Lonely at the Top: Why Success Can Still Feel Empty
15 Nov 2025 · 54 min
Jesse Pujji and Dave Kashen discuss why extreme success often brings loneliness, responding to Brian Chesky's viral post about the gap between achievement and fulfillment. They explore imposter syndrome, the drive to prove worth through work, and how founders can stay connected to themselves and others through vulnerability and peer communities.
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All right, welcome to Heart of Entrepreneurship, where me, Jesse Pujji, and Dave Kashen talk all about building businesses from heart. And we want to stand in this podcast for being able to be ambitious and build your dreams and live your 10 out of 10 while being alive and loving and happy. And, you know, it doesn't, doesn't have to be a grind and doesn't have to be depressing. There was a, there was a a post this week that went around the Twitterverse or the Xverse now, written by Brian Chesky. And I just thought of this to start this way. And for those who don't know, Brian Chesky is the founder of Airbnb.
And he— Fairly successful entrepreneur.
Yeah. A guy I think a lot of founders look up to. You know, Airbnb, it's sort of YC darling, $100 billion company. I think it's a the most successful company out of YC, or certainly one of them.
Certainly one of few.
And, you know, he read about this and I think his net worth is $10 billion. For those, you know, for those who care about that. And, you know, he— I'll just read it. As I became a CEO, I started leading from the front at the top of the mountain. But then the higher you get to the peak, the fewer people there are with you. No one ever told me how lonely you would get, and I wasn't prepared for that. I had this guilt about not working because so much of my life was about being successful, probably if I were to dig deep, because I thought it would make people love me. And the day of our IPO, we reached a $100 billion valuation. I remember after going public, I was like, oh my God, there's this amazing exaltation. It was amazing that I'd gone to the mountain, and then I woke up the next day and my life was exactly the same. I'm alone. I wake up, I put on my sweatpants, I go onto my iMac, and I have 10 to 12 hours of Zoom meetings. And I just don't really have much of a life outside of work. My work was my life. I didn't know at that time that I was lonely. I knew I was isolated, but I didn't know that also meant loneliness. And I thought, have to have all these people around me, how could I possibly feel this way? There were a couple people who entered my life and gave me some awareness and consciousness, one at a deeply personal level and one at a more professional level. And then he goes on, and there's a discussion and some of the stuff around just, you know, I think there's a lot of interesting pieces of it, but he's, you know, I think he's saying one of these things of he basically reached arguably one of the most high pinnacles of professional success and found it to be completely empty. What jumped out to you on that, Dave?
Could you read the line again about, I thought I'd feel loved?
I had this guilt about not working because so much of my life was about being successful. Probably if I were to dig deep, because I thought that would make people love me.
Mm-hmm.
Resonates. Yeah.
First, I just— I noticed sadness as I hear that. And first, just empathy. Like, I really connect with the, the, the part of him that for so long believed that I had to achieve a certain level of success to be lovable, or for people to love me, or maybe for my dad to love me. And, um, oh wow, I just, I really appreciate his vulnerability in sharing that. Um, And like, so you asked what stood out. That's what stood out to me, I guess. And I don't think they're unrelated. Like I think that sense of I need to achieve in order to feel loved. There is kind of a loneliness in that, in the sense of, I can't be loved just for who I am. And that sort of lack of, like, in a way, lack of authenticity. And that's the trap, I guess, of— I mean, what's so striking is the magnitude of his success. Yeah, like, it's, you know, what happens to most people, I think, I think, first of all, I think most people hold that belief at some level. Certainly most people in our world, most entrepreneurs, that I'm not inherently worthy and lovable, you know, but I can become worthy and lovable by achieving enough. You know, I certainly know I felt that and believed that for a long time. And it's, um, it's funny, even if like you intellectually see through it, there's a way that that pattern is very sticky, um, you know, because I think there's some feelings we don't want to feel. And so what happens with most people is they get to a modest level of achievement, like the thing that their mind said was the 'I'll be happy when' or 'I'll be right' lovable when, and then they don't feel it. And at that point, they can still fool themselves and say, okay, all right, maybe it wasn't $3 million, maybe it's $10 million, you know. And so they keep playing the game until they get to the $10 million, and they're like, ah, huh, maybe it wasn't $10 million, maybe it's $50 million, you know. But he, he achieved such a magnitude, right, of success that it's almost more confronting because it's like, okay, well, shit, if, if I built a $100 billion company that, you know, is serving millions and millions of people and impacting their lives, and I personally made $10 billion more money than I could ever spend and my children's children's children could spend, like, it gets, it gets pretty hard to still believe the, that, you know, illusion that something outside of you can make you feel whole and loved.
So, you know, certainly something financial. I mean, I feel like there's tons of stories of people then taking the money and trying to— can I be alive?
If I donate enough, then I'll feel—
yeah, I think the, the— I think this The, like, on some deep level, he thought it would make people love him. I think that's good self-awareness. I think the other thing that I say this a lot to people, and I actually was walking with a founder yesterday and he really, really characterized it well. He's like, literally, I feel like I've built my perfect life, but I'm not living it.
Hmm.
