Why High Performers Self-Sabotage

Hey everybody, welcome to the Inner Circle. It's myself, Kevin Dahlstrom, and Mike Brown having the conversations we have anyway. Uh, and today we've got a, uh, juicy topic, um, to discuss, and it was really inspired by an article you posted on X with the title of How Losing $1.5 Million Set Me Free. And I read that article and it really, it triggered like a very specific thought that I just thought was fascinating. Um, and, and so in the comments, I'm just going to read a couple of our little comments discussion to kind of set you up here. But I said, sometimes, sometimes I think high performers play with fire, in your case, buying that business that lost $1.5 million, because some subconsciously we want or need to experience failure. And you said, I definitely think that's what happening. And then I posed the question, is there such a thing as constructive self-sabotage? In other words, I was asking, you know, is, is there actually like a method to the madness when we, when we sabotage ourselves sometimes? Yeah.

Let's, let's dig in here and I'll, and I'll give context for the, for the folks that didn't see the article. Um, and I, I grew up, uh, as a gifted child. School came easily for me. I worked hard. I got good grades. But things mostly came easily. And so I went to the Naval Academy, prestigious college. I went and flew jets in the Navy, tested myself in combat. And then I came back and started a company, sold that company. And by 38 years old, like, you know, I don't say this from a place of arrogance, like I had really never failed at anything that I truly set out to do. And then in 2021, after my exit, I bought an e-commerce company in what was supposed to be a quick 12 to 18 month turnaround. It was a distressed asset on the verge of bankruptcy. And it was an abject and total annihilation. I mean, just an absolute shit show. The wheels came off the minute I closed on it. I started injecting $100,000 a month to cover payroll and expenses. And I mean, the hole just got deeper and deeper. And, you know, a year in, I knew there was no way out. I mean, I knew that I was up the proverbial shit creek. And, you know, I went into, you know, depression, anxiety, panic all at the same time. There was days I didn't want to get out of bed in the morning. But on the backside of that, once I sold, I lost $1.5 million inside of 18 months. Once I sold, I felt liberated. I felt finally free because there was so much pressure that I was unaware of, or maybe I was deeply aware of. To be the best at anything I did, right? And this comes from childhood where somebody— you can do anything that you put your mind to. Well, if we start believing that, then the cost, the psychological cost of failure becomes greater with every win that we get, right? Because now I'm swinging, taking bigger swings, and eventually it's all going to come crashing down. Right. And for me, that's literally what happened. I mean, and I experience it now as one of the greatest gifts of my entire life.

I think this wasn't necessarily something you were talking about in your article, but the question it begged for me was, you know, did Mike in some strange subconscious way do that on purpose? I mean, you wouldn't consciously choose to go because I know the kind of pain that comes with a failing business. You wouldn't consciously, but I think of like an image of like, you're, you're in shackles, like you're in this dungeon and you're in shackles and like, you have to just like rage and pull against the chains and like kind of go nuts to break free of those chains. Like it can't happen in a smooth, controlled, pleasant way.

Yeah. I mean, I look at this as divine assignments, so the universe will give us lessons. Over and over until we answer the phone and hang up the phone and get the answer, right? And the reality is, I had been making bigger and bigger bets. And somehow I would always pull a rabbit out of the hat, and it would always work out. And so I just kind of never learned the lesson until, you know, this, this massively failed company landed at my doorstep. And there was no way out. And so to your question, did I do it on purpose? Well, obviously not consciously. But I think from a subconscious perspective, I think that I certainly had a part of me that wanted to engineer this failure to find that freedom, to actually feel what it would be like not to be able to do anything I put my mind to. And that experience, what it truly taught me was humility in a way that I carried the arrogance of someone who had never lost anything. I mean, I had this fighter pilot, athlete persona who wins at everything. And look, that was really cool in my 20s and 30s. But I think as we kind of get to midlife, that stops serving us, right? And so, what this taught me was deep empathy. And the other thing it taught me was that we actually can't do anything that we put our mind to. Sometimes, the universe delivers a lesson so harsh that we can't get out of it. And how cool, like what, like what a neat experience that part of life is. Like, that's something I had never experienced was, was being in that kind of depths of despair.

