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I see with brand new eyes.
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No.
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I've never been so sure Take my head let's run into the unknown this is the beginning.
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You are listening to the Kristen Boss podcast. I'm your host, Kristen Boss. As a best selling author and performance coach, I'm on a mission to share about sustainable and purposeful approaches to both business and life. Each week I bring relevant topics that I believe are necessary to create a life of purpose, significance and meaning. Entrepreneurship is about so much more than growing your bottom line. It's about who you are becoming in the process and building a life that is truly extraordinary. Entrepreneurship is really just the beginning.
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Hey friends, welcome back to another episode of the podcast. Glad you're back. Hey, if you notice that I sound a little different, that is because I am without my podcast mic. I am not in my recording studio. I'm in the basement of my parents house because we have no Internet and in this day and age it's not very convenient. It's not very often you hear that you're not going to get Internet for the next like one to three weeks. I'm like, I have a business from home. Can you like do it yesterday? So anyways.
And we also had like two back to back snow days the past week. And so we, our kids were having like 90s snow days and like not streaming anything. Like, hey kids, you're gonna have to figure it out if you're bored. Oh well. So yeah, so I'm having to drive up to my parents every day and record on my laptop. So if it sounds different, that's why. So hey, so I want to talk about something that I think is really important as we are getting to the end of the year and you're probably starting to think about, you know, 2026, what you want to look different. Maybe you're moving into some reflection this year. Maybe this year has been about surviving. Maybe this year has been a winning year for you. But here's the thing. When I, when we talk about transformation and change and results, because you know, this is a personal development podcast, that's probably why you're listening is, you know, we, I find we are emotionally bought into two parts of transformation. We get excited about the start, the dreamy, exciting place. And I kind of talked about that in the last episode with Hope Hustling. And if you haven't given it a listen, I highly recommend. But this idea of like the, the beginning is always exciting, exciting. We have this, you know, dopamine of a fresh start. Um, and then we of course are Excited about the end goal. You know, we put it on your vision board, you write it down, you're like, I'm gonna get there. Can't wait for the end goal. Um, but the part that we have little to no buy in with, emotional buy in with, is the messy middle. Um, this is the middle phase. And this is when people tap out, they quit. Um, and it is the most important part of any transformation, any journey that is worth doing. And so this year, this entire year has been a messy middle for me. And I've just been thinking about, like, I think we have some years where.
You know, when I think about, like, what we're. If you're building something or changing things, I think about the bigger the change is like building a skyscraper, and the higher the skyscraper has to go, the. The deeper you have to dig the foundation. And I feel like this year has been digging a foundation far longer than I wanted to and feeling like all there is is a hole in the ground. Nothing impressive, but I know that it's building reinforcement for a future that I can count on. And no one wants that. Like, we, we wanna. We wanna get to the fun stuff. And so this middle phase, I think it's important to have an honest conversation about it because I've. I've been, you know, I've been in many phases and, you know, in starting a new thing, I find that the messy middle has been.
Really. It's your training ground. This is when your character is built. This is where all your lessons are. We don't learn our lessons in the beginning. And oftentimes when we're at the end, we're looking back hindsight, and when we're looking back hindsight, we're looking at the middle, the messy middle. Right. Um, so I want to talk about this. That long, awkward stretch where it doesn't feel new anymore, it doesn't feel exciting, fast, and no one's cheering for you. There's no recognition. And this is the part where people. I think people avoid this part. We don't want the messy middle. We want. We want recognition. We want to feel like things are happening. And I will say in the middle is when you. It's so easy to believe the narrative that nothing is happening, nothing is working.
