Episode 16: How to Have Hard Conversations Without Making Everything a Fight with Kyle Depiesse

In this episode of the Scar Tissue podcast, host Melissa Dlugolecki interviews Kyle Depiesse, a former corporate executive turned high‑school teacher, grief‑focused entrepreneur, and creator of the Guy’s Trip retreat brand. The conversation opens with a discussion of men’s mental‑health crises, especially the high suicide rate among men, and identifies isolation as a primary driver. Kyle shares his personal story of burnout in retail e‑commerce, a career shift to teaching, and the accidental founding of Guy’s Trip – intimate, low‑key retreats that blend physical challenges, sobriety, and structured reflection. He explains the retreat’s core tools: a “personal balance sheet” questionnaire and a “ladder” visual that helps participants prioritize life domains. The dialogue explores the concept of sonder – recognizing that every person carries unseen stories – and stresses the importance of surrounding oneself with honest, truth‑telling friends to avoid echo chambers. Melissa and Kyle discuss the destructive loop of people‑pleasing, the need for non‑confrontational communication, and practical tactics such as frequent expectation‑checking checkpoints. Kyle uses the mangrove‑vs‑oak metaphor to illustrate why relational interdependence (horizontal growth) beats solitary vertical achievement. The episode concludes with concrete resources: a PDF guide for partners, the guystrip.co website, and Kyle’s preferred LinkedIn presence, encouraging listeners of any gender to engage with the retreats or apply the discussed frameworks in their own lives.
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The one thing that comes to mind is isolation. Leaders tend to surround themselves with people who agree with them. And most guys just, they don't know how to do that, so we just don't end up doing that. I have prioritized work over my girls for their entire life. I'm making a change from tonight. I was climbing a ladder and you get towards the top of the ladder and you're like, maybe, maybe my ladder's on the wrong house. Is this the life I really want to live? I just want to let you know that I lost my daughter.
All right, you guys, I am so excited to welcome Kyle Deppes to the show today. He is a wealth of wisdom, knowledge, and truthfully, you know, the podcast Scar Tissue was built on resiliency and opportunities that come from our challenges, but also on the notion that it's a choice and that we get to choose to be the creators of our life and our realities. And, and that's going to come with challenges, right? And so here on Scar Tissue, we talk about the real, we keep it real, we keep it raw, we keep it authentic. Um, and Kyle's work in particular, as I mentioned, in supporting men is just so needed. And so get your notebooks out. Uh, we have a heavier community of women, so share this one with your husbands, um, your boyfriends, your brothers, your colleagues. And pass this along because this message needs to be shared. Kyle, welcome to the show.
I'm excited. Thanks for having me, Melissa Dlugolecki.
Absolutely. Now, as I was, you know, preparing for our conversation and, you know, we don't script anything and I know that you're the same way, but I found myself really thinking about the statistics that I have heard myself, which I'm sure you're well more educated in terms of mental health for men and the suicide rate for men. And I just found myself thinking about that a lot, how the suicide rate was, I believe, 4 times as much men, 4 times more men than women. And I just found myself wondering why. And what is it that, you know, you think, and obviously this doesn't necessarily have to be to the level of, you know, suicide, but if somebody chooses to end their life, I mean, that is a lot. I mean, it's a lot of grief. That they've been carrying. We talk a lot about grief here, grief that they've been carrying before that decision is even made. And so what do you think in your experiences is it that is creating a lot of suffering, whether it's all the way to the level of somebody doubting if they want to live anymore, or just suffering as they're going through their day to day? And also, I'm just acknowledging the fact that we just went right in and went real deep.
