com/subscribe

If this episode helped you, share it. That’s how we grow.

SPEAKER_01

And bro, they handcuffed us and took us to juvenile detention center. I was handcuffed at 11 years old out of the elementary school, but had a jumps tube put on me, fingerprinted, like I was a fucking criminal at 11 years old, bro. And I just remember being in the cell and I just remember thinking to myself, like, we have two paths. Either this is what's in store for us if we keep fucking around and making mistakes and doing stupid shit, or we could take a different path, one that could be more rewarding and has a bright future ahead of you. And that should change everything for me.

SPEAKER_00

Failures podcast. Today we're talking about the broken overachiever. Now, listen, not an atypical topic for Failures Podcast. Because if you're an overachiever, you're probably thinking to yourself, Well, Justin, this episode ain't for me. My life is good. I made it from the worst conditions. Look at my car, look at my house, look at my girl, look at my job title, look at my portfolio, look at my bank account. How the fuck can I be broken? Well, if you're successful and you're not broken, this episode's not for you. Shit, if you're broken but you've dealt with it, this episode is definitely not for you either. But this episode isn't for the guy who's failing or successful or has stability. No, no, no. This episode is for the other side of the coin. This episode is for the high achiever, the guy who lives in a silent contradiction. The one young man who sees himself as successful has all the accomplishments, but deep down inside is conflicted. He still feels empty, he still feels unfulfilled, he still feels like something's off. That guy is masking success with hard work. He's fueled by fear, fueled by anxiety. He's up at 3 a.m. laying up, thinking to himself at 3 a.m. Damn, what did that guy mean when he made that criticism of me? These little things that live in your head rent-free, a comment that someone made, if that can keep you up, then this episode is for you. You are a broken overachiever. I didn't make that example up in the intro of this episode. That is a real life example that came from someone in our community. Rich, do you know who that person was in our community that had that issue?

SPEAKER_01

That person was me just. Man, listen, a couple episodes ago, we finished recording, and I remember just venting to you, like, man, I have a lot of built-up anxiety. And you were like, what about? And I'm like, I have this presentation the next day, Monday, and I felt like the stakes were really high. You know, I've done this presentation before. It was met up with some criticism as to like me reading off the slides. So I really felt like I was being personally attacked. And I just felt like, man, I don't want to feel like a fraud to you know, my employer who I've I've only been in for a year. I just had a lot of built-up anxiety. I felt like I was dealing with some imposter syndrome, and you were like, Rich, calm down. Like, do you know your field? And I'm like, yes. You're like, did your employer hire you? And I'm like, yes. Then you're like, so why are you doubting yourself? And man, that was exactly what I needed to hear in that moment. But more importantly, that's what we're here to unpack. It's like, you got the job, you got the money, you got the success, but there's moments in your life where you feel like maybe you're not supposed to be here, or maybe you don't belong, or maybe you got lucky, and this is why you're here. It's that weird gap between how the external world views you versus how you view yourself internally. So I'm excited to jump into this one, Jess.

SPEAKER_00

Yeah, Rich. I have a few SEO terms that I was able to find from doing research, and SEO is just, you know, the common phrases that come up when you look up a topic like this. And I'm gonna read a few to you, and you just kind of, you know, let's go back and forth on why you think these terms come up so often when we talk about this subject, because it's a nuanced subject. It's almost like you survived a plane crash, you should be happy, but for whatever reason you feel guilty. And you mentioned the first one, which I wanted to bring up, which is imposter syndrome, survivor's guilt. Those are two. Another one that came up was the title of the episode, The Broken Overachiever, and then Toxic Hustler. What is it about those words that feels fitting for this episode and which one of them stands out to you when you think about yourself and why this episode is so important for our community?

SPEAKER_01

Listen, man, all of those terms fit the mold for me. And it's this weird thing, right? Like you can feel all these things, these labels, and still be accomplished, right? And still be motivated and still be disciplined. But just like the doubt monster, right? Which we also uh discussed in a previous episode, there's always that doubt that creeps in. There's always you questioning yourself as to are you supposed to be here? Should you have what you have? Like, did you stumble upon some luck and this is how you got to where you got to? And I think a lot of that comes from how you grew up, right? The things you were exposed to, circumstances monetarily, right? Like, did you come from a place of wealth or did you come from a place of poverty? And your entire upbringing sort of shapes your worldview. And unfortunately, when you evolve as a person and you do reach a pinnacle of success, you carry that old identity with you to this new life. So I think that's a common mistake that shit I'm still dealing with today.

SPEAKER_00

Yeah, yeah. I mean, the one that you discussed more, and I feel like there's a different part of this conversation that I think it feels more relevant to me. I can feel the salt on the wound of the phrasing the toxic hustler. That one, when I read it, I immediately pushed back on it because in my mind, it almost makes sense to work hard. It's like chasing something feels a lot better than standing still. But that's a me thing. And I I've learned the hard way that shit, most people that I work with, most people that I'm surrounded with every day, my friends, my family, they don't agree with this phrasing. Chasing an unrealistic goal feels better than standing still. And that one hit me deep, the toxic hustler, because I push it back every time I hear it. But there is something about it when you do the research, it's like, are you sure you're a hustler or you're just an adult trapped in the insecurities of a young version of yourself's body? And when you put it that way, that unlocks a whole door of truth that is behind it that I want to get into on this episode. So that one to me is big. I feel like I've trapped myself in a jail of someone that just doesn't want to be insignificant and doesn't want to be poor and doesn't want to grow up in an area that is violent. Or yeah, a lot of the childhood trauma I have, I think it shapes who I am as an adult. And then I've defined myself. And I think if you're a young man listening to this and you're in your early 20s or even your late teen years, and you're starting to define who you are based on all the validation that you get, be careful because that ego becomes something that you use to protect healing from these problems that you may have had when you were younger.

