168. Crushing Procrastination
15 Nov 2025 · 19 min
Kenny Chapman explains procrastination as avoidance of uncomfortable feelings, not laziness. Three concrete fixes: set clear outcomes and prioritize, batch work with breaks, and kill distractions. An attorney mentor story shows how this plays out in real work.
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Foreign Kenny Chapman here, your host of Leadership in a nutshell. Super pumped to be back with you. I'm feeling a little froggy today. I don't know what that means or where that came from, but I'm just in a super great mood and I'm enjoying this opportunity to connect with you here today. Episode 168 crushing procrastination how many of us feel like, if I could just get myself to do that thing, then everything would be great, and how many of us kind of do that thing and then feel like, oh, man, but, you know, there's another thing. If I could just do that. No, I'm going to put that off. I'm going to wait. Let's call time out for a minute, my friends, and let's just kind of look at this and let's see what this procrastination thing, it, you know, challenges a lot of people. I've talked about this concept on the podcast before, but, you know, we're going to continue to circle through things that. That matter, that affect you, that. That influence your behavior, that impact the results that you. That you may or may not get, that you want to get. Sometimes we. We don't do things, and that prevents us from getting what we want, and then other times we do things, and that also prevents us from getting what we want. And so we got to kind of take a step back and look at this whole procrastination thing and just decide, like, what does this mean to me? And first off, you know, I'm not big on specific definitions or what, you know. Well, let's see what the Thor is. The Thor. Can I say that? The. So the thesaurus. It's pretty funny if I can't pronounce a dictionary name or something, right? That's why I'm just here cracking this code of this driven mind that you all and I have together and we look at, you know, I don't care what. What. What it means to have procrastination. All I care about is that you and I are moving our lives forward in a direction that makes sense, that is supportive, that is fulfilling, that drives contentment, that drives growth, that drives my own conscious evolution as a leader in business and family, in finance, in, you know, different areas that I want to lead in, that I want you to look at where you want to lead in and just look, is this. Is this action or lack of action optimizing my life? That's the question. This thing that I think I want to do, why am I not doing it? What Is it? Let's fill in what you know, oh, I need to have the conversation. That's always a good one, right? The quote, put that in air quotes. The difficult conversation. I'm putting it off. I'm procrastinating about it. Right? Well, one of the things that we want to get clear on is the perception around everybody that procrastinates is a terrible person. Well, hang on, wait a minute. Number one, no, that's not accurate. Number two, what if procrastination isn't this evil thing that everybody says it is? You go, well, hang on, wait a minute, Kenny, you're recording a podcast you're sharing with me today about procrastination, and we're talking about crushing it. That's right. I want you to crush procrastination when it comes to the things that are not optimizing your life. However, if I have a tendency to overeat cookies, let's say, and I procrastinate eating cookies, you with me? Then it can be a really good thing, right? So that's where I want you to just look at. We. We beat ourselves up. We create these rules, we create these regulations. We create these things. And you're a leader because you wanted to challenge the rules, right or wrong. Like, give me a head nod if you will. Right? Like, one of the reasons you're in the role that you're in, regardless of what that is, is because you wanted to challenge conventional wisdom and heavy on conventional and not always so heavy on wisdom. Right? So, you know, there's the collective agreement that most of society plays by. And then you're probably listening to this podcast or watching it, if we're putting it up online somewhere because you're interested in doing things a little bit differently, in realizing that you're creating your own reality. And the challenge that you have when you procrastinate is that, you know, that's a blocker to you creating your own reality, right or wrong. Okay, you with me? So all we're looking to do when it comes to crushing procrastination is to get leverage. The brain is a meaning making machine. It's a habit forming machine. And if we come to the realization, which we have multiple times during our 167 prior episodes of Leadership, in a nutshell, we know the subconscious brain is running most of what we do on a daily basis. And so what I want you to challenge yourself on is procrastination. Is that a habit? Is that a subconscious response? Or is there something consciously that's saying, wait a minute, this might be dangerous. I don't know that I want to do this. And you know, and again, danger. Not like you're going to go jump off a building, but danger like I might not feel good if I have this fill in the blank type of a conversation. Let's say I've got a coach up, a team member. Let's say I've got to talk to my spouse. Let's say I've got to, you know, talk about money with somebody, whatever that. Oh my gosh, I don't want to do that. I don't want to do that. Now understand, it's not that you don't want to have the conversation. The conversation is simply an event. What you're avoiding is the feeling that you may get or you're presupposing that you're going to get from having the conversation. Okay? Now stick with me. Give me a head nod. You with me still? Okay. So it has nothing. That's what I want you to understand with procrastination. It has nothing to do with