Emotional Readiness

Learning From Conversations Podcast Host: Welcome back to the show. Today’s conversation is a little different. We’re talking about what happens after the transaction, after the congratulations, after the wire hits the account, after everyone tells you that you’ve reached the ultimate definition of success. My guest today is a 64-year-old entrepreneur who sold the company he built after decades of hard work. It has now been 14 months since the sale, and he’s here to talk openly about something many owners don’t spend enough time thinking about: what happens when the company you built is no longer yours. Thanks for joining us. Frank: Thanks for having me. I think this is an important conversation because when you’re building a company, almost everything is focused on the business, growth, employees, customers, solving problems, creating value. The idea of selling becomes this finish line. But what I’ve learned is that selling the company isn’t the finish line. It’s actually the beginning of a completely different chapter, and I don’t think I spent enough time preparing for that chapter. Podcast Host: Let’s go back to the day after the transaction. You had accomplished what many entrepreneurs spend their entire careers working toward. What did you think life would look like? Frank: Honestly, I thought I had it figured out. I thought, “I’m going to play golf six days a week. I love golf. I’ve always loved golf. Finally, I’ll have the time.” But what I realized was that my relationship with golf was different when it wasn’t a choice, when it wasn’t squeezed between business meetings, customer visits, and responsibilities. During my career, I probably only played about one round a week, and many of those rounds were with customers or business relationships. Golf was connected to the business world. After I retired, I had unlimited time, but I didn’t necessarily have unlimited motivation. I found that I wasn’t motivated to playing six days a week. Sometimes I play a couple of times a week. That was a surprise. Podcast Host: Why do you think that happened? Frank: I think I underestimated how much purpose came from the business itself. The company wasn’t just a job. It was my identity. It was relationships. It was challenges. It was waking up every morning knowing there were problems to solve and people counting on me. For 38 years, I had a reason to get up. Now, I can sleep later if I want. Nobody is waiting for me to make a decision. Nobody needs me to solve the problem of the day. And while that sounds great when you’re working 70-hour weeks, when you lose that structure, you realize how much energy came from being needed. Podcast Host: You mentioned before the show your wife wanted to travel more, and you’ve done more traveling together. How has that transition been? Frank: Actually, it’s been good. My wife always wanted more travel, and we’ve definitely done more of it. The challenge is that travel means different things to each of us. My whole career involved a tremendous amount of business travel. Airports, hotels, meetings, being away from home, I did that for years. So when I retired, I was thinking, “I finally get to be home.” My wife was thinking, “Great, now we can go everywhere.” (Laughs) She loves exploring new places. I enjoy it, but I don’t have the same appetite for it because I spent so much of my life traveling. Podcast Host: You’ve also talked about how your wife has adjusted to having you around more. Frank: Yes, and that’s been an interesting part of this transition. For years, I was gone a lot. She had her routines, her friends, her activities. Now I’m home much more. She loves me being around, but I think the reality is that going from having your own separate rhythms for decades to suddenly sharing almost every day takes adjustment. She has weekly groups and activities with friends, and sometimes she feels guilty leaving me home alone. I keep telling her, “Don’t stop doing those things. You need your friendships and your independence.” But I understand why she feels that way. We’re both learning what this new version of life looks like. Podcast Host: You mentioned mornings have been difficult. What does a typical day look like? Frank: The interesting thing is I still do things I’ve always done. I get up early. I take our dogs for a three or four mile walk every morning. That routine has stayed with me. But I’ll admit there are mornings where I wake up and think, “What am I really getting up for today?” That’s something I never experienced when I owned the company. There was always a mission. Now I’m trying to create a new one. Podcast Host: Do you miss the business? Frank: More than I expected. I miss the challenges. I miss the people. I miss the employees who were part of the journey for years. I miss sitting across the table from customers and solving problems. You spend decades building relationships, and then overnight, you’re no longer part of those conversations. That’s been harder than I anticipated. Podcast Host: Looking back, do you think selling was the wrong decision? Frank: I wouldn’t say that. The transaction was successful, and I’m grateful for the opportunity. But I do question the mindset that led me there. There was a lot of outside messaging: “You need to sell now. The market is strong. This may be your last opportunity. You need to maximize your value.” And I listened. What I wonder now is whether I was making the decision because it was truly what I wanted, or because I was trying to meet other people’s definition of success. Was I trying to prove something? Was I trying to show the world that I had made it? Those are questions I’ve thought about. Podcast Host: Do you think you could have continued running the company longer? Frank: