Sometimes You Need to Say Yes to the Big Chain Ring: Embracing Boldness in Business

In July 2023, I spent a week bicycling across Iowa. I wasn’t alone. I was one of the thousands of riders taking part in RAGBRAI — the Register’s Annual Great Bicycle Ride Across Iowa. This week-long bicycle journey across Iowa is more than just a cycling event. It’s a vibrant community on wheels, a celebration of fitness, friendship, and discovery in America’s heartland, drawing thousands from all corners of the globe.

This wasn’t my first time participating in RAGBRAI; it was, in fact, my third. Each ride has been a unique experience, offering new challenges, perspectives and insights. This time, as I navigated Iowa’s rolling hills and expansive plains, the journey resonated with me more deeply, revealing lessons about resilience, adaptability, and the crucial importance of perspective. The ride became more than just a physical feat; it transformed into a metaphorical journey through the world of entrepreneurship. Every mile, every hill, and every flat stretch provided a moment to reflect on the broader aspects of running a business and the mindset required to navigate its uncertain terrain.

In this series, I will share with you five key insights gleaned from this remarkable journey. Each one is framed by a specific event during the ride, reflecting on how these moments resonate deeply with the entrepreneurial spirit. These stories, born from the rolling landscapes of Iowa and the camaraderie of RAGBRAI, offer a unique lens through which to view the challenges and triumphs of the entrepreneurial journey. Whether you’re a seasoned business leader or a budding entrepreneur, you’ll find valuable lessons in resilience, strategic thinking, and the importance of balance, all gleaned from an unforgettable 530-mile cycling adventure. So join me on this reflective journey as we delve into these entrepreneurial insights.

Sometimes You Just Need to Say YES to the Big Chain Ring

Have you ever wondered how cyclists tackle different terrains with ease? A key player in this game is the big chain ring. It’s a gear mechanism on a bike, commonly the larger one out of the two or three at the front. Cyclists use it on flat or downhill stretches to gain speed. It’s about efficiency – more distance covered with each pedal stroke. Simple, right? But it requires more effort, more push. There’s a perfect moment for it — when the road ahead is clear, and you’re ready to fly.

I’ll admit to not using that chain ring often. Maybe it’s the hills — we have a lot of those here in Tennessee and you don’t use the big chain ring to climb a hill. Maybe it’s that I’m comfortable going with the speed I’m going and the effort I’m spending. But one morning in Iowa, that changed. As I was pedaling out of one of the many small towns we passed through, I was feeling good, feeling energized. The morning was gorgeous, with the sun shining and the road stretching out in front of me. I decide – shift to the big chain ring. Suddenly, I’m powering forward, eating up the miles with renewed vigor. At that moment, it hit me. Sometimes, you need to say YES to the big chain ring, to step up and see what you’re capable of.

The Big Chain Ring in Your Business: Executing with Boldness

This isn’t just about cycling. It’s a business metaphor too. In the world of small businesses and solopreneurship, there are moments crying out for the ‘big chain ring’ approach. Think about launching a new product or scaling up your services. It’s daunting, right? But what if you embraced that boldness, said YES, and pushed forward with all you’ve got? Think about how much ground you could cover and the growth you could attain.

Starting your own business is the quintessential big chain ring moment. It’s the decision to pedal harder, knowing the road ahead is long and uncertain. Think of it as standing at the edge of a familiar path and choosing to step onto a new, uncharted one. It’s a leap of faith, fueled by courage and a belief in one’s potential. This initial push sets the wheels of your vision in motion, transforming ideas into reality. It’s about embracing the risk, knowing the reward lies not just in the success but in the growth and learning along the way.

Then, there’s the big chain ring moment of launching a new product. This is about seeing an opportunity in the market – a downhill stretch, if you will – and deciding to go for it, full speed. Embracing innovation and offering something new to customers is a strategic decision, even if it means exploring uncharted territory. This decision requires not just vision but the boldness to act on it, to accelerate with all your might in pursuit of a breakthrough. It’s a test of your entrepreneurial spirit, pushing you to outdo your past achievements and set new benchmarks.

A Balanced Approach: Knowing When to Shift Gears

However, just as a cyclist cannot always stay in the big chain ring without risking fatigue, an entrepreneur cannot always operate at maximum capacity. The key lies in recognizing when to push hard and when to conserve energy, ensuring a sustainable journey towards your goals. It’s about strategic boldness – knowing when the time is right to accelerate and when it’s prudent to shift down, gather strength, and prepare for the next push.

Embracing the big chain ring in business, whether by starting your venture or launching a new product, symbolizes a commitment to bold, strategic action. The entrepreneurial journey is about highs and lows, courage, resilience, and knowing when to push and when to pace. As I reflected on my own moments of acceleration across Iowa’s varied landscape, I was reminded that the most rewarding journeys are those approached with both boldness and balance.


Each stretch of my journey across Iowa offered unique insights into the parallels between long-distance cycling and entrepreneurship. The lessons I’ve shared in this series reflect the diverse experiences and challenges encountered along the way. If you found the insights in this article valuable, I invite you to explore the other articles in the series, where we delve deeper into the principles of resilience, strategic thinking, and balance. These stories not only illustrate the physical journey across Iowa but also the metaphorical path through the landscape of entrepreneurship. Click on the links below to continue exploring how each moment can transform challenges into opportunities for growth and innovation.

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