SPEAKER_01

Yeah, that's a great point. And I think we've attached our identity to the accomplishments, which is why we work so hard. And it's such a weird topic to discuss, right? Because in one end, you tie yourself to the accomplishments, but why are you doing that? In my mind, the accomplishments suppress the trauma, right? So the more you accomplish, the more goals you meet, the more you climb up that mountain, the further away you're getting from that childhood trauma, right? So you feel like the the more I win, the more I move forward, the less I have to worry about my upbringing and where I came from and my like negative circumstances. And I think that's part of like the toxic loop that you that you were talking about.

SPEAKER_00

Yeah, the it's almost like the imposter syndrome, it drives your success. It is the fuel that's driving you. And it's a double-edged sword because without the mouse being chased by the cat, the mouse doesn't run to its full potential. But without the cheese that's in front of the mouse that he's also trying to get, it puts you on this treadmill that almost is fulfilling. It's like, man, I'm running away from something that can kill me, and I'm running towards something that benefits me. So you can't really blame the mouse for being on this treadmill because the faster it runs, the more validation it gets. And then eventually you just become a slave to this process. This is how I see it. At 39 years old, soon to be 40 years old, I still suffer from this problem, Rich. I've been having this issue in my life since I was a teenager, and I have it to this day. And it almost feels crazy for me to call it an issue because it's rewarded me so much. Does that make sense? Like this has gotten me everything that makes me feel stable.

SPEAKER_01

Yeah.

SPEAKER_00

But I'm trapped in it.

SPEAKER_01

Yeah, and you you know why it's an issue because you're in this loop of following your dreams, goals, accomplishments, but it's never about those things, right? Like, how many times have you accomplished something and you you got a plaque for work and you sat down to actually celebrate that moment? You don't. You look at the plaque, you're like, oh, this is cool. You hang it up on your wall and you keep it moving. Like that is toxic, bro. Like that's the part about us that I would say is a bit broken. Like you have to have the self-realization to pause for a second and enjoy a win, right? Enjoy accomplishment, enjoy a goal. And part of I believe why we don't do that is because we feel like we're still behind, right? Like we just have to continue moving forward. Like we have aspirations of hopefully one day building a multi-million dollar media enterprise. And until that moment comes, we're not going to be satisfied. And I got news for you, Jess. When that moment does come, we're still not going to be satisfied.

SPEAKER_00

So, what are we doing this for? That's really what this episode, because I felt exposed when I was doing the homework for the episode. I'm thinking to myself the whole time I'm doing research, like, wow, there are clinical studies, there are psychological studies, there are doctors that have dedicated their whole career to this feeling, this imposter syndrome, this feeling of with every win I get, the more exposed I feel because I feel like I'm undeserving because of where I come from. And that is essentially what started this episode, right? It's one criticism of adult rich, the executive that gets paid good money, kind of brought out the young version of you that was very vulnerable and couldn't handle a criticism. And then, you know, your employer got to deal with the aggro and the and the pushback. And what we're dissecting is that gap between 13-year-old you and 38-year-old you. And why is your ego so fragile that someone called you out that you felt this need to feel exposed? It's like I said, whenever you win, you feel more exposed because you have imposter syndrome. You do feel like you don't deserve half of the stuff you got.

SPEAKER_01

Yeah, I mean, that's a great question. And I think a lot of how that comes up for me is just my upbringing and my circumstances. Like, I understand, like, bro, we're smart dudes. I understand that statistically, right? If you take the urban neighborhood of where we grew up, yeah, we're not supposed to be making the income that we make. No. Hell, we could have even been deceased if we had gone down a different path.

SPEAKER_00

Yeah, and I don't need the Census Bureau to come and tell me that I just gotta go back home.

SPEAKER_01

Yeah, exactly. So I think for a long time I've felt like an anomaly in like the matrix that is where we grew up and my circumstances and my mom being on every single government assistance possible. And I remember as a young kid thinking to myself, like, there could be more for us. There is more for us. Like, who's going to stand up for the family and go after something and change our last name? Somebody has to do it. And I have a personal story just that sort of sparked that change for me that to this day it almost comes up in different moments of my life. But like PTSD, like it just comes up a lot. And I'm like, damn, that was such a defining moment for me. Like it's small in nature, but I think in the grand scheme of things, it was a big life moment. But and I'll try to make a long story short. At 11 years old, right, in elementary school, fifth grade, hanging out with my friends. We used to do this thing like, oh, who got the most hops, right? Like who could jump the highest?

SPEAKER_00

Yeah, yeah.