the task, with the thing with the phone call. One of my great mentors for many years was my attorney back in, when I lived in Colorado. Tom was such a great mentor of mine. He was about 20 years older than me. Is about 20 years older than me. And, and he taught me so much around what life, you know, in business was. You know, he formed the first deal when I bought my first company at 23 years old. And I remember when he taught me that, you know, as an attorney, he has to call clients back. And little did I know back then that attorneys don't like all their clients. Right. I wasn't around it, although I needed that. Maybe it's because I had a court appointed attorney at that time in my life. No, I'm, I'm playing. Okay. No, I'm not. No, no. Oh, I'm playing. Okay. Like, okay, we're gonna move on from that. But, but the point is, like, you know, Tom would say, oh man, I got it. We'd go to lunch and he'd go, okay, now I'm heading that part of my day where I'm gonna return phone calls and I'm gonna call fill in the blank first. Why? Because he's the biggest pain in my ass. It's the least conversation I want to have. I don't, you know, and it's like I start there and it was his way of overcoming procrastination to where he would start with what he didn't want to do the most. And then he would chunk down and then like, okay, this person isn't quite as rough as that one. And then down, and then down. And then get to the end of his day when he's calling people that he enjoys and working with and whatever. What, you know, whatever that looks like. That's simply one area of somebody that implemented a strategy to help putting off the inevitable. You're going to make the call anyway, right? You're going to have the. Back to our example here. You're going to have the conversation anyway. So stop avoiding the thinking. It's about the conversation. And that's the main thing that I want you to take away today. I'm calling this crushing procrastination because it has nothing to do with what you think it has to do with. That's the amazing part of the human brain is it tells us stories, it feeds us events, it feeds us scenarios, it ties us to previous experiences. It looks at the habits that we run, and we then think dangerous things sometimes, right? Then we think it has to do with this. Like, oh, my gosh, I don't want to have that conversation. It has nothing to do with that. I don't want it. Let's say this. I don't want to be in an uncomfortable situation that's different than having the conversation. Now we're starting to tell ourselves the truth. I don't want, let's see, the other person to feel bad. Ooh, okay, now I'm starting to get somewhere. Oh, I don't want to expose the fact that maybe I should have given them more coaching, more training, more ability to do their job. Oh, now it's going back on. Now we look at. Well, of hell, of course you don't want to have the conversation in your mind. You're going to make somebody else feel bad. You're going to embarrass yourself over some things that you did or didn't do that you kind of could have helped that. You follow me. So let's just get clear about this. And obviously, that's just one example. That's one thing that's on your mind when it comes down to it. But let's back this up and realize, hey, procrastination isn't good or bad the way it's framed. And you could probably Google all kinds of blogs and probably find all kinds of podcasts about procrastination. I challenge you to find any that are about what I'm talking about here, which is stop telling yourself a story. Stop giving yourself labels that allow you to generalize yourself I'm a procrastinator. No, you're not. You're a magician at staying away from bad feelings as long as you possibly can. And then you go in and you have the feeling and go, oh my God. And then you get done with it and you go, oh, man, that feels better than when I went in there, actually. How many times have you said this? That wasn't as bad as I thought. And sometimes I was recently with a client where we ended up letting somebody go and went, oh my God, that was way worse than I thought it was going to be. And that happened too. So what's the point? There's no point in presupposing. There's no point in building this story around a story that may or may not happen. And yet. And we wonder why we're stressed out. My gosh, let's simplify. Let's simplify our emotions, simplify our feelings, realize the brain's an incredible tool. It's doing its job of keeping you out of harm. In this case, you're viewing the harm as, I don't want to feel this way. Of course you don't. Who wants to feel like crap? Who wants to make someone else feel bad? And some of you just said, my mother in law. And that's not what I'm saying. I'm saying that some people, you know, it's like, hey, some people are wired to make some somebody else feel bad. And you go, yeah, that's how bad they are. That's not how bad they are. That's how they're trying to feel better. And they're not intentionally trying to hurt people. And that's a whole nother. Maybe I'll make a note of. That's a. That's an entire, you know, another podcast or whatever. But I wanted to give you just three things to be mindful of, okay? So first of all, if you're procrastinating, be easy with yourself. All of us have times when we don't do what we planned on doing, when we don't do what we said we were going to do. It's part of the human experience. Be easy with yourself. Guess what? You're human. None of us are perfect. Get over it. And guess what? We're all absolutely perfect because we're having a human experience and we're doing the best we can every single day. Having the conversations, having the emotion, having the feeling, building the businesses, growing the team, leading by example, leading by what not to do. Sometimes as an example, if I go back to my young leadership Career. So we just, we look at these things. But I'm going to give you three things today. Number one, set clear outcomes