In this episode of The Inner Circle, host Mike Brown talks with guest Kevin Dahlstrom about the necessity of making bold, scary moves to reboot one’s life. Kevin shares his personal story of leaving a high‑paying corporate job in Dallas, moving his family to Colorado, and enduring marital strain before ultimately finding a more authentic, fulfilling life. Mike recounts his own painful divorce and the dismantling of his "have‑it‑all‑together" identity, describing how confronting that mask freed him to pursue new paths, including coaching. Both emphasize a pragmatic approach to major change: first identify the underlying pain point, apply a "minimum effective dose" or test‑drive the change (e.g., sabbaticals, short‑term relocations) before committing to a full reboot. They discuss psychological concepts such as Jung’s masks, the ego, and the role of fear versus courage, noting that fear biases decisions toward the status quo. The conversation concludes with a shared mantra that it is better to regret actions taken than opportunities missed, urging listeners to clarify their desired life, adjust for fear, and act boldly.
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Hey everybody. Welcome to The Inner Circle. I'm Mike Brown, joined by my dear friend and member of my inner circle, Kevin Dahlstrom. Today we're diving into a tweet Kevin posted yesterday about his life reboot. And, uh, he received over 40 DMs, which is, which is absolutely wild. And essentially what he said is life is never perfect, but I finally built the one that I, the real me, wanted. So here's my message to you. You can do the same, but only if you muster the courage to make bold, scary moves. There will never be a good time to do it, and there are no guarantees it will work out. Kevin, how do you think about bold moves and maybe unpack your reboot a bit?
What I posted yesterday, which seemed to hit a nerve, uh, as you said, I got more DMs from that post than I, I, I can't remember the last time. It's been probably a couple years or, or more. And the post relates to one of my very closely held beliefs, which is that inevitably over time, um, we tend to drift, right? Like we get into a routine, we get stuck, we get complacent. And I believe that it's very hard to have a great life if you're not willing to make at least one big, bold, scary move in your life. And so, um, I think a lot of people who listen to this probably know my story, but I'll summarize. You know, I grew up in Texas. Um, I'm a Gen Xer, so we're notorious for, you know, we don't ask questions. We put our heads down and we just go. And, you know, um, over the course of you know, um, my 20s, 30s, and even into my 40s, I built the life that society told me to build. I did what I was supposed to do. I got my college degree, I got married. I joke that I had 2 and a half children. Like, you know, did I did whatever, like the white picket fence, worked my way up the corporate ladder. And so on paper, through a lot of hard work, I built the life that That looked great. Like it's in some ways the dream life. It's exactly what I was told success looks like. And then I had a bit of an awakening and I realized like, this isn't my definition of success. And I mentioned in this post yesterday, there was a vivid moment for, there was a few like kind of catalyzing moments, but one of them was, I remember sitting in my executive office in Dallas, looking out the window thinking like, What the hell am I doing here? Like, I just don't want this. And again, huge salary, prestigious job, big house in the suburbs, all these things. And so, um, I hit the reboot button, which is, you know, it was very scary and moved the family to Colorado, quit a very high-paying job, walked away from a ridiculous sum of money. And, um, you know, it all sounds glamorous when I tell the story. The truth is, and, and, and Mike, I know you've experienced this and we're gonna get to your, your reboot in a little bit. There's smiles on the outs. I posted a picture of us, you know, sitting on our porch the day we, we landed in Colorado and we're all smiling inside. It's probably the worst I've ever felt. Like my marriage was falling apart. Uh, my kids weren't happy with me cuz I just uprooted them from the, the only life they ever knew. I was so disillusioned on the inside. I didn't know what was next. I was, kind of discovering who I was. But I had a strong sense that we needed something different and we needed a major change to force a reboot. And so fast forward 8 years and it worked. You know, I say all the time, and it's true, like I've got the best life of anybody I know. Of course it's not perfect, but it's worked out really well. And so that informed my belief. And so I'll stop there. I mean, that, that's just an example of, you know, I think at some point everyone needs a major change, whether it's by choice or whether it's forced upon you. So let me stop there and then I'll, maybe you can talk about, uh, a major reboot that you've experienced and then we'll get into how to process, yeah, how do you do, how do you make a, a major change?