SPEAKER_01

So one friend, there was like this device on the ceiling. One friend taps it, five seconds later, the fire alarm goes off. Fire department comes, they check the whole building, they don't see anything wrong, right? We were happy because we had to evacuate the building, we'd have to go to class. So about 15 minutes later, we all go back inside, we resume the game. And it was my turn. Tap the little device, alarm goes off again. This time, the fire department actually got into a car accident on the way to the school. Oh shit. Right? So it became an even bigger moment because it's like, why do we continuously have to come to the school because the fire alarm is going off, right? Bro, turns out that those devices were actually smoke detectors, right? And a couple kids snitched on me and the other kid who hit the smoke detector. So we got grilled for like two hours in the room with a police officer, fire department, and the principal. And bro, they handcuffed us and took us to a juvenile detention center. I was handcuffed at 11 years old out of the elementary school, taken to a juvenile detention center, but had a jumpsuit put on me, fingerprinted, like I was a fucking criminal at 11 years old, bro. And I just remember being in the cell, calling my mom, collect, and being like, yo, I don't know what I did, but like I know I'm in big trouble. Damn. And the next day I had to go to court. You know, I spent the whole 24 hours, but it got cleared up in 48 hours. My mom had to pay a crazy fine. And I just remember, bro, like my mom took me on a shame tour. Like, we went visiting like every single family member. Like, do you know what Rich did? He went to jail because he touched this, that, and the third, right? And I was I was so shameful about that moment. And I just remember thinking to myself, like, all right, we have we have a path here. We have two paths. Either this is what's in store for us if we keep fucking around and making mistakes and doing stupid shit, or we could take a different path, one that could be more rewarding and has a bright future ahead of you. And that should change everything for me, bro. Since 11 years old, since the moment that I was put in handcuffs and had a jumpsuit on, I made a mental decision to operate in a way where I'm going to be a positive member to society and not end up in jail like I did at 11. Damn.

SPEAKER_00

I I I did not know that.

SPEAKER_01

Yeah, it's not a story I share often, but I felt the need to share it for this topic and this platform because these are the type of moments just that you have in your life that shape who you are and who you end up becoming, right? So when I had the anxiety of doing that presentation, I'm just thinking of like my 11-year-old self. Like, I went to jail at 11. Like, like, like I'm not supposed to be here. I'm having this presentation with my manager and the senior leadership in the organization, and these folks trust me, right? They trust me to give them the right information. So it's it's just so weird how the external world views you a certain way and you've reached a certain pinnacle in your life, but deep down you're like this 11-year-old kid who's walking on eggshells who doesn't want to make a mistake because he feels like every mistake could be devastating to like the overall goal and mission in his life.

SPEAKER_00

Yeah, that made me think of something that I know I still struggle with, and that is a lot of my operating system now, they're just childhood survival tools that I've always used since I was a young, frightened kid growing up in the hood, and I was defenseless because I was small, and a lot of the adults around me, my father was involved in a lot of fuck shit, my brother was involved in a lot of fuck shit. Shit, my mom and my grandmother were even in the mix. So when you're exposed to that level of day-to-day hood stress, I think as a little person, I just built up these tools that helped me survive. And it was like almost an animal in a dangerous environment growing horns, like a porcupine that grows quills. It doesn't do it to hurt anybody, it does it to defend itself. So when you talk about childhood survival skills, as you get older, those things that help you survive become your friend, they become allies. You lean on those things when things get crazy. But as you get older and life becomes less chaotic, these survival tools are less significant, they're not as important, they're not as useful. So the best way I could explain it is in your brain, your old programming is fighting a threat that no longer exists, and you're approaching every confrontation in life with that level of fire. And that's kind of why I enjoy confrontation. I know I do, because once upon a time, confrontation was expected. There was always a bully around the corner, there was always a cousin that was older cousin that was gonna fuck with me. There was always my father saying, Hey, there's some the police are on their way, like make sure everything's good. And I have that programming in me. But as a taxpaying, high-earning, good member of society, kind of like you said, what do I do with these fangs? What do I do with these claws? What do I do with these horns? I don't know. But every time there's smoke, I become the firefighter. I I run towards it because I'm almost missing confrontation. And it's a weird thing to say out loud, but it's like I need the adrenaline, I need the dopamine of something that's difficult, challenging, hard to figure out. My whole brain and my eyes light up when I think about like, oh, this person has a problem. I could fix that because that's what I'm designed for. Man, most people don't want that. Most people just want to chill. They want to, they want to get their check, they want to go on vacation, they want to take their summer Fridays off. And I I don't know why, but I don't know. In my heart of all hearts, I'm like, oh, that's fucking weak. That's weak. That person doesn't want more in life. Who the fuck said they want what you want? So the the real conversation we're having here is I've made the life I always wanted my own jail. Now I live in that jail because I tasked myself to run a triathlon and I did it. And now I'm looking for, I don't even know what comes after a triathlon, but now I'm looking for more because I want to challenge myself and I want to prove to my younger self, man, you're worthy. You're worthy, you deserve it. And that to me is being as vulnerable as humanly possible. And I don't know what the answer is, Rich. This is a very difficult episode to get into because I don't even know if I have advice for a young man watching this, other than maybe some self-realization, which I guess is what we're doing here.

SPEAKER_01

Yeah, I mean, this shit is very it's it's very nuanced, but like you said, bro, we've made this jail for ourselves, but we're happy in this jail.

SPEAKER_00

That's the scary part, right? Yeah, because my fear is that we'll talk the next Steve Jobs off of that edge that makes them great. I don't want to do that. I don't want right, this is not the platform. I'd be a hypocrite if I were to say, like, yo, you're too driven. Don't become a billionaire. That's crazy that you want that. You're talking to a guy that put at 17 years old, I drew a check on my wall that said 250 million dollars. A check, and I wrote it out to myself. I understand that I'm broken, but I'm also not guilty of feeling bad about being broken. But I do understand that some people gotta pay the price, and I think that's what I'm here for. To talk through the price that I make other people pay for the prison that is my success or is my drive. It's not even about success, it's about the drive.