Like, in other words, it was almost like he had built like the dream house for himself, but he didn't feel like he was living inside of it because he was so and he's had a lot of success financially and whatever, but he just, he wasn't present. Like, he was just miserable because, because he was orienting himself. And there's a version of the, like, 10 to 12 Zoom, 12 hours of Zoom meetings. And like, here's a guy who worth $10 billion who puts his sweatpants back on and gets on the iMac. And like, and I think there's a lot of founders running around who, who sort of live that life. And I don't just mean, you know, the, the sort of worldly stuff, but like they're actually not solving for what does their day look like? What does their week look like? What is an actual joyous, you know, what would it look like to live, be fully alive? But it was, yeah, it's a sad, it's like a sad, it's a sad quote.
Yeah, I also get really, I notice I'm really curious about the loneliness. I get, you know, I can At the surface level, I can kind of get the, you know, having coached lots and lots of CEOs with great, you know, as they have greater and greater degrees of success. One, there's a sense of like, I can't complain about anything because I got $10 billion. Who's gonna, who's gonna listen to me complain about, you know, uh, my fear of losing the money or investing it poorly or having a bad day? Because like you know, I'll play my violin for you, you know, billionaire. So there's a little bit of a sense of like, I can't relate to regular people. And sometimes there's a sense of like, I don't— I can't trust that people love me for me because they just want something from me because I have a lot of resources. So I think there's that piece. Um, I also think there's often— and I don't know, I don't know Brian, and I'd be curious, but there's often this sense that, um, I have to play this role in this— in the right way, right? And I think some of what creates the loneliness is the lack of authenticity, the sense that like, basically I have to put on a mask and go be this certain way that's not actually who I am. And I heard this quote and I posted on LinkedIn the other day that was like, "The only way to become confident in yourself is to be yourself." Right. You know, which is sort of like, on the one hand, kind of a tautology, but there's wisdom in that, right? It's like, oh great.
Yeah.
You know, if I go try to be loved by achieving all of these things, Well, then how do I know if I'm loved for me or if I'm loved for having achieved all these things? So it's sort of a fool's errand in that way. And I think there's something in that that creates that loneliness.
Um, I just thought of— it's so funny, I like— this is a random aside, but I go to school, like my kids' schools, and like schools are really inspirational places. Like all the quotes they have on the walls and all the little sections, like, you know, it's elementary school. But when you said that, that one of the quotes in my son's homeroom is Be yourself because everybody else is taken.
I love that. I happen to have on my wall here something my older son made a couple of years ago. It says, "Be yourself. Your uniqueness is far more important and valuable than your ability to conform," which I— So, there's something here around authenticity. Again, my guess and I've heard a little bit like people who No, Brian Chesky, I— my understanding, they would describe him as a pretty authentic person. So I don't, you know, I don't want to give the impression— I don't know— but like that he's sort of trying to put on a face.
But even just at this deep level, if he's accurate in his self-assessment that like there's this deep sense of, you know, trying to be loved by being achieving and being successful, there is just a natural way you disconnect from your authenticity Yeah, well, I think one version of it, and we could talk about this since we're kind of going like, I don't know if you and I have ever talked about this, but I remember when I started my first company, Nick and I used to talk a lot about how selfish entrepreneurship felt because, because you become single-mindedly focused on success. Most founders do. Like, that's how you— I can't fail. Yeah. And so like all my energy has to be organized to being successful.
Yes.
And I mean, I'm picking up pieces of what he says. He's like, well, he had lived his whole life to be successful and it's like, yeah, then you don't have— you're not, you know, you're not married and you maybe don't have children. If really, if all your energy is going towards being successful, you don't— you know, like, I remember I was just like, wouldn't make time for my family or friends, like, for the first several years. I, I— we were just being like, damn, man, this is— you are, you know, you have tunnel vision and you were just trying.
Yeah, you got myopic.
Totally. And, and it's— and it does— it is kind of selfish, um, in a sense.
Yeah, well, ironically, because if it doesn't actually give you the experience you want, it's like a, it's like a bad version of selfishness where you, you end up unhappy.
But yeah, but that's, I guess that's like when in success, I mean, this is a thing I think a lot of self-oriented for sure. Yeah. When, but when success, that the need to be successful overrides all your other impulses.
Yeah, that's a good—
and that's where it becomes inauthentic, right? Because to your point around authenticity, yeah, not like there's authenticity in the like level 1 authenticity, like, hey, I meet this person and they seem like they're, they're honest. They're not like, like they're not trying to sell me something or so. That was like, are you living authentically to what your whole self wants, or is this other— it kind of reminds me, I've been doing this IFS thing and like this concept of the— there's one part that tends to override you, your whole system, for a long time, or can forever. And like, oh well, the— because I resonate with that for myself of like, man, needing to be successful was the thing. And it was like, okay, if I wasn't going to be successful, it just— and to your point, then it wasn't— I wasn't living authentically my heart. I wasn't being a great husband. I wasn't being a great friend. I wasn't being a great son. None of those things.
Yeah, I think I almost lost my wife because of this. So yeah, I, I hear you. Like, I— the way I often tell the story is I was so busy trying to become worthy of my family that I almost lost them.
Yeah.
And so I, yeah, I know very deeply what you're speaking of, you know, from my time as an entrepreneur, like, and that's super lonely, right?
I mean, that's kind of ties back to the loneliness concept of you're living in this sort of weird vortex and then, you know, you're not— it's kind of what you were saying earlier, like not authentic because you're not actually connected to your, your real self.
