This is the first installment in a new series about learning hard things as an adult—and the freedom that comes with letting yourself try.
When I rolled up to the range at my local community college in White Bear Lake, Minnesota, I was the only woman in a class of 10 men—and the only student with no prior motorcycling experience. My newness was so obvious, one of the instructors had to show me how to properly fasten the D-ring on the chin strap of my helmet.
I spent most of that first day trying—and failing—to coordinate the clutch and throttle on the stripped-down Suzuki TU250X that the Motorcycle Safety Foundation loans to students. Shifting gears felt impossible. I lurched, stalled, and barely made it into second. By the time I left, utterly humiliated, I couldn’t stop wondering: What on earth had I gotten myself into?
In the grand scheme of milestone birthdays, 44 is a nothing age. But turning 44 last December felt seismic because it kicked off what I’m calling My Year of Why Not?—a personal commitment to saying yes to things that challenge me, terrify me, or both.
Why not lift heavy like the gym bros? Why not try sex therapy? Why not learn how to ride a motorcycle? Doing hard things reminds me I’m still alive—and if we get only one go-round, I better make it count.
My obsession with motorcycling began on a lark last spring, when I set what felt like a modest goal: take a solo motorcycle trip to Badlands National Park and the storied Black Hills of South Dakota, places I’d only skimmed by car a decade earlier.
I kicked off this old-dog-new-tricks experiment by enrolling in the MSF’s Basic RiderCourse, a five-hour online class followed by two days of closed-range instruction. I’d ridden automatic scooters before and thought, How hard can it be? Then I learned that most motorcycles have manual transmissions. I was shaken.
One wouldn’t expect to sit down and play Ravel’s Gaspard de la Nuit or pass a Mandarin fluency test after a few hours of instruction—so why had I assumed this would be any different?
My husband tried to be encouraging, but he also clocked what he called “typical Ashlea behavior.” Whether I’m taking my toddler on a three-month trip around the world or diving headfirst into a new skill, I have a history of just assuming I’ll “figure it out”—a combination of ignorance, arrogance, and classic American optimism.
This time, however, I worried I’d gone too far. The fear was compounded by creeping mom guilt. You don’t belong here, I told myself. You should be home with your 3-year-old, making Pinterest art projects or whatever it is good moms do.
Then another voice chimed in.
No, eff that. You don’t have to give up everything adventurous in life just because you have a child. You can figure this out—and set an example for him in the process.
The next morning, I showed up to class with renewed determination. I went back because I want my son to see his mom do hard things—and to know that women can be strong and capable and also imperfect. That it’s okay to fail on your first or fifth or 87th try. Just shake it off and start again.
Day two went slightly better, but I still failed the license endorsement test. After sulking for a spell, I signed up for private lessons with Serena Rebechini, a local Rider Coach recommended through MSF. She’s warm, funny, and a take-no-prisoners badass who rides a gorgeous white 2020 Harley-Davidson Street Glide Special plastered with stickers tracking every U.S. state she’s ridden in.
“For women in particular,” she told me, “learning to ride is empowering. When it finally clicks, the opportunities that open up are endless. But the biggest thing is realizing, If I can do this, I can do other hard things too.”
We spent hours working on fundamentals—shifting, braking, U-turns—but also talking about work, motherhood, and life. She helped me untangle my despotic impostor syndrome and gently pointed out my habit of apologizing for every little mistake.
“Nobody expects perfection,” she said. “Men don’t apologize for stalling.” Some, she said, even “get fancy” on the range—leaning hard, scraping pegs, and demonstrating a bravado I’d be smart to channel when panic and self-doubt crept in. “Anybody can go fast in a straight line,” she reminded me. “The best motorcyclists are made doing slow-speed drills in parking lots.”
Overthinking, I learned, is the enemy. The more we tell ourselves we can’t do things, the more we start to believe it. Get in your head and you plant the seed for self-sabotage. At the end of each lesson, Serena instructed me to go home and tell my husband everything I got right that day. Nailed one U-turn out of 10? That’s the one I talked about.