SPEAKER_01

Yeah, and I think your drive is what makes you you, it's your defense mechanism for everything else outside of your life that you have no control over. It's like at least Justin, you know, and set into. Individual, right? If you're watching this, you have control over your life. You have control over your destiny. You have control over your ambition and your discipline and your knowing and your knowledge. What happens outside of that? You have no control over. So I think you like to be the guy who's driving the car as fast as possible to like the most optimal destination for you. Yeah. Right.

SPEAKER_00

And you know what's funny? What you said, that analogy. When you said driving the car, I was like, yeah, I drive cars. I don't sit in no passenger seat. This is not good for somebody that has to have a romantic relationship with another person that has autonomy and wants their own word in the relationship, but they want to exist. This is not good for someone who manages a team of 20 young people that needs to lead them to success. This is not healthy for someone that has family that loves them and they're just normal people. They don't look at the world the way I look at the world. This is what the episode is about. You know, something that I just looked at in our research, Rich was a quote from a very high achieving successful man, which I want to get your feedback on. He said, Self-work is for people who are failing. I'm not failing.

SPEAKER_01

Damn. Self-work is for people who are who are failing.

SPEAKER_00

Meaning I don't need therapy. I'm successful. I don't need to be introspective. I'm successful. What y'all are talking about, it doesn't have anything to do with me. Look at my car, look at my girl, look at my bank account. I'm winning.

SPEAKER_01

Yeah, I mean, that's an interesting angle, right? Because everyone has their own definition of success, right? You have yours, I have mine, we have ours together, right? And building this platform. And I think for the outsider looking in, it's hard for them to digest like why you go so hard, why I go so hard on uh accomplishing our goals and completing different tasks. And I think it's important for us to sort of help educate those folks. Like, listen, I know you think that I'm being miserable by spending three hours writing a podcast script, but I promise you I'm okay. I'm not broken.

SPEAKER_00

I'm actually in We were about to say it's again. It's almost like working out or seeing somebody in pain from doing something physical. Like, I know it looks like from the outside I'm getting punched in the face in this octagon during this MMA fight, but I'm actually kind of happy in here. It's a weird thing. I think you gotta be of that cloth to really understand the dichotomy and how sadistic that even sounds.

SPEAKER_01

Yeah, and listen, you have to, if if you're in this world, right, if you're the ambitious man who's always going after something and you have tunnel vision and you can see the prize in every goal that you're trying to accomplish, that is fantastic. Like we will never take that away from you. This is why we're encouraging all of our audience members to go through our catalog where we speak about many different failures because we don't want you to repeat the same mistakes we've repeated and you can accelerate your growth, right? But it's important for you to understand that not everybody will understand your journey. Not everyone is as ambitious. Sometimes your girl just wants to sit on the couch and watch Netflix with you. She don't want to hear about the 20 different business plans that you have in your head swirling, right? Or that you just closed on a real estate deal. Like it's the truth, you know. I I hate to say it just, but like it's so hard for you to be comfortable around other people and not share everything that you're working on, right? And sometimes they're not trying to hear it. Sometimes they're really just trying to kick it, but you're so fucking overachieving, uber successful. I want to share all my wins and I want to speak on how to make a hundred million dollar business.

SPEAKER_00

So we're that guy at Thanksgiving that people are avoiding. Is that what you're saying? Potentially. They're feeling judged by us when we're like, oh, what so what do you got going on?

SPEAKER_01

Yeah, or you become the guy who everyone shares their business plan to. Yes. And now you're yes, you're you're filtering every fucking play that your family is trying to do.

SPEAKER_00

Rich, I like the angle you took, and I actually think we're gonna settle on a few topics that can be helpful to a younger guy who is not listening to this podcast to hear us go on about how conflicted we are because we're successful. Like, like who the fuck wants to hear that? But I think one thing that you mentioned and it made me think about this phrase that I heard, which is relevant here and we should discuss it, which is internal scorecard versus external scorecard, intrinsic success versus extrinsic success. Meaning when I achieve what I achieved that was a personal goal of mine, do I feel the need to constantly tell everybody about it? Or am I at a phase in my life where I can internalize it, keep it to myself, and keep it moving because it truly is something that I want for me. And I think that was a breakthrough I personally had in the last five years that is the evolution of a broken overachiever, which I self-identify as. I am broken, but I am an overachiever, and I'm conflicted by those two things because there's no better feeling than the feeling of being counted out and being an underdog and someone that was left on the side of the road to die, that comes back and rebounds and gets their life together and then achieves the unthinkable. That journey is so validating that younger me wanted a shout on the top of every motherfucking mountain like, look at me, look what I've become. I did it. I felt like I've made a good transition last five years where I've internalized it. And it's like, man, you know what's really telling, Justin? If you can achieve something and not post it on social media, you cannot tell anybody about it, you don't have to brag about it. That's how you know it wasn't something that you were seeking validation for. It was something that you truly, truly internally wanted, and you're not playing a game of status. You're playing a game of getting right with yourself. That internal and external, that's a slippery one, but I'm curious to know if, you know, you're 38 now, Rich. You just turned 38. How do you deal with that conflict where you want to talk about these wins, but you know, maybe you're conflicted?

