The Messy Middle
Ep. 266
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Messy Middle

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In this episode, I dive deep into the concept of the messy middle – the space where most of life happens, filled with shades of gray rather than absolutes of right or wrong. Our brains often gravitate towards black-and-white thinking because it feels safe and certain, but this episode explores how embracing the ambiguity of the middle can lead to personal growth and understanding. From the way we perceive truth and engage in discussions, to our political beliefs and the pursuit of success, I encourage you to let go of the need for clear-cut answers. Instead of striving for an unattainable perfection, I suggest finding beauty and learning in the messy middle. By acknowledging that life is a continuous journey without an ultimate destination, we can release ourselves from the pressure of always being right and open ourselves to new perspectives. So, let’s explore the gray areas, accept our imperfections, and thrive in the space where life truly unfolds.

Show Transcript
Hey! Welcome to Lessons from a Quitter where we believe that it is never too late to start over. No matter how much time or energy you've spent getting to where you are. If ultimately you are unfulfilled, then it is time to get out. Join me each week for both inspiration and actionable tips so that we can get you on the road to your dreams.
Hello my friends. Welcome to another episode. I'm so excited you are here. I wanted to talk about this phenomenon that I'm seeing now, now that you know, like when you notice something, you start seeing it everywhere. Well, I'm noticing this everywhere, but I first started realizing it with a lot of people that I was coaching and the way that I was coaching on their problems and this false idea that I think causes so much pain and so much resistance and fighting within us. And so I wanted to talk about the messy middle. And I've been really thinking about this concept for quite a while and I've been watching it play out in different arenas on social media, in politics, people fighting with each other in coaching thought work. And I'm going to hopefully wrap it all up together so you get an understanding of what I mean.
But one of the things I was realizing is that this, so much of our suffering, so much of our resistance to the way the world is or to the way a situation is, is simply because we don't understand this concept. And I call it the messy middle. I was thinking about it just as the middle, like thinking of things in the middle, but here's what I mean by it.
Everything really, the vast majority of things, including our lives, are taking place in the middle. What do I mean by that? Our brains love to believe that things are black and white, that things are right or wrong. Success or failure, right? One way or the other. That's it. That's all we have. All or nothing. Those are the options. We love that because it makes us feel safer. Because if I know what success, then I can go after it. I can try to avoid failure. If I know what is right, then I can try to shoot for that and avoid what is wrong. So much of our society is set up like this. So much of religion is set like this where like they are, here is the prescription for what is the right thing to do and here's the prescription for what is the wrong thing.
And it actually weirdly is a comforting thing for us. So we seek it out because we want certainty, right? We want to know like tell me the black and white, so I don't end up in the gray area. Tell me what is right? Tell me what I should go for. Tell me what success looks like. Tell me what I should want. And then we take on what other people tell us and we go after it, right? We go after the career, we go after the job, we go after the white picket fence and you know, the big house. We go after all of these things because somebody has told us that's the end goal, that's the end zone and we just march towards it, right?
And I think that we think we still are under, even though we've had tons of experience and tons of evidence to the contrary, we still operate from this understanding that there is this all or nothing, that there are these two competing poles and like we have to get to one and avoid the other. And I've realized how much, like I said, resistance and suffering comes from resisting the fact that it's not like that. That it's just the messy middle, that there is no black and white, that it's all gray area. What I'm observing more and more in the world, and I'm realize it's, is that it rarely exists if it's black and white. I'm not saying it never does. I'm not saying there's some things and there's some things for us within our own values and stuff that become very black and white for us, but it is still all mostly gray area.
And the more we embrace that, the easier things become. I know it doesn't seem like that, so I want you to stick with me, but I promise you the more we give up the idea that there is a right and wrong and that I have to then kill myself to be that, right? I have to be that perfect. I have to do it the way that is, you know, the good noble whatever way, then it opens me up to questioning like, What is the way I want to do it? What do I think about this? What actually do I want? What does success look like for me?
And so I'm going to talk about this in two different ways that I see this. I see it both in like the way that we live our lives, which I'll get to later, but I, what I've really been observing for a long time is like looking at the quote unquote truth, looking at how people think of the truth. I see this every single day, every fight on social media. And it's fascinating to me to see people kind of dig their heels into whatever position they have, know within their bones adamantly that they're the right one and the other person is wrong. And then spend all of their energy fighting these other people.
