Lunch Ride

Chessin Gertler
6 min readOct 29, 2022

I’m sitting on Justin’s wheel, pedaling up an undulating wet gravel road somewhere in Southern New Hampshire. It’s 41 degrees F with wind conditions perfect for sending little pebbles of ice under my glasses, leaving them to either freeze on my eyelashes or in the wind on the edges of my beard. I drop back a few feet, cock my head, and blow my nose into the ditch to the side of the road, then pick up the pace to find his wheel again. In the parking lot where we met, we looked up at a blue sky and smirked at the rain in the forecast. To be fair, we didn’t see much of it over the next four hours — mostly hail and sleet with little breaks of snow flurries. Five miles in, I was worried that I was overdressed. Fifteen miles in and I’m worried about my toes. So much for our spring day ride. April in New England.

I glance over my shoulder for cars and pull up next to Justin who’s checking the route on his computer. One hand on the bars, another pecking at his screen, pedals spinning like there’s nothing going on.

“I think it’s hailing,” I say. Irony intended.

“I think so…” he returns with little inflection, countering my dryness. We continue to climb.

“I actually love this type of weather,” I confess.

A pause as we hit a hill and both get out of the saddle.

“I know. This is epic” comes through with a glance upwards, the slightest hint of a smile, and a genuine aura of appreciation that’s uniquely him.

Riding with Justin is special. A former pro cyclist at the highest level of the sport and expert mechanic, I feel lucky for every ride we share. He messaged me the day before that he had a ride in mind, sent me a grainy screenshot of the route and a pin drop in the parking lot where we were to meet. I was all in.

Watching Justin pedal a bike is like watching Roger Federer swing a racket, or Ray Allen sink a three. There’s a rhythm and economy of motion that looks fundamentally different from that of a civilian. Tens of thousands of hours on the bike, an unwavering goal-oriented work ethic, compounded with a foundation of immense talent translates into an appearance of abject effortlessness — souplesse in cycling parlance — that makes him look less like he’s riding a bicycle and more like he’s hovering between two wheels, floating up a mountain. The fact that he can hammer up a hill like this in his forties on a bike significantly heavier than mine, having not ridden in any serious manner for the better part of the year as I struggle to hang on to his wheel after a winter’s training block that I should be peaking for at this moment, adds to the respect.

I love riding my bike. I love the feeling of connectedness to the machine — the endorphin rush of the elevated heart rate and proprioception required to go fast and stay upright. I love being outside; I love watching farms pass, seeing animals at pasture, sprinting when dogs spot me and beeline it for my ankles. I love moving over rolling terrain, letting my legs react to heavier riding as hills pass under me, giving way to the weightlessness of the descent. I love stopping at cafes and having a scone and coffee that taste three times as good as they would otherwise. I love the clarity of thought while I’m on the bike - or the complete absence of it, depending on the moment and my heart rate. I love going home after I ride and standing in the shower, feeling my cold skin tingle under the warm water like I’m stoned. I love sitting with my family at dinner after with a beer and plate of food, my daughter on my lap, happy to be motionless, appreciative of the meal. Not wanting anything more. I love being able to hit my pillow and go right to sleep, even if I wake up in a couple of hours to eat a bag of cookies.

Justin loves riding his bike too. More than anyone I know. His bond with cycling is complicated. With immense expectations and a career that didn’t pan out the way it was expected to, he has remained remarkably loyal to the relationship. When he rides, he seems to be distilling the act down to its most fundamental pursuit, that of pure enjoyment and appreciation to be able to experience this incredible machine. He feels no need to compete, no need to posture. It’s infectious.

a cyclist on a dirt road in the woods stops to look at a sign indicating that he’s about to enter an unmaintained road

Over the course of our four hours in the saddle, we don’t speak more than a few minutes in total. We take turns pulling (setting the pace and creating a draft, making it easier for the rider behind) and riding side-by-side on the quieter roads, of which there are many today. We laugh about the weather, exchange a few sentences about the beauty of New England, chat a bit about our bikes, and make some decisions about route adjustments when we end up at the end of a dirt road in front of a house with a bunch of questionable lawn signs. Justin answers my compulsory one-per-ride question about what it was like to race in the Giro (it was fast) and we take an uncharacteristically long time choosing snacks in a country store.

This ride is the antithesis of a power lunch. Twenty-four hours earlier, I was being peppered with questions about customer acquisition costs and smiling politely to comments on prep school preferences over a steak that simultaneously left me feeling uncomfortably full and profoundly empty inside. I pause for a moment to think about the fact that as I feel my ears freezing from a thousand icy beestings and wipe icicles of snot off my face, my legs throbbing and my hands now numb, I’m the happiest I’ve been all week. I try not to think too hard about it though, and pedal on. Too much clarity can be tricky.

We make it back to the parking lot with enough sensation in our hands and feet to drive home. I discover that I left my phone on the roof of my car - definitely component to the enjoyment of the ride. It’s sunny again, the precipitation dissipating right as we pull in, of course. I sit in my passenger seat and peal the sweat and mud-sprayed layers of black lycra off my body, while Justin disappears into his van before emerging in his street clothes looking like he hasn’t sweat. A few summary comments and we go our separate ways.

These rides last weekly through the spring. We ride Central Massachusetts: loops around Mt. Wachusett, the quieter roads outside Boston, and more of Southern New Hampshire. As late summer roles in, heat, humidity and the particularities of life finally succeed in breaking the rhythm. A missed week turns into two and eventually a death spiral as work unravels the ritual. Justin gets a new job in manufacturing after a brief though personally informative stint in retail and an approaching autumn signals more awkward lunches and superfluous Zoom calls for me.

It’s warm for late November — sunny in the high fifties. I roll out towards Blue Hills on an impromptu pre-lunch ride, Froggering my way through Mattapan’s potholes, bike lane parking violations, and jaywalkers in what’s become my de facto neuromuscular warm up. Over the Milton line, the vibrancy of Boston fades instantly. On the winding ascent of Chickatawbut Road, I follow the last bit of sunshine as it disappears into grayness behind the upper branches of the reservation’s now leafless trees. By the time I turn onto Summit Road for a quick climb up the ski hill, the temperature has dropped another twenty degrees. Half way up the six-minute climb, it’s hailing. I turn around at the top and zip up my jersey, cursing myself for not bringing a vest, spinning my legs in vain to keep warm as I bomb down the hill. At the base of the service road, I unclip and blow hot breath into my hands until I have enough feeling in my fingers to grab my phone from my back pocket. I abort trying to type and tell Siri to text Justin.

“You wanna ride to Provincetown tomorrow? If we leave real early, we can make the ferry back. It’s supposed to be nice out.”



Chessin Gertler

Founder @ Slé - | Tech futures in mobility, sport, and the human experience …and sometimes just stories about my dog and riding my bike