SPEAKER_01

Yeah, I think certainly in my early 20s, I did things and accomplished things and posted them a lot on social media, and I purchased a car and here it is. Purchased a house and here it is, right? Because you seek that validation from the world that, like, oh man, because remember, it especially folks like us who tie their identity to accomplishments. This is part of who you are. So if people see the accomplishments, they're just like, oh, we expected that from Justin. We expected him to be in a publication variety magazine or a billboard or whatever, right? So certainly, early in my early 20s, I suffered from that. I think post-30, bro, and I the only thing this comes by proxy of maturity. I think you care less about that external validation. And like you said, it's it becomes more about your internal scorecard and what you're looking to accomplish for yourself, what will feel fulfilling for you and your own personal journey. If people end up witnessing that or hearing through the grapevine that you did set accomplishment by proxy, then so be it, right? But it's not something that you're publicizing. And I think it removes the pressure off of you and your journey when you're not sharing this information with other people, because then there's added criticism, there's opinions, you let these outside forces like influence your journey. So I've always found it advantageous to just bro, whatever you're working on, work on it in silence, building stealth, like they say, and then let people see the progress once you're done.

SPEAKER_00

But I I do want to mention that's why to a younger man who wants to prove to his younger self and maybe a fucking bully that he had at 11 years old, I'm not weak anymore. I'm strong now. That's why the winning feels hollow because you're chasing validation from fear that you had at 10 years old, 11 years old, 12 years old. If I do right, my mom usually validates me. But as an adult, I want the world to validate me. That is a very fucked up loop that you're trapped in. It's a deal with the devil. The I will be happy when deal is a deal with the devil. That is a contract that you're actually never going to be happy. I'll be happy when dot dot dot never comes. And I learned that shit the hard way, man. I have had an insane amount of debt looking for the validation of people that I no longer speak to just to tell me, man, I love that car, man. It's a really cool car. One compliment forty thousand dollars. Yeah, I'll be happy when. You won't be happy when. It's almost like we sit around planting seeds for fruit. But if you've ever planted anything, you know it takes time to see the fruits that bear. But what happens with guys like us, Rich, broken over achievers, is that when the fruit comes six months later, a year later, two years later, you don't even want it. You don't even want it because you forgot you started that mission a long time ago. And I know we're trying to give advice, but me and you are very guilty of that. You mentioned something about this in the pre-show. It was just like when we get what we want, we're probably not even gonna want it anymore.

SPEAKER_01

Yeah. And listen, there's this weird thing where a lot of your decisions are based on fear. And where does that fear come from? It comes from the fear of being broke again. Facts. Of not having enough to get the things you want, right? So we're far removed from being broke, but we still feel like we are, or we feel like one wrong move, one mistake can get us back to that moment of like, damn, I made a mistake that I cannot come back from. And living in that fear, bro, it's a double-edged sword, bro. It's what drives you, but it's also what holds you back at the same time.

SPEAKER_00

Rich, you saying that reminded me of this really crazy television show, teachable moment that I had, I want to say last year. You had mentioned variety and billboard. And if you Google my name, and you'll see that those two platforms have given me credit for things that I was involved with in the last four years. And with that, Billboard of the Year, executive of the year comes award shows. And I remember working on the project that I was working on, I was so invested that I felt the need to be acknowledged more than they were acknowledging me. It was like a little blurb in the article, and I was so fucking annoyed. I did an interview and they only published like one line. And I was legitimately upset about that for like a week. And that right there was what we're talking about. 18-year-old Justin who wrote the quarter million dollar check in his small ass two people max bedroom in my mom's basement, wouldn't even believe that a publication like Variety Magazine would even write about me. But I've become numbed to the success that every seed that I planted led to fruit that I ignored when the fruit was bare because I was constantly looking forward for something more. And the level of arrogance that I had, I didn't feel it until my nephew, who wants to be in the music business and comes from the same place I come from, he flew out to LA and I lined up a whole week for him where he got to see the fun stuff that I do in my business because he wants to be in the music business. And when he got back, my brother called me and was like, Yo, you have single-handedly changed my son's life. He was emotional and inspired and so excited about seeing what you do every day. And you've lit a fire in him that he needed just from living a week in my life. He didn't get no award, he didn't get none of the money, he didn't get to drive in my car. He was just existing. It was like Justin from the past met Justin from the future, and the level of gratitude and happiness that he had just to see how a Duran could be living. And for my brother, my idol to call me and tell me that made me feel this small, Rich. Because that was the same week that I was mad that I didn't get more of my interview in the variety magazine. Like, who the fuck do I think I am? You get what I'm saying? And that right there is a perfect example of I'll be happy when. For someone that is a broken over achiever, that happiness will never come if you're constantly looking for validation from the world. But if I was at peace with myself and I was cool with whatever success or awards or acknowledgement came, but the only thing that made me happy was knowing that I did my best work, then I would have been good because I would have been able to see and not overlook how inspired and how happy my nephew was when he came to visit me and got a chance to see the way I was living. Because that would have been a truth grounded in reality. But I wasn't living in reality. I was living in my ego because I was living in the prison called success. I was living in the jail that was my pre-programming as a young man. And when I was writing out the notes for this episode, I was thinking, like, damn, this is the life I always wanted, but why do I feel unfulfilled? And I don't know, man. This is a very complicated topic, but that moment with my nephew was very important for me for sure.

SPEAKER_01

Yeah. Listen, I think part of the process, too, that we don't really analyze, but we should break down is just like we're also in love with the journey, right? Not so much the awards that come by proxy of being on said journey, right? But here's the problem, just the journey never ends, right? So the the journey is a continuous thing that is your life, and you will continue to receive accolades, awards, money, success, accomplishments, right? Sure, God willing. God willing, right? And unfortunately, you will continue to be numb in those moments because you are in love with the journey. You have fallen in love with the process of achieving something. You know what the best way to handicap you is? Is not giving you a goal to accomplish. It's putting you in a room and saying all you have to do is do nothing. Sit in silence, watch TV. You will deteriorate and you will die within a week because that's anti-you. You know, that's anti-the overachiever. So yeah, I can't emphasize that enough, man. The journey is what overachievers fall in love with, um, not so much the rewards and accolades.