One of the things that I'm seeing, and this is just random but you know, it comes up is, because in my world I'm in the coaching world, there's a lot of like discussion about people coming out and being like, coaching is a scam or coaches are scams or whatnot. And then other people wanting to fight and be like, you know, coaching is the best thing since sliced bread and it's changed my life. And don't listen to anybody that's saying this and whatever. And there's all of this back and forth. And I see so many people who want other people to acknowledge like that it's a scam and that, you know, I don't know, coaches are trying to get people to pay them money when they're not really giving them any result or whatnot. And then there's other people that want to dispel that so badly. And I look at that and I'm always like, yeah, the truth is somewhere in the middle, right? There's scam artists in every industry. There's always people ,if there's money to be made, that will find a way to try to make money from that. And it's also true that it is very life-changing, but not for everybody. And maybe it was life-changing for you, but maybe it's not for someone else. And like, can we hold that truth? Can we be okay with that? Can we not keep fighting this like all or nothing? It can only be black and white. It doesn't all have to be a scam. Clearly there's a lot of people that have had their life changed and there's a lot of people that find really good use out of it and there are problems with it.
And this is for any industry, right? You could look at doctors and therapy or anything where it's like, we want to like I see this now, you know, there's like railing against western medicine and again, yeah, there's something in the middle. There's a lot wrong with western medicine. There's a lot wrong with, you know, what we do know in science and how maybe big pharma, the control it has within our country. Like that's true. It's also true that it is a phenomenon. And western medicine is, you know, obviously we all know like responsible for saving so many people and extending life expectancy and all these other amazing things like both can be true because it's something in the middle. It's nebulous, it's gray. It isn't one thing.
And I think we feel so scared to admit that because then it's, well, how do I know what is right? How do I know which coach is a scam artist? How do I know if going to this doctor is the right thing for me to do? Or if it's just going to lead to a bunch of nothing? How do I know if you know what whatever the, the fight of the day is?
And so we seek this answer because we have a really hard time trusting ourselves. We have a really hard time if we don't know the answer. We have a really hard time failing. We have a really hard time trying things and seeing what happens. And so we're desperately trying to find one side where our view matches with theirs and then we hold on tight, right?
We all have confirmation bias. Our brains is wired like that. Like if I believe something, I'm going to look for evidence that that is true. And so I'm going to find more people in my own echo chambers that say the same thing and be like, see, yeah, I knew this was true because it makes me feel all like safe, that I'm right and they're wrong, I'm good and they're bad. And the problem with this beyond the fact that it makes you very rigid in your thinking and it makes you very unforgiving and judgmental and all of these other things because if there can only be one truth, everybody else that doesn't agree with your truth is somehow wrong now. When we don't have the ability to hold this nuance that there can be multiple things, one aspect of the harm that we cause ourselves is that.
But the bigger thing, the thing that I think is so much more harmful is that we then typically can never be in the right column all the time, right? Like if, if there is good and bad, well there's parts of me that are bad because I'm a human being. There's parts of me and I say bad, like quote unquote not actually bad, but what we deem in society is bad. Every human is a hypocrite, is a liar, is greedy, is selfish, is jealous. Those are natural human tendencies and emotions, especially in our society, right? And obviously we try to work towards like leaning more towards our good side and like every human is I think inherently good, right? Depending on what happens in their traumas, maybe they don't act out from that way. But we have both within us. And if I've created this dichotomy that you only get to be good or bad and I know within me resides some bad, whether I'm admitting it or not, I create so much shame for myself and my life because I know that I will never be that good all the time.
It's the same thing when you think of like success and failure. When you look at this all or nothing thinking. If you can only be a success in one way, like one definition of success, most of us won't hit that. Even if we do hit that we don't feel like we've hit it like so much of imposter syndrome where it's like I do get the job, I do get the income, but there's still something missing because I don't feel good all the time. But I've told myself that this was the definition of success. So now I'm just going to tell myself I'm a fraud. Or let's say I do hit it, but I don't make as much as these other people or I don't have as prestigious of a title. I quickly find ways that I don't fit within that very high standard that I have set.
And so if that's the truth, then that means I'm a failure. And so many of us grapple with this because we're unwilling to see that. Like what if we all just kind of fall in the middle there? What if parts of us are successes and parts of us are failures? What if parts of us are good and parts of us are bad? How can when I understand this, open me up to understanding other humans, understanding their, their plight and knowing that even if we don't agree that we're likely coming from a similar standpoint, right? We likely are coming from inherently being good, wanting the best, but just thinking about it differently.
I know, and this obviously leads me to like even talking about politics and I know politics can be very emotional and triggering. And as somebody who was extremely rigid in my thinking when it came to politics as someone who was like, there is only one way and it is my way.
And if you don't believe the things that I believe, then you are not only like wrong, but you're evil and you're mean and you're whatever, all these other terms I would think of. And it took a lot. And I have to say like I was in such an angry place and I realized the more I'm judging other people, it's because I'm also judging myself. If I wasn't a purist, if I didn't do everything in my power to give back to other people because that's what was required to be good, then I would rake myself over the coals, right? I would, my inner critic would unleash on me because I would think like, if you're going to be a good person, this is what you have to do. If you're going to be a good liberal or a, you know, whatever it is, whatever your political leanings might be.
And obviously I wasn't meeting that because I'm human and so maybe I didn't, you know, canvas or knock on doors or do whatever it is like doing and then I would feel guilty about it because I'd created this insane standard. And now when I look at this, I really, this is a harder arena and I don't think like we all need to start in politics, but I truly want us to understand that like most people want the same things. Most people are born good and want, like don't necessarily just want bad for other people, right?
But we are influenced our thoughts from when we are children. And I realize this, like for me as a liberal, it's, I'm very liberal in my, in my beliefs. That's not surprising giving my upbringing. I, I'm an immigrant to this country. I have lived in other countries. I have very liberal parents. I had parents who, I had one non-religious parent. My mother was religious, but I grew up in a household that religion wasn't really forced on us. Or talked about that much. I have been othered, I've had a lot of experiences that I think other people that have, were not born outta the us haven't had I constantly hear would hear about other countries. I would listen to news from other countries.
I have a lot of experiences that clearly influenced how I think about the world. And I started realizing like somebody who grew up, let's say in the, a small town in America who had highly religious parents who were very conservative and had never left the country and had never seen any diversity in their hometown, likely has been fed a lot of different thoughts than I have, right? Which is just the basis of where we've likely ended up in our thought process. And that's not to say that there aren't tons of people that grow up like that, that change their minds on both sides, right? We obviously have free will and we obviously can learn things and we can change, but the barrier, the obstacles to that changing are much different, right? There's a, when you have to unlearn and go against everything that you've kind of been brought up in, you absolutely can have that reckoning and you can learn. And that's the beauty of the human mind. But it, it is disingenuous for me to believe that we have the same exact access to the same information. And so we just, this person is just choosing to believe something different than me. And I'm right and there wrong, right? Again, I say this not being like a purist here. I'm not saying I get very angry when people have different political beliefs than me. Because I truly obviously believe they're right. That's why I believe them. So I understand where it comes from, like when I have my set of values and I vote according to that and I get upset if other people have different values.
But what I, what I would always work towards is because I would think when I was really rigid in my thinking, it always came with, well how could they believe this? And you see a lot of this posturing in political discussions where it's disingenuous like it's not even trying to understand the other side. It's very much like, well then you just want to kill babies or, you know, I mean something equally ridiculous or like, well then you just hate all immigrants or whatnot. And it's really trying to understand like if most people are just operating from their own fears about their own lives and the world and whatnot, and we all have had different upbringings and different thoughts and different programming and we are given certain set of facts and we watch different pieces of news. Like what is the real reason that this person thinks this thing? And maybe, I know for me one of the biggest realizations was when I sort of had this moment when I was like, wait, I think that I'm right about my politics and I think I'm right about religion and you know how much religion people should practice or not practice. And I think I'm right about how people should parent and how people should drive and how people should act towards their spouse or their families and how people should deal with, you know, uncomfortable conversations and how people should be in the workplace.
