When Everything Goes Wrong, Keep Moving Forward

Finding Strength in the Struggle: How Vehicle Disasters, Production Delays, and Life Challenges Become Stepping Stones

When you're an entrepreneur, especially one who takes their business on the road, challenges aren't just occasional hurdles—they become part of your identity. This week at the Windsor Fair represents our third consecutive year participating in this incredible event, and remarkably, our third consecutive year facing significant vehicle catastrophes. It's almost comical how consistently the universe tests our resolve exactly when we need everything to work perfectly.

This year's adventure began with a shipment nightmare that's all too familiar to small business owners. Despite meticulous planning and scheduling for production, two vendors dropped the ball, splitting shipments and delaying critical inventory needed for the fair. After paying extra for overnight shipping, only half the order arrived on time, with the remainder trickling in throughout the week. This pushed production schedules to midnight and beyond, forcing last-minute setup plans and team coordination that resembled a military operation more than a family business.

Upon arrival at the Windsor Fair, we discovered our vendor location had been moved—not drastically, but enough to cause concern when you understand that in the fair business, "location, location, location" truly matters. Sometimes your spot can be more important than overall attendance numbers. A good location at a moderately attended fair can outperform a poor location at a heavily attended event. The twenty-foot move was enough to create anxiety, though we managed to find silver linings.

The real drama began when our transportation—a converted school bus—decided it had other plans. First, the shifter linkage disconnected, leaving us unable to change gears. While addressing that issue, we discovered brake fluid pouring out at an alarming rate. We managed to limp the vehicle to our camping spot, but it's now completely immobilized, requiring emergency roadside assistance from friends who will drive nearly two hours just to assess the damage.

What's most remarkable is that this isn't an isolated incident. Every single year at Windsor Fair, we've experienced vehicle breakdowns. The first year, our farm truck's fuel pump died mid-intersection, followed by AAA losing our vehicle entirely and requiring parking lot repairs. Last year, with my wife nine months pregnant, our radiator hose blew on the interstate while towing our camper, stranding us for hours until friends rescued us with parts and tools. This year continues the tradition with our immobilized bus creating yet another chapter in our vehicle disaster anthology.

Despite these challenges—or perhaps because of them—we've developed a resilience that's difficult to explain to those who haven't lived through similar trials. When you've faced enough setbacks, you eventually reach a point where panic gives way to pragmatic problem-solving. You learn to distinguish between what you can control and what you can't, focusing your energy where it matters most.

The Windsor Fair holds special significance for our family beyond business opportunities. Last year during this fair, our daughter Paisley was born, requiring a mad dash from the fairgrounds to the hospital. Now, she's celebrating her first birthday at the same event, complete with her own vendor badge that will be updated annually—creating a unique tradition that perfectly encapsulates how our business and family life have become beautifully intertwined.

Perhaps the most powerful lesson from these ongoing challenges is learning to maintain perspective. When facing vehicle breakdowns, shipping delays, and logistical nightmares, it's easy to become overwhelmed. But remembering the bigger picture—that we're building something meaningful, creating family traditions, and serving our customers—helps transform frustration into determination. The struggles become not just obstacles to overcome but stories to share, lessons to learn, and eventually, badges of honor that prove your resilience.