The Hero's Journey of Becoming A Good Leader

Mar 22, 2022

A huge part of what kind of leader we become is how we react to our experiences. Even though we plan our actions ahead or we create safety nets in case things go South, failure might surprise us along the way. Or perhaps we don't fail, but the final product is entirely different from what we had in mind when we created the project in our heads. Whatever the case might be, in failure, just as in the deviation of our projects' direction, we learn, acquire experience, and become wiser. 

Defeat is a great teacher. Every time we fail at work, in business, or in our lives, that experience teaches us a lesson, and if we decide to learn from that experience, we'll become better leaders and better followers. 

Today's episode is about the value we can get from failure and how every time we give something another try after failing, we are not starting from scratch; we start from experience. We delve into the importance of learning from our mistakes and incorporating those experiences into our leadership toolbox. We analyze a past experience I had with sales, where pushing through my fears helped me land a fantastic deal and, at the same time, taught me about teamwork and leadership and changed my mindset completely. 

In This Episode, You Will Learn:

  • Failure is relative. How to deal with the expectations in our mind when we fail (2:15)
  • What can we learn from our experiences (4:52)
  • An enriching experience from one of my first jobs in sales (7:18)
  • What can pushing through our fears teach us (11:42)
  • We get to choose what kind of leader we become (14:10)
  • The importance of recording our experiences and having access to them when we need them (18:40)


  • Quote: Randy Pausch, professor at Carnegie Mellon University (CMU) - "Experience is what you get when you didn't get what you wanted. And experience is often the most valuable thing you have to offer."
  • Quote: Unknown - "Don't be afraid to start over again. This time you're not starting from scratch; you're starting from experience."
  • Quote: Marjorie Pay Hinkley - "Everything you are learning now is preparing you for something else."
  • Coaching with Clint Consultation Call - Book Here
  • Download my free One-on-One Transformation tool

Let's Connect!


Clint Hoopes: Experience is what you get when you didn't get what you wanted. And experience is often the most valuable thing you have to offer. 

Welcome to the Flavor of Leadership podcast. Excited to have you here once again today. As we often do on the podcast, we speak about continually improving in your life just a little bit, a little bit better each day in your life, in your business as a leader. And we are doing the same thing here on the podcast – seeking to be just a little bit better all the time. So, in an effort to be just a little bit better and serve you even better, we're making a few changes to the podcast. And I can't quite announce all the changes yet, but over the coming weeks, there'll be some fun changes that will help to enhance your experience even better when you listen to the podcast. So, stay tuned. Over the coming weeks, we'll be announcing more and more of these fun changes. So, as we get started today, I want to start out with a question. So, think of yourself here. Have you ever made huge plans for something that you wanted to accomplish and it didn't quite turn out like you had planned? Maybe it was a learning or a fitness goal, something you want to do that way – like learning an instrument, learning a language, learning something else, or running your first marathon or a triathlon, or doing a 5K. Whatever it might be, but there was something that you were wanting to do that you failed, or it didn't turn out quite as you planned. Failure is all relative. Perhaps it was becoming a manager or leader for the first time. And you had these expectations in your mind of how it was going to be, and how you're going to lead. And man, maybe people didn't follow as readily as you thought they were going to. Or maybe you started your own business and that business didn't take off quite as quickly as you thought it would, or not in the way you thought it would. The business that you had, in the end, was not the business that you set out to create in the first place. I imagine all of you have had something like this happen in your life where you imagined something was going to happen a certain way, and then it didn't. So, when you're thinking this in your mind, “Did it go according to plan?” The answer is most emphatically no for most people. 