SPEAKER_00

Yeah, and one other thing I wanted to mention is worth dissecting because it's a layer within a layer within a layer of this subject of the broken overachiever is ego and identity. How I tie my identity to what I mean to my family as someone who has done better for themselves. The identity and the ego and the adrenaline rush I get when my mom introduced me to her coworkers or her friends as my son who made it. Look at this. My son, he's doing so good for himself. Man, nothing charges me up and fills the ego. Fuck the doubt monster, the ego monster. And my brain is like, yeah, that's who I am. That's what I mean. But you know what happens when you fail or you fall short. That guy is right there being like, man, what happened? I thought you were the guy who gets it done. I mean, you relate. I can tell you do.

SPEAKER_01

Oh, yeah, for sure. Listen, that external pressure from family to have you live up to the identity that's been built for you, that you've built for yourself, ends up being that, right? Like a lot of pressure. Well, you know what's a funny thing that my mom does, bro? Like, I've had parties for my my daughter, right? Like I had a baby shower for her. I threw a party for her one-year-old birthday, and I'm renting halls, like I'm spending some bread on this, right? Like, open bar the whole nine. And she'll always invite two or three of her friends, right? And I know why she does this. It's her way of showing the world, like, look what I birth. Like, wow, like this is how accomplished my son is, that we could have these moments, everything paid for, and enjoy a great event. So I think that's just a funny thing that our family just views us in a way that of the life that we've built for ourselves, right?

SPEAKER_00

Yeah. When you're wrapped in your ego and you see yourself as I'm the guy who gets shit done. I'm the successful guy. That's what I am. Slowly that crown becomes a cage that you live in. And it's weird how it can quickly go from being proud of yourself to being locked in your own jail of your ego and who you think you need to be. It's an identity thing. It's an identity thing, and one comment, this is how you know it's fragile ego and not reality. Because one comment, one negative comment, one critique, one person that takes a strike at that ego, that identity you built for yourself, your whole world collapses. And you become angry, you become vengeful, you want to fight the person for not buying into the identity that you need to upkeep because you've already sold yourself that lie. And there's no solution to that. The only thing we could say is, as some sort of advice for our overachiever, is you can only get as high as you fall. It's like a roller coaster. The feeling in your stomach could only feel terrible if you allow your pride and your ego to take you that high. Keep a level of reality in these moments, like you said, Rich, where your mom is bragging and boasting about her son. But you know, in some weird way, that's her ego. Because she's like, look at what the fuck I birthed. That is me right there.

SPEAKER_01

Yeah.

SPEAKER_00

You ever ask yourself why parents are so proud of their kids? Because it's a version of them. That's why. Why do you think parents are so delusional when it comes to having realistic judgment and discernment about the level of intelligence of their kid or the level of talent of their kid? Why do you think softball programs and youth programs for parents that care a lot make so much motherfucking money? Because you're not gonna quit on your kid because your kid is an extension of you. So once you put$20,000 into little Edito's softball program and he sucks at softball, the last thing you're gonna do is kill your$20,000 investment. You're gonna say, you know what? I was like him when I was younger. It just took me some time. And you're gonna keep putting up more money. Why? Because it's an investment that you're making to your own ego, because you can't believe that you birthed a child that fell short. And I think that is something that is wrapped in a lot of us. And most people don't get to live that truth. So you're living that truth. So in some weird way, everybody gets to partake in the identity that you have in yourself. But tell your mom that she can't invite her friends, see how she reacts to that.

SPEAKER_01

Yeah, but listen, bro, I am broken. I am addicted to winning, I'm addicted to accomplishing my goals. I'm addicted to having more money. If either of these things don't happen for me, I feel absolutely terrible. Like these things are tied to my identity and who I am as a person. If my bank account has less money than I expect it to have, I literally feel a pit in my stomach. Like I feel bad emotionally and physically bad. Like we need to save more money or we need to get this uh account back up to a healthy number, right? If I don't accomplish something, if I fail at something, I feel physically bad. That is a broken person, bro. That is not a normal emotion to feel when you're feeling like you can't get something over the line.

SPEAKER_00

Yeah.

SPEAKER_01

We're making the assumption that there's overachievers out there in our community that feel the exact same way that we feel, right? We're not saying we're millionaires and we're these uber successful. Uber rich people. We're saying that we feel like from where we came from, we've accomplished more than what our family has, more than what some of our peers have. And we're doing pretty well for ourselves. But the journey to get to where we were came with a lot of flaws that we still live with today.

SPEAKER_00

Rich, that that leads me to a question. And you can just answer it off the top, because I feel like that's what you're talking about right now. And why do you think for the overachiever, his identity when he was younger never really matches who they are currently? What is it about that? Even in your story that you said to open up the show, what is it about the person that the world sees you as? You're a grown-ass man, you're 38 years old, you're decorated, you're accomplished, your resume says so. But in that singular moment, you felt like a kid. You felt like young rich, you were vulnerable. Why is that?

SPEAKER_01

Man, I think it's part of your upbringing, bro. And I don't say that to put blame on your parents. I say that to say that we're all born with different circumstances. And when you aggregate all those different circumstances, it outputs a certain feeling, right? And when you aggregate me feeling like I was abandoned because my father left at two years old, me going to juvenile detention center at 11 years old, me filing for bankruptcy at 19 years old, like, bro, these are the scars that I carry with me into being 38 years old. And I can't shy away from those failures, bro. Like those things about my past shaped who I am today. And I'd be lying to tell you if I didn't feel like any wrong move I make from this moment going forward will affect my future because I do operate in that fear.