What comes to mind for me is that I think almost everybody has some daydream about the life they're not living, right? And the real question I think that we're unpacking here is if you have this secret life or this secret fantasy of making this change, what's the difference in the people that keep that a fantasy and the people that take big, bold action, right? And I do think sometimes it's forced upon you and sometimes it's chosen or a combination of both. Uh, you know, for me, I've had several through business. I've reinvented myself, uh, many times. And in, in some ways I've, I've made sort of a hobby out of burning down my identity and rebuilding. But the scariest one by far, um, was my first marriage. I got married very young when I was in the military, you know, also kind of following the track, uh, just, just doing what I was supposed to do. And, you know, the military, you move a lot and, and I was dating this woman and moved and wanted her to come with me and basically, well, if she's going to come, you have to get married. So it just kind of unfolded, I think, kind of, you know, unconsciously. Um, and, and the reality is that at 26 years old, you have no idea who you are and no idea who you're going to become. And, and over time, It just became very apparent over, you know, the next 13 years that we were dramatically different people. We were not a match and there was a lot of hurt there. There was a lot, you know, I didn't have the tools to even know how to build a successful marriage. I didn't have the tools to work on myself. And so, you know, rather than placing blame on anybody in particular, it just It became apparent, you know, that this was not the marriage that I had imagined. And for years I tried to cover it up with everything else in my life. Um, so I just poured myself into business. I poured myself into sports and hobbies and travel with friends. I had all this stuff and I, and, and I, I have this distinct memory. We, we, we moved to Colorado in 2016. And met all these amazing friends in our neighborhood. And, you know, my ex was not particularly social. And I remember sitting by myself with these other couples and just thinking, you know, man, I built a great life and I don't need that. I don't need my partner to be here with me. Like, I'm really happy. I was convincing myself of how happy I was until one day I truly had I was in a group retreat with my coach and who eventually became my mentor, Philip McKernan. And I was sitting at a hot seat in the front of the room and just all of a sudden blurted out, I don't love myself. My wife doesn't love me. And I think I want to get divorced. And I don't even know where it came from. I started crying and I was like, Whoa, like I never even voiced that out loud to myself, much less a room of people. And it was the scariest thing I've ever done. You know, it was, it was programmed into me deeply. You know, I, one of my family patterns was like, never be messy in public, right? Like you can fight behind closed doors, but we put on a front that everything is good. Going through a very messy and very public divorce. That facade was just completely ripped away and it felt very exposing. And I mean, it was truly terrifying. I mean, you know, and there were times when, you know, I would say like, if I knew how painful this was going to be, I probably wouldn't have done it. And, you know, now I look back and see that as one of the greatest gifts I've ever given myself, but it was terrifying. And, and now I met my, my new wife, Claire, who is a total match. I married the female version of myself. Gift of, of being able to rebuild a relationship at 40 with these tools. I knew who I was. I, you know, I, I knew how to invest in a relationship properly. And difference is so stark and is so fulfilling to have this relationship now. But it was on the other side of, you know, 3 to 5 years of really painful personal development. And, um, you know, it was tough. And so I look back at that and the crazy thing is, and, you know, from this bold decision, I didn't know that it would work out. And in fact, it was worse than I thought it was. Would have been. And yet now I look back at, you know, and see that as one of the biggest catalysts to also living the best life of anybody I know, as you like to say. But it was terrifying and it got worse before it got better.
That's, um, first of all, uh, thank you for sharing. I think your story hits very close to home for a lot of people who will be listening to this. And I think, you know, I made a few notes while you were talking because there's a lot of powerful stuff there. I actually got a little emotional when you were talking about your session where you kind of had that epiphany. But, um, and by the way, having directly observed Mike and Claire, uh, uh, uh, you know, for many hours, the thought that came to mind even before today when I would just observe you guys is that's what love looks like. Uh, so I love, that's really beautiful to see. So congratulations on coming out the other end of it. But you know, the thing is, um, hard things are hard, it turns out, and hard things are messy. Hard things are uncertain. If they weren't those things, it wouldn't be hard. It would be easy and everybody would be doing it. But the reality is kind of back to my core point, you have to do hard things if you want a great life. My story of relocating, which was really more of a relocation, it was, you know, it was a catalyst for rebooting everything. Um, that was, um, you know, that triggers every fear in people for some reason, like the idea of uprooting and moving. But walking away from a relationship is, trumps that, like that's even, even harder. And so I want to transition into like, how do you process it? I think this idea of like getting worse before it's better holds a lot of people back. And I often say that, you know, it's all about fear. I mean, you and I talk about this all the time. It's like all these things ultimately come back to courage and, and overcoming fear. And I tell people, uh, like the post I posted yesterday, a lot of people The DMs I got, a lot of them were like, I'm on the fence. I've been thinking about doing this forever. And my standard response is, if it feels like a 50/50 decision, it's not because you have to adjust for fear. And fear always lands on the side of maintaining the status quo, even if it's miserable. So like fear is what kept you in your relationship probably longer than it should have. Um, So if you adjust for that, it's actually not a 50/50 anymore. It's like an 80/20 that you need to go make the bold change. And so I don't know, man, how do you, how do you pro— like, how should people think about if they're contemplating a big change or they feel like they need a big change? How do you process that? Like, what do you, how do you guide your clients when they think about, when they talk about this?
