Neighbor­hood reps
Neighbor­hood reps
Neighbor­hood reps (Jessica Chou)

My Month of Doing 100 Wheelies a Day


In her quest to master a quintessential cool-kid trick, Outside contributor Kim Cross found the sweet spot at the crossroads of work and play


A wheelie is the bicycling equivalent of hanging ten on a surfboard or spinning a basketball on your finger—a skill as profoundly cool as it is functionally irrelevant. Pedaling around with one wheel in the air won’t help you win a race or bomb a gnarly descent. Unlike a front-wheel lift or a bunny hop, it has no business on a trail. 

What the wheelie lacks in utility it makes up for with pure, unfiltered radness. There’s something thrilling about a skill that isn’t a means to an end but the end itself, whose value in doing it is just doing it, simply because you can. Yet it’s more than showing off. It’s about seeking an elusive, almost mystical state of precarious, dynamic balance. You’re chasing a sweet spot, a moving target that’s constantly shifting in every dimension, including the one inside your head. 

In 20 years of mountain biking, this skill has always eluded me. So in January 2020, I hatch a plan: 100 wheelies per day for 30 days—3,000 attempts, all told—spread out over two or three months. I’ll consult some experts about technique, but mostly I’ll just put in the work. And I’m willing to fail prodigiously. 

How will I define success? The ability to wheelie indefinitely, until I choose to put the wheel down. I’ll simultaneously tackle the manual—a different method of one-wheeled cruise control—because maybe the moves will inform each another. And also because: Why not? 

It’s a juvenile pursuit for a professional writer with a mortgage and a 12-year-old boy. There are more productive uses of my time. But maybe, just maybe, there’s some value in tilting at your own quixotic windmill.

Project Wheelie begins at Idaho’s Boise Bike Park, in a session with my friend Kenny Woodall. Kenny is my age, but he rides with the effortless finesse of someone who grew up on a BMX track. 

My son tags along. A seventh-grader, Austin is transitioning from building with Legos and waging Nerf wars to building bike ramps and playing Metallica riffs on the guitar. He races on his middle school mountain-bike team and has stood on a podium more than once. But he’s still learning the meaning of the famous adage “Hard work beats talent when talent doesn’t work hard.” 

I’m riding my favorite rig, a full-­suspension Yeti SB5 with 27.5-inch wheels. On Wheelie No. 1, I execute the technique I’ve been taught in the past: I punch the pedal, straighten my arms, and lean back. The front tire rises off the ground two or three inches. After a few more tries, the wheel floats up to eye level, hovers for three or four pedal strokes, then thuds onto the ground. Kenny nods, poker-faced. 

Next we take stock of my manual—a more difficult maneuver. It involves standing on the pedals while the bike is rolling, shifting my weight behind the saddle, and lingering in the “float zone” by moving my hips from front to back. Unlike the wheelie, the manual is done at speed—­riskier and therefore scarier. When I watch teenage boys manual the waves of dirt on a BMX track, a little voice whispers, Maybe in your next life.

But it’s worth a try. Coasting downhill at a jogging pace, I pop the front wheel too enthusiastically and “loop out,” flipping the bike past vertical on the rear wheel. I leap off the pedals and land on my feet, but I’m moving so fast that I stumble, throw the bike, and grate my knee on the ­asphalt. Kenny looks concerned.

By Wheelie No. 60, my arms and legs feel like overcooked pasta. Other riders swirl around, executing manuals with disgusting ease and Mona Lisa smiles. Kenny says the last thing a frustrated novice wants to hear.

“Just keep practicing.”

Cross takes a water break while practicing manuals on the dirt jumps at Boise Bike Park.
Cross takes a water break while practicing manuals on the dirt jumps at Boise Bike Park. (Jessica Chou)

The wheelie has been vexing riders since the late 1800s, when the penny-farthing—with its giant front wheel, tiny rear wheel, and saddle four feet off the ground—gave way to the more user-friendly “safety bicycle,” with wheels of equal size. 

The father of the wheelie was a telegraph messenger named Daniel J. Canary, a “fancy riding” champion who figured out how to coax the penny-farthing’s rear wheel off the ground. In August 1890, he used a safety ­bicycle to pull off “the feat, then regarded as impossible, of riding on his rear wheel, with the front wheel elevated.”

That’s how the Chicago Tribune described the wheelie in 1896. The article, titled “Wizards of the Wheel,” chronicled the origins of “trick riding” and noted why the discipline had but a few bold pioneers: “The union of strength and agility with perseverance and self-confidence is not common enough among men.” (It said nothing of women.)

“Like the art of the contortionist, trick riding requires an extraordinary suppleness of body and limb,” the author wrote, adding something that rings as true today as it did 125 years ago: “United with this must be the patience and perseverance for long and unremitting practice.” 

