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The Inner Circle · Episode 9

Why High Performers Self-Sabotage

For successful people who feel restless and cannot explain why.

Mike Brown and Kevin Dahlstrom · Feb 25, 2026 · 16 min

About this episode

Kevin asks whether Mike, on some level, set up the failure of the business he bought. Mike talks about the pressure that builds when you believe you can do anything, and how the collapse let him shed a mask he had worn for years.

They describe failure as liberating, and Mike offers a tool he uses with clients: separate knowing something from acting on it.

Key takeaways

Full transcript

Automatic transcript, lightly corrected for names, with profanity masked. Some passages may contain transcription errors.

Hey everybody, welcome to The Inner Circle, I And so in the comments, I'm just going to read a couple of little comments discussion to kind of set you up here. Sometimes I think high performers play with fire, in your case, buying that business that lost 1.5 million dollars.

Because subconsciously we want or need to experience failure. And you said, I definitely think that's what happening. And then I Ve

In what was supposed to be a quick 12 to 18 month turnaround, it was a a distressed asset on the verge of bankruptcy. That I was up the proverbial s*** 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 dollars 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 I was deeply aware of. To be the best to anything I did. Right. And this comes from childhood where you can do anything that you put your mind to, well, if we start believing that, then the psychological cost of failure becomes greater with every win that we get. Because now I'm swinging, taking bigger swings. And eventually, it's all going to come crashing down. Right. And that's literally what happened. And I experienced 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 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 shackles 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 so to your question, did I do it on purpose? Obviously not consciously. But I think from a subconscious perspective, I think that. I think that that I I certainly had a part of me that wanted to engineer this failure to find that freedom. I actually feel what it would be like not be able to do anything I put my mind to. And, and, you know, 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 this this fighter pilot, you know, athlete persona who wins at everything. And, look, that was really cool in my 20s and 30s. But, you know, I think as we kind of get to live life like 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 like 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 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 way with your identity. But I'm sure that was part of it. And it is a tempering if humbling if you will, that everyone will get eventually you're not going to make it to the deathbed without being humbled a

bit. I say all the time like 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, you know, I had wealth stored elsewhere that was inaccessible to me at that time. But I didn't have to start completely over right 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 on it was it was a mask. I mean, the reality is right. The reason

I learned that from Esther Perrell 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 let me spin this in a way that I think a lot of guys will connect with is Carl Young talks about this concept of masks that you mentioned and masks are

we think of a midlife crisis as someone becoming a diferent person but actually what it is is it's the masks coming off and the true identity being revealed. It's interesting because my story is sort of related to that where like I was in my mid 40s I was at the top of the corporate world 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 in my marriage was on the rocks like you know the behind the scenes of course I would you know publicly looked great.

But I started doing stupid s*** like just you know nothing major but just like weird behaviors that are very 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 just going to start blowing s*** 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 s*** 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 unful

our ego is going to cling to all of that stuff that we built that fortress that we 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 mid life chrysalis. Yes, you have to walk through this this midlife fire fire to figure out what you really are and since we've been on the young kick right life starts at 40 and everything else is just an experiment and I really do believe in some ways that life life starts at 40 like I don't have it all, I'll figure it out but at 45 like I know a whole lot more than I did it 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 back to your the kind of the comments on your article. Another guy that I, I've interacted with a lot online Drake Smith who lives hereopter and-Boulder said about your your failure and kind of 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 back 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 the sort of sabotage what we're really seeking is liberation.

That was definitely my experience and that that word was very intentional it was liberating because once I could separate my ego from my accomplishments my self hood from my accomplishments 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 five kids in my family and if you. Really get attention from my parents at the dinner table you better have won your swim meet or scored a goal in the soccer field or gotten an A on a test so very quickly you know I learned that achievement. Was how you garden 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 this is an awesome core wound to set you up for success.

And yet there were there were shackles in that right because then if I failed that means I wasn't worthy of love right. 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 your biggest limiting factor. Alright 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 great conversation Kevin and Mike what are we supposed to do about this and in other words

the best my simple answer would be you know maybe it's a necessary process but minimize the collateral damage I mean looking back on my big pivot I probably needed to go through that process regardless but had I been mindful and over it about it I could really minimize the collateral damage what what would your advice be like okay I hear you know what do I do about this. I think what you're talking about is bringing the subconscious forward into the conscious right, how you can I recognize this this restless a feeling right so what 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. Okay well what is out of alignment here what are my values and 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 an 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 like I don't like where I live it doesn't mean I need to go put a for sale sign in my front yard on Monday right.

I actually engineer a plan maybe over two three five years to to go somewhere else and minimize that collateral damage so I, I think that's exactly it is number one. Stop lying to yourself right become radically honest with. And learn the process of what finding your truth actually feels like. And once you got your once you've gotten to the truth. Only then you start putting the action plan in place and hopefully that minimizes some of that collateral damage you heard it here first folks constructive self sabotage. I love this is hard. Maybe I'm maybe I need to launch a new coaching program 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.

More from The Inner Circle: all episodes. Mike’s book Be Rich Now covers the same ground in depth.