No, it's a great question, but it's like, it's a great jumping off point because I don't know if I can pinpoint one thing, but the one thing that comes to mind is isolation because there are a lot of numbers as well on how isolated men feel. And I, you know, I have some theories on that, but those are just personal working theories and I'm happy to share some of those and I can speak to my own experience. So I, in high school, I played 4 sports and then I was also involved in every extracurricular activity our school would offer. So from 7:00 AM to 7:00 PM, I was with my friends the entire time. And then you go to college and not quite the same, but similar. You have proximity to your friends and they're always around you. And now you fast forward a little bit, you're working. And as you continue to go out, maybe you get married, maybe you have kids, I don't know, but you no longer have that proximity. Maybe you've moved away from your friends. And so now as an adult, the question is, How do you make new friends? That's a really hard question to answer. And a lot— something that guys struggle with because it's something that was just always there for us. But the key is now we have to be intentional to go make new friends. And most guys just— they don't know how to do that. So we just don't end up doing that. And so I think the thing that's really taking men out is isolation, because the people, the other men that are in our sphere— I'll look at myself as an example. It's, it's maybe other flag football dads. And I'd see them on the sidelines for my son's game. Maybe it's colleagues, but who are those do I actually get to choose versus who's just around you? And most guys just don't ever take the intention and the step to building their own community.
Hmm. That is such a good point. And my background is in education, so, um, me too, 10 years in the classrooms. Yeah, that's right. And, you know, you think about it and that really is curated circles. For you from literally the moment you get up until you go to bed. And, and then as you move on, if you go to college, you're now living with your friends, you know, um, in many cases. And for me, I played sports in college, so it was the same thing. We'd go to classes and then we'd go to practice, right? And we'd have games, we'd have road trips. That's such an interesting— I never actually put that together of like, when does that happen? How does that happen? Where does it start? And it's almost that loss of connection That's so powerful. So you mentioned that your background is in education. I let the, you know, the listeners know about your work and your expertise, but talk a little bit more about what you do now and how you got here.
Yeah, well, I stumbled into it. I kind of call myself a bit of an accidental entrepreneur, but my background is corporate America. And so like corporate America, I got really sucked into this whole climb the corporate ladder thing. And when I got really burned out of that, it was about 2015. I said, I'm just done with this. I was at that time, I was working in retail and e-commerce. And so, I'm sure most of the listeners are familiar that that industry, like our Super Bowl is Q4. We do so much product in that season. So, while everyone's home with family or whatever it is, or they're traveling or taking time off, Thanksgiving, Christmas, I was working. And I'm not just working for a couple hours checking my email. Like, I'm talking 12 to 14-hour days. And I just got to this point, Melissa, I'm like, what am I doing? You know, I was just really good at putting my head down and just grinding and working. And then all of a sudden, you just look up and you're like, wait a minute, like, how did I get here? Like, what am I doing here? Is this where I really want to be? And so, I kind of stepped back and in 2015, I said, I don't want to do this anymore, and I want to start living a life that I'm fulfilled by. And so I became a high school business teacher, and I, like I said, like, probably like you, like, I love teaching, but I love to uncover the process of learning for people. And so taught for a couple years, and then, um, my wife and I had our son 2017, and we decided that I'd take the promotion to a stay-at-home dad. And it was awesome. It's still awesome. But you have this gift of being home with your child. But the unexpected gift that I found was I've got a blank canvas, a white sheet of paper. What do I want to create? Like, what do I really want to do? And I spent a lot of time and I kind of went back to like my days in corporate America. I would always go to leadership conferences and, you know, those seminars, and I sought out personal growth stuff. So I went to like John Maxwell conferences and I— there, there's so much of them are the same thing. You're stuck in a Marriott Hotel conference room for 3 days, you know, 4 concrete walls, and it's speaker after speaker. And I'm like, I'm introverted and I don't learn that way. Like, that's like— forced networking is really hard for me. And so I thought, well, what if we just flip this model on its head? And instead of hundreds or thousands of people, what about 12? So instead of seeing someone's name on a lanyard and listening to their elevator pitch, what if you got to like truly know their full story? That, that doesn't happen in, in those types of environments. So how do we reverse engineer this thing? And so in 2019, I just, I created this event on the North Shore of Minnesota along Lake Superior, and we dropped a helicopter on the resort. They've never done it before. And we, I had the guys go in and we hovered over waterfalls on, on some state parks and this really cool thing. And I put it out to my network. I said, this is what I want to do. Who wants to come? And, uh, 12 dudes showed up. And you'll get a kick out of this because of your background. Like, I didn't market it for guys. It was not meant to be a guys-only thing, but that's who showed up. And so I just was observant, and I listened to the conversations. It was a part of the conversations, and I, I was just blown away, Melissa, because men were usually like sports, fantasy football, like that. Those are the things that we talk about. But those were not the conversations that happened on that trip. And these guys had meaningful and deep con— and you could just tell these guys are carrying a lot. We all carry a lot. There's a lot of pressure and responsibility. And like, where do you go to put it down? Like, where can you go to just be Melissa Dlugolecki or whomever and just be you, but not your title? You don't have to perform. You're not going to be judged. You could just be you. And so it was really refreshing, and I said, I guess I'll do it again. So, you know, now fast forward 7 years later, and, uh, it's turned into this brand called Guy's Trip. And we take a handful of trips per year, uh, some are US, some are throughout the world. And I've kept it small intentionally and on purpose because I love it. And, uh, that's just kind of what it's turned into, this fun little brand.
