120. How Much Planning Is Too Much Planning?
15 Nov 2025 · 14 min
Kenny Chapman identifies four ways over-planning backfires: it kills productivity, enables procrastination, masks low self-esteem, and feeds perfectionism. He offers a four-question checklist to stay on track without spiraling, then says the goal is to get directionally correct and go.
Chapters
Foreign. Hey, my friend. Welcome back to leadership in a nutshell. Yes. Cracking that code of the driven mind. We've got a driven mind and we've got a code, and we're here to crack that code, just like the code on a safe. And we're here to unlock your unlimited potential once again. A few minutes today together for episode 120 of How Much Planning is Too Much Planning? Let's talk about this today in episode 120. By the way, before we jump in, if you could just share the podcast with somebody that you care about, somebody that might be able to benefit of taking 5, 10, 15 minutes out of their week to just think about their thinking a little bit, to challenge their thought process. I'm not looking to epically change your life every single week. I'm looking to epically challenge you to slow down and think about your thoughts every week. And I would love it if you'd help us share this, this movement that I'm creating around just how to feel better as a leader and how to enjoy life more in when it comes to ultimate success, which is how you define success. So episode 120, let's go right now. So here's the thing. When it comes to planning, yes, we want to be prepared. Yes, we want to have a plan and we want to have everything structured and we want to do right by everyone and we want to have everything squared away. And I get that. And you know, you, you want to be prepared, you want to be ready, you want to execute perfectly. Isn't that what we want? A couple episodes ago, I remember talking about business planning a little bit. And we want it all, you know, is talking about certainty and uncertainty. And just like with planning, like, I'm going to set the plan place so everything happens exactly how I want. And my ego wants me to think that's how it's going to go. That's how it should go. And the reality is the plan only gets us started. And I just really want you to be clear of how over planning can hurt things and kill creativity and some different things like that. I've heard the quote, you've probably heard the quote multiple times as well. There's this saying about don't try to boil the entire ocean, right? And so I love a good hot springs in the mountains of Colorado or different places. And it's like, man, that that water comes out hot right out of the rocks or whatever it is. And you think about, well, when there's hot springs in the ocean, it's just the little Spot a little area that you start with, and that's what I want you to think about in life. There's a lot of challenge that comes from overwhelm. Right now, we're living in a time in history where there's more at our fingertips than ever before. We are absolutely barraged nonstop with information, with marketing, with advertising, with social media, with comparison mindset with who we should be that we're not with all these different types of things. And from all that, we're looking to have control. And planning gives us a sense of control. And so when, when we think about last week when I was sharing about accepting uncertainty, I want you to frame a little bit this week around accepting when enough planning is enough. So obviously, the lovely Christie and I do road trips, and we just got back from our summer trip this year, and I mean, shoot 5,000 miles or something and multiple states and a bunch of national parks. And God bless. The lovely Christie does a bunch of planning and knows a lot about different areas. But no matter how much planning she does before we arrive in a new town, in a new situation, in a new national park, there's always things that happen. Maybe a restaurant is closed, maybe there was a flood in the kitchen and we can't eat at a certain place. Maybe the. The Airbnb isn't how it looked in photos. Maybe we're planning to go on a specific hike in a national park and it rains. Whatever the case might be, there's always wild cards that happen. And my friend, that's one of the beauties of life. And so, as leaders, yes, we are tasked with planning. And planning is important. Don't get me wrong, this is not an episode about not planning. This is an episode about you deciding for yourself when is too much planning, when is enough. How does that look for you and your business? And for me, I'm a visionary. So I rely on my executive leadership team to help lay out and execute my vision. So I have a vision of where I want the company to go and what I want the company to look like. But I'm not the one that puts together the specific, exact plan of this is going to happen. That's going to happen. So that's kind of how it shows up in business. So I have other people that get involved in planning. And as a visionary, sometimes planning can frustrate me because I just want to get going. I just want to rock and roll. But when I look at my amazing ops director and she's like, no, I need to know a little more of the Direction and of the plan and what it's going to look like. And then we come to common ground. And the president of the organization is like, okay, well, I get the overall vision. I get that there needs to be a plan. And then he's able to blend those together in his role effectively for the rest of the company and our clientele. And so the same is true for you in your life. Depending on what your role is, you may have different levels of how much planning is too much planning. So back to the lovely Christie and I for travel. We love to travel. I travel all over the world. Any chance that I get, for me, when I think about somewhat of my level of planning would be, okay. We get out of Arizona in the summertime, so let's go in this direction this year and let's be gone. Let's take five weeks. Okay, that's about the planning I do. And then I might say, well, okay, so this summer we did the Pacific Northwest, and we're going to hit certain parks, and that's the type of deal that we're, okay, fine. And then Christie kicks in with a different level of planning. Her level of planning enhances the trip, enhances my life for sure. No question about it. But it's not my DNA. It's not how I'm wired. So for me, if I try to get that granular with planning, it frustrates me and I might not do anything for her. It can be over planning, and there can be a point of where it just turns into frustration, because at certain point, enough is enough. And so the whole point of today's episode is just really, for you, depending on where you are in your life and in your business, as well as the team around you and who your supporting cast is and supporting roles around you in your personal and professional life, how does that work? How does it show up? Because when we get to where we're over planning, there are different forms and like masks, if you will, of where, oh, well, I'm going to make sure that I have a plan, but really it's masked and it's a form of different things. And there's four things of forms that that over planning shows up in. Number one, it shows up in the form of a productivity killer. If I'm just going to plan, I'm never going to get off the couch and