Now, some of you might have things just perfectly planned out in every way. And typically, even when you have things planned out that way, it doesn't always go according to plan on these big dreams, these big things we're trying to accomplish. Leadership is one of those big things – running a business – but it applies to all parts of our life and what we're doing. I love this quote by Randy Pausch, who was a professor at Carnegie Mellon University. Now, he said this: “Experience is what you get when you didn't get what you wanted. And experience is often the most valuable thing you have to offer.” Isn't that so true? Experience is what we get when we planned so well and went to execute, action happened, and it didn't quite work out like we thought. Now, do we fail? Or did we fall flat on our face? Maybe, or maybe it just didn't have quite the effectiveness that we thought it was going to have, whatever we did, or we didn't accomplish the goal or the thing as much as we thought we would. And then we would define that as failure, depending on what metric we're using. But in the end, something we did gain that wasn't a failure, that's never a failure is the experience that we gained. In that quote, it says that experience is often the most valuable thing you have to offer. And so when we're working with other people and we're a leader, that experience that we've gained by failing – and not just failing at work and in business, but failing in any part of life – it teaches us something. And it's that experience that helps us learn patience, helps us learn to be a better leader and a better follower, when that's needed in a business. 

All of these different things that we have from our experience are things that we have to offer an employer, the market, or anyone that we're needing to lead or serve. So, a great friend of mine shared this with me. And I don't remember where this quote came from. I searched it up, and it looks like it's an unknown quote, one of those that's attributed to a few different people. So, I don't know, we're going to call it Unknown for now. If you do know who it is for certain, go ahead and send me a message, I would love to know so I can attribute this to the right person. Says this: “Don't be afraid to start over again. This time, you're not starting from scratch, you're starting from experience.” So, anytime we attempt to do something, whether we fail by the metrics that we set up or not, doesn't really matter. In the end, we're learning something. We're learning something from what we're doing, even when it doesn't go as planned. And the next time we go to start something again, or we go to teach someone else, we're not starting from scratch, we are starting from experience, we have already experienced so much of what there is to offer. I often think of professional sports players. So, whether it's someone in basketball, football, baseball, doesn't really matter, somebody who's in the Olympics – these people who have been there before, they have an edge, they have something to offer other team members and themselves as they go back to compete at these incredibly high levels of performance and these huge events like the Super Bowl, like the Olympics. When they go back, the experience they've had in the past, those same places, makes them so much more valuable in the future. 

We as leaders are in the exact same boat. When we have been there, even if we've failed, by different metrics, the experience that we've had is so valuable. And if we let that experience drive us forward and help us improve, and make better decisions, and lead better, that's when the experience has actually helped us. But if we let those experiences remind us of the way that we failed, remind us that we couldn't do it before, that's not going to serve us nor the people we lead, because that experience is the way we can adapt, and they are our most valuable experiences. 

So, these experiences where things didn't go as planned, they can define us in one of two ways, like we said. They can show us and remind us how we failed, or they can show us how we can succeed in the future. And if you are listening to this podcast, you are one of those, I know, that is looking to succeed even more in the future and up your game. 

Thinking of this principle, it actually takes me back a number of years to one of my first jobs where I was starting a business, and I was doing sales calls. And goodness gracious, any of you that have done sales, if you're in business, you're in sales one way or another, always. But I was doing sales calls, that was a big part of the business at that point as we were starting up. We didn't have a lot of business. So, what did we need to do? We needed to get more business. So, what did I do? I was out pounding the pavement, so to speak. Literally, out there, pounding the pavement, trying to get people – these businesses that we were marketing to – to use us, to use our services. But guess what? They didn't know me and I didn't know them. And in my mind, I knew that our service was fantastic, what we had to offer was amazing, and it's what these people needed. They just didn't know it yet. So, I was there, and I was pretty confident that I was going to be able to help these people see that our product is what they needed, and to use us, to use me, to trust me. But guess what happened? Any of you out there that have done sales in the past know where this is going. I didn't get the sales. They didn't come. My phone didn't ring off the hook. I had a few calls here or there. We made a few sales and it was great. But there were so many places where I was stonewalled, I wasn't making the progress that I needed. And in this particular business, there weren't a tonne of potential customers. And so I had to keep going back over and over again to some of the customers that were not incredibly kind to me. 

