Before enlightenment, get on and pedal; after enlightenment, get on and pedal. (Photo: Stephen Matera/Tandem)

The 6 Stages of Cycling Enlightenment

Before enlightenment, get on and pedal. After enlightenment, get on and pedal—but we do pass through several transitional phases along the way.


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There’s a Zen saying, you’ve probably seen it online superimposed onto a photo of a sunset:

Before enlightenment, chop wood and carry water; after enlightenment, chop wood and carry water.

The same thing applies to riding bikes. Before enlightenment, get on and pedal; after enlightenment, get on and pedal. But we do pass through several transitional phases along the way before arriving pretty much where we started.


Think about when you first fell in love with riding bikes—not necessarily when you learned how to ride a bike (though it could have happened as early as that), but when you really began to appreciate that one way or another that this was going to be your primary recreational pursuit going forward. For me, even though I grew up riding bikes and racing BMX, I really began to understand this in college, when I started heading out for longer road-ish rides just because. Career, relationships, money—I had no idea what the hell I was going to do about any of that once I graduated, but at least I’d figured out how I’d be spending every one of my weekends for the rest of my life.

When we do have this moment of realization, we all look ridiculous, at least by the arcane equipment and sartorial standards that inform our sport. In my case, I was riding a hybrid that was at least a size or two too big, pedaling in sneakers, and shielding my eyes from the sun with a pair of gas station wraparound sunglasses. When it got too hot I took my shirt off and put it in my fanny pack. (This was decades before the fanny pack underwent a dorkiness inversion and finally became cool.) A shirtless guy on a hybrid wearing a fanny pack is pretty much the epitome of velocipedal cluelessness, but I felt great, and I was too stupid to know better.


Adam and Eve once frolicked naked in the Garden of Eden, then they ate from the Tree of Knowledge and felt shame. Similarly, when roadies passed me in the park, their matching kits bearing the names of sponsors and their shorn legs glistening in the sun, I looked upon my sneakers and my bare torso and despaired. Granted, there are some riders who never experience this embarrassment, either because they were born into a cycling tradition, or because they don’t have whatever pesky gene that causes self-consciousness. However, for the majority of us, there’s a painful period during which we realize we’re doing it all wrong, and we want nothing more than to get it right.

Hunting and Gathering

As you ride more, learn more, consume more bike-related content, and begin to follow the elite levels of the sport, a Platonic ideal of what a cyclist should be begins to form in your mind, and the considerable gap between it and you can weigh quite heavily on your brain. In my case, this compelled me to work as a bike messenger, and ultimately to race, which at the time seemed like the purest expression of my love for cycling.

Regardless of whether you take up racing, or bikepacking, or bikerafting, or any other all-consuming bike-based pursuit, when you truly love riding your bike, components and clothing and techniques that promise to heighten the experience are profoundly tempting; a wheelset that once would have seemed unthinkably expensive now seems absolutely necessary. Spending a week’s pay on a pair of handlebars soon seems eminently reasonable, and you implement austerity measures in other aspects of life in order to acquire all the stuff it takes to make riding a bicycle as close to perfect as it can be.

But it’s not just about the stuff. In addition to wanting to have, you also want to do—the big miles, the epic bikepacking trip, the leg-and-lung-searing gravel race. Strava overtakes Facebook on your Social Media Importance Pie Chart. You binge on riding experiences, and when you’re not riding you’ve got 15 browser tabs open and are binging on other people’s riding experiences while you’re supposed to be working. It’s a period of intense transformation, as both your physique and your bank account are stripped of their excesses and you learn how to run lean.


In [insert your favorite war movie here], the hero arrives at boot camp a naive recruit, but he’s soon trudging through the jungle with a pack of filterless cigarettes in his helmet strap while making sardonic comments with an M-16 slung insouciantly over his shoulder. This is you now, out for a quick 60-miler to shake out the legs from yesterday’s big ride. Those well-equipped riders no longer look intimidating—now you know half of them, and you nod subtly as you pass. As for the new recruits on their pie-plated road bikes and ill-fitting internet fixies, you know what lies in store for them, and you smile bemusedly to yourself as, in your mind, you see a brief flicker of the rider you used to be. Then you take both hands off the bars, stretch, take a drink, and get in the drops for the descent.


The feeling that you’re finally locked into the cycling lifestyle is intensely satisfying, like clipping into the pedals for a long ride on a beautiful day. But it can also get…boring. Not the riding of course—that part never loses its luster—but everything that comes with it. The matchy-matchy clothing, the scrupulous data recording, the genre bicycles each in their neat little boxes: road, mountain, gravel. Whereas you once saw the well-turned riders and coveted them, now they seem almost comical in their conformity. Slight variations in seasonal jersey patterns only enhance their sameness, and tire widths go in and out of fashion like men’s neckties. You’re no longer tempted by the newest and latest stuff, and you’re letting your equipment wear in and even wear out before replacing it, often with something cheaper. Why even bother trying to keep up? It’ll come back in style sooner or later anyway.

Devouring miles becomes less of an imperative, too; you’re riding just as much, but you’re savoring it rather than binging on it. Having tried and failed to quit racing in the past, I know how hard it can be to stop turning yourself inside out over and over again like an old sweatsock. But eventually you become okay with stopping every now and again, and with sitting up and letting the rider ahead of you go. “What’s the big hurry, anyway?” you ask yourself. The faster you go, the sooner the ride is over.

In my own experience, you know you’ve reached the disenchantment phase when you start feeling silly in Lycra.


You’ve changed, and your bike has changed. You no longer need to be stretched out over your cockpit, and your bicycle and wardrobe reflects this. At first glance, an actualized rider might mistake you for an innocent, riding an unremarkable upright bicycle with a metal frame while wearing casual clothing and footwear. But you’re no innocent. You’re now the incredibly rare rider who can transition seamlessly between life on and off the bike. Not only are you as comfortable on the bike as you are on the couch, but you wear pretty much the same thing in both places. For you have learned one of life’s greatest secrets: If you ride a bike in flip-flops and a T-shirt, even for long distances, not only will you survive, but you’ll also be totally comfortable.

As for me, I’d never presume to call myself enlightened, but I do look more like my innocent self than ever these days, and I’ve never been happier. The main differences are that my bike fits me now, and when something goes wrong with it I usually know how to fix it.

Oh, I also don’t ride shirtless—but hopefully I’ll get there eventually.

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Lead Photo: Stephen Matera/Tandem