The making of a cyclist: 10 epiphanies on a 10,000-mile journey

Epiphanies sure can strike at odd moments.

Mine occurred as I barreled down a steep and winding mountain pass in Baja California during the annual Rosarito-Ensenada ride, one of Mexico’s most popular group cycling events, on the first Saturday of May. 

Thousands of riders converged on the town of Rosarito Beach, a bit south of Tijuana, for the ride. There was a stage near the start line, and the emcee asked passing riders to state their hometowns. People named locales from all over Mexico, Central America, and the American Southwest, on what already felt like a festive day. 

The ride’s first couple hours were spectacular: Killer ocean views. A cool sea breeze. Spring wildflowers in full bloom. A tailwind. Friendly townsfolk lining the streets, waving and cheering as you passed.

Then we turned inland: The breezes and crowds vanished. The temps under the midday sun suddenly felt like someone cranked the thermostat all the way up. There was little shade to be found.

Oh, and then there were the hills: A long and winding 800-foot climb. A desert plateau for a couple miles. Then a shorter but considerably sharper 400-foot climb.

I’m no pro. This ride was less than two weeks before my 45th birthday. I’ve written in the past about my story as someone who weighed nearly 300 pounds on a 6-foot-2 frame in my 20s. I’m much fitter now. I love and appreciate all that cycling has done to improve my quality of life. 

But I still hate every second of hill climbing and I’m not going to pretend it is something I will ever enjoy.

Right up until the hill is conquered, and a feeling of accomplishment sets in, that is. 

This time, though, the descent turned out to be just as challenging as the climb. All of a sudden, I found myself in middle of the sort of scene that would make a casual television viewer of the Tour de France question the riders’ sanity.

I hurtled rapidly down and around twisting corners, on what was not exactly the world’s best-maintained road, moving so fast I was afraid to even loosen my grip on my handlebars for fear the slightest false move would send me hurtling to a severe injury.

Occasionally I’d hear what sounded like approaching cars, only to have other bikes absolutely fly past me. I’m not yet experienced enough in these situations to let myself go with what seems such reckless abandon. I tensed up and found myself wishing the descent, which on paper sounds so much more fun than the climb, was done.

Then came my moment of clarity. 

Malcolm Gladwell’s “10,000-hour rule,” wherein it takes that amount of time to master a skill, flashed into my brain. Somewhere toward the end of the Rosarito-Ensenada ride, I was going to surpass the 10,000-mile cycling mark, at least since I had started keeping track via MapMyFitness in the summer of 2014. 

Maybe 10,000 miles makes a cyclist. Maybe four years after you decided it was time to pick up biking as a hobby, you’re a for-real, all-grown-up cyclist now.

I smiled at the thought. I relaxed. I released my death grip on the brakes just enough to allow myself a little more speed and, more importantly, allowed myself to enjoy the ride. 

From there, the journey again became a tremendous experience as it wound back toward the Pacific Ocean. The breezes returned. As did the cheering crowd. I crossed the finish line, claimed my medal and T-shirt, joined the post-ride street festival, and treated myself to a cerveza or two and a plate of Ensenada’s world-famous fish tacos. 

It was a hell of a way to surpass a milestone. But it wasn’t my only such moment of clarity. A handful of smaller epiphanies paved the way for my big one in Baja. Here are the top 10:

1. Los Angeles, April 2014: I need to start riding again

It all started inconspicuously enough. I attended a Sunday matinee Clippers-Lakers game in April 2014 at Staples Center in downtown Los Angeles, and as I walked back to the train station (yes, we have those in LA now), I noticed Wilshire Boulevard was for some reason closed to traffic.

I went to investigate. I discovered the street was shut down for an event called CicLaVia, modeled after a similar deal in Colombia called Ciclovia, in which main thoroughfares are closed to motor vehicles for a day and opened to cyclists and pedestrians.

I took a look around and saw a whole lot of people having fun: Individuals, groups of friends, and families, all out on their bikes, enjoying what’s usually a traffic-choked street on a sunny Sunday afternoon, with food trucks and entertainers along the route.

