Running the Long Race: Lessons from Generational Succession in Family Business

The Business of Long Days

When people ask me what it was like starting in our family’s businesses, I have to smile because, as we shared in this episode, long days and late nights were the rule, not the exception.

Back when my parents, Tom and Shirley, were at the helm, a “long day” often meant starting before sunrise, going strong until midnight, and doing it all again the next day. Whether it was managing the grocery store, running the car wash, or juggling side ventures (like our infamous cookie distribution), family time wasn’t a separate category, it was woven into every task.

What stands out from our conversation isn’t just the hours we put in, but how those hours shaped our work ethic and sense of responsibility. Both Shirley and Tom agreed: fun and fulfillment came not in spite of the hard work, but because of it. And despite the hustle, there was always time carved out for family, laughter, and the occasional unconventional solution (“Hope you went to school anyway,” as Shirley joked).

Evolving Responsibilities: Passing the Baton

Succession in a family business rarely happens overnight. In truth, it’s a gradual process that evolves as both generations grow. For Tom and Shirley, the decision to step back and let Kim and me take the reins wasn’t the result of a formal meeting or master plan, it unfolded organically as they began traveling more each winter.

What really prepared us wasn’t a single moment, but a decade of “test runs” managing the business alone for a few weeks, then a month, then an entire season, always with the safety net of a phone call to Mom and Dad. As Kim pointed out in the episode, by the time the transfer was official, she and I had already been running things part-time for years.

One priceless (and funny) lesson came in the form of payroll. Shirley hung onto the payroll account for years, long after she’d let the rest go. When she finally handed it over, she did so with impeccably balanced binders, though Kim admits she didn’t reconcile them again for five years. That highlights something every family business should keep in mind: there are some hats people are reluctant to give up, and patience is essential.

Gradual Growth: Balancing Pressure and Support

A recurring theme in our discussion was the importance of gradual, intentional growth for the next generation. I love Tom’s analogy: just as you wouldn’t expect someone to run a marathon their first day, you shouldn’t expect a successor to handle every aspect of the business right away.

Kim added another critical point: every person learns and adapts differently. There’s no one-size-fits-all template for developing leadership. Success depends on observation, communication, and a willingness to let people take on responsibility at their own pace, aiming for “slightly uncomfortable” without pushing them into overwhelm.

Shirley and Kim also stressed the importance of exposing future generations to the business from an early age, even if they’re not formally involved. Family dinners, convention trips, or half-days at work can plant seeds of interest and understanding that may not sprout until much later.

Creating Opportunity, But Not Pressure

One of our biggest takeaways was the necessity of offering, not imposing, opportunity. Not every family member wants to be an entrepreneur, and too much pressure can breed resentment or drive them away. As Tom joked, “Not everybody wants to be an entrepreneur,” and sometimes, even those who think they do change their minds when reality hits.

Instead, our advice is to keep the door open: share information, encourage curiosity, and provide experiences, but let each family member find their own path.

Looking back, our family’s journey wasn’t perfect, but it worked for us because we adapted, communicated openly, and trusted each other to figure things out. If you’re navigating the succession maze in your own family business, take heart: build in time for hands-on experience, share your wisdom, and remember, success is a marathon, not a sprint.

Don’t forget to check out the full episode (81!) for more stories, laughter, and lessons from our crew! And make sure to check out our other blogs for more insights into our business story.