The Constant Climb Of Entrepreneurship

Today, as I write this, I am sitting on a veranda with the most magnificent views of Jamaica. I came here to speak at the annual Business Summit event in Kingston, and my wonderful host has me staying in a villa at Strawberry Hill.  My room sits on top of a mountain (a hill for Jamaicans, a mountain for New Jerseians), over looking other mountains in all directions. The drive up here was fascinating.

I am not sure if you have ever navigated the back roads of Jamaica. But, for myself, I consider it old hat. (That is, as much as a passenger can say “old hat” when it comes to driving.) I would never drive these roads myself, they are fast, they constantly twist and turn, 18-wheelers careen down them, people drive on the left side (which gives any American driver a heart attack every time another car approaches), and there are mammoth pot holes everywhere. If that doesn’t get to you, the fact that mere inches to your left or right are gorges that drop as far as the eye can see… and railings seem to be optional here. Yet with all that, the drives are the most beautiful and invigorating thing you can experience.

During this particular drive to Strawberry Hill I noticed something. Almost every time we completed a turn and the road leveled out, I was momentarily convinced we had finally reached the top of the mountain. But then, another turn would come, and we would start to climb again. We’d level off, I would think that this time we were in fact at the top, and that’s precisely when the next climb would begin.

I couldn’t believe how high up in the mountain we were, yet we always climbed higher. When we reached the summit (I thought) we entered the Strawberry Hill property, and I was assigned my villa. From there I walked up higher! Climbing 30 plus steps to get to my room. I entered. It was gorgeous. I walk onto the veranda to look down. But I had to look up. The distant mountains we far higher than I.

Welcome to entrepreneurship. Or a drive up a Jamaican mountain. It’s basically one and the same. The climb never ends for entrepreneurs. There is always a higher summit for us. When you think you are at the top, you haven’t even started yet. You can always climb higher. You must always climb higher.

Strawberry Hill Jamaica - Looking out from my balcony

Looking out from my villa at Strawberry Hill into the Blue Mountains of Jamaica. You can see my laptop, where I wrote this post, in the bottom of the picture (below my stinky feet).

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4 thoughts on “The Constant Climb Of Entrepreneurship”

    1. This most certainly has been my experience. I have always been a positive person, bordering on idyllic optimism. My parents instilled in me that no dream was off limits, and in youthful zeal I fully believed ‘I could be an astronaut too’. I know now that running a small business is perhaps the most difficult thing I could have chosen, as it has tested the limits of my strength and brain power and confidence. It is a litmus test, revealing who you are and the stuff you are made of, and it was good for me to be tested. Despite the revelation of every one of my warts through the last 25 years, I am thankful. Why? I’m convinced that we learn things in small business that we can learn in no other way. Like: no one succeeds single-handedly. (CS Lewis said ‘Humility, after the first shock, is a cheerful virtue.’) Small business teaches you not only what you don’t want, (which is often the occupation of our youth), but what you DO want. And thirdly, I would have never known what I really was capable of doing had I just sat back and watched everyone else have all the fun. These are all things that people that have laid nothing on the line will never know. “It isn’t a calamity to die with dreams unfulfilled, but it is a calamity not to dream. It is not a disaster to be unable to capture your ideal, but it is a disaster to have no ideal to capture”. Benjamin E.Mays Appreciate your blog.

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