Number one, and this is almost counterintuitive to what we have been talking about. But I actually advocate for minimum effective dose first. Let's try to pull the small levers before we go nuclear and hit the big reboot button. Right. And a great example is a lot of time clients will come and they're contemplating selling their business. And the first question I ask is like, do you want to sell because it's the right time to sell because you've grown the business as far as you possibly can and the market conditions are right? Or do you want to sell because you're burned out? And 90% of the time it's because they're burned out. I say, cool, let's try to reconfigure your role inside of your business to see if you can fall in love with it again. Right? Minimum effective dose. Let's, let's try and fix the business first. And then if you want to sell on the backside of that, cool. That's a different decision. So, so I would say first thing is figure out what the actual pain point is you're trying to solve. And like, so if you're fantasizing about this big dramatic reboot, What's, what's actually underneath that? What, what is the pain point that you're trying to alleviate? And, and try to make that minimum change first and then evaluate. And then sometimes the thing might reveal itself as like, okay, yeah, no, I do need to make this big decision.
Incredible advice. Um, and our, you know, I would label that as like test driving the change. You can't do that with all changes. But with a lot you can, and our mutual friend Paul Millard writes a lot about the transformative power of sabbaticals, for example, like taking a break from work. Let's say it's 3 months and going somewhere, ideally overseas, experiencing a different life, getting a taste of it often makes the answer very, very clear. And in fact, I did that. I didn't realize I was really doing that at the time, but, um, we did a, a, uh, a, a one month, uh, we came to Boulder for a month before we relocated and it was like trying it on for size. And of course the answer was what I knew all along, which was yes, we absolutely need to, to be here. So I think that's incredible advice, this idea of like either taking a baby step or of, of like trying it on for size for a little while.
But let's say, okay, you do that and you realize the big bold decision is the one that's actually, you know, staring at you. Um, I think it actually comes down to a question of identity, right? We, because we tend to wrap our identity in, in what we do or what we've built, you know, and, and my identity was largely tied to being seen as the guy that has it all together. Well, the guy who has it all together doesn't get divorced, right? And so it actually had very little to do with the dynamics of my marriage or, or, you know, what I knew I needed to do is the thing I was most afraid of was shattering this identity as, as the guy who has it all together. And again, burning that identity was actually one of the best things I've ever done because The reality is no one has it all together. And, and all of a sudden letting that loose created so much freedom for me of not having to maintain this carefully manicured image. Uh, and really was a catalyst for changes in so many areas of my life that actually gave me the courage to, you know, get out of the oil and gas industry and become a coach. And, and I, you know, I've done so many things as a result of no longer having to be the guy that had it all together. Um, but, but it was that first big bold step of just burning that, that whole idea. Yeah.
I think you say, uh, something like, I reserve the right to be a, a completely different person than I was 5 minutes ago. I think that's a good mindset to have.
Yep. From that, my favorite quote from Alan Watts.
One thing that, um, I happened to stumble across when I was contemplating my big change was, um, Carl Jung's writing about masks. Carl Jung wrote a lot about. Uh, midlife crisis, actually. And, um, the way he described a midlife crisis was he basically said, like, we think of midlife crisis as, oh, Kevin's becoming a different person, and it's actually the exact opposite. Your true nature is revealed. And he talks about this concept of masks where, you know, we all wear masks just to, to exist in society. Like, you can't be completely unfiltered at all times. Right. But, uh, and so masks aren't inherently bad, but masks become a problem when you lose the person behind the mask, which is when I read that, I was like, that's me. Uh, I have like, I'm wearing this mask that, you know, looks great from the outside, right? Allows me to thrive in society. But this person behind the mask is actually crying. Uh, he's, he's, he's pretty miserable and. I can tell you, you know, there's nothing more liberating than removing the masks and living your true nature. And I think that's a connecting thread between both of our stories is I, through my reboot, was able to express my true nature. And you, through your relationship change, same applies.