The scene made me decide on the spot that it was once again time to start riding a bike. I was more than 15 years removed from the last time cycling was a regular part of my life, when I was a college student in Boston and trying to get in shape. I had simply fallen out of it, but the fun everyone seemed to be having on this day reminded me how much I enjoyed biking up the Charles River, or along the Cape Cod Canal.

CicLAVia

I was 40 and found myself yearning for something new. I wanted to take up a new physical activity while I was still young enough to accomplish something. I couldn’t have known it at the time, but stumbling on the 2014 Wilshire Blvd. CicLAVia changed my life in profound ways which would take awhile to manifest.

2. San Clemente, Calif., Oct. 2014: Sheer enthusiasm will get you a long way

A couple weeks after CicLAVia, I bought a used bike for about $150 (My advice to anyone who inquires about wanting to get into cycling is to get a cheap used bike first and see if you enjoy it, then upgrade from there if you do). I biked along the LA River bike path, or around my neighborhood, or down by the beach in the South Bay, and steadily built to my first 15-, 20-, 25-mile rides. 

I knew the old beater bike I had wasn’t going to last forever, so at the end of the summer, I bought a new Trek FX hybrid ... and started to dream big.

Somewhere along the way, the idea of biking from LA to San Diego got stuck in my head. I wasn’t sure why. It just seemed like an audacious goal worthy of pursuit, even if it seemed outrageously beyond my capability.

I Googled “LA to SD ride” sometime in the late summer of 2014 and found a route on MapMyFitness. 

I knew I wasn’t going to make the jump from 25-30 mile rides to 135 miles in a couple months. 

But as I took a close look the route map, I noticed there was a train station in San Clemente, about halfway between LA and SD, and riding there and then taking the train back seemed like something I could aim for in the fall of 2014, before the days grew short.

So I made this a goal, and worked toward it in the fall, doing my first 50-mile ride around Labor Day and first 60-miler a few weeks later.

A few days before Halloween, it was time. In hindsight, I didn’t know just how much I didn’t know. I did so much that would be considered “wrong” on this ride.

Experienced cyclists will laugh at this: More than 70 miles on a hybrid bike, not a road bike. Sneakers and flat pedals, not clipless shoes and pedals. T-shirt and cargo shorts, not a cycling jersey and cycling shorts. I hadn’t even figured out how to properly adjust my gears going uphill at this stage.

But ignorance is bliss, and I proceeded on my merry way: Through Boyle Heights and East LA. Down the San Gabriel River path. Huffing and puffing my way up and down the hills of Orange County, though Newport Beach and Laguna Beach and Dana Point, sweating through my shirt as my lungs felt like they were going to explode.

Final descent into San Clemente.

Despite everything I was doing "wrong," I finally made it to my destination, the San Clemente Pier, exhausted and elated.

I’ve done LA to San Clemente about a dozen times since. It remains my favorite ride. It’s long enough to be a solid challenge without being overwhelming. There’s 50 miles of flat riding, followed by about 20 of quite challenging hill terrain, ending with a blissful final five miles along the beach and out to the pier. 

And the reward at the end is magnificent: An absolutely beautiful area, ending in a rare Southern California beach town that hasn’t been overrun by annoying bros and chain stores, with a view of the ocean, wonderful little bars and restaurants, and maybe the best Amtrak “station” in the country, which is simply a platform overlooking palm trees and the beach.

I still crack myself up thinking about how I did this “wrong” the first time. And yet my naivete in its own way made this one the most fun.

I also had about an hour-long phone conversation with my parents on the pier after the ride. The significance of this wouldn’t hit home for a few months.

3. Los Angeles to San Diego, June 2016: Cycling can help you heal

If you’ve been following my exploits, then you already know the tough part of my story: In a six-week span in the winter of 2015, I lost both of my parents and one of my closest friends.

In June 2016, I made the LA-to-SD ride a reality and raised nearly $6,000 for charity in my Dad’s name. I’ve already written extensively about this ride and you can read about it here. 

4. Prince Edward Island, Canada, Aug. 2016: You revisit old goals you thought you gave up on and achieve them after all

Bike riding was a pivotal part of my regimen when I made my first effort at getting in better shape back when I was in college. They weren’t long rides, maybe 10-20 miles at a time, but it was a solid start for someone who hadn’t been able to walk up a flight of steps without running out of breath.