It's so easy to believe that all of your effort is in vain. But in my experience with people I've coached and with myself, like the messy middle, it's like you're not just building the thing like, you know, your business or habits or transformation. You're built, you're rebuilding yourself. That is, you're. You're getting to know another layer of yourself. And so this is also the season where you get humbled. This is where you learn what you're not good at. This is where you learn about your skill gaps, where you're like, wow. In order for me to get from point A to point B, I'm actually missing these skills, and I have to put in the reps and the practice to get good at these skills. And no one. No one's excited about that, especially as adults. And my daughter, she's. She's playing the piano this year, and every time she gets a new song, it's. It's our first couple practice days together because I played as a kid, so I instruct her between her. Her days when she sees her piano teacher. And so the days when she has a new song, I know that I have to buckle up for a more emotionally charged piano session. And my daughter, you know, she gets so frustrated at her first attempt of learning a new song when she makes mistakes. And I've had to tell her, and it's like it surprises her every time. And I. I'm like, hey, of course you're making mistakes. This is your first time. This is why we practice. And. And eventually she gets to the place where she can play it through perfectly, and she's so proud of herself. And I'm like, hey, remember when you started this and you just kept making mistakes and you got so frustrated? And so I feel like sometimes as adults, we don't grow out of that version of ourselves that gets frustrated at the piano when we're making mistakes of our. Our first run through. We get emotional, we get frustrated, we stand up and walk away, and we forget to tell ourselves, like, oh, of course I'm making mistakes. This is my first time trying this. I don't know where it was handed to us, where we think we need to get it right the first time, and we beat ourselves up when we don't. And obviously, it's not fun when we're making a bunch of mistakes, but this is where. This is where we're learning, and this is where we feel. We don't feel like a rock star. We don't feel like an A player. It's just like, this is where we see where our. For lack of a better term, but I think it could be a highly charged word. We see our inadequacies or our shortcomings, and we have to learn how to meet ourselves with compassion and how to what. What we get to think about those things. And you could choose to make it like, oh, I'm wrong. I. I'm not cut out for this. Or it's like, oh, I have. I have some new skills to learn and I got to put the reps in. You don't go. You don't get to be good right away. But unfortunately, when we have social media, all you're seeing is everyone's highlight reel all the time. Honestly, this year for me, I just feel like I have nothing. Like, what's the opposite of a highlight reel? Like a downer. I feel like we had so many things happen this year that was so hard, so emotionally exhausting, from, like, health issues to losing our dog, to accidents, to things not going to. To plan, lots of things falling short of expectations and just like, over and over again. But who's. Who's wanting to broadcast their shortcomings? No one. So, of course, everywhere you look, you see people posting their wins. What you don't see people talking about is the messy middle. That's 100% where I am. And I'm like, listen, it's. I have to, I have to, like, remind myself how important this phase is. Because this is where you build new habits. This is where you build confidence. This is where you, your identity starts to shift. This is where you grow resilience. This is where you become the person who gets the results. When you start out, you're not the person who's able to get the results. It's the process that builds you. And so the middle is the transformative part of the process. It's what transforms us. We are shaped in the process. And so, you know, I believe, you know, everything in life, any change, it's. It's about, you know, the work we're willing to do on ourselves and the, the things we're willing to face and the conversations we have with ourselves. And so.
Here'S why I think so many people struggle with the middle phase. I find especially high achievers who have maybe had success in some areas and they're going into a new area. I also think that's why some successful people are terrified to try new things, because what if they're not successful at the next thing that I had to work through that being like, oh, my gosh, I built this really successful one thing. What if the next thing I build isn't successful? And I've had to sit and remind myself, like, and there are billionaires who have gone bankrupt. There are billionaires who have had many ventures, and not all of them have Worked. And.
I think. I can't remember. I don't know if it was Warren Buffett, but there was like, hey, out of all the investments I've done, it was only out of, like, hundreds of investments. It was only this tiny little percentage that actually built all of my wealth. And so we. But we focus only on those things and not the 98 losses. We focus on the two wins, but not like, okay, but who are you becoming? And what was your conversation and grit and resilience like with the 98 losses? So this is why I think high achievers can struggle with the messy middle is one you might be used to being good at things fast. So when you're not instantly great, you want to run away and be like, this sucks. This is horrible. It's the same with my kids. Like, some things, like with my son, things come. Some things come very naturally to him. And then if some things, anything that he isn't naturally great at fast, he wants to check out. And we're like, oh, no, no, no, no. This is a really important skill for you to learn. Maybe another one is you rely on excitement to fuel you. So obviously there's. There's very little excitement in the messy middle. It is painful, it