See Jack Run: From One to Twenty-Six Point Two
Growing up with asthma, I was the kid on the sidelines, clutching an inhaler and armed with a doctor’s note excusing me from any kind of strenuous activity. Running one hundred feet no less a mile was unfathomable. But life has a way of pushing us toward what we once thought impossible. What started as a casual jog around NYC’s Financial District turned into something much larger—a journey that would reframe my entirelife.
A Fresh Start in New York
After my 25-year marriage ended, I found myself living alone in NYC. Friends suggested I start dating again, which sounded simple enough until I actually thought about it. Dating was far from my mind, but getting out there was probably a good idea. They suggested joining a group—ideally one where I could meet people (meaning women). Living in the city offered plenty of options for a recent divorcee trying to reconnect.
Given my limited athletic background, I considered tennis, but in Manhattan, finding a tennis court is as rare as a rent-controlled apartment and nearly as expensive. So, I settled on jogging—not running. Real runners know the difference, and at that time, I was no runner. But to my surprise, I actually enjoyed it, something I never thought possible.
So, when I decided to join something to meet people (women), I came across the Achilles Track Club in the NY Cares volunteer booklet. Achilles, so I thought is the organization behind the one-legged runner at the front of the NYC Marathon. I figured, if a guy with one leg could do it, maybe I could, too. In April 2004, I made my way to my first Achilles meeting at the New York Road Runners Club on West 89th Street.
The First Steps to Something New
I sidled up to an open spot in the group and introduced myself around. Everyone was dressed for a beautiful sunny day, ready to run. I wound up next to a guy named Chris. He thanked me for volunteering and casually asked if I’d like to run with him. “Sure!” I said, explaining it was my first time “running” and mentioning that I’d also never been in Central Park before. “Come with me,” he said confidently. “I’ve been doing this for years.” Just as I was getting comfortable, the team leader called out, “Okay, everyone, let’s head out to the park!”
Chris turned to me, asking if I was ready, and as I nodded, he leaned over, reached out, and gently grabbed my elbow. OMG. My life flashed before my eyes. Everyone was wearing sunglasses—Chris, me, half the room. It took me a second to realize: he was blind. My mind raced. Where’s my one-legged guy?!
Chris must have sensed my reaction because he started laughing. “All you people who can see have no idea where you’re going,” he teased. I laughed, trying to relax, but inside I was a bundle of nerves. As we walked to the park, he gave me a quick tutorial on running with a blind partner: hold one end of the tether while he holds the other, keep him between the lines, lift it up for elevations or depressions in the road, and keep the line taut. He sounded confident, but I still wasn’t buying it. In my mind, I was going for my first real run—and I was going to kill a blind, 55-year-old guy from Trinidad & Tobago.
We finally reached Engineers Gate, where the group met for announcements and stretching. Chris and I got ready, and he reassured me we’d start slow—a four-mile loop, he said. “Four miles?” I balked. “The furthest I’ve ever done is two.” But Chris shrugged it off. “Hey, who’s the disabled person here?” he joked. And with that, we set off.
My First Real Run
As we made our way up the east side of the park, Chris turned into a tour guide. “The ball fields are on the left…coming up to the 103rd Street Transverse…” He knew every twist and turn. I couldn’t wrap my head around how he knew exactly where we were. Is he counting steps? At one point, I even waved my free hand in front of his eyes just to make sure he was really blind. No reaction. The man was a walking GPS. We crested a hill, and he mentioned we were going to stop at a water fountain coming up on the left. Sure enough, there it was.
Step by step, I felt my initial fears slipping away. Here was a blind man trusting me to guide him through a park I barely knew, and he was narrating landmarks like he’d designed the place. His confidence was contagious. By the time we completed that four-mile loop, I felt a sense of accomplishment I hadn’t known before.
As we got back to Engineers Gate, both of us alive and now best friends, Chris said let’s get another drink of water. There’s another water fountain to the left along the gravel path. I was proud—not only for surviving four miles but, for not killing this guy! Confidently, I walked toward where I thought the fountain was, striding forward until I heard Chris call out with the deepest Trinidadian accent, “Man, where you going?”
“Uh, to the water fountain!” I said defensively.
Laughing, he responded, “Turn around, you passed it.” With what little dignity I had left, I turned around and walked back, only to hear him say, “STOP. It’s right in front of you.”
“Son of a bitch” I muttered, and Chris burst into laughter, tears rolling down his cheeks. And that’s how I started running.
From Jogging to Marathons
That first run with Chris was just the beginning. What started as a casual jog evolved into regular runs, then longer distances. One mile turned into four, four turned into ten, and ten eventually became my first marathon. Every run, every mile, was a reminder of how far I’d come from the kid who sat out of gym class. Running was teaching me not just physical endurance but mental endurance, too. And through Chris and other Achilles athletes, I discovered a community of people defying their own limitations every day.
Twenty Years Strong
Looking back, it’s clear to me now that every step of this journey was about more than just running. It was about finding my way forward, discovering my own “next” chapter. Running became an unexpected gateway to healing, self-discovery, and resilience—a journey of letting go of old limitations while pushing toward new ones. And though I might have started running to meet people (women), I ended up meeting myself.
April 2024 marked our 20th anniversary of running together. In those two decades, I’ve completed 11 marathons, 38 half marathons, and seven triathlons—pretty remarkable for a guy who once couldn’t run 100 feet. I even convinced Chris to run the 40th NYC Marathon with me.
The path to finding what’s next often takes us in directions we don’t expect. It may not be comfortable, it may be messy, and it may challenge everything we thought we knew about ourselves. But with each step, each mile, we find the courage to keep moving forward. So here I am, from one mile to twenty-six point two, embracing every step of the way.