Extraordinary suppleness is overrated. Those last four words mark the difference—then and now—between Wizards of the Wheel and wannabes.

It turns out that long and unremitting practice hurts. After day one, I feel like I’ve been flagellated with bars of soap in tube socks. I quickly call upon some experts. 

Lindsey Richter, founder of the Ladies AllRide women’s mountain-bike camps, says the wheelie is primarily about torque—getting the back wheel to accelerate with enough power that the front wheel rises. To make this happen on a motorcycle, you either rev the engine and dump the clutch, or simply rip open the throttle. On a bike, it’s a seated, slow-speed procedure initiated by a powerful pedal punch. Your arms don’t lift the front wheel, she says, so much as they “encourage it.”

Braydon Bringhurst, a Canyon Bikes ambassador who can land a backflip in a wheelie, instructs me to drop my saddle two inches, lowering my center of gravity, and practice by placing two objects—cones, rocks, gloves, whatever—a few feet apart as a ­target distance. Once I can wheelie that eight out of ten times, he says, I should move them farther apart.

When I watch teenage boys manual the waves of dirt on a BMX track, a little voice whispers, Maybe in your next life.

From my buddy Lance Trappe, who rode for Cirque du Soleil, two shows a day, 478 shows a year, for 14 years: Move your knees from side to side for balance. Also, practice on a smooth surface and an uphill slope. But the secret sauce, he says, is the rear brake, which brings the front wheel down to guard against loop-outs. 

So my mission for the next few hundred wheelies is to train my right index finger.

Not to brag, but I have an extraordinarily supple index finger. It can strum a guitar, pull a trigger, deadhead daisies, maneuver a paintbrush, give directions, and pick anchovies off pizza. It knows damn well how to feather a brake. 

But something short-circuits when my front wheel takes flight. All I ask of my digit is a crummy millimeter or two of precise modulation. Under pressure to save me from looping out, it chokes. I spend hundreds of wheelies yelling at my finger like a drill sergeant. It’s as useless as a football bat. 

Meanwhile, the manual seems even more hopeless. After my crash, I buy knee pads and practice on a baseball field. The grass scrubs my speed, which makes my handlebars wobble. I land on a turned front wheel and am ejected into left field, where I pick dead grass out of my teeth. 

At the next session, Kenny arrives with two gifts: a full-face helmet, donated by a buddy who works at Fly Racing, and the suggestion to look into a manual machine.

A manual machine is basically a float-zone simulator, designed to help you locate the balance point while a static contraption holds your rear wheel safely in place. Sender Ramps, a company in Seattle, ships me its Core Skills Trainer manual machine, which Austin and I assemble with a power drill and minimal bickering.

In the safety of the garage (my husband vetoes the living room), I find the balance point after six tries on the manual machine. The sensation reminds me, unexpectedly, of my days as a competitive water-skier. My muscles begin to memorize the dance of opposing forces—pulling on the handlebars, pushing against the pedals—and the hip action that occurs in between, a quick and thrusty motion that mortifies my husband when I mime it in public. 

The manual machine bewitches my son, who sees it not as a training tool but as a giant toy. Austin suddenly opts in to the wheelie quest. Like most kids, his athleticism far exceeds his patience, and any skill that doesn’t come easily is soon crabbily abandoned. But as we try and fail, heckle and laugh, I notice a new quality sprouting within him: perseverance. 

When the pandemic hits in March, wheelies become therapy. The bike park shuts down, so Austin and I practice in the street, where we’re cheered on by neighbors. Our ritual gets my kid out of the house and me out of my anxious head. 

My first big breakthrough comes with Wheelie No. 681. I enter the sweet spot—and stay there, for 12 pedal strokes. My gleeful cackle is a noise I haven’t heard in a while. The stoke rubs off on Austin, who also has a quantum leap in the float zone. 

When I head to a mountain cabin for a writing retreat a week and a half into the challenge, I bring my bike and practice alone in the snow. On the edge of a frozen lake, with a light post as my target, I keep Wheelie No. 1,086 in the float zone for what feels like an eternity. After, I pace off the distance, counting each stride: 17 steps, around 34 feet.

At the bike park
At the bike park (Jessica Chou)

When I return home, the air in the house is prickly. Quarantine living has lost its charm. Austin joins me for day 14, but his surly attitude curdles my mojo, and we both regress. He challenges me to a duel on the manual machine, which he’s been training with all week. When I win, he sulks for hours. 