I can think of this particular day where I was sitting in my car and I needed to go in and follow up with this particular referral source, and I needed to go in there and say, “Hey, please use our services.” And I needed to present a couple of things to them. And I was terrified. I knew what I was going to say when I went in. And yet, it still terrified me because they had not been overly kind to me. But really so much of that, I realized now, hindsight, looking back, was in my own head. They did not need me at the time, I didn't think, as much as I thought I needed them. And so that was playing with my head and it put all this fear inside of me. So, I sat there and I was frozen. Until finally I just cut over my fear and went it. Went in, and it ended up going actually very well. It was one of my better times. It was amazing. It actually not too far later they ended up using us, they ended calling us and giving us business, they end up being an amazing customer in the future. And it all started when I pushed through this fear. Mark Twain said this: “Courage is not the lack of fear, it is acting in spite of it.” For me, on this day, I had fear, and I acted in spite of it and I was rewarded. I often think back, what would have happened if I hadn't pushed through the fear and went in? What would I had not learned? Having that fear and having to push through that taught me so much. Because up until that point, I'd had what would be deemed a bunch of failures. I wasn't having as much success as I thought I was going to have. And it was so much harder than I thought it was going to be. And pushing through this, even in spite of the fear, and then in the future, starting to get business from these people; helped me realize and helped me learn so much. I think it'd be hard on the front-end, and then having the great reward on the back-end taught me so much. It helped shape my experiences for the future. My expectations changed, my preparation changed in the future when I was doing other similar sales activities. I was prepared in a different way. I learned how to work with people in a way that I didn't know before. And all of these things made me better in the future. I wasn't starting from scratch, I was starting from experience with these future businesses that I was helping to run. And I'm telling you going through the struggle at this point in my career was amazing. 

Now, looking back, at the time, it hurt so bad, it was so hard. But now looking back with a different lens, I am so grateful that I was able to learn those things. And it's made me better today in so many ways. The experience that we gain is truly wisdom, it's not just knowledge. Knowledge, we can pick up anywhere. Wisdom is a little deeper, it's something we internalize a little more, it's something that will change us a little bit more. Wisdom is often the thing that we acquire when we didn't ask for it. Knowledge or all of those things that we seek to learn often, but wisdom, we often acquire what we didn't ask for it. So, it often hits a little bit deeper for us. 

Another quote that I love is by Marjorie Pay Hinckley, and she said this: “Everything you are learning now is preparing you for something else.” So, what are you learning right now? What's a trial you're going through? What is really hard? What are you working through? And what is it preparing you for? Something bigger, something better. If you're listening to this show, you're not someone who likes to live small, you're someone who wants to do something great, be better. So, the experience you're having, how are they shaping you into the person that you need to be in the future? The person that your people at work need you to be. What kind of leader you becoming? So much of it depends on how you react to your experiences and how you let them shape you. It reminds me of heroes. You have heroes all over in history, real people, as well as fiction stories. And so many of these stories are based on what we wish we could do or what someone has actually done, actually accomplished. And we look at these heroes and we think, “That is what we want to do. That is who we want to be.” We look at those heroes in our lives and we think, “That's what we want to be.” But we often forget that the heroes in real life or in fiction always were prepared to be the hero, through their trials and their experiences. 

The stories that we see follow through principles most of the time. These people had to struggle and be prepared so they could be that hero and fulfill their ultimate purpose, what they were meant to do. And so these stories are not just for heroes and for fairy tales. Our trials are preparing us for our purpose, for what we can accomplish, what we want to accomplish. Once again, we get to choose how we view the trials, and the struggles that we have, and the failures that we have. We get to choose if we're going to get back on the horse, so to speak, and start again with the experience that we've gained. What we do when we don't have experience in something and we're trying to lead, it's a little harder. Have you done that? Where it's hard and you're like, “Man, I am trying to lead somebody, but I've never done that.” And that's okay, too. We can still lead people. There are so many different ways. And that in and of itself helps teach us and learn. I know, I've had times, as I was starting my career, and even till today, where I'll be speaking with people that have had experiences that I've never had, they've been through things that I've never been through. And so we can learn from each other. And so, don't be intimidated, don't feel like you need to always be the smartest person in the room. We can get knowledge from all the people we have and don't have to have all of the answers in order to lead, and lead well. We'll have to make all the mistakes in the book to be able to learn from others. We get a chance to learn in so many different ways. 