That's amazing. And I think it's funny I say I stumbled on it. I did not plan on doing what I do now, you know. And it's like I always say the best entrepreneurs are see a problem, solve a problem. Yeah, right. And you saw from a place of curiosity, like witnessed a need. I think, I think that is the way I truly believe that is when it is in service versus like, I have this great idea, I want to force other people to buy into. Yeah, right. But you see a lot and people wonder, why isn't the selling, why isn't the selling? And I'm like, because people don't even want it, you know.
Um, yeah.
And so I know I, I segued a little bit there to the, the funnels and marketing side. I can't help myself. But, uh, that's really how I think. I know, it's really how I think though. The best businesses are born from looking at, um, because entrepreneurship for me is just service, it's humanity. And, and you touched on something, how everyone's carrying a story. And that is, I want to say, chapter 14 in my book, Scar Tissue, uh, and there's a term called sonder. Have you heard of sonder?
I don't know, I don't think so.
Not a real—
I'm gonna write it down.
So it's— yeah, you can look it up. It's actually in dictionary of like not real words that need to be words. I don't— I'm butchering the name of it, but there's a dictionary that is words that were not created that we need to have a word for this. And sonder is the idea that every passerby is carrying a story you know nothing about. And that was so pivotal— well, I just got chills— that was so pivotal for me and my grief journey because I think so often we think, why me? How did this happen to me? Like, hey, the more you lean in, you more you realize everyone's got something. Yeah, something. How can we be more curious and more compassionate, more committed to humanity? And so, yeah, I just really resonated with that.
Can I tell you a story? And I did. I just got goosebumps too. And this is why. So the first trip that I did, so this is 2019, I had a guy show up. I'm just going to use a random name because just in case he listens, Paul. And he showed up very reserved. And you could tell like he was just holding on to something. And I didn't know what it was. The last night night, uh, we're sitting around for dinner and we kind of had these hot seat conversations. It was his turn to talk, and again, you could tell like he's almost kind of shaking a little bit. And he went on to tell us, he's like, guys, I've got two, um, teenage daughters, 18 and 16. And he told us, he says, I have prioritized work over my girls for their entire life. And like, you could hear a pin drop. I'm like, I don't know what's going to come next. And he says I'm making a change from tonight. And he went home to our resort that night. He called his daughters. He said, tomorrow night I'm making dinner. I'd like to talk to you girls. And so he told us later on that he went home, he made dinner for the girls, and he apologized. He said, I've just come to know that I've prioritized work over family. I'm not doing that anymore, and it's going to look different from here on out. Now here's where it gets interesting. In October of last year, 2025, he sent me a text. He said, Kyle, I just want to let you know that I lost my daughter. And like, I just, I cannot tell you like how powerful, you know, to hear that because we all carry something like you said, and we just need these moments and containers where we just can stop You know, put, put this phone to the side, stop distractions, and let, let bubble up to the surface what needs to bubble up to the surface. Deal with it in a loving way with people who care about you, and then go make whatever needs to happen after that. But we don't give ourselves that gift enough. And I just— when you mentioned that, I was like, you know, I had no idea. None of those guys had any idea that he was carrying— they were all carrying something, but that sticks out, and I will never forget that story because His life was changed from there. And just to be a part of that journey, like, that's why I do guys trip. That's, that's what it means. We travel to amazing places, but it's stories like that where you have an impact that that's why, that's why I do it.
