21. Leadership: Retirement
15 Nov 2025 · 13 min
Kenny Chapman argues that driven leaders should retire from guilt and unfulfilling tasks, not from work itself. He shares how his stepfather Richard's early dementia shaped his thinking, and offers a worksheet to help you identify your primary purpose.
Chapters
Hey, my friend, welcome back to Leadership in a Nutshell. I'm your host, Kenny Chapman. I'm super excited to talk today about retirement in episode 21. Today we're going to be breaking down this little, what is it, five, six letter word? I don't spell. So I'm going to let you figure that out. Right? Retirement. What a terrible word. What a word to be stricken from the driven leader's mind. If you're a driven leader like you and I, Leadership in a nutshell. Cracking the code of the driven mind. We are not wired like most people. Most people think we're crazy, okay? I'll give you that. Sure, I'm crazy and I'm proud of my crazy and I embrace my crazy. And one of the things that I think is crazy is what some people call security, what some people call, you know, Social Security. Let's go there for a minute and go, well, wait a minute. I'm going to work until I'm 65, and then I'm going to wait and I'm going to retire. And then the government's going to send me a check because the government's always had my back, right? Why would it change when I'm older? I have no idea why that might change, but I'm just going to go ahead and I'm going to go through my life. One of these days, I'm going to stop working and I'm going to put it in air quotes, my friend, retire. And then I'm going to get on to my golden years. Then I'm going to live my life of my dreams. Then I'm going to become the person that I want to become. Then I'm going to engage the relationships that I want to engage in. Then I'm going to be free. Stop the insanity, my friend. Retirement is not for you. If you're listening to this and you have a driven mind like me, you know that you cannot retire now. What does that mean? Maybe you're in a sales career. Maybe you're in a job where at some point you leave and you're going to embrace this quote, unquote, retirement. Here's what I know. Retirement is not for you. Why? Because you're not built to retire. The way the world sees it, when we think about the word like stop moving, slow down, all those different. I'm not talking about running and playing full out. I'm talking about staying in purpose, in purpose, on purpose, with passion. You know, people talk about, oh, you're passionate, Kenny. I wish I had passion. If you Want passion? Take some action, my friend. People, these kids today are seeking passion. Well, I want to find. I'm not going to take a career. I'm not going to choose anything until I really connect with what I'm passionate about. You want to get passionate? Go do some stuff. Go have some experiences. Find out what really sucks in life. Find out what you really don't like. Find out what is really painful. And you'll realize I'm passionate. When I was sitting on a jail cell floor in Lake Havasu City, Arizona, when I was 19 years old, what I knew I wanted to retire from the jail system. How about that? I knew that I wanted to. I had tremendous passion about not ever going back there to a point of. I did not go back to where I came from. I did not stay in Havasu, where we were doing a lot of illegal activities and the cops were watching our house and all the. I. I retired from that, if you want to use that word. And I got myself in the military and I said, I can never go back to the way that it was. If that's what you think about retirement, that's exactly where I want you to go with this. What I want you to think about. You're a driven leader. I want you to retire. Air quotes in it. I want you to retire into your life. I want you to retire into doing what you really want to do. I think about my late stepfather, Richard, who was diagnosed with early onset dementia around 60 years old. 62. I'll never forget the night we were at a dinner at an Italian restaurant in western Colorado. My wife and I, the lovely Christy and I, my mom and Richard, and Richard and I were splitting the bill. It was Christmas Eve. My mom's birthday is Christmas Day, and we generally go out, do something. So we were out together for a dinner around Christmas time. So we don't celebrate mom's birthday on Christmas, so we kind of break it up. And I remember looking at Richard kind of struggling to do the math on the check, and he was having a hard time figuring out the 20% tip. And I went, huh, that's interesting. I didn't think much about it. I knew he had a glass of wine, but he's not a big drinker. I don't think anything's going on there. Like, huh, that was really odd. I don't even remember if I said anything to the lovely Christie. But I drove home and I look back now and I realize that was the beginning of his shift in his mind. And then from there, it Built to different things and he began to forget certain things and he began to not perform in his job. And it came to a place of forcing his retirement and he wasn't able to do anything. And the next thing you know, within a few years he was in a home and he couldn't take care of himself. And my mom wasn't able to live with him any longer. And all these things happened. And then he died. Yep, Richard tapped out. Is it too early? Absolutely it's too early. I wouldn't wish it on anybody. But what it does is it reaffirms to me why we're having this conversation today. It reaffirms to me there's no such thing as waiting for your golden years. You don't know your golden years are right now. You woke up today. You're a leader. You have an opportunity to influence. You have a responsibility like no other. Not to come from a place of heaviness or concern or fear, but from a place of abundance, of fulfillment, of opportunity. You get to say, I'm going to retire in it today. I'm going to do the things that I love to do. I'm going to find out the things that I'm not very good at that I don't love to do. And I'm going to retire from those specific things. But I'm going to retire into my business, I'm going to retire into my team. I'm going to retire into the things that that makes sense for me. My friend, retirement is not for you stopping doing stupid crap that doesn't make sense. That's what's for you. And if you want to call that retirement, cool, let's do it. I know when I was in the army I would watch 40 year post sergeant majors. Been in the military 40 years and then the military finally forces them out. They're leading 10 mile post runs before they're forced out of the military because they've been in too long and they have to stop doing. They retire air quotes. Six months later, drop dead after running 10 miles of