An impulsive move that took thirty-five years: A conversation with Lili Dobert

Who is Lili Dobert? A psychotherapist from upstate New York who got her motorcycle license at fifty-three and ten years later rode into history on the first female-led Legacy Lap at the Isle of Man. Four bikes in the garage, a pit crew of engineers who don’t ride, and a habit of saying yes before she knows how it ends.

There is a community college two miles from Lili Dobert’s house in upstate New York. For thirty-five years she drove past it, and for thirty-five years she saw the same thing in the corner of the parking lot: little motorcycles, moving in slow circles, with people learning to ride them.

“I call it an impulsive move that took thirty-five years,” she told me.

Her kids were grown. And she did the math a lot of women in her generation never let themselves do out loud: if I die, they’ll be fine.

“My husband could take care of the kids. He’s a grown ass man. My other boys are grown ass men. Like, I can do it. They don’t need me anymore.”

So she signed up for the class.

“Honey, I need a helmet.”

“What do you need a helmet for?”

She didn’t have a bike. She hadn’t told anybody. She just went. After she passed, they rolled out with a brand-new Kawasaki Vulcan S.

I taught the range in Pennsylvania for years, and there was always one of her in the group. The older woman at the back, quiet, absorbing everything, replicating it with a precision the younger riders rarely showed.

“We come with this wisdom,” she said. “I don’t want to get bogged down with ridiculousness.”

After the class she accumulated five hundred miles of experience. Five hundred. Then she loaded up the Vulcan S and took a two-week trip to Nova Scotia.

Then COVID hit, a trip to Pakistan appeared as a blip on the Women Riders World Relay board, and Lili signed up for that too. She had never ridden dirt in her life. Not once. Liza Miller, running the thing, called her the wild card.

Husband comes home. Same doorway. Same script.

“Honey.”

“Now what?”

“I signed up for a trip to Pakistan.”

Here’s what gets me. I interviewed Liza months before I met Lili, and she told that story from the other side: one rider with no business being there on paper. She never used a name. I was on this call realizing I’d been hearing about Lili Dobert for months.

“I do better when I just wing it. If I have to think a lot about it, I freak myself out.”

The best ride of Lili’s life is not the Isle of Man. I asked her straight, expecting the Legacy Lap and she went somewhere else entirely.

Pakistan. The Himalayas. She and another rider, Arlette, missed a turn near a river crossing and rode forty-five minutes in the wrong direction.

They did not know they were lost, exactly. What they knew was that four boys on a single hundred CC motorcycle were riding alongside them, in sandals, on terrain Lili could barely handle solo. The boys said yes, this is the main road. And it was. It was the main road to their village, not the main road Lili & Arlette were supposed to be on.

Meanwhile, there is a rule: if you go ten minutes without seeing your group, you stop. Their guide, Moin, found them by riding up to villagers and asking if they’d seen two women on motorcycles. People just pointed.

“He goes, the rule was ten minutes. If you don’t see anyone in ten minutes you stop. And I go, I thought it was ten minutes. He goes, no, it was forty five!”

She was not scared. She has ADHD, loses track of time, and was, by her own admission, having a great time.

“That’s the ride I remember. It was dirt, it was in the Himalayas. It wasn’t touristy. Can you imagine riding a hundred CC motorcycle with four kids on it? I could barely navigate that road with me. And here he’s doing it with four people in sandals. Those are amazing riders.”

By the time the Legacy Lap came around, Lili had a role. Hayley Bell called her before the thing was even approved. Then Liza. Then a side group formed with Ruth and Dr. Amanda Knapp, and it snowballed.

Lili and Liza took the logistics. Specifically, the bikes. In the UK, theft is real enough that riders lug ten-pound chains around. Lili, who comes from a place where she leaves her helmet sitting on the seat without a second thought, took one look at that and said no.

So they researched. An underground garage in Liverpool. Motorcycle campsites in the middle of nowhere in Wales, one above a pub by a river. Another by a castle. Not once on the entire trip did they chain up a bike.

“So your legacy from the Legacy Lap is that nobody had to carry chains?”

“We carried the chains because the rental company made us but never once did we have to use them. Yes. Liza and I figured all that out. Imagine that.”

A win is a win….

The lap itself broke her open. She arrived feeling like the smallest person in the room. Carolynn Sells. Erin Sills. Liza, Hayley, Amanda.

“And who am I? I have nothing, other than I’m kind of friends with them. That’s all I have.”

Then they rolled out.

“I think it was five minutes in, the tears were rolling down my face.”

Because she looked at the side of the road, and it wasn’t what she expected. It was mothers. And it was little girls, placed deliberately at the front of the line so they could see. That’s the image she carries out of the whole week. A town lined with people, a curve coming up, and the children pushed to the front.

“I’ve never seen little girls out there before. That many, ever. In my riding of the ten years, ever.”

Ask who she was riding for and she’ll tell you it wasn’t herself.

“I think I was riding for a generation. There’s a generation, and let me call myself a boomer, whatever, that we did not have that permission to ride as a kid. It wasn’t even in my vocabulary.”

Her brother has ridden for fifty years. She has cousins who ride. Not one woman in the family, to this day, has thrown a leg over a bike.

“I stood at that edge for thirty-five years, because I’ve always wanted to do it. But I followed society’s prescription. And to be able to step over it, and we told those girls, you can step over it. It’s okay. And it’s not only about motorcycling. It could be anything in life you want to do.”

Where She’s Going Next

Colorado in September. And then, maybe do more in America. She grew up in Japan as an expat kid, moving through countries until she was sixteen. “I don’t want to say I know the world, but the world is my home. My childhood was living and moving from country to country: an international way of life.” Pakistan wasn’t a leap for her. The United States, oddly, is the frontier.

And when I asked what’s pulling her west...there’s a Navajo Code Talkers museum inside a Burger King in Kayenta, Arizona. “Burger King’s my favorite fast food and I want to know about this. This is how I think. Two in one. This is great.”

Typically I end a story with takeaways, but Lili actually wrapped this one up as we were finishing our interview, so I will let her take it from here.

“I just want to invite everyone to tap into their courage and curiosity in whatever you do in life, and have fun with it. And you might get there and say, ‘I like this,’ or, ‘ooh, I don’t like this.’ That’s okay too, because that gives you information about yourself. You’ve learned something really important about yourself.”