The Link Between Cycling, Entrepreneurship and Effective Leadership for Founders

I’ve been thinking about this comparison lately, which seems like an odd thing to be thinking about in the context of everything else going on, but here we are. Ever since I was a kid, I was one-and-one with my bike. Throughout my teens and 20s, I spent a lot of time shredding one trail after the other in some of the most pristine – and awesome – mountain biking locations around the globe. 

Every once in a while, I’d take a nasty spill, break something (on my bike or my body), but I’d get back up. Heal. Then get back on my bike to do it all over again.

And then a few years went by. Then a few more. Over time, I could tell that I was losing my edge mountain biking. I started to fear falling. When fear creeps in, you stop jumping those tree roots with authori-TAY and those doubts leave you unfocused on the trail ahead and unable to think strategically or methodically about your next move.

At that speed – at least at the dizzying speeds that I used to attack the trails with – you can’t afford to lose a microsecond of focus. Because, when you do, it’s ass-over-teakettle you go. As you get older, your bones don’t heal as well and you start to realize that you may be mortal after all. So you find a new way to channel your energy.

Enter road biking. “Cycling” as most refer to it. There’s something compelling about it that attracts riders of all ages. In that regard, it’s a sport that has a lot in common with golf. We could debate the athleticism of each but we’d like agree that it takes patience, planning and execution.

Does that sound like something you’d say to a founder of a startup? 

We might even find agreement on the point that it also takes maturity, strategic thinking and the fortitude for failure. I’m not a regular golfer (although I do like to watch the bunnies and birds on the course but have admittedly run from the crocodiles) but I do love to cycle. Other entrepreneurs, female founders in particular, seem to like cycling, too.

So I asked a few of them why they like cycling and if they see parallels to starting and running a business. Indeed, they do. Why?

The Similarities Between Cycling and Entrepreneurship

There’s freedom to chart your own course (another reason why I don’t like golfing; too many rules and no flexibility on how to get to the 18th hole, it’s all very linear and prescriptive). As you cycle uphill you have to catch your breath, focus and channel all your energy through your legs, into the pedals to turn the gears to turn the wheels to propel you forward. There’s a lot of gear grinding as you shift and make adjustments to make that uphill climb as smooth and efficient as possible. At least in my case, there’s occasionally some huffing and puffing, too.

As the entrepreneur, you see the long road ahead but you have a vision for where you want to go – you have a destination in mind. You have a general plan how to get there but you may not have mapped out every intricate detail to know exactly what the incline grade is of every hill and how long it will take you to complete the ride. And you may have to make adjustments along the way if there’s traffic, construction or whatever else. This is where leadership comes in – being able to navigate the unpredictable road ahead, make quick decisions, and guide the team towards the ultimate goal.

But one thing that you do know is that there WILL be hills. Along with some low points. Not to mention a (precious) few exhilarating downhills where you can coast, sometimes at breakneck speeds. 

However, intrinsically, you fundamentally understand that there will be a hill to climb the second that you’ve finished coasting your way down. And, as you’re rapidly descending down the hill, tucked to minimize drag and to maximize the freeing experience of it all, you’re thinking about the possibility of crashing. 

Am I going to fast? How will I stop? Or, better yet, what will stop me?

Maybe other riders don’t think about crashing, but I do. My legs tell the story of many wonderful vacations and biking experiences. Somehow, my vacations are frequently punctuated with a new body marking. I slough it all off: every mark is another story that just adds even more to the character that I am. 

Getting Back Up: Resilience and Perseverance in Cycling and Entrepreneurship

Last summer, I had an epic wipe-out. This wasn’t your average “meh-a-bit-of-roadrash” kind of spill. It was the, “OMG, I can’t move my legs” kind of spill. The kind where the ambulance comes and the x-rays show that parts of you are broken. And your helmet? To some, a badge of honor. To others, a PSA regarding why you should wear one. 

It took me 11 months to get back on my bike. I was tenuous at first and making my way slowly through a route that I knew well. No sense trying to prove anything to anyone. The objective was simple: ride and return home, upright and unscathed. Mission accomplished.

A few days later, I got back on my bike again (owing some of this feeling of rejuvenated hootzpah to Coach Mary Foley). This time, I was a little more confident and assertive. “Hill? Ha! I see you and I challenge you! May the best gal win!”

Each time that I rode, I felt more liberated, more on point, more like my old self. And then I decided that it was time to cycle with my toe clips. Let me pause right there – who was the brainiac who decided that it was a good idea to bolt your feet into a vehicle capable of moving at high speeds but wholly lacking any protection for the driver? They say there is no such thing as coincidence but there is, indeed, irony. The inventor was Eugene Christophe, a French cyclist who – wait for it – happens to share my birthday; only that he was born (1885) a little before I was! He invented toe clips around 100 years ago. Maybe it’s time for some innovation?

Yup. You knew where this was going. My leg has yet another story to tell.

Uphill Battles and Exhilarating Downhills: How Cycling Mirrors the Ups and Downs of Entrepreneurship and Leadership

I took a few days to heal and rode again. Then again. And I’m going to keep riding, keep grinding up those hills and keep making my way forward. Because that’s what entrepreneurs do and what leadership is. We find ways to overcome obstacles, invent around them and strategically think through a route that brings us closer to our destination … make that, our goal. And along the way, we also need to develop our soft skills like communication, empathy, and adaptability to navigate the challenges that come our way.

Look out. You’re going to see me on the road more and more. Occasionally bloodied, frequently bruised, but UPRIGHT and moving forward.

#resilience #unstoppable #grinding 

Photo by The Lazy Artist Gallery from Pexels

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