Freedom Friday Focus - Leadership: Is it Time for an Executive Checkup?
15 Nov 2025 · 4 min
A short Freedom Friday Focus podcast by Kenny Chapman urging leaders to perform an "executive checkup" of their business and personal life. Chapman argues progress depends on asking better questions and regularly examining areas like processes, systems, cash flow, marketing, relationships, and personal routines; he uses analogies (Groundhog Day) and cites Socrates' "a life unexamined" line to emphasize that routine without examination leads to stagnation. The episode closes with a call to subscribe and visit leadershipinautshell.com.
Chapters
Foreign. Welcome back to Leadership in a Nutshell. I'm your host, Kenny Chapman. This is Freedom Friday, Focus Version, where Let me ask you a quick question. Is it time for an executive checkup for that business? Think about it. We get to certain ages as I'm approaching, and they say, hey, you got to get in and get your executive checkup, and you got to check in on these different types of things and you got to get an exam, an examination of certain things. Certain. And yet when we look at our businesses, when we look at our livelihood, when we look at our finances, when we look at our closest relationships, sometimes we don't look at examining what's really serving us, what's really working well. Why is that? Sometimes perhaps we don't want to know the answer. What we know is that all solutions lie within the questions that we ask. The quality of your life, the quality of your business, the quality of your relationships, the quality of your finance, the quality of your health all depend on the questions that you ask. When you stop asking questions, you stop making progress, my friend. And today I just want you to really take a moment and take a step back and go, huh? Wait a minute, Kenny. When is it time for me to really examine a little bit? Let me ask you this. Have you ever just wake up, it's Monday morning, here we go again. It's like dust off the dust from the weekend. And like, okay, you drive the same route to the same place for coffee on the same way to the same business, to the same team, to the same strug, to the same situation, to the same quote unquote shoulds that you're going to fix, the same projects that have been on your desk for a little bit, the same things you're procrastinating against. And then you go, well, wait a minute, let me roll some of that task list to Tuesday. And then it becomes Wednesday. And the next thing you know, it's Friday afternoon. You're headed to your. Your afternoon. What? You know, I know it's only in Colorado. Sometimes we call it fac, Friday Afternoon club, whatever your happy hour situation is. And the next thing you know, you are pushing into the weekend, forgetting about the week that happened to get up and do it again and again and again. Bill Murray was in a great movie called Groundhog Day. And I don't think you want Groundhog Day to be your life and business. You know, I'm not going to go all philosophical on you here today, but I am a fan of certain things that Socrates said. Amazing Greek philosopher born in Athens, credited to a lot of kind of Western thinking originally. And one time he said that a life unexamined is a life that is not worth living. I want you to think about that and let that land for a moment. A life unexamined is a life not worth living. Think about your business. A business unexamined is obviously a business not worth operating. And yet sometimes we come in and we do the same thing day after day, week after week. I want you to think about today. What if you were just completing an acquisition of your business? What if you became the primary stockholder? If you're a manager and you're watching this, if you're a leader of a church and you're watching this, if you're a leader of your family, you just came into this position of power and leadership, however that looks for you and whatever your role is, today's your first day. How would you do it differently? Not knowing what had happened in the past? Would you not start asking questions? Would you not examine things as the way they are? Would you not look at processes, systems and start going, why do we do things certain ways? Why am I operating this way? Why is my cash flow challenged? Why is our marketing team not getting it done? Wouldn't you start asking those questions? It's time for a business checkup, my friends, and it begins with you as the leader. That's ultimately what it's about. This is Freedom Friday, focus episode of Leadership in a nutshell. I'm your host, Kenny Chapman. I want you to take a step back, check into the things that really make a difference for you. Until we talk, make it a better than fantastic day. Make sure you subscribe, watch us on YouTube, go to leadershipinautshell.com and stay in touch.