Yeah. Now I love that. I mean, that's powerful. And that's why we do the work that we do. As much as I love— my brain works and you can see whiteboard in the background if you're watching, but my brain works in funnels and whiteboarding. But what really motivates me is helping really good people, authentic good, pure people amplify their impact and reach. Because there is— there's so much competing attention for consumerism, for things that aren't real, for superficial. And we can't stop that, but we can amplify the good, you know. And so it's just an honor to, to see, you know, to be part of your work and what you're growing. I remember when, um, you know, when Nick told me about, you know, your trips or something. And it was like, you know, oh, it's a guys weekend type thing, right? And so the ladies, you're listening on here, when my boyfriend said, oh yeah, I got this guys weekend thing, you're probably thinking like, oh God, like, what, what are they doing? Like, yeah, guys weekend, they're all getting away from their wives, their kids, their significant others, they're gonna be shot they're gonna be doing whatever. Uh, what do guys' trips actually, uh, consist of? I know, but I want you to share because I just think it was so powerful. And now I'm just like, Nick, go on all of them.
Yeah, yeah, yeah. We have a loyalty punch card for Nick coming up pretty soon, right? Um, I think, you know, we have that perception that we have to overcome, you know. And honestly, it's— as men, it's our fault. Like, we— the perception is real. What's interesting though, Melissa, is most I'd say at least half the guys that go on guys' trip don't— they're sober. They don't, they don't drink. And the others are like, you know, at the end of a long hike in Patagonia, I'm gonna have a beer. And that's, that's fine, you know. So alcohol is not really a part of it, and that's also very intentional. I don't want to be a part of it. I want distractions to be put to the side, and I want clarity to come forward. And that's, that's hard when you numb it out with alcohol. Um, they're usually pretty physical in nature because I think men connect best by and through movement. And so when we move our bodies, when we're doing workouts, when we're putting sweat on the floor, um, that's how guys connect shoulder to shoulder. So there's always a physically challenging element to it. My favorite part is I will ask guys to do something they've never done before. So there will be an activity or something where the guys will have to be a beginner because as men, we also have ego and bravado. And if we can just get past that because, hey, no one's going to be the expert at this. We're all first-timers. Well, who cares what I look like? I'm just going to go do it. Like the last one that we did in California, we all went to this Lagree studio and no one's ever done a Lagree Pilates class.
I was going to say, if you're not sure what that is, it's Pilates.
Yeah, yeah. I'm familiar with it now. I got the grippy socks and everything. But, um, so those are the elements to it. And then I've got this, um, I've got this, you know, brand IP, which is a personal balance sheet. And I ask guys before they come on a trip, it's one sheet of paper. It's very simple. And it's just, here's all the categories in life that are important. Let's track them. Let's measure them and let's rate each other on it. How are we, how are we showing up as, uh, as partners in our relationships? How are we showing up at work? Where's our health at? What needs attention? And how can you help the group? And so every guy gets a chance, usually fireside, to just share. Here's where things are at. And in an honest way. And if you give guys like, just fill out this piece of paper, here's the question to answer, you know, as opposed to, hey, tell me about your marriage. You know, it's just easier if guys have some prompts. And so we give that to them to make it easier for guys to do. But that's where the magic happens. I mean, we've done some cool things. We've visited amazing spots, but every guy I will tell you, it's those conversations that are the most impactful and why they keep coming back.
Yes, 100%. And I borrowed your questions that you had last time at the, at the guys trip that you had. And you had these very thoughtful, intentional questions. And I was with a couple of women and Nick had shared them and I was like, ladies, Let's do this. Let's go.
Cool. How did it go?
And it just— it just— oh, it was amazing. But you know what's interesting is like, I think the question in itself is such a lesson because you see a list of questions, you think you have to get through them all. That's how our brains work, right? We got to get through all the questions. But it was like one question would lead to a detour and a detour and a detour. And all of a sudden we're in this like 40-minute beautiful discussion to one question. Yeah, right. Uh, and I, I just think that's so powerful.
Yeah.
Um, okay, so one of the things that I saw that you wrote, and I wrote this down, so I'm going to read it off of my own screen. I love this. I'd love for you to elaborate on it. It said, the tendency to complicate our lives comes because we confuse the definition of success and what living a full life looks like. So So we basically, what I hear you saying is that we complicate our lives because we aren't clear on what success is. So I'd love to hear you speak into a little bit more how you've seen maybe people find that clarity on what success is. If the listener's like, well, I'm kind of chasing the wrong thing. I think I'm chasing the wrong thing. I don't feel fulfilled. I don't feel connected. Like what might that be coming from? And maybe walk them through that. Yeah.
I had the, I, alluded to it in my brief intro story, that I was climbing a ladder and you get towards the top of the ladder and you're like, maybe, maybe my ladder's on the wrong house. And the whole point, the whole point is like when we're busy and we're just busy being busy, we don't actually take time to step back and say, is this the life I really want to live? And Honestly, that, that question and that answer might change from time to time. Like, my life changed when I got married, and then it changed, it changed, it changed again when I became a father. And you have to ask yourself those questions on a, on a somewhat semi-frequent basis to make sure that you're still in check. And then I think another really important thing, Melissa, that doesn't get talked about enough— leaders tend to surround themselves with people who agree with them. Now, whether, whether they do this intentionally or not, I don't know. But if every day— if every idea is a great idea, then how do we know if we're on the right track or not? I think putting people in our lives who are willing to tell us the truth is so important. There's a great proverb that I love that says, kisses from the enemy are deceitful, but faithful are the wounds from a friend. So who in your life is willing to have the courage to wound you for good by telling you the truth?
I love that.
Most people don't have that in their lives. And I can't— it's— that's wildly important, because if you've got a handful of guys or gals, whatever it is, who's willing to say, man, you're off track a little bit, like, you said you were committed to this, or I saw you, you know, looking at something inappropriate. Like, are you— should you be doing that in a committed relationship? You need people like that in your life because we sit in these echo chambers and, uh, we just end up down the wrong path. And so I think if there's one thing to take away from anything I've said today, hopefully it's that, because I think that's very important to have the courage to put people in your life who are willing to tell you the truth.
Yeah, that is so powerful. You know, I've always said to my clients, especially when I used to do group coaching— so I used to do group coaching before really the agency was birthed— and I would always tell them, like, I care about you too much to tell you what you want to hear. And people would come with these business ideas or these objections or these things. I'm like, I don't need you to like me. Like, my commitment isn't to being like you being my fan. My commitment is to your greatness. And I think if we're really committed to somebody's greatness, we're willing to say the uncomfortable thing. Because this is something I'd be curious to know your thoughts on. I always say people pleasing is so misunderstood. I was like, oh, I'm a people pleaser, poor me, I'm a people pleaser. I think people pleasing is selfish because people pleasing is— yes, it's going to sound like, uh, Melissa, how could you say that? You're just caring about other people. No, you're making sure that that other person is happy with you because then your happiness and your validation is connected to their happiness with you. So you are seeking to kind of impact or influence how they feel about you by dismissing your own needs or your own truth so that they're pleased with you, so then you feel safe. And it all comes down to safety, right? But I see you laughing at me.
Yeah, no, you're— I'm picturing a loop. I mean, what you described is like a loop, and we're stuck in this feedback loop of try to, try to just not have confrontation. Try to just— everyone, you know, don't, don't rock the boat. Like, you don't, you don't confront me with something that's challenging, I won't do it to you. And, you know, we'll just, we'll just stay in this beautiful little circle that feels nice, but nothing ever changes or gets better, or there's no growth there. And so what you're describing, I just, I can just picture a loop, and I would totally agree with that, right?
And then that person who's people-pleasing can often go into resentment. Yeah, because they become resentful that they are choosing to put their needs aside. But I always say, and I think this is important for the listeners to hear, especially this can be— I mean, I can't speak to this as common for men, but I know it's very common for women, um, people pleasing. But we can then become resentful, but no one's a mind reader. And so your partner may just be operating like without any clue that you're stuffing your needs down or dismissing them or abandoning them. Right? Because they're not a mind reader and they're going based off of what you say, right? And so how would you describe, um, or suggest maybe somebody who hears the word confrontation, which you just said, and I think a lot of people in the air of confrontation, they think negative, bad, angry. Um, you can have maybe confronting conversations in a non-confrontational way, right? You can have confronting topics in a way that doesn't have to be volatile or angry. What would you— how would you maybe support somebody if their understanding of having those difficult conversations is intensely confrontational? Like, what other ways could somebody have that conversation or speak into the things that they need to speak into that maybe they're avoiding?
What comes to mind for me when there's conflict is usually a misalignment of expectations. Usually the expectations are unspoken. And so to me, I kind of giggle a little bit because I just think of my— in my marriage, and I'm like, whenever there's conflict, it's just, well, I thought she was going to do this and she thought I was going to do this. We never talked about it. So now we're both like, hey, why don't you do— so it's just, to me, it's just a little bit silly because like, if we could just talk, if we could just talk about it, we probably could— number one, this wouldn't happen, or number two, we could resolve it really quick. And I think carving out— this is going to sound really silly, but everyone lives busy and really filled up lives. And so even if you just have small checkpoints throughout the day, whether it's morning, maybe lunch, or obviously one at night before you go to bed, like, hey, how are we doing? Or, hey, is there something I did today that, you know, wasn't having those really small touch points, which is— I think it would keep us out of a lot of conflict, to be honest. And then if there was, it would resolve it really quick. And so I'm an over-communicator and my wife's a bit of an under-communicator. So I guess we got opposites. Certainly do opposites, certainly do attract. Um, but, and so I think I probably drive my wife crazy in that. Um, but anyway, I don't know, I just, I giggle. Maybe you do too, because maybe you're similar to me, and I think I just, I just over-communicate. I don't know.
Oh yeah, I know where I'm like, yeah, because I think opposites attract. And so, yeah, uh, someone listening, likely you are more of the heavier communicator, or not, right? Probably wearing one of those. Uh, and I think you can find calibration in relationship, you know. I think, uh, through Nick I've learned not everything has to be urgent or immediate, right? Like, there is a level 2 of, like, discernment and timing and patience. And I think, you know, with, with me, he's really embracing the power of communication and just speaking our truths, right? But we have to create environments, and it's very important, we have to create environments where the other person feels— for, I don't know if it's lack of a better term, or I'm not sure what other word I'm looking for— but feels safe ultimately. In articulating their truth. So many times, even people pleasing or any of that, as much as I was like, hey, be responsible for communication, uh, we also have to look at on the other side, are we showing up as a partner that you would be— I would be comfortable communicating my truth with? Would I be comfortable coming to me with something difficult? And if not, I gotta fix that, because how could I expect anyone else to come to me me if I wouldn't be comfortable coming to me. And I think that's very important. I, I, I— my whole book, and even though it's about grief, it's really the guiding principle is radical responsibility. Yes, personal responsibility. Because, um, no one was coming to save me in grief, and that was the life lesson. No one was coming to save me. And, and even in the gender constructs that our, our world has, you know, and there's some biological in that of the protector, provider, more, you know what I mean, like different things. A lot of it's constructed, but it was very much like looking for my daughter's father to just save me, fix me. And then it was this wake-up of, oh, this individual has their own individual way of grieving. Yeah, they need to individually grieve too. And I tend to attract a lot of people through grief, so that's why I speak into it a little bit more. But You know, understanding that was a big lesson for me, was that I had to be really responsible for my grief. No one was going to save me, no one could fix it. And honestly, in hindsight, I am so glad that nobody did, because if somebody put a Band-Aid on and I could kind of get by, I wouldn't have done the deep work that I did. I wouldn't have learned the lessons that I learned. And so I'd also offer, like, there's a beauty to that level of responsibility.
So can I ask you a question?
Sure.
I want to ask you a question. Okay. Did you— it's such an interesting topic to me to get to the point where you took the responsibility and said, it's my responsibility, not someone else's. Can you explain? And maybe you have in your book, and I apologize, but I would love to hear it selfishly, and I'm sure someone else listening would too. Did you get to that over time, or was there like a— did it happen like that? Do you know what question I'm asking?
I do.
Okay.
