When Your First Time Is Your Worst Time, Keep Going Anyway

The Road to Syracuse: Lessons from a Small Business Journey

When you're running a small business, especially one that requires constant travel and events, the journey is rarely straightforward. Our recent trip to Syracuse Nationals demonstrated this reality in vivid detail. What should have been a triumphant weekend turned into a masterclass in resilience, adaptation, and maintaining positivity in the face of setbacks.

The adventure began long before we hit the road. Production issues plagued our preparation when a new t-shirt design I'd worked on for weeks arrived with unexpected modifications. The outline that was supposed to highlight certain elements had instead filled in the entire design, making it too heavy for the breathable, wearable aesthetic I aim for. To make matters worse, the image quality had been compromised during the template conversion process. This wasn't just a minor inconvenience – it meant all the funds I'd allocated from the previous event toward this special design were effectively tied up in a product I couldn't use for the Syracuse event as planned.

The old version of myself would have spiraled into despair, letting this setback poison my mindset for the entire trip. But growth means learning to respond rather than react. I couldn't control what had happened, but I could control what came next. So I pushed forward, restocking items I knew would sell and setting my sights on the journey ahead.

The drive itself presented its own unique challenges. Imagine traveling six hours in sweltering 100-degree heat with a malfunctioning air conditioner that cycled between cool and hot air every 20 minutes. Add to this a 10-month-old baby experiencing her longest car ride yet, and then, as if orchestrated by some cosmic jokester, hitting a rough patch of Massachusetts road construction that caused our entire merchandise display to collapse. Clothes and products went flying with every subsequent bump, forcing my wife to shield our baby from falling items while I navigated through traffic and heat.

Despite these obstacles, arriving at our destination provided immediate relief. The hospitality of our friends in Syracuse – Paisley's godparents Lance and Jen – was nothing short of extraordinary. They welcomed us with prepared meals, comfortable accommodations, and even loaned us their vehicle for daily commutes to the event. Their support, along with that of our entire Syracuse circle, became the foundation that kept us going through challenging days.

Setting up our booth became yet another test when powerful winds threatened to send our tent airborne. What should have been a simple hour-long setup stretched into a full day of struggling against the elements, only made possible by friends rushing over with weights to help secure everything. This experience reinforced a crucial lesson for small business owners: nothing ever goes exactly as planned, and your ability to adapt determines your survival.

The event itself delivered a hard but valuable lesson. Despite impressive overall attendance, our booth location kept us isolated from the main flow of traffic. The humbling experience of watching tens of thousands of potential customers just a couple hundred yards away – visible but unreachable – tested my resolve. Yet instead of allowing disappointment to consume me, I used the slower periods to walk the event, seek inspiration, and set new goals for the business.

This exemplifies the entrepreneurial mindset that separates those who succeed from those who surrender. Finding opportunity within disappointment, I discovered a vendor with a souvenir trailer that could potentially transform our business model, allowing us to attend one-day events and increase our visibility at larger venues. What began as a challenging weekend evolved into a vision for future growth.

The true measure of success isn't found in short-term results but in your response to adversity. Despite not meeting our financial goals for this event, we still made money, gained invaluable experience, established our presence at a major national show, and set ourselves up for greater success next year when we can request a premium location.