One day around this time, at a Barnes and Noble, I thumbed through a book about cycling in Prince Edward Island, off the Atlantic coast of Canada. And I vowed to myself I’d get in shape to bike around the island some day.

As it turned out, it took 20 years to make this one happen. As I scanned my brain for new challenges after the big San Diego ride, I remembered PEI. After an internet search, I signed up for a week-long trip through a Massachusetts-based outfit called Easy Rider Tours. 

I still wasn’t entirely sure of myself as a cyclist, even fresh off the success of my charity ride. As I waited to get picked up for the tour in downtown Charlottetown on a Sunday morning, I imagined joining a bunch of professional-caliber riders sneering at me and wondering what this big guy thought he was doing trying to be a part of this.

My fears were instantly alleviated when I met the group. I was the youngest person on the tour. Everyone was friendly. No one judged me. I started making new friends almost immediately.

The week turned out beyond anything I could have imagined when I leafed through that book 20 years prior. I spent my time cycling through some of the most breathtakingly beautiful terrain on earth, during the best time of the year to visit. The locals were friendly. The inns and hotels along the way were charming. The fresh PEI seafood every night was out of this world. 

My new favorite people were a duo named Pam and Millie, retired friends from the Bay Area on the tour who took up each day’s ride with gusto. After seeing my parents pass, it was a pleasure to experience such vitality and joie de vivre among older folk.

PEI National Park, before the rain.

My favorite moments of the tour, though, came on the final full day. We pedaled through the immeasurable beauty of Prince Edward Island National Park. I was part of a group of four who had congregated together over the week since we were of similar biking skills and pace: Myself, Pam, and a couple from Massachusetts. Pam had taken to calling us “The Family.” On this day, The Family had decided to take in an extra ride out to the very edge of the park, adding a few miles to our scheduled route. And while we were there, the heavens opened and we got absolutely soaked in a pouring rain, the first real precipitation of the week. 

We stopped for a moment to take stock of things. We had about 10 miles left until we reached our housing for the evening, a five-star resort in Dalvay-by-the-Sea. We could have hitched a ride with the tour’s support van, but we took a vote, and it was unanimous: We hadn’t used the van at any point all week, and we weren’t about to start now. 

So onward we went, soaked to the bone, the rain falling in sheets. And it was one of the most exhilarating, satisfying experiences I’ve ever had, as we splashed through puddles and laughed like little kids. We finally pulled up to the prim-and-proper lodge drenched and muddy, which must have been quite the sight.

The ride I imagined for 20 years became a reality, and it was more fun than I ever could have envisioned. So here’s my plea to you, dear reader: That thing you swore to yourself you’d do when you were younger, but never got around to? Do it. You just might find it was everything you thought it would be, and make memories and friends to last a lifetime in the process. 

5. Killarney, Ireland, Aug. 2016: Cycling is a great way to see new places

Some day, I want to go back to Southwest Ireland and bike the famed Ring of Kerry. But my first time pedaling in the Emerald Isle was pretty solid, too. On the same trip as my PEI tour, I made my first-ever visit to Ireland, spending four days in Dublin before taking a train out to my grandmother’s breathtakingly beautiful hometown of Killarney in the southwest part of the country.

For about $25 US, I rented a cheap hybrid for an afternoon, and took a short-but-fantastic ride around Killarney National Park, biking up to centuries-old castles, around ponds, and up to the majestic Torq waterfall.

Take a bike instead of walking or driving and you may stumble upon a 16th-century castle.

The lesson for this one was simple: Big, challenging rides are great, but a rental and a short ride is a hell of a way to take a tour, too. I’ve since done similar short explorations on cheap rental bikes in Montreal, along the North Saskatchewan River in Edmonton, over the Golden Gate Bridge in SF, and along Lake Michigan in Chicago, and I’ve never once regretted incorporating these rides into my travel. 

6. Los Angeles, April, 2017: You can get hurt doing this

It seemed the least likely day to have an accident. I had simply pedaled about two miles on Saturday afternoon from my place in downtown LA over to a coffee shop in Boyle Heights. It was the sort of short trip on my hybrid -- which had become my "around town" bike after I bought a legit road bike -- I had made dozens of times without a second thought.