We find a new practice spot for wheelies, one with a mellower slope. I place my gloves 17 paces apart, but I can’t even make it halfway. My brake finger is finally doing its job: I haven’t bailed off the back in hundreds of tries. But now, instead of freezing under pressure to save me from looping out, it has become trigger-happy. My front wheel slams down repeatedly. 

This off day is followed by another off day. Then another. And another. Austin and I both seem to be going backwards. Meanwhile, I throw out my shoulder, either from overenthusiastic manualing or by shoveling a cubic yard of gravel. Unable to lift my right arm, I have to put manuals aside. I’m frustrated, discouraged, and mopey. I can practice wheelies, but now they feel like work.

My confidence has eloped with my pride, but I still have tensile faith. I have learned the hard way, from competing in more than ten sports, that skill building is a nonlinear process. Big breakthroughs often happen after long plateaus punctuated by setbacks. Harder feats require more repetition—and more failure. 

When I was Austin’s age, I obsessed over learning a backflip on a trick water ski. It was still a relatively new feat in the sport, and only a few elite women had mastered it. I fell eight to ten times every training day—brutal spills that left me seeing stars—for five years before I landed my first flip. If my math is right, I failed at least 6,500 times before my first success. It took several thousand more falls before I perfected the move and nailed it at the national championships. 

But that was more than two decades ago. Now I’m a middle-aged mom trying to resuscitate her inner badass without alienating her son. 

As a kid, Austin has an advantage in our wheelie quest: superior neuroplasticity—the brain’s ability to reorganize itself in response to new demands. What we call muscle memory is actually the strengthening of neural pathways. The greatest window of opportunity for learning new motor skills opens during youth, when your gray matter and synapses are increasing in size and number. Neuroplasticity peaks in your twenties, then declines with age, making it harder for older dogs to learn new tricks. Which means I’ll need more practice than Austin.

While age may not be in my favor, I refuse to call it my foe. I’m with the Irish playwright George Bernard Shaw, who said, “We don’t stop playing because we get old—we get old because we stop playing.” In my thirties, I learned to do headstands on a paddleboard, at night, in the Gulf of Mexico. For my 40th birthday, I taught myself a backflip on a trampoline. I know I have the ability to master the wheelie—eventually.

But I also know that the price is long and unremitting practice. 

And I ask myself: Is it worth it?

Austin nailing a wall ride
Austin nailing a wall ride (Jessica Chou)

Halfway into my experiment, I dis­cover Ryan Leech’s 30-Day Wheelie Challenge. A 41-year-old Canadian professional mountain biker and coach, Leech has produced more than 600 coaching videos, available with a subscription through his website. When the world shuffled into quarantine, he generously made his wheelie course free. Around 20,000 people signed up. 

The course builds the skill through a smart progression of drills and movement patterns. I’m energized and hopeful. But by day 23, I’m nowhere near my 34-foot record from day 11. Most days I’m either spinning in place or backpedaling.

Leech is not surprised. 

“You’re getting in your head and getting frustrated,” he tells me during a video chat from his home in British Columbia. “It feels like you’re further away from the goal than when you started.”

This insight can also help describe the status of his own quarantine pursuit: learning to juggle four clubs. It’s a skill he’s been trying to master for years, stuck on an endless plateau. This part of the learning curve can feel like failure—unless you keep going.

“It’s the fight-or-flight moment,” he tells me. “Most people give up and create the belief that ‘Oh, I don’t have the wheelie gene.’ Those who fight turn their way of thinking into ‘OK, this is just part of the process.’”

But what’s the point, I ask, of spending so much time and energy on a useless skill? 

“These things are extraordinarily healthy for the brain,” he says.

Leech is right. Research has shown that learning to juggle increases the density of gray matter—the brain’s computational infrastructure, which declines with age. The process has also been found to change the architecture of white matter, which shuttles messages between different parts of the brain. Other studies suggest that these changes are not unique to juggling but are also involved when learning any new skill, regardless of real-world utility. And the degree of neural improvement has little to do with the level of skill acquired. In other words, it doesn’t matter how accomplished you become as long as you’re learning. At least I’m flexing my gray matter. 

“When did you learn how to wheelie?” I ask Leech. “How long did it take?”

“I was a teenager,” he says. “It was a ­couple-year journey.”

Wait a minute. It took Ryan Leech—and his teenage neuroplasticity—two years to master the wheelie? 

At the start of this experiment, 3,000 wheelies seemed like a lot. But with an average of 100 wheelies an hour (or a half-hour if I’m rushing), the 30-day effort amounts to less than a standard workweek. 

Even Cirque du Soleil Lance didn’t learn to wheelie overnight. He says it took “many hundreds of times” over “many months” before he mastered the skill as a teenager. 

And then he kept at it. On a typical workday at Cirque, he performed about seven wheelies. Over a 14-year circus career, that’s 46,844 wheelies. And he still practices every week.