build a business. I'm never going to fix the sales department. I'm never going to do a ride along. I'm never going to train my management team. I'm never going to Take a trip. I'm not. Whatever it is, right? It's a productivity killer. So you can over plan and you can overthink into not doing anything. Over planning can also be a form of procrastination. So. Meaning that, well, I need to know this more. Little bit. Back in the day we used to do a lot less planning. Grab a map book and hit the road. You don't even know where the gas stations might be. In today's world you can drive yourself crazy because we live in information overload. Just like your business can drive you crazy and pull you unconsciously out of ways that really drive the business and really matter because you just have data overload. Oh, there's so much data. Well, just like planning, too much data. It can be a form of procrastination because I'm not gonna do anything until I get this report. I'm not gonna do anything. Be mindful of those things. So it can be a form of productivity killer. It can be a form of procrastination. It can also be a form of low self esteem or self judgment. So I need to plan. I gotta have everything in order because I need to control. Why do I need to control? Because I don't want to be judged. I don't want to judge myself. I don't want others. I don't want to fail. I don't want to. It's a function of low self esteem. If you're over planning a lot of times. So be mindful with that and with yourself and be easy with yourself. As you look at when enough planning is enough planning. Don't get me wrong again, I'm not saying planning is a bad thing. I'm saying when you're obsessive about it and it stops you from doing these things, that's when it can be a challenge. It's also a form of perfectionism. Much like the self esteem is tied to perfectionism. Much like procrastination is tied to perfectionism. You're trying to be perfect in the world. If you're over planning and trying to control every little thing because that's where you used to get validation as a child in your early career, whatever it is. But it's probably not relevant any longer. Good enough sometimes is good enough. 80%, sometimes is 100%. And that's a challenging concept for a lot of you to understand or a lot of you to grasp. And that's okay. Part of my thing in this podcast is to connect with you and challenge you on some things. And if you're over planning, I want you to challenge on what you're doing, why you're doing it, and what you can do differently. So here's four things I want you to think about today. I always try to give you just a few things to think about, a few things to focus on in between our time together. Number one, just get desire. Like, get clear on what your desired intention is. So what is the intention of what I want to accomplish for me? Like, okay, so the plan for me is, like, I want to go, okay, this summer, I want to go to the Pacific Northwest, was the deal. Okay, fine. And then depending on who you are and how you plan and what your role is, then you go, okay, well, then the lovely Christie's going to go, okay, well, we're going to have this many Airbnbs. She had to book. I forget what it was. 12 Airbnbs or something like that over the course of our five weeks. Like, okay, so I need these. I need to know this town and where we're going to stay. And then maybe a restaurant or two. Like, okay, fine, then once we get that, then we're good. What does that. So just get clear on your desired intention. Second thing, what are you wanting? What do you really want from this plan that you're putting together? Are you looking for specific Fill in the blank? What is it that you want? Three, how do you want to feel? How do you want to feel? Like, that's a huge key when it comes to every. Remember this. Everything that you do in life, you're doing it for a feeling. I want to make more money. No, I don't. I want to feel better. Oh, I want to be secure in my relationship. No, I don't. I want to feel better. Oh, I want my kids to get a good education. No, I don't. I want to feel better. I'm not saying, no, you don't on those things, but that's not ultimately the core. You want to feel better. You want your kids to feel better. You want to be financially secure because you want to feel that you're financially secure. Everything is about a feeling. So when you're planning, then what are you looking for when it comes to how you want to feel? And then last and certainly not least, the thing that we kind of get lost on sometimes, I think when it comes to planning, what does success look like? That might be the most important question you can ask when you're starting planning or when you're doing planning. Like, and I'm talking like, we could break this down to the granular of you're going to do a team meeting this week or you're going to do training for your frontline team, you're going to do a sales training in house and so you're building your plan of what that's going to look like. You can over plan it. I know I've been training and coaching in this industry for what, 20 something years now. I'm like it's been a long time now that I've been planning meetings and planning trainings and now I plan podcasts and you've been with me for a while. I don't over plan this podcast because I just, I get literally I'm doing this, I get directionally correct. What is the direction I want to go. What do I want from this? And what do I want you to have from this? How do I want to feel? How do I want you to feel? And what does success look like if you share it with somebody? If you give us a rating, a review, an email back. If you're feeling good and you're sharing the information, if you feel good, then that's what success looks like to me. But for you, like oh this training meeting, well then what would success look like for me? Well if we doubled our, doubled our sales by noon that today, like let's look at it. What does success really look like? Because that'll help you when you need to stop planning, perhaps. So it can be a productivity killer. It can be a form of procrastination, it can be a form of low self esteem or self judgment. It can be a form of perfectionism, remember? So what do you do? Get clear on your desired intention. Decide what you really want, decide how you want to feel, decide what success looks like and then my friend, to quote Kris Crew, the president of the blue collar success group, get directionally correct and then just go. Just get directionally correct and go. The plan is going to change and you planners on the line. That wrecks you when I say that the plan is going to change. But no, I've got to get it. That's why you get it close, you get it good enough and then you get going and then you alter the plan as you go. How much planning is too much planning? That's up to you to decide for yourself. I just wanted to give you some thinking points. It's about thinking about your thinking. The quality of your life has to do with the quality of your questions. And I'm honored to be able to ask you some of these questions each and every week. Do me a favor. Share this episode with somebody. Come back next week. This has been episode 120. How much planning is too much planning? Up to you decide until we talk again, my friend. Make it a better than fantastic week and I'll see you next time. Thank you.