And I started realizing like, what if I could be wrong? What if there's some things that I, maybe I'm not right in, right? And I think it's a really humbling thing to be able to have that cognitive dissonance where it's like, I believe in one thing, but I'm willing to hold that maybe there's a possibility I'm not seeing something. Or maybe there's this is in the middle and it's gray and we don't know. And there's other arguments. Now that's not, again, not to say that you can't have your beliefs. I have very strong beliefs in what I want to believe. It's just that when I see other people, I'm not shocked anymore that they have some other belief, right? I truly like understand like of course they have those thoughts that led to that. Where do those thoughts come from? What are their thoughts? And I think that when I started realizing that we're all somewhere in this middle that it, there isn't this one right way and one wrong way. And even within our political beliefs, like I see within liberals within the left, there's so much cannibalizing and so much infighting and so much arguing about the right way to do something. And you can never please anyone obviously because anything you think somebody else is going to think something different. And the reason it gets so heated is because everyone thinks that theirs is the, you know, pinnacle of right–it has to be that way. And I always wonder like, what if we just came to understand that none of these are really the right way? There's suggestions, there's possibilities.
I was thinking about this with respect to capitalism. There's a lot of anti-capitalist kind of sentiments on social media and there's a lot of people that talk about money and you know, and obviously inequality that's in, in the country and in the world. And I was, I was, it was fascinating to me because I was thinking about like as someone who I, I would say like through my youth and in college and stuff, I was more anti-capitalist and I was more of the belief of like, we have to change the entire system. Which I still believe to a certain extent I've realized that what was interesting is that I had thought that the only way to do it was to change it by completely scrapping the system. And now my beliefs are very different. And it's not that I don't think it's just that, that we should do that. It's that I don't think we really can. And so I believe like we, me working within this system, I have to find ways to try to change it within it, right? I can do it while making money and using that money to make changes I want to see to run businesses the way that I want and and whatnot.
And I see so much of people fighting about this as if there's one way as if just choosing to do it. Like if you decide that you think that the entire system, like you want to, you know, reject all kinds of capitalistic structures and you don't want to be a consumer and you want to not buy anything and you want to you know, work and vote and create a dream of something outside, great. But also if you want to work within it and decide like, listen, I actually think it might not be as bad as some other systems. And yes, it's, it can be terrible and there's inequality, but we can work to try to fix that. And I want, like, I'm stuck in this system so I might as well make money and use them that money in a way to help alleviate something like. Both, again, there's no right or wrong and I just, again, I know this is like the fourth example.
I wasn't going to give this many examples, but like, it just keeps coming up. Like I keep watching it and I keep seeing people, like somebody talking about wanting to make money and change it within, and then somebody saying like, oh, well that'll never work. Like way to give in. And it's like this, okay, but what if there was like somewhere in the middle here that all of these are just us trying things.
And it's like to bring this back home to like thought work. And what I see and what I've been seeing in my coaching a lot is that it's the same thing. Like I try to teach a concept and I try to teach like let's say how to do less, right? And I try, try to teach people about how much we do in our society, how much we do in capitalism, how much we do because of hustle culture, how much we're all doing, doing, doing. Like the to-do list never ends. And we're all so exhausted and burned out and I'm trying to get people to do less. And inevitably the question I always get is like, well I can't do less. What if I become a lazy lop? What if I lose my job? Like we immediately go from all to nothing. Like as if I'm saying, when I say do less, it means stop your work, stop feeding your family, stop making food, don't exercise, just sit on the couch. Like obviously that's not what I'm saying.
And like what if there was a middle there? What if we didn't have to worry about like if I let myself go, I'm never going to do anything again. And we have this fear about ourselves. We all do. Where it's like we think like we have to hold ourselves on a short leash. If I let myself go, I don't know what's going to happen. And I always laugh at that. I'm like, like, what if you could just trust yourself that it's not going to get that extreme? Or I tell people they need to say no more at work. And I, we work in the quitter club a lot on boundaries and like, how can you set boundaries? And I always hear people say like, well I just, what if I become like the selfish person? Like what am I just supposed to say no to everybody? And like, you know what if I lose my relationships? And it's like, well what if it just doesn't have to be that extreme?
What if what we're saying is not that you have to say no to everybody all the time and that you can never do anything, even if it's just to like please someone in your life. What if we're saying like, Hey, once in a while figure out what you want to do and say no, right? Like what if there was a middle there? So it's not like we're going to get rid of people pleasing, we're never going to people please again, we're going to get rid of perfectionism. That's not possible. But what if we just bring the pendulum back a little bit?