SPEAKER_00

Yeah.

SPEAKER_01

And I think other people operate in that fear as well.

SPEAKER_00

Yeah, there's a very simple trick that I try to do whenever I get overwhelmed in a moment of frustration or anger, and that's sitting in silence for a few minutes and truly trying to disconnect from everything. And I ask myself, is this making me upset because I'm truly upset? Or is this making me feel away because someone is attacking the person that I want them to see me as? Is someone's attacking my ego, someone's attacking my identity? It's almost like you're sitting in a car and everybody in the car is safe. But if somebody sat on your car or bumped your car or scratched your car, you jump out of the car and you want to get into a fight with them. But in all actuality, if if you're safe inside, why is it that you overwhelm yourself and overconcern yourself with what's happening on the outside? That's something that I try to do more and more. And I feel very fortunate that in the time I didn't think it was fortunate. But post-pandemic, I came out to LA and I wasn't around a lot of my family. I wasn't around a lot of the people who knew me since I was younger. So it put me in a weird spot because everything I did or everything I said, I had to ask myself, am I doing that because I want to upkeep an identity? Or am I doing this because I actually want to do this? No one I met out here even knew the old Justin. So I was starting from scratch. And it gave me this unique opportunity to really think about why do I do what I do? And is it because I want to keep a persona going? Is it because I want people to like me for these things that other people have liked me for? And it was almost like a reset. It was like a simple life reset that I can check back in and I can get rid of the old programming. I can get rid of the old software and be like, I have to update this for who Justin is at 39 years old, at 40 years old. And doing that, Rich, has helped me out a lot because it's removed a lot of the baggage that I used to carry around that was built on this old identity.

SPEAKER_01

Yeah, that's a great point. And it's sort of weird how we all carry our own sort of defense mechanisms. And this is our way from shielding ourselves from the world and from who we used to be. And it is such an interesting concept where who you used to be versus who you are, like there's a big disparity between those two people. And it's really up to you to self-reflect on and identify that, hey, this is who we used to be, this is who we are, and close that gap. I don't feel like you'll ever be able to close the gap completely because shit, we all have trauma, we've all been through some shit in life, but at least try to find different tentacles that you could put between your old life and your new life and find positive ways to reinforce that. That yeah, I came from poverty, but guess what? I got some some nice coin in my bank account, right? Yeah, I came from a one-bedroom apartment, but I have a house now, right? Like these are there's this like weird thing that you have to do with yourself to relearn who you are in the present moment and not so much live in the old identity that you came from.

SPEAKER_00

Yeah, yeah. One counterpoint that came up from our notes, and I actually agree with it, and I'm curious to know what you think, is yeah, I hear you. All this therapy talk that you and Rich are going into about healing yourself is easy for you to say you're in your late 30s, early 40s, and your life is already good. You're stable, but I'm young, and me being an overachiever gives me an edge. What's your advice to someone that doesn't want to lose their edge?

SPEAKER_01

That is absolutely your edge, but listen, we're we're not healed, bro. I think the cautionary tale of this entire episode is that listen, the more you accomplish, the more you're going to feel various different feelings, imposter syndrome. You're gonna feel like you're a fraud, you're gonna feel like any failure can bring you back to where you used to be or where you came from. And you're operating in this fear of like feeling like you're not enough. You know, when you are enough, because we've already touted that if you clicked on this episode, you are an overachiever, right? So there's a lot of weird mental things that happen when you're operating in the world and operating as a young man where you're just trying to decipher, like, man, I'm progressing and I'm doing well, and I feel like I'm on the right track. But there's this always side feelings that make me feel like I'm inadequate or I'm not enough. And that's the cautionary tale that we want to share with our audience that it's normal to feel these feelings, you know? And listen, I I'm speaking from experience.

SPEAKER_00

When you are a broken overachiever and you get older and you achieve more things, you quickly realize that the void doesn't fill itself. If you are building on a hollow foundation, if you're building an empire that is your life, a skyscraper that is your career on a hollow foundation, eventually everything's gonna cave because the foundation is hollow. And I think fuck it, get rich, get money, be obsessed. Rich and I would be lying if we told you that wasn't the formula that helped us. But what we're saying is the minute you start realizing that you're creating new goals, new things to do, new milestones, and you have everything you want, but you're still not happy, that's when it's time to check in and ask yourself, what is this void that I have? What's wrong? Why am I not fulfilled? Why am I not happy? Why can't I just sit peacefully at dinner with people I love and not think to myself, man, these people are not driven. These people don't want it. This is why this person is overweight. This is why this person doesn't have what they want in their life. I know the answers. I'm saying that because I'm speaking from experience. It's this fucking chronic, judgy ass monster in my mind that's constantly asking me, what are you doing, Justin? What are you doing? Why are you not doing more? And what we're saying is in your early 20s, that may be what drives you, and that's okay. But be cautious. That same Ferrari that drives 180 miles per hour on the highway is the same Ferrari that if it hits a slight speed bump, can flip a thousand times and be your demise. So just understand, take a little bit of time every now and then, when you get your wins, to take a deep breath, understand that you're happy about what you have, have gratitude. There's nothing wrong with that. You deserved it, you earned it. But understand why can't I fill this void? What's wrong with me? And again, we're speaking from experience. And most of the time, that void comes from early programming. When you were younger, something is missing. Go find out what's missing before you achieve more.

SPEAKER_01

Just and everything you just said is exactly what makes us broken because we don't follow none of that shit that you just said.

