The portfolio and writerspace for Al Gentile

500 Words on Jumping

I’ve recently rekindled my love for hiking. Navigating an upward trail, getting closer and closer to the clouds, and breathing the thinning and ever-clearing air is something that at once exhausts and rejuvenates my entire self.

On one excursion, I was trekking Mt. Monadnock in New Hampshire when, about 2,000 feet up, I looked over my shoulder at the wide expanse of rolling hills and surrounding peaks. A familiar feeling set in.

It first pulled at my ankles, an invisible force goading me to consider in the deep recesses of my mind whether or not to jump. It’s a frightening feeling, but one that is exhilarating and ultimately electrifying.

It started to swirl around in my stomach, course through my legs, and stiffen my shoulders. I was really high up (for my standards at least), but the fear of losing traction and falling to my untimely death started peeling away layers of the comfort I felt on solid ground. I looked back to the peak again, and continued to climb.

A recent émigré to the world of freelancing, I remember feeling a similar pull at the ankles, wrenching of the stomach, and dizziness as witnessed the peak—several thousand feet and some unknown amount of time away—of where I wanted to end up.

Self-sufficiency, stability, and boundless optimism from the realization that I am truly the master of my own success.


You are about to enter the realm of self-righteousness.


This fear is a constant reminder that I am truly alone in determining my own success. Much like witnessing the firmament at 2,000 feet, I am seeing the world much differently than I had before, with the limits of my vision bounded by my cubicle walls, or the edges of a stuffy office. The diminishing returns of time put in over time paid for, and the shackles of a job description that would constantly pose the question, “Why?”

With desperation clawing at every moment, my circumstances pose a new question, that in my limited experience has led to some incredible insights on my part, even in the last few weeks.

That question is, “Why not?”

I’m constantly asking myself why I haven’t studied technique and form in writing before, and why I should start doing so again. For me, the above question is the answer.

Thinking about whether I should prospect a certain client, again, the question is the answer.

When asking myself whether or not I deserve to be successful, the rhetorical question rears itself again as an almost self-evident truth. But, not in the way that you might expect—as in the question is a direct answer. It forces me to think about my own circumstances and, as someone who generally believes everyone deserves happiness and the methods to get there, I come to the same realization time and time again.

Much like how I looked on that breathtaking horizon, I’m making leaps forward into a land unknown. But I did—I jumped, and it’s great.


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