Episode Summary:
In this raw and relatable episode, Kristen invites listeners into an honest conversation about one of the most overlooked—but essential—parts of any transformation: the messy middle. From career pivots to personal growth, Kristen shares why this unglamorous phase is where true change actually happens.
Using stories from her own life—unexpected setbacks, frustrating gym reps, snow days without WiFi, and even a drooping houseplant—Kristen makes a powerful case for why resilience, self-compassion, and showing up when it’s boring and hard are the keys to sustainable success.
Whether you’re building something new, working through a tough season, or just tired of not seeing quick results, this episode is a must-listen. Kristen gives practical mindset shifts to help you stick with your goals after the excitement wears off—and before the big wins arrive.
What You’ll Learn in This Episode:
- Why most people quit in the messy middle—and how you can be different
- How boredom, frustration, and slow progress are actually signs you’re on the right track
- The importance of building “frustration tolerance”
- How to retrain your brain to spot micro-wins and signs of life
- Why downsizing your goals can help you actually follow through
- How to find purpose and pride, even when the results aren’t visible (yet)
Key Takeaways:
- Progress is often quiet, slow, and unsexy—but it’s still progress.
- The “messy middle” isn’t a problem; it’s the process that transforms you.
- You don’t need motivation to stay committed—you need consistency.
- Building something meaningful requires boring, repetitive reps over time.
- Boredom is a gateway to creativity, not something to run from.
⏱️ Timestamps:
0:58 – Recording from the basement: Life without internet
2:45 – Why we love beginnings and endings—but struggle with the middle
4:44 – What Kristen’s “skyscraper year” taught her about digging deep foundations
7:34 – Lessons from her daughter’s piano practice (and adult frustration tolerance)
10:13 – Why high achievers struggle when they’re not good at something right away
13:18 – Training your brain to look for signs of life
15:21 – How to stay in the game when results are slow
17:23 – 5 ways to thrive in the messy middle
20:03 – Reflecting on 2025: Measuring internal wins, not just external results
Connect with Kristen:
Visit www.kristenboss.com for coaching, courses, and more resources.
Loved the episode?
Send it to a friend who’s stuck in the messy middle and needs a dose of real talk
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Resources & Links:
If you’re in The Messy Middle, you need to be at the 3-Day Success Rewire Challenge – it’s not to late to join us!
“The middle is the transformative part of the process—it’s what shapes us. You’re not just building the thing; you’re becoming the person who gets the result.” – Kristen Boss
Transcript for episode 242: The Messy Middle
Kristen Boss (00:03):
I see you with brand new eyes. I been So you are listening to the Kristen Boss Podcast. I’m your host, Kristen Boss. As a bestselling 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.
(00:58):
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, Mike. 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 one to three weeks. I’m like, I have a business from home. Can you do it yesterday? So anyways, and we also had two back to back-to-back snow days the past week. And so our kids were having nineties snow days. I’m not streaming anything. Like, Hey, kids, you’re going to 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.
(01:49):
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 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 we talk about transformation and change and results, because this is a personal development podcast, that’s probably why you’re listening is 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 the beginning’s always exciting, exciting.
(02:45):
We have this dopamine of a fresh start, and then we of course are excited about the end goal. You put it on your vision board, you write it down, you’re like, I’m going to get there. Can’t wait for the end goal goal. The part that we have little to no buy-in with emotional buy-in with is the messy middle. This is the middle phase, and this is when people tap out, they quit. 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, I think we have some years where when I think about if you’re building something or changing things, I think about the bigger the change is building a skyscraper and the higher the skyscraper has to go, the deeper you have to dig the foundation.
(03:42):
And I feel like this year has been digging a foundation far longer than I wanted to and feeling like all there 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. We want to 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 been in many phases and 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 messy middle. So I want to talk about this that long awkward stretch where it doesn’t feel new anymore.
(04:44):
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 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, the messy middle, it’s like you’re not just building the thing like your business or habits or transformation, rebuilding yourself. That is 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 in the practice to get good at these skills.
(05:48):
And no one’s excited about that, especially as adults. And my daughter, she’s playing the piano this year and every time she gets a new, it’s our first couple practice days together, I played as a kid. So I instruct her between 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, 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 am like, Hey, of course you’re making mistakes. This is your first time. This is why we practice. 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?
(06:45):
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 first run through, we get emotional, we get frustrated. We want to 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 we’re learning and this is where we feel we don’t feel like a rockstar. 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.
