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A Motorcycle Journey’s Unexpected Lesson

Life on two wheels isn’t just about reaching a predetermined destination. It’s about the joy of perpetual acceleration, the roar of the engine beneath you, and the lessons learned while on the journey. The road you are on may change along the way, and the ultimate arrival that you thought was the goal may end up being totally different, and better. When entrepreneurs approach their ventures with the same mindset, they find deeper fulfillment and lasting success. Forget the finish line for a moment; it’s time to savor the ride.

Journey > Destination

One hot summer day on vacation in Phoenix, I rented a Harley Davidson Deluxe to explore the surrounding picturesque desert mountain landscapes, unique to Arizona. I picked a town on the map that looked like a nice day ride and hopped on the bike for what I thought would be a straightforward trip. Little did I know, that ride would be nothing but straight forward it would change my perspective on life and business.

The ride started out exactly as I imagined. Flawless fresh tarmac, cacti right out of central casting and ghost towns so perfect It thought I had actually stumbled upon a movie set.

The route I had planned would take me to the Roosevelt Dam. I passed a few other bikers and felt reassured that I was on the right route. However, the “Tarmac Ending” signs would foreshadow what lay ahead, but I persevered without any hesitation. The road turned to gravel and I was passed by some sport bikes going in the opposite direction. If they can ride on this, so can I, or so I thought.

The Apache Trail (as I would later learn) is a winding dirt trail without lanes that traverses the face of the canyon rising from the tailwater of the dam. Suffice it to say that this was NOT the bike best suited for this kind of riding. But it did force me to explore the limits of my riding. As the shoulder of the trail dropped away into the canyons below, It felt like I was crossing the Pangi Road in India.

I was too far into the journey to turn around, and after several hours of slowly and gingerly coaxing my softail cruiser along, I arrived at the visitor center, out of gas. As I walked past the rows of T-sShirts that said “I Survived the Apache Trail” I felt like a bit of an adventurer, covered in dust and sweat and with a new experience to take home with me. If I could get home, that is.

When I asked the information desk where the nearest gas station was, they pointed in one direction of the only road I could take from here. 25 miles that way, 40 that way. I wasn’t sure the bike would even start again and get me out of the parking lot.

Luckily, there was a marina on site and I was able to convince the attendant to sell me some gas. “You rode through there, on that??” She asked as we splashed some much needed juice into the tank. I shot her a cheeky dusty affirmative nod.

The Destination Mentality

In business, many of us are fixated on the end goal—revenue milestones, market domination, or the ultimate liquidity event. This destination mentality, while seemingly productive, can drain the joy from the entrepreneurial process. When we focus solely on outcomes, we often overlook the daily victories and learning moments that define our path. Entrepreneurs caught in this mindset might find themselves feeling unfulfilled even after reaching their goals.

I recommend James Clear’s excellent articulation of this concept in his essential reading book Atomic Habits. In i, he questions the merits of focusing on goals. For example, when two basketball teams show up to play a game, they are both seeking the same outcome. To win. Yet only one does, every time. So what differentiates the winners from the losers? Those who focus on building excellent systems, communication and collaboration in preparation for the game.

You can read more to explore Systems > Goals further in this article James has on his website.

The Drawbacks of Chasing Outcomes

Focusing only on the destination means constantly living for the future. This can lead to burnout, as the present moment is perpetually sacrificed for some future payoff. Additionally, when the outcome doesn’t meet expectations, the sense of failure can be devastating. The destination mentality also narrows our vision, making us less adaptable to changes and opportunities that arise unexpectedly.

The Journey Mindset

Shifting to a journey-centric approach means valuing the experiences and lessons gained along the way. It’s about being present and finding joy in the process, regardless of the outcome. Not only is this mindset more fulfilling but it also cultivates resilience and adaptability. When you enjoy the ride, both successes and failures become part of a larger, enriching experience.

The Joy of the Process

Whether riding a motorcycle through deserted backroads or building a startup from the ground up, the thrill lies in the process. It’s in the small wins, the camaraderie with fellow travelers, and the growth that comes from overcoming obstacles. When I launched my first venture, the sleepless nights spent brainstorming felt like an adventure. Each challenge faced was a story worth telling.

Practical Tips for Shifting Your Mindset

  1. Mindfulness Practices: Incorporate mindfulness into your daily routine. Simple practices like focused breathing or mindful walking can help you stay present.
  2. Systems > Goals: Instead of setting rigid, outcome-based goals, focus on process-oriented ones. For example, aim to improve your customer service skills rather than merely increasing sales.
  3. Celebrate Small Wins: Take time to celebrate small achievements. When I completed my Apache Ttrail expedition, I thought I knew what Shackleton must have felt like.


Learning from Failure

Failures aren’t setbacks; they’re stepping stones. When Thomas Edison was asked about his numerous failed attempts to invent the electric light bulb, he famously replied, “I have not failed. I’ve just found 10,000 ways that won’t work.” Every failure offers a lesson that brings you closer to your ultimate goal. Viewing failures as part of the journey reframes the experience from failure to perpetual learning.

The Value of Detours

Just like my unexpected trek in Phoenix, life often throws us off our planned course. These detours, while initially frustrating, can lead to new opportunities and insights. In business, being open to these deviations can uncover ways to navigate you hadn’t considered. The key is to remain flexible, curious and realistic about the spot you are currently in.

Building a Resilient Mindset

Resilience stems from understanding that both highs and lows are integral parts of the entrepreneurial ride. By accepting that setbacks are temporary and that they are learning experiences, you build a mindset capable of weathering any storm. This resilience isn’t just beneficial in business but in all aspects of life. If you are in perpetual motion, you will have no choice but to rack up the miles. With miles comes experience, and one day you wake up as a seasoned explorer ready to take on the tallest of peaks.

No Plan Survives First Contact with the Enemy

As with my well thought out route to the Roosevelt Dam, I had never actually been there so I was unaware that the Apache Trail had a whole line of T-Shirts taunting travelers with its viciousness. I love this quote about first contact with the enemy, much like Mike Tyson’s famous statement that everyone has a plan until you get punched in the face.

You can never know what lies beyond every corner, and sometimes it will be smooth cruising just as you had hoped. Other times, it will be an outright fight. I’m not writing about my easy rides almost 15 years after the fact: it’s the fights that stick with us, that we learn from and make us better. Win, lose or draw.

Ride safe, ride far, and make the journey count.

ABOUT THE AUTHOR

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Ross O'Brien signature

Ross O'Brien

Venture capitalist, Author, Entrepreneur, and Lifelong Motorcycle Enthusiast.

Check out Ross's first book on venture capital.

The Journey So Far On...

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