On my way back, I crossed the First Street Bridge over the LA River back into downtown, heading toward Alameda St. and back to my apartment. 

The Metro gold line, which runs from East LA to Pasadena via downtown, crosses over First Street from Alameda, cutting across the actual street to reach a separated platform in the middle of the bridge. 

At precisely the wrong moment, a jerk driving a sports car came way too close to me at too fast a speed. Fearing I was about to get sideswiped, I made a split-second decision to pull off into the area where the trains begin to cross over, away from the main street.

Next thing I knew, I was on the pavement. The jolt I felt when I hit the ground was was so sudden that I couldn’t place where exactly I had hit. 

After I staggered to my feet, I realized there was blood. Everywhere. On my shirt, all over the ground, and still dripping in alarmingly large drops.

I reached up, touched my chin, and felt a bloody clump of raw flesh.

Soon enough, after managing to stem the blood flow from a wide-open faucet to a dripping one, I realized that a. I needed to go to a hospital and b. I wasn’t so bad off I needed an ambulance. I must have been quite a sight as a pedaled the last half-mile home. I cleaned up as best I could, showered, then drove to the hospital. My ribs started to get sore on the drive.

As I waited in the urgent care reception area, I was finally able to piece together what happened. The front wheel of my hybrid got stuck in the groove of the train track. I went over the handlebars and got my hands up a split second before my head made impact, which was enough deflection to simply have my the area just under my jaw scrape the rough pavement and slice it open. 

Had I landed a few inches in any other direction, I could have ended up with broken wrists, a broken jaw, or both.

The damage, ultimately, was six stitches in my chin, a tetanus shot, badly bruised wrists, and sore ribs from the spot where my ribs hit my bike frame on impact. Bad, but could have been so much worse. 

I made a vow to myself as I left the hospital: The lane in which I was biking on First Street was marked “cyclists may use full lane.” I had always stayed to the side of the lane in these situations, not wanting to be “that guy.”

But urban planners designate certain lanes as eligible for bike use for a reason. While it might be counterintuitive at first glance to use the full lane when you can stay off to the side, fact is, a driver is far less likely to flat-out blast you when you’re in the middle of the lane than they are to come dangerously close to you if you’re off to the side of the lane. 

So guess what? If I’m making your commute last an extra 30 seconds because I’m using a full lane for a block or two, you’ll get over it. I can live with your momentary anger a whole lot easier than I can endure another hospital trip. 

6a. Los Angeles, April 2017: This deserves its own mention: I spent most of the day following my accident sore in bed. But I knew that I had some big bike goals up ahead, and that if I stayed off my bike too long, the accident would get into my head and live there rent-free. So, I made it a point to get out of bed that Sunday and get on my bike, stitched chin, sore ribs and wrists and all. I even wore the same bloody t-shirt I had worn the previous day. 

I was only out there about 20 minutes, but I made it a point to go back to the scene of the accident, where there was an astounding number of blood stains awaited.

Returning to the accident scene a day later. Those large spots on the pavement over my shoulder was my blood.

I took it in. Vowed to never let it happen again. Promised myself I wouldn't be afraid. And never looked back. 

7. Boston to Provincetown, Mass., June 2017: You can go home again

After my LA-San Diego and PEI rides in 2016, I began to conceptualize meaningful journeys for 2017. And I settled on the idea of riding in the two places I’ve lived besides Southern California: Boston and Washington State.

My cousin Kathy back in Boston, an avid cyclist, pointed me in the direction of an annual ride done by Outriders, an LGBT-friendly cycling group, 130 miles from downtown Boston to Provincetown, on the outer edge of Cape Cod. It didn’t take much investigating to know this was the right call.

I rented a road bike in Boston. On the day before the big ride, to make sure the rental handled okay, I took it for a short ride around the city. That in and of itself was an awesome experience, as I biked down to Dorchester, along the water, out to South Boston's Castle Island, made a pit stop to visit my 90-year-old great aunt Flossie, then went back through downtown and looped up the Charles River.

I cannot tell a lie, here: I’m often a nervous wreck the night before a big ride, especially if I’ve never done the course before. It poured rain on Friday night into Saturday morning. I lied awake imagining myself flying across the country just to get absolutely drenched on the longest ride I had ever done, and got just a few hours of fitful sleep before I had to get up for the ride.