Yeah. One way we could say it. Oh yeah. I love what you just said. You just said it like We're both disconnected from ourselves, and then by being disconnected from ourselves, we end up feeling disconnected from other people, you know, both because we're just— we don't feel connected to them, but also because that disconnection has us become myopic of like, I need to— at least for me, I need to prove that I'm worthy by, you know, achieving this external success. And so any given marginal decision of like, oh, should I go home and spend this hour with my wife and young children, or should I do one more hour of work? It always felt like the extra hour of work was the more marginally beneficial thing to do because there's a potential tangible outcome. And so I think that happens a lot.
It's funny you were even thinking about that, maybe because you had kids. I didn't have, but my crazy period was pre-kids. I didn't even think about any of this stuff. This was after I had kids.
Yeah, I'm reflecting on it now. I didn't even know in the moment. It wasn't, It wasn't, I don't even think it was like a super conscious choice. It was just sort of like, well, we're not, you know, especially at a time where we felt like we weren't winning, we're like, obviously we just have to work harder because we can't fail, you know?
And— Well, my conversation, I remember, and Diesel remembers, I'm like, yeah, I just, I don't know when I'll be home. Like, if you're hungry, eat. Like, that was like, I remember having that as a fight and it was like, dude, don't, she would make dinner and stuff and be, and I'm like, dude, but I don't, I don't know when I'm gonna be home. I have no, like, You know, there's that. That's an interesting one. And then there's also just like thinking how much— this is a funny one too. It relates to this. It's like, I remember feeling— this is back to loneliness. I remember feeling how little, how nobody understood what I was going through because I was so in myself and what was going on. And I was like, she doesn't understand the pressure. None of my employees understand.
Yeah.
Nick was the only person really who could understand, right? Because we were sort of in it together. And then we started working. But it's like interesting. Part of what creates loneliness, to your point, it's like you're not connected to self. You're— this success thing comes up and then that's the only thing you're connected. It's not even— again, for me, it wasn't conscious. I didn't know I was trying to prove myself. I was like, I need to be successful. What do you mean? That's, that's the— that's what we're doing here. And, and then, and then nobody understands me either. Yeah, because you could— how would you understand what I'm going through unless you're a founder?
I mean, literally, unless you were a founder, I was like, there is a weight of responsibility that you take on that, you know, I think most CEOs take on that weight of responsibility, but there's like an another level as the founder where it really feels like it's your baby and in some way your identity. Like, this is me, right? I created this, just like your connection to your children is different than your connection to maybe, you know, a kid that you're mentoring, right? So like, I'm using that metaphor for like founder versus like a hired CEO or something. Like, it feels like it's your baby and you just, you care so much about it and really see yourself in it, you know, in the sense of like your identity, your value, your worthiness depends on how impressive it is and how successful it is. So yeah, I think that is part of what creates the loneliness. Also, the like, I often, the belief is, and we can talk about, you know, is it right or wrong? And you know, there's nuance, but like, I can't tell my team what I'm really thinking and feeling. Like I have to be strong for them. I have to put on a good face. I can't tell my investors that I'm scared and like, they're not gonna give me more money. Right. They want the tough, confident, you know, one. And then, I don't, my wife, you know, or spouse doesn't necessarily, I don't want to burden them with all my issues and they don't have enough context. So, there's also that. And this is why, by the way, you know, I lead some of these groups sometimes and, you know, you've been a part of them and there's YPO. Like, I do think some of these groups for founders are really valuable because at least—
I think they're amazing.
—it normalizes like, oh, I, you know, I'm not actually alone. I'm in a unique, relatively unique situation in terms of the weight and the pressure and the sense of like, this is my identity, my safety, my freedom, my inner, it all depends on it. But also there's lots of other people who are in that experience and the self-doubt, my gosh, the like, this idea that like I'm the only one who has self-doubt is just so, It's so tragic because, you know, as you know, I've coached the most incredible, impressive, successful founders, CEOs in the world, and I've yet to meet a human being who doesn't experience self-doubt. Um, I really, uh, um, Joe Hudson did a podcast recently on imposter syndrome that I highly recommend. I thought it was great. And one of the things he said, which just I thought was so brilliant, was that If you're a high achiever, you're an imposter. Hmm. Like, by definition, like, you're doing things you don't know how to do. If you always do things you already know how to do, you're not a high achiever. You're just right, right, bumping along. And so being an imposter is not what creates imposter syndrome. Thinking you shouldn't be an imposter creates imposter syndrome, right? Right. So that's all wrapped up.
Like, you're being honest with yourself and you're just like, yeah, of course.
Another people— I don't— guy I've never done this before. I don't know what I'm doing, but I'm gonna make the best choices I can. And here we go. So, I do think there is this, there's a bit of an over, over, I guess, emphasized idea that you have to be like invulnerable somehow, like Teflon, like nothing. And I think that vulnerability is underrated and most almost every time that, you know, a CEO or founder I was working with chose to be vulnerable instead of try to appear invulnerable, it led to some great breakthrough, more connection, more buy-in. Like the people, you know, the story in her or his head that like, oh, my team's gonna leave and they're not gonna believe in me, or even investors, they're not gonna back me, was almost always the opposite was true. They're like, oh, well, thank you for being real. And of course you're feeling that way. And how can we, you know, support you?
Or so it reminds me, I mean, that's— I think we've talked about this story before, but when Rick was buying like the billion-dollar company and he was like, well, I have no— we have no idea what we're doing here. And he kind of said it in a way, to your point, it's like, yeah, that's true.
How could— how would they? They never did.