Yeah, absolutely. And I mean, the, the reality is, is, you know, at, at that point, I had no idea who I was without the burdens and obligations or even the stories placed on me by society. You know, I was just like you. I had gotten everything I was supposed to want that society says will make you happy. And I woke up and realized like, oh no, this didn't work. Like, who am I without all this stuff? Who am I without my achievements? If I stop being this driven type A, high performer, military business guy, who am I actually underneath that? And it's, you know, it's taken a decade to continue to burn those identities and continue to let go. The power truly is in the letting go of realizing like, actually, my identity is just a collection of stories and patterns and emotions that kind of fit together in this thing that we call ego. But none of that is who I am, right? It's like, who I am is what existed before that. And so a question I love to ask clients is, you know, who were you before the world told you who to be?
That actually reminds me of one of my favorite movie quotes of all time from Up in the Air. Do you know the quote I'm going to refer to? Um, so, uh, in the movie, um, George Clooney is basically like an HR executive and he's, he's firing this employee. Who's like your classic, like burned out middle-aged guy. And, um, George Clooney asks him, uh, how much do they pay you to give up on your dreams? Yeah. And I think that hits hard for, um, for a lot of people is that's the drift I talked about is like we never intend to give up on our dreams. It happens slowly, like death through a thousand cuts, and suddenly you wake up and you're 50 or 55 and like, Who am I? And, um, you know, I think the earlier you can force that discovery process of understanding who you are, um, either by choice or, you know, through a catalyst, the, uh, the better.
Maybe I'll close out with one of my favorite quotes and, and a, a rule that I tend to live by, which is, I would rather regret something I did than regret something I didn't do.
100%. Yeah. Far more people suffer from the consequences of inaction than taking too much action. And I'll close out about, because when I tell my story, one, the most common pushback I get on it is, oh great, like here's a guy who made a bunch of money and then moved to Colorado. How, how is that hard or bold? You know, that's not practical for a, a regular person. What I'd say is that, I mean, yes, having the, the financial success I had before my reboot, you know, in a, in many ways made, made it easier. But I will tell you, very few people in my situation do it. And so if money was the only obstacle, lots more people would be rebooting. Fear is always the, uh, much bigger obstacle. And look, it's a privilege that's earned. Like if you wanna make a bit major change in your life, it doesn't mean you're entitled by birthright to have that life immediately. You know, people often lose in my story that there's a 25-year period where I had my head down grinding to, to, to get ahead. And yes, that bought me a ticket or the privilege of rebooting. So it's not a birthright, but what I, what I always say is just get clear on the life that you want and It might take years, decades to get there, but get clear and do things that move you closer to that life. Do not do things that move you further from it.
Absolutely. And, you know, I think it really does come down to the courage, but, you know, at the same time I say, you know, there were, there was a period when if I knew how painful it would've been, uh, I wouldn't have done it. Now, you know, 7, 8, 9 years later, if I knew what my life could look like, right, I would have done it years earlier.
Yeah, in a way. Yeah.
And, and that's your—
that's ignorance is bliss, because things are all— things always turn out to be harder than you think. So even though it seems scary, it's probably going to be even scarier when you're in the midst of it, um, but it's also probably going to be even better on the other end than you imagined.
Yeah, I, I think that really is the takeaway, is that, you know, if I could go back now and tell that version of me the life that I'd be living today, I think I wouldn't have been able to even process or hold how unbelievable things are on the backside of—
Likewise, when I started having these feelings of disillusionment years before I moved, I would tell that guy to take aggressive action. So I guess that's our message here is be bold, you know, test drive it if you can. See what it feels like, um, adjust for courage and then take action.
Yeah. I mean, as, as my meditation teacher likes to say, like, you only get to be this version of you once. So, uh, you know, the regrets people die with on their deathbed are rarely action and almost always inaction. So take that, be bold, make big choices, and, uh, and then roll down if you need to. Good one. All right. Talk soon.