post runs and different things, why did they drop dead? Because they stopped their purpose. They stopped living. If you're stuck in a situation, if you don't like your business, if you don't like your team members, if you don't like what you're selling, if you don't like how you go to market, challenge that and retire from that now so you can get in to something that you have passion about so you can get in to your greatness, so you can get into embracing and living life. Look at people that were taught the 40, 40, you know, like the, oh, I'm going to work somewhere for. I'm going to. I'm going to take them until I'm 20 and get out of. Get out of college, 20, 22, and then I'm going to get a job for, you know, 40 years, and then I'm going to be in my 60s. And then. Those days have sailed, my friend. They're long gone. But when you look at people like that, you don't retire from the great conversations around the water cooler. You don't retire from bringing some value to the world. You retire from the commute that you can't stand. You retire from the people that you don't want to interact with. You retire from the dumb tasks that don't make sense for you. You retire from those things. You and I are business leaders. We have the opportunity to create that. And not only do we have the opportunity, our team counts on us to create that. If you don't have the best seat in the business, what is your team looking at? What does it look like for them? What is their path? If you're in the way going, oh, man, I just can't wait until I sell this thing, then sell it today. You're not doing anybody a favor. I know I'm coming at you strong. I'm excited because this is so passionate. I can't talk about Richard's life without finding passion within me because every day I'm alive is a day that he's not here. It's a day that he doesn't get a chance to wake up and play the game. Sure, he's probably in a better place than you and I right now, but what's the point? Let's make this place the most amazing place right now, today. And that's making different choices. What do I want to retire from? I want to retire from guilt. I want to retire from shame. I want to retire from, you know, the shoulds of my life. That's what I want to retire from. And then I want to retire into my unique ability. I want to retire into my primary purpose. I want to retire into those things that make so much sense to me. If you're listening to this, if you're watching this and you need some help with this primary purpose, send me an email. Kennyennychapman.com Kennykennychatman.com I'll send you my primary purpose worksheet with the. With a video that will help you identify some of this stuff, life is too short for you not to live in purpose. On purpose, my friend. And if you're just waiting for one day to tap out the time we're recording this. I'm about to turn 50 years old. And people think that 50 is old. And that is, it's just absolutely mind blowing to me. I remember the days when I was younger and I thought 50 was old. I am just getting started. I'm going to live to 146 years old. I'm barely a third of the way into my life. That's what I know, that's what I believe. That's where I'm headed because I'm living a different life. I'm choosing a different future. I've got bigger plans. I'm making my future bigger than my past. When you're looking for retirement, when you're waiting for something else, you are making your future smaller than your past. Why would you do that? Help me understand. Why would you not make your future bigger than your past? Regardless of age? This isn't about like, oh, I'm doing all the shoulds and the different things. It's about energy. See, when do most people retire the traditional way? Most people retire when they have enough money. Because we're taught that we are trying to play the game to where we have enough money. I don't believe in playing that game. I believe in creating enough value in the world to where I can create cash flow, economic independence, to where now I can do anything that I want, whenever I want, with who I want. Does that not mean that I have responsibility 100%. I've got things that I need to do every single week. But guess what? Each week they're more and more. Each year there are more and more the things that I want to do. Because what happens? You retire from the job that you don't like, you sell the business that you don't love, and what do you do? You, you go volunteer and you create a job. I look at people, they're so busy in their church, in their community. Now all of a sudden they're sitting on boards, they're doing all these things. Guess what? It comes with schedule conflict. It comes with responsibility. It comes with certain things that you need to do. Why wouldn't you just go ahead and do that while you've got your own business, while you've got your ability to create the career you want within a business, that honors entrepreneur mindset within the company? I want everybody on my team to be free to create their dream life on this team, that's the reason this company exists. Everybody's coming in different places, different growth opportunities, different levels. That's what it's ultimately all about. If my team can retire into their positions, into their careers, great things happen. It's about tapping unique ability, it's about tapping primary purpose, and it's about playing to win. See, once you. Yes, when we think about, oh, I've got to have enough money to live on. Yes, you got to have enough money to live on. But. But money is simply energy. Money is a currency for you to create energy in the world and do different things, and the world will pay you dividends on your energy. If you're so worn out, if you're so tired, if you're disconnected from your purpose, from your spirit, from your community, it's time to take a step back and realize people like you and I, sorry, you. You can't retire. You've got to get clarity. You've got to retire from a few things. I say you can't retire. You can't retire in the traditional sense. What can you retire from? From guilt, from shame? From presupposition, from the shoulds in your life? From the fear that you're not enough. Retire from that stuff and watch your world explode. I'm your host, Kenny Chapman. Leadership in a nutshell episode 21 super honored to be with you here. Please give us a rating. Would like. I love the 5 stars. Would love to have a review. Help us grow this community. Stay in touch. Kennychapman.com group again. Shoot me an email. Kennykennychapman.com put purpose in it. Tell me you want the purpose worksheet and video. I'll send you that training system so you can get into your greatness. Until we talk, my friend, make it a better than fantastic day. We'll see you next time.