Yeah, he's never done that before. And it's like actually giving it voice, it made it less scary, I think, probably for him and probably for everybody. And it's also—
I've been Even in my coaching role, I've been noticing how often my mind says like, there's something you should know that you don't know. Right? Like I have one of my patterns is like comparison. Like, oh, you know, as you know, I really respect Joe Hudson, Diana Chapman, Jim Dettmer, you know, some of my mentors. And often my mind will be like, oh, what would they say? If only I knew what they would say right now. They would create a breakthrough for this client. And it obviously gets in the way of me being present. Gratefully, I'm, I'm, I'm more and more quickly able to notice that and just come back into myself and trust. And then, you know, gratefully, what, what comes through me is often quite, you know, useful. Yeah, creates lots of interviews. Uh, but my point was, this, this little pattern of I should know something that I don't know is such a pervasive problem for founders and any, you know, really any high achievers, which is— it relates to that. It's that same idea of like, I'm an imposter, but I shouldn't be, right? Like, I should know the answers when I don't. And, um, that like—
yeah, I think trying the healthy diet of I don't know is a liberating, liberating—
yeah. And honestly, it creates connection and, and allows you to feel supported as a leader. Like, I think like again, I don't know Brian specifically, but I wonder if he had a pattern of like, well, I'm the guy, I'm supposed to have the vision, I'm supposed to know the answers. And so, if he didn't allow himself to be as supported as he could have by his team, because I certainly see this pattern with a lot of leaders I work with that like that sense of I need to know the answer actually gets in the way of like, no, you just need to harness your team's collective wisdom and creativity to, you know, navigate and, you know, make the best choices you can.
I want to pivot a little bit, so I'll try to tie it in. But like, there's this orientation. I'm sure if you're founders listening, go, my God, success. And anybody really is a high achiever. It's like, I got to have success and I'm trying to prove something to somebody, probably at some level, at least if that's the energy, it's like, I need to be successful. And that's kind of what this quote talks about. And, you know, oftentimes I guess the question is, and there's this thing, you know, I want to talk about the drama triangle, but there's— how do you know when you're, you're coming from that energy versus the energy? And I think, you know, one of the big things I've talked to a lot of people about this, and obviously you have too, and oftentimes when people hear these things, they make them very binary. It's like, oh, I'm either really success-driven or I'm like loving to my team. And the reality is almost every human is both. And it's like, well, you know, even me, like back in the day, I was like really successful, but like, I don't know, probably 1 or 2 out of 10 times I was— my heart was open. I was trying to help someone. And I like— and the awareness for me was actually realizing like, oh, I do both. But like, if I want to choose, if I want to be more authentic, I choose one. How do you like— let's— I want to talk about how to build— know the awareness through the lens of the drama triangle.
Well, I'll come— okay, let me first share the thoughts arising and then go into the drama triangle specifically. Um, I really liked your phrase like heart open, and one thing I want to clarify is that doesn't mean soft and nurturing and nice and kind, right? And I think that is a place to, to your point about binary, people sort of think of it as like either I'm like hard charging and harsh and hold my team accountable, or I'm just like soft and gentle with no accountability. And I think that's totally a false trade-off. I think you can bring ferocity. Is that a word? Ferociousness, ferocity. You can be fierce with your heart open. And you can even say like, that is not okay with me. I expect more. And certainly you can create accountability with your heart open. So I think that's an interesting— I just, I think there's something with that.
I think that's a great episode. We should, we should put that down as a, as a, cause that's been a challenge for me for—
and how do you, how do you create accountability with your heart open?
Yeah. Or just the oscillation between the two. Like I can either be, you know, like those two have been, that's been a journey for me.
Yeah. And, and I forget if we talked about this, but there's this nuance, you know, sometimes a simple, a way people simplify The distinction is like, am I leading with fear or am I leading with love? And the challenge of oversimplifying it that way is it might give you the impression that you shouldn't feel fear and your team shouldn't feel fear. Right. Which ironically is a way of closing your heart, right? Because we're human and sometimes we feel fear. And if you don't want to feel the fear, then you close your heart. So to me, that's the big aha is it's the closing your heart. I'll just use that as a metaphor and we'll kind of unpack like, what does that really mean in a moment? That tends to be the, well, what creates loneliness, what creates constriction, what creates drama, what creates internal angst and all of that. So the sort of paradoxically like, Sometimes we're scared and our team is scared sometimes and fear is really useful 'cause fear points you to like, okay, there's something to pay attention to here. There's some edge we need to move beyond or there's danger, you know, like obviously that's what fear is initially intended for. It's our body's signal, like there's danger here. So I don't want people to think like, don't feel fear, you know, 'cause I do think again with the self-doubt and that like there's this kind of macho thing of like you should be fearless, right? And like, I like the word because people sort of mean courageous, but sometimes people think that literally means you should not feel fear. And I think that's a setup for—
there was a clothing brand called No Fear when we were growing up, remember?
