About This Video
I’ve sat down with dozens of business owners who are thinking about retirement. Some are 55, some are 70. Some have clear plans, others are just starting to wonder what’s next.
And you know what? They all wrestle with the same three questions. Not the technical stuff about valuations or tax strategies. The real questions. The ones that keep them up at night.
Video Chapters
- 0:00 Introduction: Why these three questions matter
- 1:15 Question 1: What do you actually want to do with your time?
- 3:20 Question 2: Who will take care of your people?
- 5:10 Question 3: What does success look like in 5 years?
- 7:00 Wrapping up: Why these questions come before everything else
Question 1: What Do You Actually Want to Do?
Not “What are you going to do?” That’s what everyone asks at barbecues. I mean: What do you actually, genuinely want your life to look like?
Most business owners I talk to haven’t let themselves think about this seriously. They’ve been so focused on the business for 20, 30, 40 years that imagining life without it feels strange. Some say “golf” or “travel” but you can tell they haven’t really thought it through.
Here’s why this question matters: If you don’t know what you’re transitioning TO, you’ll never feel ready to transition FROM the business. You’ll keep finding reasons to delay.
Question 2: Who Will Take Care of Your People?
Your employees. Your customers. The relationships you’ve built over decades. When I ask owners what they’re most worried about, it’s not usually the money. It’s this.
“Will the new owner treat my people right? Will they keep the same quality? Will they honor the relationships I’ve built?”
These aren’t small concerns. These are the things that make selling your business feel like you’re abandoning something important.
Question 3: What Does Success Look Like in 5 Years?
Picture yourself five years after the transition. What would make you feel like you made the right decision?
For some owners, it’s seeing the business still thriving. For others, it’s having financial security and freedom to travel. For some, it’s watching their former employees advance under new leadership.
This question helps you figure out what actually matters to you, versus what you think is supposed to matter.
Key Takeaways
- Start with the personal questions before the business questions. Valuations and deal structures matter, but they’re meaningless if you don’t know what you want your life to look like.
- Your concerns about your people are valid. Finding the right buyer isn’t just about the highest price. It’s about finding someone who’ll protect what you built.
- Define success on your own terms. Not what worked for your neighbor or what some article said. What actually matters to you?
- It’s okay to not have all the answers yet. These are big questions. But starting to think about them now is better than waiting until you’re forced to make a decision quickly.
Want to explore these questions for your own situation? That’s what we’re here for. Not to give you a sales pitch, but to help you think through what you actually want and how to make it happen.