Like, was it a light bulb moment, or like, did you have to get there? I think it's probably both, right? But two flash, very teachable moments that I had that were life-changing. And also, I love that you're asking me. This is— we just have— we just converse. This is how it is. Um, but this is powerful for, for anyone listening, and so thank you. And very relevant to your work, and I think very relevant to whether, uh, you know, you're resonating with the work that Kyle does. Perhaps you're a guy who's looking for connection. I'll let you know where you can find more about Kyle about his work, maybe join one of his trips. If you're a woman who wants to support, um, whether it's your brother or your partner or your husband in doing this work, we'll make sure that you know about it. Or maybe you just want to show up more powerfully for your partner. These two lessons help me show up more powerfully in relationship, uh, in life, because I think everything, Kyle, is just energy. So whatever— it all applies to business. Everything helped me in my business, right? People want the magical business fix. When you're an entrepreneur, I always say entrepreneurship is humanship. Anyways, my two moments. One, I was walking, um, outside of Boston Children's Hospital. And so in hindsight, it was really sad. I didn't know what to do. It was after my daughter passed away, and I literally would just go to the hospital and walk outside of it to feel something connected to her, right? And I, I, I promise you, I like looked up and there was like this light coming down, and like I just heard in my head I heard a voice and it was like, Melissa Dlugolecki, it was tough love. Talk about tough love. Melissa, you've been walking around like you are entitled to a healthy child. You can grieve not having one. You can be in pain and you can heal. You're worthy of one. Remember that. You're worthy of one. But you have to remember you're not entitled to anything in this world. And I remember— oh, I just got chills. I remember it was like, this is the message I'm actually meant to share. Because how often do we walk around, to your point, expectations that can also be very cousins to entitlement? And like a very simple example, I lived in Boston and I would remind myself if I'd be driving on Storrow Drive, very congested highway in Boston, and there'd be traffic and I would have to say to myself, well, your frustration is coming from some unagreed-upon expectation or entitlement that no one else is going to be on the road. What do you think? Because you didn't plan your time well, Melissa, everyone else is going to clear Storrow Drive for you. And I started doing that everywhere. The second was— um, simplified paper for anybody who's tuning in on video— um, the second was in my grief counselor's office. And I went in like she was— I was the prosecuting attorney, okay? And I had my courtroom the invisible courtroom in her office, and she was going to be the judge, and she was going to sentence my daughter's father to life in relationship prison because he was not showing up the way that I wanted him to at that time. And, um, she had me do— draw two things. I'm gonna draw this for you right here.
And for anyone watching, thanks, teacher.
Yeah, I know, right?
I love it.
You can't take the teacher out of me. Oh no, my pen just died. Here we go. So she had me draw this. So if anyone's— I've had people tell me that this has changed their relationship, by the way. Two ladders, mine and his. Melissa, what's the most important thing in the rungs of your ladder right now? And I was like, well, my grief, right? Then what? Probably my relationship. Then what? Probably my health. Then what? Probably my job. I had a great career. Was an athletic director at the time. Okay, cool. What does he have over here? Well, he has a living daughter from his first marriage, probably here. Then probably his grief of, you know, our daughter. Then he was looking for a job. He was unemployed at the time, looking for a job, and then like something else. And so it was like, long story long, was that the rungs were not aligned. And instead of looking at a right or wrong, I now constantly create ladders. And when I see people, like invisible ladders, you know, uh, I'll just say this, for example, for those of my entrepreneurs listening, if somebody doesn't get back to me, I never take it personally. Like in, in sales, for example, people are like, that person ghosted. I think, I wonder what's on the top of their ladder. It's probably not hiring me, right? And it's just this level of humility and like empathy and compassion that, uh, that really resonated with me. So I don't know if that makes sense, but it was, it was really that moment was like, oh, so if this person isn't going to fix my grief, and grief is my number one rung, I gotta. And I had one moment where— I'll share this and then I'll stop here— but I had a one moment where I remember when I was going to my grief counselor and I had to pay for it, and I was like I have to pay? I have to pay for grief therapy now? My daughter's case was termed a catastrophe. She wasn't supposed to die. We just spent 99 nights in the hospital, and now I have to pay for someone to help me fix this? I was so angry. Then I was like, of course you have to pay. Why would you think you don't? And so it was all these lessons, I think, that just kind of stacked on each other that just kept calling me into a new level of responsibility. I don't know if that resonates with you or answers your question.
Yo, the ladder visual, I just— I'm blown away. Like, that— what a way to reorient yourself. And that's a wonderful visual. I'm glad, I'm glad that you shared that. Hopefully people are watching that because that is— that's brilliant.