So, one thing we need to be careful of, I will tell you – well, that I've been guilty of in the past – is when working with people that are struggling and they're in the midst of the struggle, it's hard to share a flowery story where you were struggling and then prevailed in the end. You have to read the situation just right. Sometimes that can go a little south on you, where you're sharing these examples with someone but they're not in the right place to receive it. So, this is where you, as a leader, have to read the room, so to speak, and know how best to help people. Sometimes, just because you learned an experience, doesn't mean that you have to share it in exactly the same way. But you can still use your knowledge to help and to lead. Sometimes the best thing you can do is ask better questions so that people can discover the right direction for themselves. Sometimes using your knowledge that you have and the insights you have that you've learned from your past really can help you ask the best questions. And though that's often the best way to help the people around you, and those that you're leading. 

Often the experiences we have in the past will happen, and we'll repeat them again. Have you ever done that? Where you have failed at something in the past, then you've repeated it again when really you could have connected the dots. You could have connected the dots and seen your experiences from the past, but you didn't. So, that is why I love journaling and recording my thoughts and insights. And I love to do it in a few different places along the way. I love to do it, record my insights when things are going well. I love to record my thoughts and insights when I'm in the midst of struggles. Many of the stories that I've shared on the podcast have all come from experiences I've had and from journals that I've written to help record where I'm at and what I was doing in the middle of the struggle. And as well as at the end of a struggle, when I have the hindsight view of looking back and seeing the progress that I made and some of the things that happened at the end of that tough time. And all of these different insights can be useful and helpful to you. The problem is they're not going to be there for you if you don't record them. And the best time to record them is as they're happening. So, where do you record your insights that you receive? Right now, I'm going to specifically talk about business insights. But this can be true for all parts of your life, all different insights that you receive as a parent, as a friend, as just somebody trying to improve and be better. But in business, tough times will come, you know that. You know it's going to be tough. And you know there are going to be times when things go really well, and this cycle goes, it ebbs and flows. 

So, where do you record your insights for work? Do you write them down when things are tough? Do you write your thoughts that you came at the end of a tough struggle? And even if you do capture these thoughts, could you find them if you needed them? Do you have them in a method where you could search, or there's a table of contents in a journal or the method that you use? If not, this is the challenge for the week. If you have not been keeping a journal of these types of things, these types of insights, start with now, don't overcomplicate it. It can be a note on your phone. It can be a handwritten journal, which is one of the things I prefer with these types of insights. There's something about it that helps to internalize it in your mind when you handwrite it. Don't worry about getting a fancy journal, do it in a notebook and write “Business Insights journal” to write it down. And when things happen, write them down. Put a simple table of contents on the front page if you want, write the page you're on, so you can go back and quickly access and find the things you need when you need them. Right now, when you're thinking about this, you're thinking, “I'm writing this so that years into the future, I can look back.” I'm telling you, sometimes looking back a month, or looking back a few weeks, or six months; man, can provide amazing insight to see the growth you've had and to see the trials you've been able to overcome. Things can shift so quickly. 

Once again, the importance is to record it, don't overcomplicate it, but then to go back and read it. Go back and read it, that's when you'll have the benefits of the insights, it’s when you go back and see that. For me, during this time, part of the reason I remembered this time where I was struggling so much that we shared, when I was doing those sales calls. Part of the reason it's so vivid for me is because I went back and relived that by my journal in the past. It's helped me remember how tough it was to be at that point in my career and in my journey. You can gain the same thing yourself. So, go and do that today if you don't have something. Get some words, write these things down, you will be grateful that you did. You got this. Until next week.