The Frog Pond
The Frog Pond (Jessica Chou)

In the final days of Project Wheelie, I struggle to huck myself up off the plateau. My grim tenacity kills the vibe, and soon I’m alone. When the fun stops, so does Austin.

I ask my son what made him decide to join my quest in the first place. 

“You looked so lonely doing them out there all by yourself,” he says with a mostly straight face. “I wanted to spend time with you.” 

An infinitesimal twitch in his nostril triggers my bullshit-ometer. 

“Are you sure you just couldn’t let your mom out-wheelie you?” I ask. 

“Noooooo!” he protests.

The nostril says otherwise. 

This is when I realize that as much as I long to master this skill, there’s something I want even more: to have Austin along for the ride. 

So I lighten up. We make a pact to prioritize fun over discipline. When the wheelies aren’t going swimmingly, we stand on our saddles or ride with no hands. We cross-train for balance by monkeying around on a slackline, an Indo Board, and a makeshift trapeze hung from a tree. We juggle tennis balls. A neighbor offers us stilts and a pogo stick. The front yard becomes a circus crossed with an American Ninja Warrior course. He picks me purple flowers and I stick them in my braid. 

I’m frustrated, discouraged, and mopey. I can practice wheelies, but now they feel like work.

A filmmaker pal asks to capture our final session on day 30. Austin is grumpy and tired, and he doesn’t feel like doing wheelies. But it’s the grand finale, so I drag him out. It wouldn’t be the same without him. 

As the sun paints the foothills gold, I have yet another ho-hum session, still maxing out at six or eight pedal strokes. 

Austin, meanwhile, has a breakthrough. 

Under pressure from the camera and a hovering drone, Austin wheelies out of the shot, up the hill, and off into the sunset. Afterward, he paces off the distance: 43 strides, more than twice my personal best. I may be growing gray matter, but Austin’s wheel is growing wings.

“My form isn’t perfect here,” Cross says. “My arms could be straighter, my hips farther back. But I found manualing between dirt jumps much easier than on flat ground.”
“My form isn’t perfect here,” Cross says. “My arms could be straighter, my hips farther back. But I found manualing between dirt jumps much easier than on flat ground.” (Jessica Chou)
Austin and a frog
Austin and a frog (Jessica Chou)

When our wheelie quest ends, Austin starts teaching himself some new skills of his own—gapping dirt jumps, tail whips on a scooter, Metallica guitar solos—by practicing over and over and over.

I come away with the competence (and, more important, the confidence) to work on wheelies at the now reopened bike park, where I’m occasionally mistaken for a teenage boy in a full-face helmet. There, about six months after the end of Operation Wheelie, something surprising happens. 

The manual has been back-burnered for months, but I decide to give it a go on the dirt jumps. On my second attempt, I nail it. With a dozen more tries, I own it. Now the jump line, the trail, and every dip in the dirt begs to be ridden on one wheel. 

In learning to do a manual at full speed, I achieved one of my boldest pipe dreams. Like learning a flip on a water ski, one of the hardest parts was to believe, all evidence to the contrary, that I would succeed. 

But ultimately, it was the combination of practice and play that made the manual possible. After establishing the skills, I had to embrace the spirit of childlike imagination to even attempt something that otherwise seemed impossible. 

This revelation hit me months before, on day 27. In the middle of a 100-wheelie session, the quest started to feel like a chore. For the first time, Austin and I ditched The Plan. Instead, we roved the neighborhood like kids playing hooky, hopping curbs and popping wheelies, not bothering to count them.

“Mom, I want to show you something,” Austin said. “We’ll have to stash our bikes.” 

We stuffed them in some bushes and crawled through a tunnel of shrubs. We emerged into a clearing with a little pond choked by cattails. 

“This is the Frog Pond!” he whispered. 

The Frog Pond! Here was the carefully guarded secret spot where he came with his friends to capture frogs and poke at snakes. I had never known its location. It felt like some magical otherworld where adults aren’t allowed, where children reign and anything is possible. Like Neverland or Narnia.

Austin showed off a homemade tree swing—a fallen limb hanging from a frayed rope. It looked like a one-way ticket to the emergency room. But at his urging, I climbed onto the dangling branch, polished smooth by countless pioneering butts. Austin gave me a push, and I swung into the float zone.

That moment has nothing to do with wheelies and everything to do with wheelies. 

For years I’ve wondered when, if ever, I need to start acting my age. But what if play is a portal to some part of us that, like baby teeth, gets lost in the process of growing up? 

Maybe Neverland is a frog pond. Maybe the doorway to Narnia isn’t a wardrobe but a wheel, spinning free in the sky.