Yes. No. Yeah, there totally was. I had their shirts. I run a venture fund called Fearless Ventures. But what we mean by that is, you know, it's like more in the realm of like courage and lots of love. Yeah, you know, courage is not the absence of fear, feeling fear, doing it anyway. So all that is to say, um, what, what the real distinction is, is are you motivating yourself by, um, resisting the fear? Like, I don't want to feel that fear or shame or something, and And so I'm gonna work my ass off so that I don't have to feel that. That's actually the toxic fuel that we speak about, dirty fuel. And so, even the sense of like, I need to prove myself, 'cause if I don't, what would I have to feel? Shame, disappointment, fear, sadness. And the more that you can learn to allow and welcome those feelings, the less you're driven by like this compulsion to avoid. So in a real— the shorthand for all that for me is, do I feel constriction in my body or do I feel expansion in my body? That's— I find that a really useful distinction that kind of is a way to cut through all the other stuff because there's so much like when people learn conscious leadership or these distinctions of like being present versus being in threat, or being, you know, fear versus love. There's— we— our minds tend to go to like, well, I would act this way if I was, you know, coming from love, or I would say these things. And that's, that's, first of all, just kind of unknowable. Um, and second of all, you can say the same exact words from a place of like constriction and threat, or from a place of openness and love, and they'll, you know, they'll feel really different, um, to you and the other the other person. So it's really about your being and what's happening inside you.
Yeah, so the easiest way to know is to pay attention to your body in different moments.
And it's one of the easiest ways.
Yeah, feel it. Is it feeling—
do I feel like— yeah, my chest tight? Am I feeling like— again, we— I think we often conflate like the quantity of work with the quality of work. And when I say quality, I don't mean, um, how good the work is. I mean the quality of our experience while we're, while we're working, right? Right. So like the whole debate about, oh, burnout and should we work 80 hours and 996, should we work 40 hours, to me misses the mark around what are, what are you experiencing while you're working those hours. Because you could work 80 hours in flow and it'd be a one— it might be a wonderful experience and you go home, you know, with joy and a lot still to give to your people. And you could work 40 hours in this, you know, super constricted, you know, grinding feeling state. So to me, like, to grind is not a question of you working 80 hours or 40 hours. It's like how— Energy. —tight are you while you're doing it? Yeah. So yeah, what do you feel in your body? And you start to notice it, you know, at first it's like you notice the gross obvious, like, oh, I'm pissed off and I'm reacting and I'm yelling at people. But then over time you can notice more and more subtle constriction, right? Bracing against life instead of like open and flowing. And then the other test, and I'll get into drama triangle. If I ask myself, is there anything I'm wishing was different right now? That is the most reliable way to know whether I'm operating from constriction or openness because life just is the way it is. Like, somebody posed this question on a call I was on earlier, like, like, can you trust life, or should you trust life? Can I trust life? Am I willing to trust life? And I, you know, for a long time I, I would say to clients, like, are you willing to trust life? It's like, it's a, it's a really powerful idea whether you trust life or not, because if you don't trust life, you, you're constantly feeling like you have to control everything But as I thought about this morning, it just started to feel absurd, the question. It's like, well, life just is. Like, I don't know, like trust it to do what? You know, like life just is the way it is. Yeah, I'm not talking about the future. You have some influence over the future, but like life just is the way it is. That's just true. So if you're in your head thinking it should be different than it is, I wish it was different, Like, you're just, you're just creating all sorts of, you know, needless suffering for yourself. And I think that's what we, we do all the time. And then we justify it because we say, I need that, so I need to— I need that suffering so I have something to run away from, you know.
I mean, well, it goes back to why people use dirty fuel and yeah, addicted to it. Yeah, we think we need it, we're addicted to it. Something's not good today, so I need to go do something different in the future to have a different future.
Yes, because I believe when I create those conditions in the future, then I'll finally feel the way I want to feel, right? And the irony is the way you block yourself from feeling the way you want to feel right now is by telling yourself you need these conditions to feel it. Yeah.
And I think, by the way, just— you sell, you're worth $10 billion, you have a $100 billion company, and you don't feel any different. This is something I tell a lot of founders, like, if you aren't happy right now 40 million or 100 million or a billion, 10 billion, it's just not going to make you happy. Like, and, and it's— and you can start to see, I mean, I see like my peer group at our age and lots of successful people in there, it's more and more they're like, oh yeah, you're right. I mean, in that post, but we forgot to mention this, that post went crazily viral on Twitter because everyone's like, wait, like it really, it really struck home.
And the nuance I want to add just to reemphasize it is The way you're blocking yourself from being happy now is by believing you need the $40 million to be happy, right? Which is very ironic, right? It's like the whole thing is like a setup because it's like, okay, well, I don't want to feel happy now because then I won't be motivated to go get the $40 million that I need to make me happy. Well, one— yeah, so I invite you to see through all that. Okay, I want to get— you want us to talk about the drama triangle. So what, what this psychologist Stephen Karpman discovered is that when we're in a state of threat, when we're in any state other than like just fully present, open, curious, our mind seems to naturally see reality through the lens of of the drama triangle, or I've also heard it called the fear triangle. And one way to think about it is just like, I like thinking about the mind as a storyteller, right? Like, our minds are very compelling storytellers, right? It's just kind of—
they try to make sense out of things. They try to make sense out of just whatever's happening.
It's the function of the mind, yeah, to create the narrative, try to make sense of things. There's lots of research, like, even when even when like totally logically inconsistent, like as long as it makes sense somehow to ourselves. So our mind's just constantly inventing— I think is a good word— stories, um, which already is really useful because if you think you're the storyteller, you get trapped in the stories, right? So already just seeing your mind as a storyteller that's just making up stories, um, is useful. And then we start to ask like, okay, well, what makes for a compelling story? Because our minds pretty good at it, right? It captivates our attention quite a lot. First, there has to be a problem, right? That's why humans think they have so many problems, because our mind is a good storyteller, and good stories have problems, conflicts, dramas, right? Yeah, tensions. Um, and then they have these three characters, you know, a victim, a villain, and a hero, right? And If you start to pay attention, you'll notice so much of the time you're identified as your mind or engaged with your storytelling mind, believing these stories like, oh, poor me, you know, I don't have enough resources to hit my plan, right? Yeah, I didn't hit my— well, yeah. All right. It's so hard to raise money because I'm not an AI startup. And the world has changed and investors only want AI startups. So these simple-minded investors, villain, right? We blame them and poor me. And then the hero, sometimes there's a person in your world that's like, oh, it's okay, it's all gonna be fine, right? They try to make you feel better, create temporary relief. Or sometimes we hero ourselves through some actions like, well, just, you know, go have a drink or, you know, yeah, watch Netflix.
One of my classic ones was like selling, like sales development. Like, I know, no, no. Like I would, I would like when I was feeling nervous about something, I would like send 10 emails out to potential prospects and clients and be like, can we get on a call? Because I would like, I was like, I don't like this. What's this feeling happening right now?
And yes, you know, the hero, the whole Um, uh, impetus of the hero is to not have to feel something and you don't want to feel, or to protect somebody else from feeling something you don't want.
Temporary relief.
Yeah, the temporary relief, uh, of, you know, basically a way to avoid feeling it. So that's a great example, like, oh, I don't want to feel this fear, I'm going to go again, hustle, build the pipeline. Yeah. And then, you know, and it's, it's really a cycle we get in, right?
And, you know, if you look at Any relationship, when I ever introduce this to people, by the way, like the first inclination is always like, okay, I'm one of those people. You're one of those people. Or like, they always go like, okay, well, I'm the victim now. And then like, so-and-so is the villain. And then so-and-so or such-and-such is the, is the hero. Yes. And that's not correct. Right. It's, it's a, it's a thought pattern.
Can you, can you talk about that? Like we tend to rotate through those different roles, and the roles have kind of like a different energy and mindset to them. So when we're in the victim role, in some way they're all flavors of victimhood, but you know, when we're in specifically the victim role, the energy is like, oh, poor me, right? Um, and, or we could even say the storyteller, right? If you imagine a storyteller who's like, part of their storytelling art is they, they play the different roles, right? So your storyteller mind goes goes into victim and it's like, oh, poor me, poor us, you know, poor me. This is happening to me. Oh, my team, it's all on my shoulders. My team is letting me down. And then the storyteller switches roles and switches into the villain role and it's like, it starts blaming. And you could even blame yourself, right? Like, oh, if God—
If I just hired that person that I thought I needed to hire.
If I just hired that person.
I should've raised more money.
Your investors told you to, or if you were a better CEO, If you were more visionary, right? It just starts to— it's like your mind starts to bully you and criticize you, right? That's the villain role. Or someone else. So, your mind is kind of playing the role of victim, then your mind is playing the role— that's a nice way to think about it— of villain. And then your mind might play the role of hero. Well, it's okay. You did your best, you know, or whatever. Let's just— or just, let's just go sell. We're going to get there.
Well, the guy I was talking to yesterday was like, well, I've already had an exit, so I've got plenty of money. I've got plenty of money.
I shouldn't really be worried about this. I don't need to worry, or spiritual bypass. It's all good, right? Sometimes stoicism is used that way. Whatever, it just is the way it is. Like, even I was advocating for that, but there's a way you can use that as a hero move. Like, well, it'll just be how it is, and abdicate responsibility.
And I think that— I think this, this is one of those, uh, tools or frameworks that I think every single person I've ever explained it to, once they know it they cannot unsee it. Because I think we— everybody knows, everyone has the experience of their mind looping. Like, we call it loop. Oh, my mind is looping.
I'm spinning. I'm ruminating.
I keep going on the same thing. And then you go— and then you go, well, hold on. Like, once you explain this, they go, oh shit. Like, I, I'm going— I'm going through— that's the loop. That's the loop. And then the hero says, well, I've raised money, but like, I'm still— yeah, but I'm still mad about this, but I wish this was different. And it just goes on and on and on. And the reason I— the reason I wanted to bring it up or just talk about it is just like to me, one of the ways I've used it as in my life as a husband, founder, father is like, oh, anytime I notice one of those stories, it's like an immediate way that I can like, especially the blame, like anytime I'm blaming myself or something else or someone else, I'm like, oof, I'm in threat right now. Like I can tell that that's the case. Nice. And that tends to be more, you know, and I think people sit on those places more often, I think, right? Like, so I'm not often victim, like I don't let myself feel victim.
Yeah, we tend to have favorites. Like, um, and, and the one that's our least favorite is usually our blind spot. Like, like, we actually do it. We don't really— like, I, I realized at one point, I was like, I definitely go victim, I definitely go villain, but I don't really— I don't think I do the hero thing that much. And I realized, like, for years I was heroing all my clients by being like, oh, you know, you're not— like, there's nothing wrong. Or, you know, I was like using the tools to help them avoid feeling shame or sadness. Instead of just allowing them to have their experience. So, so, um, but yes, we tend to have a favorite. And, um, I like what you said that, uh, I want to connect the dots here around, um, it starts with something's wrong here, right? Again, good stories have a core conflict. So our mind goes into this story mode. It Perceive like life just is the way it is, right? Like the facts just are the facts. But then our mind goes into story mode and it goes, something's wrong here. It shouldn't be this way. Yeah. And then automatically we go into who's to blame? Poor me. How do we fix it? Right. This is such a cool analogy.