Well, I can tell you, I have only known Mike 2.0 from the stories I've heard. I hear stories about Mike 1.0 and I'm like, that doesn't sound at all like the Mike that I know. So clearly, you know, I'm sure there was more than just that one experience that, you know, caused you to maybe pivot in a way. Um, with your identity, but, um, I'm sure that was part of it. And it is a tempering, a humbling, if you will, that everyone will get eventually. Uh, you're not going to make it to the deathbed without being humbled.

I say all the time, like, uh, with love, I wish upon everyone a failure that brings you to your knees, that doesn't make you start completely over. And that, that was the real silver lining in this, is that I had other investments. I had I had wealth stored elsewhere that was inaccessible to me at that time. But I didn't have to start completely over. I wasn't out on the street. And so, I got to learn the lesson without total and complete wiping out. And the lessons that I learned now, I really do value as some of the greatest gifts in my life. And it was sort of the catalyst to this shedding of that old identity that was— it was a mask. I mean, the reality is, right, the reason that I projected that arrogant person to the world is because inside, I didn't feel like enough. And what I learned was that, you know, I was enough regardless of any accomplishments, and that I am not my wins, and I am not my failures, right? If we can detach ourselves from our failures, the other side of that coin is that we also have to detach ourselves from our wins. I learned that from Esther Perel. I had the opportunity to sit with her in a therapy session with my business partner. You know, I had always worn this like captain of my own destiny armor. But, but, you know, sometimes there are market forces, there are broader things at play that we actually can't control. And letting go of that was so liberating.

Let me spin this in a way that I think a lot of guys will connect with is Carl Jung talks about this concept of masks that you mentioned, and Masks are not necessarily a bad thing. You need them. Like, you can't just be your true self all the time, completely unfiltered. You're not gonna be very popular. It's not gonna be very functional in society. Um, the problem only comes when you start to lose yourself behind the mask. And the other interesting thing that Jung says is he thinks, he says, we think of a midlife crisis as, um, someone becoming a different person, but actually what it is is it's the masks coming off and the true identity being revealed. It's interesting because if you think about all the stupid shit men in particular do when they get in their 40s and have a quote-unquote midlife crisis. In some ways, they are sabotaging themselves in a struggle to just become their true self, right? And, and it's very misguided. I mean, my story is, is sort of related to that, where like I was in my mid-40s, I was at the top of the corporate world, you know, on paper had it all— beautiful family, big house, big job, big money, all that, all that great stuff, but I was less happy than ever. And I, and my marriage was on the rocks, like, you know, behind the scenes, of course, I would, you know, publicly it looked great, but, um, I started doing stupid shit, like just, you know, nothing major, but just like weird behaviors that are very, um, out of character for me. And when I look back on it now, especially in the context of what we're talking about right now, it was like my struggle to just like, I need something different and I don't know what to do. So I'm just going to start blowing shit up. And that's exactly what I did. And luckily I survived. My family survived that process. But in a way, it was like almost purposeful burning shit down.

Yeah. I mean, I think this is, you know, when the higher self takes over from the base self, right? And goes, hey, you're not on the right track. You're— you might look great on paper, but you're totally unfulfilled. You're totally unhappy on the inside. Your internal experience doesn't match your external experience. And our ego is going to cling to all of that stuff that we built, that fortress that we've built. Right. And then our higher self is the one that might take the wheel and actually start this constructive self-sabotage that we're talking about. I love this reframe that I heard recently is that it's not a midlife crisis, it's a midlife chrysalis. Yes. Yet you have to walk through this, this midlife fire to figure out who you really are. And since we've been on the Young Kick, Life starts at 40 and everything else is just an experiment. And I really do believe in some ways that life starts at 40. Like, I don't have it all figured out, but at 45, like, I know a whole lot more than I did at 35. And I, in so many ways, I feel like I'm just getting warmed up.