I awoke to overcast but dry skies. I set out at exactly 6:17, Boston’s area code. I was not prepared the intensity of the ride’s first hour.

As if in a movie, one memory after another was jarred out of the deepest recesses of my mind. There’s my grandmother’s place. Here’s the street we used as a shortcut to my other grandmother’s place. There’s the building where I lived on my own for the first time in my life. There’s Boston College High School, my alma mater. There’s the Boston Globe, where I worked for years. There’s UMass Boston, where I got my degree. There’s the bowling alley where I was in a league for a few years. There’s the Domino’s where I delivered pizza in college. There’s the street one of my best friends in high school lived. There’s the storefront which used to be a sports collectible shop where I sold a Michael Jordan rookie card for $700 back in 1993. There’s the bowling alley my dad took me to as a kid. There’s the tobacco shop where I used to buy wrestling magazines as a kid ... still open! There’s the Burger King my Mom would use as a bribe to behave when she took me shopping. There’s the place that used to be a bait shop I’d go to when I went fishing. There’s the park where I’d shoot hoops. 

Boom, boom, boom. One after another, in rapid-fire succession. Then, as I pedaled further from my hometown, the memories abruptly ended, leaving me with about eight hours of cycling left and a lot to ponder.  

The next couple hours were a bit of a muddle, but I perked up as we disembarked and walked our bikes over the Sagamore Bridge, looking out onto the Cape Cod Canal and the adjacent bike path where I had made my fledgling cycling efforts two decades prior. 

The ride flowed from there. I caught my first view of the open Atlantic in Wellfeet. The previous Saturday, I had done a century ride from LA to Oceanside as a warm-up, and I took a moment to appreciate cycling along both oceans seven days apart. 

There was one final hill of note in Truro, the last outpost before P-town, and when I got to the crest, I was rewarded with a view that made all my efforts worthwhile: A view of Provincetown Harbor, all the way out to the very tip of Massachusetts, on my left; an inlet and sand dunes to my right. The final five or so miles were like a dream state. 

After the ride, I checked into my AirBnB and was fully intent on spending the night out. It was a bustling PTown summer Saturday and I was going to take full advantage. But halfway through my first beer, I found myself nodding off at the bar. Oh well. I was asleep before 10 p.m., but I had proven my point: You can go home again. 

8. Seattle, Sept. 2017: Don’t let your stubbornness get in the way of doing things right

Somewhere along the way, things got a bit out of control. 

My cycling achievements became my excuse to become a bit too indulgent. If I biked 30 or 50 or 75 or 100 miles, that was all the reason to drink and eat and be just a bit too merry. 

These habits reached a critical point when my longtime friend Jared, who had flown down to do an LA-San Clemente ride with me earlier in the year, invited me up to Seattle, where he lives, to do some fall riding. 

That didn’t take much prompting, as I’d long envisioned making a triumphant return as a cyclist to a spot where I had lived for a few years.

But my Seattle trip turned into the weekend my indulgences caught up with me. We had an absolutely awesome, creative ride mapped out: A ferry across Puget Sound from Everett, followed by about 30 miles of cycling on Whidbey Island, followed by another ferry, followed by about another 50 miles on the Olympic and Kitsap Peninsulas, finishing on Bainbridge Island and a ferry back to Seattle.

Great ride, right? Well, yeah. But I drank close to an entire bottle of wine the night before the ride. And the ride had twice as much climbing as any ride I had ever done.

Up until this point, I had been cycling on a road bike with flat pedals and straps, not the clipless pedals used by nearly all distance cyclists. I noted how I struggled up Washington’s hills compared to my friend. Being hung over certainly didn’t help matters at all, but I also realized I had taken the pedals-and-straps approach beyond the point of usefulness. 

Struggling to keep up with my friend Jared on Whidbey Island.

It was a great ride through wonderful scenery -- there’s nothing like the Northwest in early autumn -- but the entire way, I pondered the realization I was shortchanging myself by not handling these rides right.

