Evolving, Unlearning, and Keeping It Real: Running Family Businesses Over the Long Haul

More Than Just Years: What Experience Really Means

I used to think experience was just about tallying up the years. Thirty years is thirty years, right? Not exactly. At a conference, someone asked if I’d lived thirty years, or if I’d just lived the same year thirty times. Ouch. It makes you think! I realized experience is all about learning, adapting, and keeping your eyes open.

Like Kim shared, sometimes experience is just remembering that, hey, you’ve seen this before, like that time the water bill went nuts because of a leaky valve. Twenty years later, remembering that little detail saved us a ton of cash. You don’t get that from just living, you get it from really doing the work and paying attention.

And Tom was cracking us up, saying if he’d had his current brain in his younger self, he could’ve run rings around everyone! But honestly, the joy is in being curious and learning every day, not just racking up “time served” in the business.

You Can’t Fake Doing: Learning by Living It

You can read all the business books you want, but you don’t actually know how things work until you’re in the middle of it. Shirley admitted she listens a lot more now than she used to, and honestly, I’m with her. The older I get, the more I see the value in listening - to people, to employees, to life - because that’s where a lot of the learning actually happens.

A good example for me was working with the Boy Scouts on leadership projects. Sure, you can read about dealing with people, but actually standing up and doing it? That’s the stuff that teaches you for real.

Outgrowing Old Habits

One of the trickiest things in business (and life) is realizing what worked before isn’t cutting it anymore. I’ll admit I used to believe I had to do everything myself. When it’s your name on the business, you just feel responsible for every detail, big or small. But if you never let go, your business never grows past you. No vacations, no freedom, just you at the center, 24/7. Not a good time.

Kim made us all laugh talking about how she kept her books on paper and computer for years, just in case the computer was lying to her. We all get stuck in our “this is how we do it” grooves. Honestly, some of us fought checklists, handbooks, and systems tooth and nail. When you’re young, you think, “Just do the thing!” But when you want a business that works without you, you need systems, even if they feel silly at first.

Unlearning Hurts (But It’s Worth It)

Handing over the books. Not being the first call when the freezer goes out. Sleeping through a weekend without checking your phone every hour. This stuff is tough. Some days you feel useless, or worse, like something’s falling through the cracks because you’re not there.

But if I’m being honest, letting go creates more relief than stress, even if it takes a while. There’s time for new things, new projects, or hey, maybe even a nap. Tom said it well, too, we’re not retiring, just shifting into new roles. Still interested, still involved, but not always knee-deep in every detail.

When You’re Stuck, Change Something

We all have those days (or months) where business feels heavy. Sometimes you need fresh info, sometimes you just need a change of scenery. Go out for coffee somewhere new. Call a friend. Listen to a podcast. The point is, break your routine to break the logjam in your head.

Shirley says it best: breathe, relax, and don’t be afraid to ask for a different perspective or just step away for a minute. Kim nailed it to the wall: if you’re stuck, your business is probably stuck too. Shake something loose and it usually starts with you.

Mixing family and business is never dull, and it’s never done. We keep learning, unlearning, and adapting. That’s what keeps us all going (and laughing) after all these years.

Check out the full episode (86!) right here!