Succession Planning: A Personal Story Every Business Owner Should Hear

This isn't just another guide about business exits or executive coaching. It's personal. It's a story I’ve lived, and one I believe every business owner should hear at any time in their business lifecycle and certainly before they step away from what they’ve built.

My dad and his partner started their business when I was around six or seven. They had worked together at another company before deciding to strike out on their own. He was the sales guy, she handled operations and customer support. I remember the hustle, trade shows, cross-country flights, supplier visits. The energy was high. My dad worked six days a week and loved it.

About fifteen years in, they bought their own building and warehouse. Business was good.

Then came 1996. That was the peak. Manufacturing was shifting to China, and direct-to-customer models started cutting out distributors like them. Over the next few years, they lost some major U.S. clients. Slowly, but steadily.

Innovation stopped. There was little investment or reimagining of what the company could become. I think my dad and his partner just didn’t see the possibilities anymore. Or maybe they were tired. He knew things were changing, but he didn’t see a way to shift course. When we talked about the future, he seemed stuck and full of limiting beliefs.

I started giving him pep talks around 1998. Reinvent the business. Adapt. He tried small things, but never really went all in. When it became clear the business wouldn’t bring the exit they imagined, he was at the lowest I had ever seen him. Thankfully, they owned the building. They rented it out, then sold it. That real estate saved them. Not the business.

What stuck with me most was how long it really takes to prepare for the end of a career, it's much longer than people think, and how often emotion clouds our judgment. Many business owners believe what they built is worth more than it really is. But buyers aren’t paying for years of hard work. They’re paying for systems, scalability, and a team that can run the show.

I wish my dad had sold earlier and done something else. We had those conversations, but he always said, “What will I do?” His identity was so tied to his work that walking away felt impossible. In the end, it came down to fear. He needed a coach. I wish I could’ve been that for him back then.

That experience shaped how I coach leaders today. Here’s what I’ve learned from watching it all unfold:

Start with your why. My dad didn’t have one. He knew he didn’t want to keep grinding, but he didn’t know what he wanted next. That uncertainty kept him stuck.

Know what your business is actually worth. Not what you hope, but what someone would pay. Buyers don’t pay for effort or history. They pay for what works without you.

Start earlier than you think. If you want to exit in 10 years, start preparing today. My dad waited way too long. By the time the writing was on the wall, most options were gone.

Don’t coast. It feels earned, but coasting erodes everything you’ve worked for. If you still care about the outcome, keep investing long enough to exit well.

Separate who you are from what you do. This one’s tough. But if your identity is tied to control, you won’t be able to lead through a transition.

Build a business that runs without you. If you’re the glue, the buyer sees risk. You need systems, a team, and proof that the business isn’t dependent on you.

Legacy isn’t what you say it is. It’s what others carry forward when you’re gone. Not the title. Not the revenue. The impact.

Don’t do it alone. My dad had me, but I didn’t have the tools then. He needed someone who wasn’t emotionally involved to help him navigate what comes next. Most owners do.

This is a tough story to tell. But I know my dad and his partner would want others to learn from it. If you’re feeling even a fraction of what he felt, uncertainty, fear, the sense you’ve waited too long, I’m here and so are many others. No pressure. Just a real conversation about what comes next, and how to make it count.