4 Lessons I Learned from Failure on My Road to Success

Hey there. Welcome back. Today I want to start by asking you a really simple question. How do you define success? For the better part of my life, I thought I knew exactly what success was. In fact, I had put together these big goals that were going to help me become successful. And after a decade of relentlessly pursuing those goals, one day I finally accomplished them. But what I quickly realized is that what I had accomplished wasn't success at all. In fact, I realized that I didn't even know what the health success meant. And that entire process is honestly one of the most depressing but game changing challenges that I've ever faced. Today I want to share that story with you and I want to share with you how that journey led me to redefining how I think about success. And it ultimately changed the way that I live my life. And be sure to stick around until the end because I'm also going to share with you the four big lessons that I learned on that journey. And I'm going to show how you can apply them to your life to help you define success and ultimately find your why. Let's go. So how exactly did I arrive at this existential crisis around success? Well, growing up, I came from a family that didn't have a lot of money. And if we're being honest, we were probably closer to the poor end on the spectrum. In fact, for the first six or seven years of my life, my family lived in a trailer. Not one of those fancy double wides. We lived in a single wide trailer in an actual trailer park. Now, don't get me wrong, I don't ever remember being scared if we were going to have food on the table on a given day or if our electricity was going to get cut off. And I'm really grateful for that. But as I got older, I became more and more aware of what we had, but also what we didn't have. And I started to dream. I started to dream about having a job where I made a lot of money and all the things that I could do if I made a lot of money. Well, how much is a lot of money? For some reason, I had it in my head that $100,000 a year was like the be all end all amount of money. And so it was just kind of ingrained in my head as I got into my teen years that one day I was going to have a job where I made $100,000 and I would never want or need for anything again. So for the first 12 years or so of my professional career, I kept advancing more and more. I kept getting more and more pay raises until one day I finally got the big promotion with the big pay raise that resulted in me finally eclipsing that $100,000 salary mark. And I will never, ever forget the Friday when I got home after that first payday when where I had $100,000 a year annual salary. You know, I'm driving home from work, I'm grinning ear to ear, I'm texting my buddies. Not while I'm driving, it's not safe, but I'm texting my buddies and I'm like, hey, big promotion happened today. Big payday happened today. We're going to go out tonight. We're going to have some drinks. We're going to celebrate. It's going to be awesome. And when I got home from work, before it was time to go out, I poured myself a stiff drink, I sat down on the couch, and I started just kind of taking the entire experience in. But what I realized is not too long after I started thinking it over, I got to this place where I was like, well, this hundred thousand dollars thing is cool. And, you know, I'm going to be able to invest this much money and I'm going to be able to save this much money, and I'm going to be able to go buy these new things. But my mind slowly started to drift into, well, what would it be like if I made $125,000? Boy, if I had $125,000, then I could do this other thing and I could go to these other places and I could drive this other kind of car. And then it was like, well, yeah, that's true, but if you made $135,000, that frees up this extra money. And it just kept growing and growing. And after just a couple of minutes of doing that, I realized that the bar was never going to stop moving for me. It was always going to be this carrot that I was eternally chasing, and I was never going to actually catch it because it was always just going to be perpetually moving further and further away. And with that realization comes this kind of awesome aha moment where I'm like, if I define success as a dollar amount that I'm making in salary and I'm never going to actually be able to reach it because it's always moving, then doesn't that kind of mean that I'm never going to be successful? If the thing that I say is how, you know, I define success is always moving, and it's impossible for me to catch it, then that means that I'm never going to be successful. And I'm not exactly sure why, but that. That epiphany really freaked me out. I mean, I got sick to my stomach. Literally physically sick to my stomach. My. My insides just kind of felt like they dropped. And in that moment, I felt like a failure. For some reason. I felt completely alone and I felt directionless. It was like, you know, I'm asking myself, like, what am I even doing here, right? If there's no way for me to be successful, then why am I actually going through all of this? This was just a really kind of traumatic, troublesome line of thought for me to work through. I mean, I mean, I had set this. This big goal, right? I had set this metric for success, and I'm chasing it as hard as I can for over a decade, and I finally get there, and all of a sudden, it felt like the rug was ripped out from underneath me. You know, I hadn't achieved success. I hadn't achieved anything at all. And, you know, now I feel completely lost. I don't even know what to do next. Not only had I not arrived, I didn't even know where the hell I was going. I think one of the reasons that all of this hit me so hard is I. I had just finished reading Start with why by Simon Sinek, and I had just watched his TED Talk. You know, all this happened back, you know, when he was just kind of going viral. And, you know, in the book Start with why, it talks about the importance of doing things not because of the what or the how, but because of the why. And, you know, we all need to have this compelling why. And here I am sitting there drinking my Captain and Diet on the couch, and I realized that I don't have a clue what my why is. And, you know, I read the book. It doesn't sound hard. I mean, he just draws three circles up on the board and bam. Oh, there's your why. And here I am completely lost, completely disconnected from any sense of why. And I think that that's a big reason why I kind of felt like a failure. So I canceled my plans for the evening. You know, I texted my buddies and said, I'm not going to go out. And I just kind of sat on the couch drinking Captain and Diet. You know, don't judge me for drinking Captain and Diet. That's what I drank back then. But I sat on the couch just drinking Captain and Diet by myself, having this whole pity party because I didn't know what success was. I didn't know what my purpose in this world was. I didn't know why I was living my life. Finally, on Sunday evening, I realized, you know what? I actually know some really successful people in my life. And I'm not talking like, you know, celebrities or athletes or anything like that, but there were people that I knew in real life that I had relationships with that I thought were successful. So I take out a notebook and a pen and I started listing out the names of those people that I thought were successful. And under each of their names, I start listing out why it is that I thought they were successful. I mean, I'm like physically writing these things out. And after just, I don't know, 30 minutes or so of