Riley Madaire: When the Breakdown Is Just the Beginning

Are you the type of person who strikes up a conversation with the traveler sitting next to you on a plane?

Well, I’m sure you can already guess that I most definitely am.

Making Friends at 30,000 Feet

When I was flying to Australia for my first solo overseas adventure, I sat in the aisle, and was beyond grateful when the plane closed its doors and no one was sitting in the middle seat. And even beyond that, I was thankful that the person sitting at the window was a girl around my age.

Obviously, I started talking to her, and learned that she was a twenty-three-year-old from Calgary, Alberta, that booked a one way flight to Australia.

During the flight, we talked about the personal adventures that were at our fingertips, we bonded over below average airplane meals and got each other’s contact information so that we could stay in touch.

Once we landed, we passed through immigration together, said our final (nervous) goodbyes, and then went our separate ways.

Since then, I have been following along on all of her epic adventures: van life, farm work, and major DIYs.

Fast forward twelve months, I asked Riley to tell me about a time she was “winging it,” and she didn’t hesitate. “I came to Australia with no plan,” she said. “I just wanted sunshine, adventure, and to see where life took me.”

No itinerary. No timeline. Just a van, a dream, and a whole lot of optimism.

Of course, as these stories usually go, there were some bumps in the road (literally and metaphorically).

The First Breakdown

Riley had been working in South Australia when she found her dream van for sale in Sydney. With only four days off, she headed North. But after picking it up and still being 400 kilometers from her destination, the van broke down. She called roadside assistance and was quoted $4000. Refusing to blow that kind of cash, she managed to get the van running (or stumbling) and made her way to a tiny town. The town was so small it didn’t even have a gas station.

Most people would’ve panicked. Riley? She headed to the only place open: the local pub.

There, over a beer, she shared her story with the locals. By the end of the night, everyone in the pub was rooting for her. Someone’s dad set her up for the night, made her breakfast the next morning, and even filled her tank, before sending her on her way. And somehow, when she turned the key the next morning, the van miraculously started perfectly. “It was very confusing,” she laughed. But this time, the universe just decided to give her a break, and so she carried on her way.

But the universe wasn’t quite done testing her.

The Second Breakdown

Not long after, she bought a new car, and within two hours of getting off the ferry in Tasmania, the clutch failed. Day one of a twelve-day trip, and they were stranded at a campground. Instead of losing it, Riley started laughing. “I’d already been through this once,” she said. “At that point, it was just absurd.”

After some persistence (and a few heated calls to roadside assistance), a tow truck finally agreed to take her car. The driver’s name was Tony. When Riley and her friend told him that they didn’t have plans while the car was being repaired, Tony grinned and said, “Well, I’m a pilot. Want to go for a ride?”

Naturally, they eagerly said yes.

That day, Riley and her friend soared above Tasmania’s northeast coast, flying over the Bay of Fires in Tony’s tiny plane. She even got to fly it herself. “It turned out to be one of the most unreal experiences of my life,” she said.

Winging It Daily – the Riley Way

Looking back, Riley told me that if there’s one thing she’s learned from all of it, it’s that you have to laugh at the absurdity. “If you don’t trust that things will work out, they probably won’t. But if you believe they will, somehow they do.”

With a sprinkle of optimism and a whole lot of embracing the unknown, Riley made the absolute most of two (car) breakdowns. What might have sent some people over the edge, ended up being some of Riley’s most cherished moments. She formed unexpected friendships, rediscovered the beauty of human kindness, and saw some of the most breath-taking views.

Would she do it again? Absolutely, although she admitted that she might actually get her car serviced first.

Because for Riley, winging it isn’t about recklessness. It’s about trust. It’s about saying yes when life throws you something unexpected, and remembering that sometimes, the breakdown is actually the beginning of the best part of the story.