The ferry ride back to Seattle was amazing, even after I made a spectacle of myself by accidentally spilling a Rainer beer everywhere. As I gazed out at the Seattle skyline and Mt. Rainer as dusk approached, I vowed to myself I was going to correct my mistakes going forward. My stubbornness and poor choices kept this ride from being all it could be. I was not going to let this happen again. 

9. Death Valley National Park, Calif., Oct. 2017: A small change of plans can make a magic moment

I had one big ride left on my 2017 agenda after Seattle. Death Valley National Park is, without question, my favorite place in the whole wide world. The combination of extremes, of beauty, of isolation makes this place like no other. I had visited a couple times per year for nearly a decade before I felt the time was right to give a long ride a whirl.

I booked a couple days in the park in mid-October, which I knew would be a crapshoot: Maybe I’d catch the first semi-cold wave of the fall. Or I could still find sweltering temperatures.

The latter was indeed forecast for the day of my ride: A high of 95 degrees. 

DVNP is hard to reach. It’s not like you can just postpone a ride for another day after you’ve gone all the way out there. So the answer, if I was going to get in the 85-mile ride I envisioned in my head, was to get up a couple hours before dawn and get my miles in well before the sun took its toll.

The problem with this plan, as it turns out, is that biking solo in one of the world’s most desolate spots in pitch darkness is terrifying. Still, I set out around 5 a.m., unable to see anything beyond the 10 feet or so lit up by my headlamp, and went on my way.

Fear slowly gave way to a growing sense of exhilaration. I shoved aside thoughts of what would happen if my bike malfunctioned in the dark, with no cell service and nocturnal creatures about, and pushed forward.

About a half-hour in, I spotted one of the most breathtaking sights of my life to the East: a crescent moon, with the planet Venus as the morning star, framing the very first hints of daylight to the East, just enough light to accentuate the outlines of the mountains to the East.

The first hints of daybreak over Death Valley.

Next, I had what seemed like the entire desert to myself as the day dawned. No cars, no other cyclists, just me, the rising sun, sand dunes, salt pans, and sagebrush as far as the eye could see.

None of these magic moments would have transpired if the temperature hadn’t caused me to alter my start time. 

I didn’t get in my planned 85 miles that day. I had the good sense to cut things short once the temps got too hot, and finished at 61 miles. A second attempt this spring ended after 67 miles, with heavy winds the culprit this time.

One of these days, I’ll do my 85 miles in Death Valley, because I’m stubborn like that. But I don’t know that anything will ever top those first glimpses of sunlight, my reward for having the audacity to go bike in the heart of the desert on my own. 

10. Baja California, Mexico, May 2018: I am a cyclist

As the calendar flipped to 2018, adjustments became my priority. I had maxed out as a cyclist doing things in the manner I had. If I wanted to conquer some truly major goals, then 2018 was going to be a “take a step back to take two forward” year.

Friends had warned me I was likely to fall at least once as I got used to being clipped into my bike. I now have scars and bruises on my left elbow and knee which attest to this. The dumbest of my falls came in Oceanside at the end of a long ride. I needed to take a left turn at a congested intersection by the beach on a beautiful Sunday afternoon. Given how busy it was, I decided to simply walk my bike across rather than go with the traffic.

 As I pulled up to the corner, I went to reposition my bike to cross -- and forgot my left foot was still clipped in. I was able to process the cognizant thought “I can’t f---ing believe I just did that” as I made the slow motion fall to the pavement.

But I also found myself improving by leaps and bounds as a cyclist as I got the hang of the pedals. Hills which had been daunting were now tamed. I cut back on the wine and dropped 15 pounds in a hurry. When I signed up for the Rosarito-Ensenada ride, the length and height of the climb on the route map gave me pause, but not enough to prevent me from giving it a shot, anyway.

I’d like to do the AIDS Lifecycle ride from San Francisco to LA in 2019 or 2020. I’ve already entertained preliminary thoughts of cycling across the country for my 50th birthday. 

Can I get there? I don't know. My cycling accomplishments to date have helped me feel like I'm turning back the clock at a time most people start to slow down. I don't know how long that's going to last.

But I also never would have imagined the adventures I'd experience when I stumbled on CicLAVia in the first place.

Maybe I'll pull off my next set of big goals. Maybe I'll finally hit my ceiling as a cyclist. But I'm damn sure going to try.

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