doing this, what I realized is that there was a common thread among all of those people. And that thread was that for me, I saw those people as being the types of human beings that make other people better for having known them. They're the kind of person or the kind of people that go into your life and you know that you're a changed person for having known them. They did something to you that made you a better person. Now, each of these people did that in a very different way, and they did it at different scales. But assuredly, all of them were people that I thought made other people better for having known them. And it was in that moment that I realized that, hey, this is my metric for success. This is my new kind of purpose. I want to be someone that is known for making other people better. And it was, you know, this really invigorating and re energizing aha moment. And I'm like super amped up. But that only lasted for a couple of minutes because slowly I start to have this, this next realization that, okay, that's great, I want to make people better for knowing me, but how the hell am I going to do that? I don't have anything that I'm exceptionally good at. I don't have any superpowers that people need. What am I going to do? And as I sat there on that Sunday evening thinking about how I'm going to do that, the only thing that I could come up with that I was even remotely good at was I had always had this ability to take complex topics and kind of break them down so that anybody could understand them. But therein lied another problem. I didn't know anything that anybody needed broken down. I didn't have any, you know, in depth knowledge of complex topics that the world needed explained to them. And I wish I could Tell you that I sat there and kept brainstorming and had another couple cocktails. And I have, you know, the light bulb eureka moment where I'm like, oh, this is the thing that I'm gonna do. This is the complex thing that I'm gonna break down for people and take into the world, and all these people are gonna be better for knowing me because of this. It just didn't happen that way. It actually took me a few more years before I started to finally get a sense of what my thing was going to be. And it came after business school. And one of the things that I learned was that 60% of small businesses in the United States fail within the first five years. Something like 83% of small businesses fail within the first 10 years, right? So that means that most businesses that start aren't going to make it to 5 or even 10 years old. And when you dive deeper into the data, what you find is that most of them aren't failing because they're providing a bad service or they're making a bad product. They're failing because they're making poor financial decisions. And so you're like, okay, well, why are all these businesses making poor financial decisions? Well, it's because most business owners never learn how business money works. And when you couple that with the fact that the United States economy is built on the back of small businesses, right? Small businesses are what drive our economy. It's not Apple, it's not Tesla. It's not Facebook. It's the 32 million small businesses in America that drive our economy, that give us hope. It's small businesses that create jobs. And those jobs are what pay mortgages and send kids to college and allow people to do amazing things. And so I started to realize that business owners who we desperately need, these small business owners, they need to understand the language of business finance, and they don't. And, you know, as a country, we desperately need them to succeed. And so I'm like, that's my thing. I'm going to take the language of business finance and business money. I'm going to break that down so that small business owners can understand their numbers and make better decisions and thrive and have these healthy businesses so that they can hire more people and there can be more houses bought and more people go to college. This is going to be my why. So after all these years of trying to figure out what success was and how I was going to be successful, I kind of finally had my answer. You know, for me now, success is going out and making people better. For having known me and the way that I do that is by working with small business owners to help them understand their numbers so that they can make healthier businesses. And if you can't tell, I get completely jazzed out by this doubt. I mean, this is why I get out of bed every day. This is why I do what I do. Getting to this point has been, honestly, it's been a very emotional journey, and it's a journey that took a lot longer than I thought it should have. But on that journey, I learned a couple of really important lessons. First, finding my definition of success and kind of finding my why took a lot longer than I thought it should have. You know, I always thought that coming up with your why was going to be this light bulb eureka moment that I would have while brainstorming on a whiteboard one day. And for me, that's just not how it happened. It was part of a longer journey that required a lot of looking in the mirror, a lot of introspection. I was in my late 30s before I finally got that kind of clarity that I was looking for. Second, I learned that if today you don't know what your definition of success is or you don't know what your why is, that's completely okay. I think the important thing is that you're asking yourself that question and you're doing the hard work of that introspection and the self reflection to figure out what it should be for you. So if you don't know what your why is, if you don't know what success means for you, that doesn't mean you're a failure, but it does mean that you're asking the important question. And the first step in this journey is just asking the question. Third, I think that there was a ton of power in me going through that exercise on the couch on that Sunday where I listed out people that I knew in real life that I thought to be successful people. There was a lot of power in, like, writing their names out and listing out, you know, what their characteristics or attributes were that made me think of them being successful. I don't think that I probably ever would have arrived at this had I not done that. So I really want to encourage you. Block off an hour sometime, make yourself a mixed drink or a glass of wine or chai tea latte and sit down and list out people that you think are successful, successful and why you think they're successful. I think that will serve you extremely well. Finally, I don't think that there is a right or wrong answer when thinking about what your why is or how you define success. That's not the important part, you know. Your why could be serving small business owners so that they can thrive. Your why could be teaching people how to, you know, breathe better so that they can reduce stress and anxiety and sleep better and have better relationships. Your why could be that you want to go out and practice law so that you can bring more justice to the world. Your why might be that you just want to make a boatload of money so that you can have three Teslas in the driveway and you can travel to Europe whenever you want to. I don't think any of those answers are right or wrong. I think the important thing is that you go through the process of just answering the question. So, look, if you're struggling to define success, if you're struggling to find your why, I hope this video was helpful for you. If it was, it would mean the world to me if you could smash the like button below so that other people can more easily find this video. See you next week.