I think the other thing I would add, I just thought of this is like good stories have hooks. Yeah. That pull you in. Right. And so like, like that's, you do that on any story. There's a thing that pulls you into it. And by the way, the same, your brain does the same thing. Like We, you know, the therapist called them triggers, right? But like as a founder, you're like, oh dude, the revenue meeting, like with the revenues down, like, oh, it's going to hook me. And then, and then I'm now, now there's a problem and now I got to tag who's the victim villain and the story now.
Or it makes up a hook. You're going to run out of money. You're going to fail. This isn't going to work. You're never going to raise money. You know, it's just like, oh, that got my attention. Yeah. Yeah.
Well, can we talk? I want to end on this. Kind of the 201 a little bit, or I'll call the 201, which is like when you're in relationship with others, whether it's your spouse or your team, there's the concept of responsibility and sort of like how it impacts relationship.
So, so, you know, yeah. Let me say one thing. Do you want to finish with that? No, go ahead. One just really tactical thing I just want to say about the drama triangle. So, I love what you said, like just pay attention, notice if you're in one of these roles, that's a good tell that you're in a state of threat and there might be something to shift. Practically speaking, for myself and my clients, if I pull out my phone and open a note and I start writing out my drama triangle, so I'll literally like write victim colon, oh, poor me, blah, blah, blah. You know, villain colon, those, oh, I can't believe hero colon, oh, it's okay, I'm sure it's all going to be fine. If I just like that, to me, that initiatory step, like if I take the time to really put awareness on it and write it down, right, tends to be the domino that then leads to me shifting. So for a long time, I knew about the drama triangle. I'm like, oh yeah, I kind of know it. I think I'm on it. But I didn't do that and I wouldn't really shift. But anytime I actually, or pen and paper, like started to write it down, I could just really see more clearly, oh yeah, wow, my mind is believing all this stuff. Like I'm in it and it feels really real when you're in it. And that was always my doorway to kind of step out of it and see it for what it was. So I just want to name that tactic. I would just like literally write down in your notes or a piece of paper, victim, villain, hero, and literally write out your drama triangle. Like, that for me was one of the biggest tells of like, I'm actually committed to shifting, or I'm just committed to like perpetuating the drama.
And in coaching, I mean, we coach, and even I use it, like, that's the first step of it, and it's actually super therapeutic for people to just let it all out.
Let's get on the drama triangle. Oh, poor me, can you believe me, right? And exaggerating it again, it just helps you see it more clearly. 'Cause when you're in it, I mean, that's the crazy thing about being human. Like our minds are so powerful. Like I'll sometimes be like, say to a client, like, hold on, like knock on your desk for a second. Like feel your, that's real. Like all this, none of that's real. You're literally just imagining shit that doesn't exist, but it feels so real when we're in it. It just feels like our reality. It's like being in The Matrix or like in a nightmare. I'm like, hey, wake up. None of that's happening.
Yeah. And it can— and the mind can go. So, so yeah, let's talk. So, you know, when you're in relation to responsibility and responsibility and, you know, I'll give an example, right? Like a workplace example, right? It's like, okay, I have my salesperson and I ask for their, for their update on their pipeline once a week. Yeah, right. And then they never get it to me. And I don't say anything to them about it. That's a great example. And, and then I'm frustrated about it. Let's— yeah, let's talk through that in the triangle. And as it relates to responsibility and, and maybe I say, well, I don't want to— I don't want to bug that person. I know they're— I know they're making a lot of sales phone calls and so therefore I don't want to bug them. Hero. Yeah. So let's talk through that, that example in the triangle and then sort of how responsibility works in those situations?
Yeah, so taking responsibility is one of the most powerful ways to shift from a state of threat to a state of presence. And, you know, like the Conscious Leadership Group would describe like being below the line in a state of threat as, um, essentially victim consciousness, right? Like it's happening to me. And being above the line in a state of presence as creator consciousness, like it's happening by me, I'm creating it. And what you'll see is that the— like, if you see yourself as a victim or any one of those roles, you, you, you sort of, you feel powerless. And so taking responsibility in the sense of seeing yourself as the creator of the thing that you previously were blaming or feeling like a victim of is actually an act of self-empowerment. So I just want to say that first, because sometimes people hear responsibility and they think of it as like self-blame, right? Like buck stops. Okay, it's my fault. I screwed up, right? That's not empowering. What's empowering is, okay, this occurred, right? Again, back to like the storyteller mind will go, right? Like, this is a problem. But if you can, if you can see through that and be like, okay, this just is. We— what was your— we hit— we missed our numbers.
Was your example just, I'm not getting the pipeline report I'm supposed to be getting? Okay, great.
Yeah. Yeah, right. It's just a fact. I want to be getting the pipeline report and I'm not. That's just what is. And then I go, okay, how am I contributing to that happening? Or how am I co-creating it? What's my responsibility in it? Not that you overstep and assume you're like the dictator of the world. Of course, other people have their responsibility. But what we tend to do when we see it as a problem is deflect. Poor me, it's happening to me, or it's, you know, we blame somebody. And when you shift and you're actively looking to take as much responsibility as possible, it's because you want to experience yourself as empowered as possible. Because the more you see how you created it, the more you see how you can do something different to create something different. So in that example, Dave Kashen.
But yeah, I think the conversation would be like, what do you mean? How am I creating this guy not sending me his report?