And that's the way I think about it right now. Like I think about it like a, a pendulum swing. And so it gives me so much more freedom because it's not as though, oh, I tried to fix my people pleasing and I failed. I didn't say no again. Like I just look at it as like, okay, my pendulum has swung way too much to this side. I'm saying yes to everything. I'm not putting any boundaries. I'm going to all these events I don't want to go to, how do I bring it back a little bit more? How do I start saying no to some things? How do I, and then maybe I'm going to go too far to the other side for a little bit and maybe I'll start saying no to too many things and I realize it's kind of affecting, you know, my relationships or my mood. Okay, great. Then I come back a little bit more and I feel like finding myself understanding that there's this messy middle understanding that it's not black and white. That there is no blueprint that nobody's telling you exactly because it's, it's not a science, it's like an art. How can I tell you how many times to say no? I don't know what your situation is or what your life is. You have to learn that and you have to be able to trust yourself to be able to do that. And the only way to do that is to trust yourself to show up as a human, which is messy, which means you're not going to do it right all the time, which means you're going to fail at it, which means you're going to mess up. That's the only way.
And there's so much beauty in that, right? There's so much beauty in allowing yourself to just be in the messy middle and to not demand this perfection of right or wrong, this perfection of, you know, one side or another. It allows you to change.
I was actually thinking about this like when, going back to the political beliefs, I was thinking about there's a reason we dig our heels in so much is because once we've picked something and we've, we have this stringent like unforgiving standard that it's, this is the only right way. You're never allowed to change your mind, which is a terrible way to live because hopefully you're learning new things and being like, Hey, maybe I was wrong when I was in my twenties. Maybe I want to think about this issue a little bit differently. Like we want people to engage with that. But if we're so terrified of being in the wrong quote unquote not being the right one and what that means about us and that means that we're terrible or whatnot, then none of us are willing to ever look at that. We're not willing to look at like, what should I be changing when you're like, if, if you're so wed to one side, right? There's no swinging, there's no like navigating. And I feel like for so many of us, our identities have been carved into stone on one side or the other. And so we feel really unmoored when it's like, hey, maybe we just let ourselves swing a little bit. Maybe we just see that like this was just an illusion. There is no one success or one right way or one good way.
I think about this, I said I was going to talk about it in two ways. Like I've talked about a lot with like the truth being in the middle, right? And, and our thoughts being in the middle. And I really think about this the second way I think about, it's like our lives are always in the middle. And what I mean by that, this messy middle is like there is no time where you get to the end or you get to some goal and you kick up your feet and you've made it, you've made it to some end and it's done now. Now you can relax nothing more to do. Like we already know that there's no time where your to-do list ends because you will put more things on it. Because there's another day, as long as you're breathing, there's going to be more things to do, right? There's going to be more things to experience to discover. As soon as you hit a goal, you're going to move on to the next thing. You're going to set another goal, you're going to pick something else hopefully because that's how you grow, that's how you keep yourself interested. That's how you satisfy your curiosities. And all of it is 50 50. Like no matter what the goal is, no matter what the next move is, it's 50 50, 50% good, 50% bad, you're going to get that job, you're going to get that raise, you're going to make that money. And then you're going to go to the new position and it's going to be a whole new set of stresses, a whole new set of things that you have to deal with. And that's okay. There's nothing wrong with that.
But when we realize that there is no end zone, there's no end point until we die, there's no end point. It's all the messy middle, it's all good and bad. It's all 50 50.
Because I think we think there's, we're doing something wrong. We think like, oh, I can never catch up. I can never get to the end of the to-do list. I can never like not have stress, right? Yeah, yeah. You can't, it's never going to happen. So what if we just give up that fantasy? Like notice how much resistance you can give up and how much suffering you can ease by just not expecting that you should be somewhere where you're not feeling negative emotion, that you think you're going to work hard enough, you're going to run on this hamster wheel hard enough to get to some place where you finally get to relax. When you know that doesn't exist, it's going to kind of be like this. Now I'm not saying that you can't alleviate some stress. You absolutely can.