The mindset worked—until it didn’t.
The next time I tested, the student ahead of me wiped out. When my turn came, I froze and then spiraled, knocking over a cone and failing again—tearful and shaking. I was furious with myself but also mortified to disappoint everyone rooting for me. The friends who’d sent “You got this!” DMs. My son asking where I’d been and me having nothing to show for it. I even pictured my late father shaking his head: Not only did his worthless daughter pursue journalism instead of going to B-school like he wanted, but she couldn’t even pass a silly motorcycle test.
I considered quitting. Repeatedly.
How do you know if you’re bad at something—or if you just haven’t practiced enough? When does perseverance border on delusion? What if the braver thing is simply walking away?
These were the questions I was wrestling with when, after a string of failed attempts and surprising new friendships, I flew to Baltimore for my first on-street riding lessons with Andria Yu, a former journalist and tai chi world champion I met through MSF. Between back-road rides, we bonded over our shared tendency toward self-flagellation and the unrealistic expectations we place on ourselves as adult learners.
Riding along the Patapsco River, on winding roads flanked by storybook greenery, I felt the self-loathing that had plagued me for weeks begin to loosen its grip. Getting out of the parking lot and into the real world changed everything—and reminded me why I wanted to ride in the first place.
I experienced a rush of firsts that weekend: my first left-hand turn in traffic, my first hill stall, my first ride in the rain. I met motorcyclists of all stripes, including a young woman who hides her passion from her conservative immigrant family. Most important, I left with clarity.
Goddammit, I thought. I really want this.
A week later, I bought a Halcyon Grey Royal Enfield Classic 350, which Serena helped me pick out. On my first solo ride, I hit 65 miles per hour—a euphoric, full-body rush.
The rest of the summer was a blur of wins and losses. I practiced endlessly. I failed more tests. Once, a goateed biker with 20 years’ riding experience failed alongside me. The quest felt Sisyphean, but I was nothing if not resolute.
By the time I boarded my flight to Rapid City in late September, the performance anxiety had given way to sheer excitement. South Dakota had always been the plan, but I no longer wanted to ride solo. I was thrilled to be joined by Andria and her free-spirited MSF colleague Rachel Lepley, a London-born, Montana-based moto influencer who gets wild hairs to do wild things like ride across 48 states in 48 days.
The three of us covered 421 miles that week—gawking at bison in Custer State Park, stopping for goofy jump shots in front of Mount Rushmore, and riding through Badlands National Park, with cliffs so towering we felt like mice among men. With the sun on my back and wind at my neck, I screamed into my helmet: “I did it! I did the thing!”
As if on divine cue, my dad’s favorite song—Chumbawamba’s “Tubthumping”—came on my playlist. I get knocked down, but I get up again.
At our hotel in Rapid City, a woman in her mid-60s approached us. “I’ve always wanted to ride,” she said. “But my parents said it was too dangerous.” Her brother, she noted, had been encouraged. “Now I’m too old.”
We disagreed. “It’s not a question of ‘Can you do it?’ ” we said. “It’s ‘Will you try?’ ”
Not every adventure unfurls the way you imagine. The learning curve for motorcycling was far steeper than I expected, but I’m grateful for every setback. If I hadn’t failed, I never would have found this fierce cadre of women riders I’m now honored to call friends.
Soon after I bought my bike, Serena suggested I name her. I settled on Rana—a blend of Serena, Andria, and Rachel. Without their tough love, I wouldn’t have made it this far.
After South Dakota, I bought myself a gold ring engraved with six words: I can. I will. Watch me. I wear it on my middle finger—naturally—and carry that radical attitude into 2026.
Motorcycling is only the beginning of my Year of Why Not? I’ll also be learning to ski, box, ride dirt bikes, dive shipwrecks, ranch cattle, and—hardest of all—sit alone with my thoughts. It will be messy. It will be glorious. I won’t succeed at everything, or possibly anything, but at least I’ll know I tried.
And maybe—just maybe—you will too.
What do you have to lose?