and prioritize your list. So what is the outcome I'm looking to have? I'm looking to feel better sooner. There's one. If that's my outcome and we take this conversation, we continue to run this through today's examples. If I want to feel better sooner and one of the only things in the way is this conversation that I've tricked myself or I've built this story around that I'm going to feel bad, then if my outcome is to feel better sooner, then guess what, I gotta go have the conversation, don't I? And that's a brilliant thing. So now, hey, let's go have the conversation. Let's see how it goes. It's gonna go better than I thought. It's gonna go worse than I thought. It's gonna go exactly how I thought. But either way, now I get to my outcome of feeling better sooner. Okay, so we look at what's the outcome. And then I set my priority task and list and go, okay, well I'm gonna do this first, then I'm gonna do this. And be easy with yourself. Don't have massive things like we build these incredible to do lists and all the different things. That's a whole nother podcast around productivity and, you know, managing your behavior. There's no such thing as time management. There's only, you know, personal management and behavior management and energy management and emotion management and there, you know, language management, communication management. Those are the only types of management. But we've coined this thing around time management. Last time I checked, I can't manage the time that passes on this time together. Right? And so we think about, number one, set clear outcomes and prioritize your list. Number two, big part of kind of really crushing procrastination when it comes to it. And I've just, I've just really been coming more of a master at this over the last couple of years, is really batching my time with breaks, especially for me in my creative world. Like if I'm going to build content, if I'm going to write magazine articles, if I'm going to be at Client Notes together, if I'm going to build presentations, I batch this stuff. When I'm in that creative zone, I batch it. But I take breaks. So number two is batch with breaks. So going back to my buddy Tom, like, okay, I'm going to make these calls, I'm going to call the first three People that I want to talk to the least. And then I'm going to take a break and I'm just going to do a walk around the office. I'm going to go outside, I'm going to get some fresh air, I'm going to heat up a green tea, I'm going to whatever it is, I'll batch my time with breaks. And then three, I'm going to eliminate my distractions. So when it comes to crushing procrastination, I've got to address my distractions. And what I've realized, as you know, I build self managing companies which there's no such thing. There's only companies that operate with self managing people and manage their own behaviors. And so as I build companies that do this through other people, then I have more and more opportunity to manage myself, which is ultimately why I do it. Right. So then the next thing you realize is I've got some time, but I'm distracting myself and I'll talk to the lovely Christy. I'll be like, oh my gosh, I don't do social media anymore. And then the next thing you know, I catch myself freaking scrolling through one of the apps or something. I'm like, what am I doing here? I'm distracting myself unconsciously. So then when I get conscious of it I go, no, don't do that anymore. What's even better? Shut it off. Turn off my phone completely, get rid of the app. If it wasn't for business, I would get rid of all of the apps. But because we utilize some of them in the companies, then it's like, okay, I'm gonna have those on there if I need to check anything or see anything or whatever. But you know, I'm not burying my head in the sand. But I'm gonna turn off as many distractions. I close my calendar, you turn off all of your notifications. You know, some of you in the plumbing, heating, air conditioning world that have your softwares now that you know, they text you every time a technician sneezes like, oh, Jimmy just turned on his windshield wipers. Like, I mean my God. From speed of trucks to close sales to non closed sales to time rings, answer to the phone like all kind like, I'm not saying don't manage your company, I'm saying don't drive yourself insane with getting notifications of things that don't really matter and you can't control anyway at the time. So look at how you can eliminate distractions and you will become more productive. And when we say, well how about let's let's crush procrastination. Well, that's the title of the podcast today. Yes, but really all we're doing is how about this? Let's become more productive, let's become more fulfilled, let's become more optimized with our thinking, with our behavior, with our actions, with the things that we get done. That's what we're looking to do. It has nothing to do with procrastination. I just duped you into listening today or watching today because I wanted you to to spend some time going, why don't I do that damn thing that I know I need to do? It's because of how you're going to feel or how you think you're going to feel doing that damn thing that you think you need to do. Take a step back, realize it's about a feeling. Build some strategies for yourself. One of them, set clear outcomes and prioritize that task. 2. Batch time with breaks. 3. Eliminate those distractions. My friend, I'm so honored. I'm so grateful. Action item for you. Do me a favor and share this with somebody. Make sure you give us a rating, a review. Just kick this. Just grab the URL and email it to somebody. Do me a favor to help us continue to grow some sanity around leadership, around mental stability, mental health. That's what it's all about for us here at Leadership in a Nutshell. I'm honored to have you. Thank you so much for being here. Until we talk, make it a better than fantastic week. I'll see you next time. Thank you, Sam.