Well, and it brings me to, you know, the statement— I don't know who said this, but youth is wasted on the young. You know, if you could have the wisdom and you could have the youth, boy, it'd be a fun combination to have. I want to maybe wrap up with, uh, back to your, the kind of the comments on your article. Um, another guy that I've interacted with a lot online, Drake Smith, who lives here in Boulder, um, said about your, your failure and, and kind of the, um, the lessons you learn. I can totally relate to this. I went through a public failure a couple years ago in the golf world. There's something refreshing about it after the pain of the moment. And you said a word that really stuck with me. You said liberating. And you wouldn't think of an abject failure as liberating, especially in the moment, but that's exactly what we're talking about. It's like by inducing this, um, the sort of sabotage, what we're really seeking is liberation.

That was definitely my experience. And, uh, that, that word, uh, was very intentional. It was liberating because once I could separate my ego from my accomplishments, my selfhood from my accomplishments, like, like my whole life, my, my core wound— and by the way, this is a great core wound to have— was achievement equals love. There was 5 kids in my family, and if you wanted to get attention from my parents at the dinner table, you better have won your swim meet or scored a goal on the soccer field or gotten an A on a test. So, very quickly, I learned that achievement was how you garnered positive attention. And I went about living my whole life that way. And by the way, that's the thing that made me successful, right? This is an awesome core wound to set you up for success. And yet, there were shackles in that, right? Because then, if I failed, that means I wasn't worthy of love.

[Speaker:MARK] Right. Way back here won't get you there.

Yeah, exactly. And so, and that's really what a midlife crisis or chrysalis really is, is I think when we start waking up to the patterns that shaped us and realize that the thing that may have been your superpower eventually becomes your biggest limiting factor.

All right, let's wrap up with one question, and I'll go first since I didn't give you time to prepare. Is, is so like, what are we supposed to do? Like, great conversation, Kevin and Mike. What are we supposed to do about this? And in other words, like, if you feel this, like, desire to play with fire, if you're feeling like you might be in a self-sabotage mode, what do you do about it? And I think the, the best, my simple answer would be, um, you know, maybe it's a necessary process, but minimize the collateral damage. I mean, looking back on my big pivot, reboot, whatever you want to call it, blow up, whatever you want to call it, is I did it in such a dramatic fashion that it caused a lot of collateral damage to myself, to my family. Frankly, like to my career, to my finances. And looking back, I'm like, oh, I could have actually done that in a much more clean way to minimize the collateral damage. I probably needed to go through that process regardless, but had I been mindful and deliberate about it, I could have really minimized the collateral damage. What, what would your advice be? Like, okay, I hear you. What do I do about this?

I think what you're talking about is bringing the subconscious forward into the conscious. right? How can I recognize this, this restless feeling? Right. So what are the warning signs? First of all, yeah, it's, it's out of character behavior. Like if, if you're starting to feel stuck and, and starting to rage against the machine a little bit, there's probably a sign that something is out of alignment. How can I bring that forward in the conscious? Okay.

Go. Okay.

Well, what is out of alignment here? What are my values? And, uh, what are the parts of my life that don't feel like they're aligned with the person that I want to be? And then here's something that I offer clients all the time, which is, as entrepreneurs, we are so wired to collapse knowing and action. Like, the minute we know something, we want to leap to action and do something about it, right? And that serves us super well in our business, but in our life, I actually want to distance those two things. Let me find my truth and then let me put an action plan in place, right? So if it's Something as simple as like, I don't like where I live. That doesn't mean I need to go put a for sale sign in my front yard on Monday, right? I can actually engineer a plan maybe over 2, 3, 5 years to go somewhere else and minimize that collateral damage. So I think that's exactly it. Number one, stop lying to yourself, right? Become radically honest with yourself and learn the process of what finding your truth actually feels like. And once you've got your— once you've gotten to the truth, Only then do you start putting the action plan in place, and hopefully that minimizes some of that collateral damage.

You heard it here first, folks. Uh, constructive self-sabotage. I love it.

This is hard. Maybe I'm— maybe I need to launch a new coaching program to, uh, to take people through the process of constructive self-sabotage.

Yeah, killer online course.

Yeah, there you go. Free 99.

That's right.

How to Blow Up Your Life.

Enjoyed it as always, my friend.

All right, thanks, amigo. Talk soon.