You can learn to manage your mind, which we do in the club and it helps so much. But truly realizing like I'm in the middle of my life. I'm in the messy middle and that's for most of my decades, right? This is life right here. Not tomorrow, not 10 years from now. Not when I get that raise, not when I have the kids, not when, none of it right now. And all of it's messy. And that's what makes it beautiful and I'm going to keep failing at it and I'm going to keep messing up and I'm going to keep trying things and I'm going to allow myself to like be in that messy middle, to not need that perfectionism, to not need that answer, to not need the right or wrong, to not need some certainty that I'm not going to get.
Whatever certainty you think you have gotten has been an illusion anyways. If you thought you were right, it's simply because you told yourself you were right. It's not because you were like some panel in the universe is going to come down and be like, you know what? You were right about these beliefs. As we see as generations go by, beliefs change, anything you're believing is just a thought. And so you get to hold onto whatever thoughts you want.
I just want you to realize that it's this nebulous place. Instead of like you think you're on solid ground and you're so scared to wade into that water, you're so scared to be in that unmoored place. And my advice to you is like, surrender yourself to it. Go in no knowing you are already in there. You haven't been on solid ground. None of us have. And understand that when I, like, when I accept that it releases so much of this pressure to be somewhere that is moored, that is certain, that is right, that is successful. It allows to be like, yes, this is good and it's bad. I'm great at this and I'm terrible at this. Like I have good parts and I have bad parts. And it's what makes me whole, it makes what? It's what makes my life whole and it's all messy. And that's beautiful.
There's so much to be learned from this place. There's so much to be learned from being humble enough to know that you don't have all the right answers and you never will and you never need to. That you can just show up as a flawed human being and navigate your way through this and that. You don't need to get to some end. And when you know that you can enjoy that middle so much more, you can enjoy that mess. You cannot need to clean it up all the time. You can know it's going to be there anyways. And that changes everything.
So my friends, we're going to embrace this messy middle. We're going to stop trying to be right all the time. We're going to just sit with the question, what if I'm not right?
I recently actually had this, I wasn't going to add this in but it just came up and I feel like I should tell you guys, one of the coaching pieces of coaching that's really shifted things for me in the last six months was this, I didn't realize with respect to this topic, but was this idea of me desperately wanting to be quote unquote good. And so anything I did was in the pursuit of wanting to be a good person, right? And that my biggest fear was what if I'm not good and I really had to sit with it. What does that mean? Like, what if I am not good? What if there's bad parts of me? Can I be okay with that? Can I accept that? Obviously it's not something that I'm like, eh, I don't care. I'm just going to be bad and hurt people. But it was simply like my whole life is being driven by this irrational fear that I might not be a good person. And so I'm people pleasing. I'm doing all these things I don't want to do because I can't sit with the uncomfortable feeling of like, what if we're all a mess? What if we're all good and bad? What if you're not good sometimes?
And so I just want you to sit with that. Like, what if you weren't right? What if you weren't good? Could you love yourself? Could you see the humanity in that? Could you decide what you want to do with all of those messy parts?
And if you want help with those messy parts, you're in luck because I love messy humans. So join me in the Quitter Club because we're all a mess in there and we're all figuring it out, and we're all learning how to manage our minds so that we don't have these insane standards of being right and wrong all the time. You can go to and sign up for the wait list. We are not open right now, but we will be open soon. And I want you to join us so that we can work on this because I want you to see that oftentimes it's not the career or the job that you're doing, it's the standard you're holding yourself to. So if you're holding yourself to a perfectionist standard that you are never going to be able to meet, you'll always feel like you're failing in life.
And it doesn't mean that you're actually failing, it just simply means that you're holding yourself to a punishing, impossible measurement. And I want you to stop that and I'm going to help you. So go to and join us. I hope this was helpful and I'll see you guys next week.
Hey, if you are looking for more in-depth help with your career, whether that's dealing with all of the stress, worry, and anxiety that's leading to burnout in your current career or figuring out what your dream career is and actually going after it, I want you to join me in the Quitter Club. It is where we quit what is no longer working. Like perfectionism, people pleasing imposter syndrome… and we start working on what does, and we start taking action towards the career and the life that you actually want. We will take the concepts that we talk about on the podcast and apply them to your life and you will get the coaching, tools, and support that you need to actually make some real change. So go to club and get on the waitlist. Doors are closed right now, but they will be open soon.