Thank you. Oh good, I'm so glad it resonated.
Yeah, well, I learned a lot today, so hopefully, hopefully the listeners did too.
I did too. Now I want to let people know where they can find you and maybe even join the next, um, guys trip trip. But with that, what would you recommend? How— what would you encourage, whether it's the woman listener and, and supporting their— we'll just go with husband or partner— and doing this work? Like I said, it could be colleague, brother, friend, cousin, doesn't matter. Um, like, I think of my brother, right? I think of my brother, and you've said some things that I'm like, I am sending him that micro clip, right? Um, or to our male listeners who are maybe wondering, like, am I living life the way that I want to live? Because as much of this podcast is rooted in grief and the resiliency, what I would love is to be able to share something that can maybe get somebody, invite them into what's something they can sit with, ask, and let's give them a homework step. We're both teachers, right? Yeah, we'll give them a homework step, um, so that they don't grieve looking back at the end of their life that they didn't live the way that they wanted to live. Yeah, that they were chasing the wrong success.
Yeah. Well, I would first say that I think what I see, especially, but this, this works for male, female too. A lot of high performers, high flyers, entrepreneurs, whatever it might be, they're built like oak trees. And people think oak trees are very strong. They are very strong, but they're not the strongest tree in nature. The strongest tree in nature is a mangrove.
No.
Oak trees grow tall. Vertical, strong, they're often standing alone. And when storms come through, they don't test how tall you are, they test your exposure. And so, mangroves, because they're interlocked and their roots are connected, they can blunt the force of a storm because they're connected. And so, I encourage people, yes, go build amazing things, go do awesome things, grow vertically, but don't do it alone. You got to grow horizontally, grow relationally. And Guystrip is just, I think, a cool way to do it. There's obviously a lot of other ways, but you can find out more information on our socials. We're Instagram and Facebook and YouTube, and my website's just guystrip.co, and I'm pretty active personally on LinkedIn as well. That's a great way to get in touch with me. Um, for the guys out there, we have something on our website where, uh, because every guy when they're like, oh, Iceland's coming up in the fall, I want to go to Iceland, I got to talk to my partner about that.
Yeah.
So we've created a little PDF on how to get your spouse on board or your partner on board with a guy's trip because they're going to have to battle the perception of what's going to happen on the guy's trip. Well, we have a lot of women that talk about how their partners come back home changed from it. And so I think that's a useful tool as well, but it's just meant to be playful and fun. But you can find that and that's on our website too. But there's a lot of ways to check out what we're doing and how to interact with me. The best way for me personally is LinkedIn. The best way to keep up with the brand is our Instagram page.
And that's guystrip.co.
Someone's got.com and they're trying to sell it. It's listed for like $10 grand and I'm like, I don't, I'm fine with, I'm fine with co. We're good.
I don't need a.com. Yeah. Especially now with so many, uh, oh, this is kind of, but so many addresses going to.ai.
Yeah.
Right now that's being used a lot. See if we can grab that one, but yeah. guystrip.co. Go scope it out. Connect with Kyle. Um, ladies, I highly recommend you not only say yes to your man going on these trips, that maybe you gift it to him. Maybe you gift it to him. What? It could be a life-changing gift— memory, relationships. Um, and I can tell you from my exposure to the work that you do and the questions that are asked and that reflections, it just creates, uh, deeper relationships and deeper humanity. So I can't encourage that enough.
Yeah, well, thank you. I appreciate that.
Yeah, Kyle, thank you so much for coming on the show. You guys, we will link all the places that you can find Kyle in our, uh, show notes here. We'll also include it in the email, so if you're on the email list, you will get that as well. And if you just can't find Kyle, go to guystrip.co or send me a DM, and I will point you in the right direction. You can also find Kyle online on LinkedIn, as he said, is his preferred, most, uh, commonly accessed platform, because there are certainly a lot of platforms out there. Kyle, thank you so much. Thank you for the work that you're doing. Um, thank you for pursuing your mission and stumbling into this business that will just change so many lives and, uh, I think lineage.
Yeah, I appreciate that. Thank you, Melissa Dlugolecki.
All right, thank you so much.