is frustrating, it is disappointing. It is. You question yourself. You start to think, like, am I doing the right thing? Did I do this right? Is this the right call? And allowing yourself to have those, what I call, like, the doubt days. Like, yeah, you're going to have doubt days, and then you're going to have belief days. And so when I have a doubt day, I'm like, okay, this is one for the books. And then tomorrow I'm going to show back up believing in this again. Another thing I think why people give up in the middle is they mistake slow things happening. Slow, slowly, as not working at all. And you have to. You have to look for the miracles. You have to look for signs of life. And I say this, I was thinking about doing a podcast about this, but I'm like, no, I'll just talk about it in this episode. This idea of, like, mistaking slow for not working or needing to abandon ship. I have this plant in my house, and it's called the Money Tree. And I've had it for a few years. And I have a podcast about it. Like, I think it was called, like, the Money tree, the two tails of two trees or something like that. And lately the money tree has been, like, wilting. And I'm like, oh, no, the money tree's dying. Is this a Sign. But I have been sitting with it. I'm like, okay, this is natural. Leaves are dying, falling off. And I could look at it and be like, oh my God, the money tree is dying. But what I decided to become intentional about is looking for signs of life. And sure enough, I started seeing new, new sprouts shooting up. And I'm like, okay, there's signs of life. So even while it looks like things are falling apart, I'm going to be intentional about looking for sign signs of life. So for you, your brain is going to look where you, where you teach it to. It's, it's, you know, confirmation bias theory. So if I tell you like, look for red cars, you know you're going to find red cars. And when you come back to me, I would say, hey, go look for red cars. You go look for red cars and you come back to me, I say, how many brown cars did you see? You'd be like, I didn't see anybody. Well, because your brain, you didn't train your brain to look for that. And so if you're, if you're training your brain to look for failures and everything that's going wrong, that's all it's going to find. But if you look for signs of life, if you look for the micro wins, if you look for the data that it might actually be starting to work, that's that, that keeps you in the game longer. Okay? Another one is why people get out hate the messy middle, is they can't stand the mundane, the monotonous, the boring. There's, there's not the high highs, there's plenty of low lows, but there's not this like adrenaline fueled journey. Um, you have to be okay with the mundane and the boring, the repetitive. And most people aren't, they want the exciting, they want, you know, they want to have faster feedback. Right. And then lastly, you know, we are a society that values intensity and not consistency. And so if it's not happening fast enough, fancy enough, sexy enough, you know, we quit. And that can be in any areas. You know, I know for me with, part of my weight loss journey is like for a while, like my, the first, I was so desperate to, I had like 45 extra pounds on me and I was so desperate to get the pounds off that at the beginning it just felt like I was putting in so much effort with so little return and I would like maybe lose two pounds in a month and I'd be like, oh, this is nothing. And I wanted to quit because it wasn't Happening fast enough and. And it wasn't exciting. It was actually really hard and it was slow. So I thought it wasn't working. Like, I can. I can tick every box at this. And like, not being good at things fast. Yeah. Learning to do a proper squat and, you know, deadlifts and all those things. And, you know, I think it was my. It was my coach at the time that said, kristen, you have to build your tolerance for fresh. Your frustration tolerance. And I, like, hated that. But I'm like. He's like, you have to be willing to. To push through your frustration and keep going. And so I think many of us have low frustration tolerance. We have a threshold and we're like, that's it. I'm done. It's not worth it anymore. And I just remember I had to keep going. And eventually, like, the tiny little things, like the signs of life, the signs that it's working, the one pound, the half a pound, the clothes fitting looser, and eventually like £5, £10, 15, 20. And it starts to compound. And then you're like, wait, hold on. This is working. So, so here's my thing, is when you actually stay in the middle, this is about building reps. This is about building your trust with yourself that you're not somebody who gives up when it's boring and hard. That this is where you kind. You build the muscle of follow through. You're putting in the reps. Like I said. You start to rewire your brain to not need excitement and dopamine to get the work done. Your brain stops looking for excitement in order to do the work. Um, you stop with your all or nothing thinking. You stop starting from zero, and you become the person that you want to be. This is. This is. These are all the byproducts of being somebody who stays in the middle. So here's. Here's just a couple things I'm going to give you of how to. How to stay in the middle without wanting to exit. So the first thing I would tell you is expect boredom. If things feel repetitive or ordinary, congratulations, you're in the right place. This is a sign that it's not wrong, that this is part of the process. You have to condition yourself to look for small wins instead of big ones. So that's number two. Condition yourself to look for smaller wins.
You have to. The next one is like, downsize your goals. Downsize the work. So make the work smaller so at least you can be consistent in your follow through instead of bigger. Bigger is about intensity. Smaller is about consistency. So if you feel yourself shutting down and not doing things and not showing up. Ask yourself, how can I downsize this enough to get me back into action?
The next one is don't rely on motivation to keep you going, because that is. Motivation is inconsistent. So if you're only working when you're motivated, you're only going to be working some of the time. Right. And then again, I know this sounds cliche, but it's important is you have to. Lastly, you have to revisit why you're doing this. Because when it's painful and thankless and not rewarding and frustrating, you have to remind yourself, this is why I'm doing this. This is why it matters. This is why I'm, you know, I'm committed to this. This is where you tap into your purpose and stop looking for excitement, because excitement isn't always readily available. So let me. I'll. I'll kind of close with this. If you're. Maybe this whole year has been the middle for you. Maybe this has been a year where you were just digging the foundation. And, you know, people are walking by the job site and they're like, wow, I thought you were building a skyscraper and there's nothing, just a big hole. And you're like, yes, I know. Just think, however deep the work I've been doing on myself is going to. I'm going to see a return on that with what I build in return. And so it's just like, we have to be willing to do the foundational work. We have to be willing to stay when we're not getting the excitement and the motivation. We have to be willing to rebuild our relationship with the boring and the mundane and the hard. Kind of like my kids had to learn to survive two snow days without wifi there. The first couple hours was awful for all of us, but once they moved through all of the negative emotions. Emotions, it unlocked creativity and they were. They were doing things and, you know, was I going a little crazy? Yes. But at least my children were learning to navigate boredom. Because I honestly think. I think we're in trouble. I think our future. If we don't know how to navigate boredom, then we're constantly going to be people that seek stimulus and excitement and dopamine. And I think. I think we have a real problem with that. I think boredom is actually important for us. I think we. We learn a lot in stillness and when things are mundane and think about all the things where you have to put in the reps in. And it's hard and it's annoying. And it's frustrating. You know, even with my. I was talking with my friend with our weight training program, I have like, of a new gym buddy. We go to the gym and it's the same leg movements every week. We just work on perfecting the movements or adding the weight or, you know, doing progressive overload in the sense of like, I'm going to work on perfecting the same movements week after week after week after week after week after week, because that is what puts in results. It's the boring, it's the mundane, it's the frustrating that compounds over time. So, friends, it. I want you to look at this year, and if it's a year where you don't have a lot to show for it, you're probably looking at the wrong things. It may not be fancy things that you can see from it, but look at the internals. Ask yourself, what are the byproducts of this year? Who, although there might be nothing sexy shiny externally, but what are the internal rewards I've been reaping with doing this work? And maybe it's like, hey, this year was the first year I went to therapy and I, I started learning some things about myself and, and that's been good for me. Or I decided to stop running to alcohol when things were hard. Like, I just want you to think about again, this is kind of like condition yourself to look for the smaller things, the things we write off because they don't seem sexy. But I honestly think the best things in life are not a product of doing really sexy things, but doing the boring, the mundane, over and over again. So, friends, that's my encouragement to you as you are thinking about, you know, making changes. I hope you're making changes from a place of self compassion, from a place of feeling proud of yourself and that you become somebody who learns to operate in the messy middle. All right, friends, thanks so much for listening. Go ahead and give a share. Leave a screenshot, leave a review. If you've never left a review on the podcast, I would love that. It just helps the show get out and, and into the hands of others and so obviously share it with some, some friends. Otherwise we will catch you in next week's episode.
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That's a wrap for today's episode. Listen, if you love what you heard here today, I would love for you to leave a real quick rating and a review. This helps the show get discovered by new people. Be sure to take a screenshot of today, today's episode and shout us out on Instagram. We'll shout you right back out. If you'd like to find additional resources or discover how to work with me, head to www.kristenboss.com.
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It starts right.
Release Date: December 8, 2025
Host: Kristen Boss
In Episode 242, "The Messy Middle," Kristen Boss offers an honest, unfiltered solo deep dive into the often-overlooked and uncomfortable transition phase in any transformation journey: the "messy middle." Speaking candidly from personal experience as both a high-performing entrepreneur and someone navigating major life transitions, Kristen explores why this challenging stretch—between exciting beginnings and celebrated outcomes—is crucial for true growth and sustainable success. She addresses the emotional complexity of enduring long periods without outward reward, how to build resilience and self-trust, and practical strategies for persevering when progress feels slow, invisible, or frustratingly mundane.
Kristen offers concrete strategies for staying the course:
Kristen’s message: Embrace the messy middle, develop compassion for yourself, and recognize that real change is forged in the ordinary, not the extraordinary.