SPEAKER_00

I was thinking about it while I was saying it. I was like, man, we are recording a podcast voluntarily with less than a hundred followers, and Rich and I have literally dedicated all of our free time to trying to figure this out. Why, Rich? We're good. We have two girlfriends that love us dearly, that want our time and attention. What the fuck are we doing? Oh, you know what the excuse is? We're helping out other people. That's my excuse.

SPEAKER_01

Yeah, that's my excuse too. I'm gonna use a line that you've always used throughout our entire friendship. Anytime we've uh been trying to accomplish a goal, or we just got a new job, or we just got put on a new project. And you always say this everybody is food.

SPEAKER_00

Oh man. You're quoting me?

SPEAKER_01

Yeah, I'm quoting you. Everybody is food. This is why we are broken, ladies and gentlemen, because we don't check in on ourselves. Everyone is food means everyone is competition. I'm going to destroy everyone around me, and I'm going to be holding the trophy at the end of all of this. Watch me work. That is how we are built. So understand that there's nothing wrong with that, but exactly what you just said, Jess, is what makes us broken because we don't check back in on ourselves. We don't look into damn, why do we operate in this aggressive manner of always trying to accomplish the unthinkable or just going and trying to reach things that seem unattainable to us? And it's because that's just the way that we're built. We don't check in on ourselves, we don't analyze our past traumas, we don't think about our childhood. Like, we're just like, no, bro, everybody is food. I came from nothing. Like, we literally got it out of the mud, and we are here now, and we will not go back to that old life going forward.

SPEAKER_00

Yeah, you got me. You got me. You got me. I know I'm a stone coal hypocrite because I'm out here giving advice to help people to fill the void that is the trauma in their life that makes them an overachiever. But in that same vein, I just watched one of my new favorite movies of all time with my girl, and it's a movie called There Will Be Blood. And there's a character in the movie played by Daniel Day Lewis that is an absolute narcissistic, sycophed, psychopath-driven man who wants to take over this entire state by drilling for oil and becoming the richest person ever. And I know that I have a foundational problem because while we were watching the movie, my beautiful girl, such a kind, warm-hearted human, and my ego-driven self, we were watching two different movies. And I didn't realize that until the movie was over. Because when the movie finished, my girl was like, I hate that guy in the movie. And I was like, Yeah, you mean the pastor that was trying to stop Daniel Day Lewis from being rich? She was like, No, Daniel Day Lewis at the end, it was so sad to see his life. He was rich, but he was alone. He was arguing with uh with a kid that couldn't even compete with him. He was competing with everyone, but nobody wanted to compete with him. I remember thinking to myself when she said that, huh? I kind of love that character. He won. He won at the end, and she was like, Yeah, but he was alone and he was sad. He even lost his own son. Why would you want to be that character? And at that moment, I realized, Rich, my girl don't know who I am. I fucking love that character. And to this moment, I still love that character because there's a scene that he had this level of pettiness, which I fucking loved. The dude that he was competing with the whole movie, it was like 10 years later. He finally linked up with him and he did the pettiest shit of all time. He explained to him every chess move on how he tricked him into being the person that was gonna give him his land. And the scene is iconic. If you haven't watched the movie, Rich, watch it. But I dare you to watch it with anybody who's a kind human, an empathetic human, a human that doesn't have an insecurity and an ego complex. And they're gonna hate the character that you love because that void is in us, and that void is certainly in that character that Daniel Day Lewis played in that movie.

SPEAKER_01

Yeah, bro. Listen, I was watching the Robert Murdoch documentary.

SPEAKER_00

Rupert Murdoch. I just watched it. Yeah, I loved it.

SPEAKER_01

Yeah, Rupert Murdoch. Yeah, and my girl was like, Oh my god, like he's so mean to his kids. I'm like, fuck them kids. Like, they're trying to take his whole empire.

SPEAKER_00

You know, let this man cook. He got got it out the mud, came from Australia. Yeah, yeah. See, we are empathetic to the fellow broken overachievers. So, you know what? Rich and I are humans, and we're not gonna get on this platform every week and act like we have all the answers. Because this one, we don't know if we have the answers, but what we are doing for the young overachiever is we're giving you a little psychology and a little bit of introspection for while you're out here cracking skulls and taking names, fuck it. That's what you got to be to be a titan of whatever it is that you're the industry that you're in. While you're cracking skulls and taking names, take a moment, have an introspective moment. Ask yourself, did my dad really ignore me this much to the point where I got to conquer everything? Then, you know, you got some work to do. But outside of that, we're not gonna stop you from being great because our problem on this show is not men who want to be great. It's men that can't even get themselves out of bed. So I'm not gonna knock the hustle for the young man that feels like an overachiever. Keep achieving over and over and over again, but be mindful when the achieving comes from a void, comes from you being broken, comes from the ego, comes from you wanting validation from other people. That is when this becomes a problem. But outside of that, keep rocking in the free world. Do do doop doop do for real, for real.

SPEAKER_01

There you have it. Failures podcast, man.

SPEAKER_00

Oh, I was I didn't even realize I was closing out, man.

SPEAKER_01

Yeah, that was the close, man. We can't get any better than that. I'm not gonna follow that up.

SPEAKER_00

Man, you know, listen, Rich and I work really hard on this on this uh platform we're building, and we don't charge anything, we don't plan on charging for anything. If this episode resonated with you, share it with a friend, leave a comment. That's probably the best thing you could do for us. Yeah, failures podcast.

SPEAKER_01

Yes, sir. We out.