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Most people who ride a bike can remember, with the clarity of a spring morning, the moment they fell for cycling. Two strong thoughts linger in my mind about my first real ride, about six years ago, as I was already climbing the hill of my forties. The first was: Where has this been all my life? The second: What an absolute dork I was.

For journalistic reasons, I was due to ride about 65 miles with a seasoned rider. A metric century seems, now, like the barest threshold of a decent day out. But for someone accustomed to short urban commutes, I had trouble comprehending the figure: OK, so I’ll take my usual run down to the coffee shop and multiply it by …40?

I showed up on my 18-speed flat-bar hybrid bike, wea­ring sneakers, some vaguely athletic (but hardly form fitting, and certainly not padded) shorts, and a backpack. Among the things I had neglected to bring were: Water, nutrition, a spare tube and pump, and anything resembling the fitness to ride more than two miles. My host looked at me with polite condescension. “I’ve got a spare bottle for you,” he said cheerily (even as his face read: Oh dear), “and we’ll stop for bagels.”

As I limped home, I knew I was hooked. I felt I had discovered some secret vice that turned out to be virtuous. But I also immediately knew I was out of my depth, that I was a total noob. A kook. A patzer. A Fred. A Barney. Or whatever word for novice you want to employ.

It is never easy being a beginner, but being a beginner at an age when you are supposed to be at the peak of your professional and life powers, is especially hard. And road cycling — not just riding a bike but a riding the right bike the right way — seemed to have a particularly daunting learning curve. Soccer, by contrast, which I had been playing recreationally for years, seemed easy. You just threw on some cleats and showed up and tried to kick the ball in the back of the net.

But cycling seemed like an endless series of decision trees. I needed a proper bike. Did I want a race bike, or something with more relaxed geometry? Did I want aluminum, carbon fiber, steel or titanium? Shimano, SRAM or Campy? What was my preferred tire width? (“Um, you know, not too wide, but not too thin”). What sort of pedals did I want — and wait, don’t they just come with the bike? Then I grappled with what to wear. I was not even close to knowing about debates over sock heights and the like, but I still felt overwhelmed. And so I bought “bike shorts” (not of the bib variety) and a fluorescent top — a veritable badge of my beginnerdom, as much as the chain-grease stamps that would soon be blossoming on my calves.

If I had only had some sage counsel to walk me through all of this, I might have avoided some of the ignominy that was to follow. But I just wanted to get out there, and wasn’t getting out of one’s comfort zone the whole reason for trying new things? And so there it was, that inaugural outing, one Saturday morning. It wasn’t even a ride, actually, just me wheeling my bike to the park across the street. First, so I could simply get used to the idea of wearing micrometer-thin pajamas in public, out amongst the old ladies pushing shopping carts and the brawny construction guys drinking coffee on the neighboring stoop (at least I had not yet shaved my legs). The second, so I could practice clipping in and out of my weird new pedals (which, confusingly, were termed “clipless”).

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But I slowly put together the barest façade of competence, and soon felt emboldened enough to join (for a magazine assignment) a “ride with the pros” event at Blackberry Farm in Tennessee. I was thrust into a large paceline for the first time — good thing it was on wet mountain roads! — and I tried to chat casually with my neighbors, even as I tried to grapple, internally, with the sickening realization that I was meant to ride within inches of the person in front of me and be totally cool with it. Of course, like many new riders, I wasn’t cool with it, and kept slipping back, losing touch — when I wasn’t overcompensating by dangerously half-wheeling the person in front.

“Oh, you’ve got a triple,” a fellow rider noted early in the ride. “Yeah,” I said, quickly realizing he was referring to the triple chain-ring on the bike the outfitter had equipped me with. Not only did I not yet know it was a device held in some contempt by hardcore riders, I had not even noticed I had one. A few minutes later, I realized I had forgotten my sunglasses. You moron. Perhaps no one would notice.

My veil of nonchalance was immediately shattered as the rider next to me, a doctor, immediately piped up. “Your eyes could get really dried out, and you could get road debris in your eyes.” I imagined a whispered chain of communication up and down the paceline. “Dude forgot his sunglasses. And he’s got a triple.” Just then, Christian Vande Velde rolled alongside and very gallantly offered up a nice pair of Oakleys. Not long after we, hit a section of the ride called “The Wall,” a big, unforgiving upward slog through the Smokeys. Even my triple couldn’t keep me off the back. The ride leader dropped back and asked if I was OK. “Yeah, but this driver behind is creeping me out. He just won’t pass.” “Oh, that’s the sag wagon,” he said. “Right, of course,” I said. Please get a clue, you pathetic donkey.

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On the many rides after that, there were any number of further foibles. Let us run the highlight reel. There was the time on that big multi-state charity ride, in early spring, where I opened my swag bag to find a jar of “embrocation,” a term that was new to me. “Keeps your legs warm,” my roommate said, as he removed wadded newspaper from his wet shoes. “Sounds good,” I said, proceeding to apply it, then adding my full-length winter bibs on top of it. I was more than warm: For the next hours I felt like a piece of raw fish that had been dropped into citric acid, a piece of human ceviche in lycra.

There was the time my ill-secured saddle bag fell off my saddle, nearly bringing down the cursing rider behind. There was the time I accidentally put my sleek carbon fiber water bottle cage on upside down. “Weird thing,” the mechanic who spotted it said, “it still works.” I unknowingly left “pie plates” on my rear wheels, and did not discard the nuts and caps from my valve stems (both no-nos).

I ploddingly changed flats (new bike builds have been done in less time) only to get another one two minutes later because I had overlooked the tiny shard of metal in the tire. After changing flats, I left the front wheel skewer open, and only divine providence kept me from not attempting a bunny hop or something that would have liberated bike from wheel. I would dodge a pothole at the last second, feeling smug, then suddenly shrink as I heard the hollow thwack of carbon being pushed to its stress-fracture limit as the rider behind screamed “fucking call it out!”

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And then, with this string of successes notched on my belt, I started racing. If you thought novice cycling was bad, novice bike racing takes it to a whole other level of stupid. There was the time, after finishing one event, that I put my bike on my roof rack and then pulled away – leaving the front wheel lying in the long grass (this Zipps for you, bud!). There was the time I rubbed against someone’s wheel and went down — a few moments after the neutral start vehicle began to pull away. There was that first race at Brooklyn’s Floyd Bennett Field, where I came around the turn on the last lap and launched a heroic solo sprint for the win, thinking I got this, then running out of gas precisely 400 yards short of the finish, ending up near last as the peloton roared past.

Being new to cycling was exhilarating — there was a whole new vast world of possibility stretching out in front of me. But it came with a cost: These constant slings and arrows, these injuries to my pride (and occasionally body and bike). Strangely, that is part of what made it feel so good; the best learning, after all, comes from mistakes. When it feels easy, you are not improving. Years later, at another charity ride, when I had a swish loaner bike and was at peak svelteness, someone told me they had assumed I was “one of the ex-pros.” I felt a massive rush, as if I had truly arrived. And then a real pro yelled me at for my poor placement in the paceline.

Tom Vanderbilt is contributing editor at Outside and Wired U.K. and author of the books Traffic: Why We Drive the Way We Do and You May Also Like: Taste in an Age of Endless Choice. João still yells at him for cross-chaining.