Making It, Managing Chaos, and Staying Flexible: What We’ve Learned from Mixing Family and Business

Defining Success: When Do You Really “Make It”?

One of the big questions I asked Kim, Tom, and Shirley this week was whether there’s ever really a moment when you feel like you’ve “made it,” not just as a business owner, but in life. It turns out, the answer is a lot more nuanced than checking off a box.

For Shirley, the honest truth was, “I’m still working on it.” Even after decades of hard work and 62 years with Tom, she joked that only when the bills are paid does she feel like she’s finally arrived, at least for that moment. Tom had a similar perspective, saying he never felt like he’d ever truly made it. “The minute you get to that point, you better be ready to retire,” he said. His experience taught him that success isn’t some permanent state but rather a series of steps. Achievements accumulate gradually, a bigger house here, a new car there, but it’s health and happiness that ultimately matter more than any material thing.

Kim reflected on her “golden period” in the early 2000s, when everything was firing on all cylinders with their Dairy Queens and grocery store. For her, the moment she really felt successful was ordering a fully loaded Suburban at the dealership, without worrying about the price. Still, she’s quick to admit that good times don’t last forever, but if you’re still standing after the tough years, that’s the real win.

For me, personally, buying our house on the lake with my wife was one of those special moments, one that comes after years of hard work. But just like my co-hosts, I know those moments are fleeting, and the journey is what matters.

Weathering the Unexpected: Business Disasters and Community Resilience

If there’s one constant in business, it’s that the unexpected will happen. Over the decades, we’ve seen our fair share of disasters. From epic storms knocking out power for days to surprise construction projects slashing our customer traffic by more than half.

Shirley and Tom shared their memories of a massive storm back in the 80s that left the entire city of Eau Claire without power. Their grocery store was the only one open, running on calculators and selling whatever they could before it spoiled. “We served the community; they got what they needed, and we were exhausted but satisfied at the end of the day,” Tom said. It was a testament to both grit and the importance of being there for your neighbors when things go sideways.

Kim told a lighter, but no less stressful, story about a power outage at the Dairy Queen. With power company crews stretched thin, she resorted to bribery: “A blizzard a week for a year, and we’ll be there in 20 minutes,” they told her. True to their word, they fixed the power, and thankfully, only claimed a single treat.

My own biggest challenge was having the power go out the morning of one of our huge meat sales, a logistical nightmare after days of preparation. We had to cancel, adapt, and reschedule, but got through it thanks to teamwork and a last-minute radio campaign.

Flexibility: The Secret Superpower in Business (and Life)

The resounding theme from all these stories? Flexibility wins the day. If you're going to be in business, prepare to adapt constantly.

Kim summed it up perfectly: “If you can’t be flexible, don’t get in business.” None of us can control the weather, power outages, or market changes. Whether you’re dealing with a pandemic, construction detours, or your equipment failing, the real question is: are you going to freeze, or are you going to say, “What can we do?”

Our advice? Don’t get so caught up in the fear of what might happen that you paralyze your business or over-invest in “solutions” for every what-if scenario out there. Build redundancy where it counts, but remember: most things will require a bit of improvisation in the moment. Hand out pens if the registers aren’t working. Use radio ads if there’s no social media. Your plans won’t always work as predicted, and that’s okay.

Celebrate the Wins, Embrace the Challenges

Running a family business isn’t easy, but it’s rewarding, and the challenges are what make the journey meaningful. You’ll hit golden stretches, and you’ll hit storms. The most important thing is to stay flexible, lean on your people, and keep your sense of humor. And, if you ever have ideas or want to hear us talk about a specific topic, reach out anytime. We’re in this together.

Brian

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