(07:34):
We see our inadequacies or our shortcomings, and we have to learn how to meet ourselves with compassion and what we get to think about those things. And you choose to make it like, oh, I’m wrong. I am not cut out for this. Or it’s like, oh, I have some new skills to learn and I got to put the reps in. 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. 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 health issues to losing our dog to accidents to things, not going to plan, lots of things falling short of expectations and just over and over again.
(08:28):
But 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 hundred percent where I’m, and I’m like, listen, I have to remind myself how important this phase is because this is where you build new habits. This is where you build confidence. This is where your identity starts to shift. This is where you grow resilience. This is where you become the person who gets the result. 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 I believe everything in life, any change, it’s about the work we’re willing to do on ourselves and the things we’re willing to face and the conversations we have with ourselves.
(09:27):
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. 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 Buffet, but there was like, Hey, out of all the investments I’ve done, it was only out of hundreds of investments.
(10:13):
It was only this tiny little percentage that actually built all of my wealth. But we focused only on those things and not the 98 losses. We focus on the two wins, but not like, okay, but who were you becoming and what was your conversation and grit and resilience 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 same with my kids. Some things like with my son things, some things come very naturally to him. And then if 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.
(10:59):
Maybe another one is you rely on excitement to fuel you. So obviously 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, 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 the doubt days. 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. I believing in this. Again, another thing I think why people give up in the middle is they mistake slow things happening slowly as not working at all. And you have to look for the miracles. You have to look for signs of life.
(11:46):
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 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. I think it was called The Money Tree, the two Tails of Two Trees or something like that. And lately the money tree has been 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.
(12:35):
And sure enough, I started seeing new sprouts shooting up and I’m like, okay, there’s signs of light. So even while it looks like things are falling apart, I’m going to be intentional about looking for signs, signs of life. So for you, your brain is going to look where you teach it to. It’s confirmation bias theory. So if I tell you, look for red cars, you’re going to find red cars. And when you come back to me, I’d 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 training your brain to look for failures and everything that’s going wrong, that’s all it’s going to find.
(13:18):
But if you look for signs of life, if you look for the micro winds, if you look for the data that it might actually be starting to work, that keeps you in the game longer. Another one is why people get out hate the messy middle is they can’t stand the mundane, the monotonous, the boring. There’s not the high highs. There’s plenty of low lows, but there’s not this adrenaline fueled journey. You have to be okay with the mundane and the boring, the repetitive. And most people aren’t. They want the exciting, they want to have faster feedback. And then lastly, we are a society that values intensity and not consistency. And so if it’s not happening fast enough, fancy enough, sexy enough, we quit. And that can be in any areas. And for me, with part of my weight loss journey is for a while, 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 maybe lose two pounds in a month and I’d be like, oh, this is nothing that I wanted to quit because it wasn’t happening fast enough and it wasn’t exciting.
(14:30):
It was actually really hard and it was slow. So I thought it wasn’t working. I can tick every box at this and not being good at things fast, learning to do a proper squat and deadlifts and all those things. I think it was my coach at the time that said, Kristen, you have to build your tolerance for your frustration tolerance. And I hated that, but I’m like, like you have to be willing 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 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 five pounds, 10 pounds, 15, 20, and it starts to compound.
(15:21):
And then you’re like, wait, hold on. This is working. 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 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. You stop with your all or nothing thinking, you stop starting from zero and you become the person that you want to be. These are all the byproducts of being somebody who stays in the middle. So here’s just a couple things I’m going to give you of 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.
(16:34):
The next one is 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. 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.
(17:23):
This is why 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 me, I’ll kind of close with this, if maybe this whole year has been the middle for you, maybe this has been a year where you are just digging the foundation and 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.
(18:26):
They’re, the first couple hours was awful for all of us, but once they moved through all of the negative emotions, it unlocked creativity and they were doing things and 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 we have a real problem with that. I think boredom is actually important for us. I think we learn a lot and 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. Even with, I was talking with my friend with our weight training program, have a new gym buddy.
(19:17):
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 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, 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?
(20:03):
And maybe it’s like, Hey, this year was the first year I went to therapy and I started learning some things about myself and that’s been good for me. Or I decided to stop running to alcohol when things were hard. I just want you to think about, again, this is kind of 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 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. Alright, 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 into the hands of others. And so obviously share it with some friends. Otherwise, we’ll catch you in next week’s episode.
(21:29):
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’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. It starts right.