Exactly. What are you talking about? So first we'll go in the drama triangle. Which would sound something like, I'll let you do it. Wait, what am I—
I'm for me. I'm not getting this guy. This guy never gets me the report. I don't know what's going on in our business. I, I, I, you know, I've told him to do it before and, and he said he would and he never does. And I just don't— there's too much, too much going on and I'm just stuck and he's lazy or he's just not doing something. Yeah. And yeah, and he's a good sales guy and he did Dave, but he's like, but you know, it's just frustrating. He's busy. I know he's busy.
I know he's got a lot of— that's your hero move, by the way. Well, maybe he's just busy, and I— okay, I could just let it go, right? So that— so, so first we just have you get in the drama triangle so you can see the pattern that you're in. And, and then, um, I'll typically say, could you accept yourself for being on the drama, you know, below the line on the drama triangle? Because you— it's important. You can't shift what you don't accept.
And then I'll say, okay, before we go on though, Which of the consciousnesses are thinking about which level of responsibility? Which— so when I'm a victim, am I, am I, am I, am I—
the victim is abdicating responsibility.
So they're taking less than 100% responsibility. Yeah, that's a good way to say it.
So is the villain, really. Um, the victim is just like, oh, it's not my responsibility, it's happening to me. The villain is like, It's your responsibility. They're trying to assign more than 100%.
But both of them are taking less responsibility and trying to, well, yeah.
Both are taking less in different ways. One is just sort of abdicating responsibility. Like, what can I do? Poor me. The other is, is specifically trying to assign response, more than 100% responsibility to everyone else or to the world or to other people.
But what about the hero? The hero's taking more.
And the hero tends to take more than 100% responsibility. And, and that's why they try to like rescue the people they see as victims from feeling some feeling. And that could even be themselves, which is interesting.
But in this example, it's like I'm a victim to this person, but then I'm heroing them also. I'm also going, well, they're busy, they got a lot going on, and I get it. Yeah. What is— what I guess— what happens when that becomes a pattern with that other person?
Um, you, you typically end up resenting them. Heroes typically end up resenting the victims that they rescue because over time it's like, okay, well, God, you know, I've asked you and you're not doing it, and, and I, I keep making excuses for you, but like, oh my gosh, you're, you know, you're still not doing it. I've been so nice about it. I haven't even said anything. I've been so kind about it and still you're not doing it, right? Like, that's kind of the cycle. So, so let's talk about how responsibility shifts that. So then you just get curious, like, okay, I say I want them to do their pipeline reports every week and they're not. Okay, how am I allowing that to occur? And if you get really curious, you'll usually see something you didn't see before, like, yeah, I guess I can be a little conflict avoidant. So I did ask them once, but I didn't really tell them how frustrated and disappointed I am that they haven't done it, or I didn't create a clear agreement around it. I asked for it, but I didn't say, will you do it? Because that feels edgy, that feels bossy. I don't want to be bossy, right? You know, so if you're willing to see, almost always you can see some way that you could have acted differently that would have likely led to the outcome you want, which is awesome because then now you have the recipe for how to create what you want, right? If you If you see how you created it the way it is now, you're more likely to see how to create what you really want instead.
And I think that like the other thing I would just add, I guess, or even my experience with myself and others is like the deeper you go in this, there's a specific activities which are actually really valuable because you'll say, how are you allowing this to happen? The first person's response, like, I'm not, what do you mean?
Then they're just not doing it.
I told them to do it. One version I'll say is like, if you had to get it or you would drop dead, Right. How would you behave? Well, I would, I would ask them 2 days before, and then I would ask them an hour before, and then I'd ask them 30 minutes before. And then like, oh, so there's a way.
Absolutely had to make it happen. How?
Yeah, you would do it, right? And but then the other thing I notice often is that underneath this, these actions are always some worldview of a person, which is often like to see them again either as a victim. The hero sees someone as either the victim or a villain, which is they go, well, and I go, well, As long as you see that person like, oh, they're disorganized, that, you know, they're— and this was a really mind-blowing one for me, is like, you're seeing that person as less than yourself, and that actually perpetuates the entire thing.
Because you start just seeing— heroes need victims. And we can— we can— exactly what you said, we can actually unconsciously, inadvertently perpetuate someone's victim story about themselves. By the way, another version of taking responsibility is Yeah, they are showing up in this kind of victimy way, but I'm co-creating that because I'm seeing them as a victim. Totally. And I keep coming in to save the day, which gives them the message that they can't handle it on their own, right? This is such a common pattern with like delegating. It's like I delegate, but then I see the client's going to be pissed off because they're missing something, so I come in, swoop in, and save the day, which tells them I don't really trust you, I don't believe you can do it, and even just unconsciously tells their system it's okay, you don't have to take responsibility because they're going to come in and save it, and then I resent them for not doing it.
And it— I mean, this comes up with, I think, parent-kids and parent relationships and spouse relationships.
Every relationship is subject to this pattern. So I would, I would challenge you as a listener, really look for like, where am I in that, right? Anything that you're frustrated about, any problem you have in a relationship, really any problem you have, notice if your, your mind, your storyteller mind is going through that victim, villain, hero. And I would, at least at the beginning, challenge you to literally write it out. And then, and then just writing it out, you'll start to get a little distance from it and, and be able to see through it.
All right, do that and we'll see you next time.
All right, thanks, Dave Kashen. Fun. Bye.
