Lessons From Going Paragliding With My Uber Driver and a Stranger From the Internet

Every connection has the power to impact and to unite people.

Paragliding in Medellin, Colombia with my Uber driver and a stranger I met on the internet

Life’s best moments aren’t always planned. They’re the ones that sneak up on you mid-trip, mid-day, mid-"what am I even doing right now?" and you can’t help but smile at the magic of it all.

One of those moments found me one summer in Colombia, paragliding with a stranger I met on the internet... and our Uber driver.

It turned into one of the most memorable experiences of my life, not because of the paragliding itself, but because of the reminder it gave me: Sometimes it IS in our power to turn an ordinary day into an unforgettable one… IF we give ourselves a chance.

We Can Make Our Own Surprises

A few years after the COVID lockdown, I found myself itching to leave the U.S. for a few months to work remotely from Mexico and Colombia. As a digital nomad, I realized it’s often difficult to meet locals or even make friends. In Mexico I made friends through a run group, but in Medellín it was harder and my days blurred together: working alone in cafés, running solo through city streets, craving connection but not sure how to find it.

One weekend, the adventurer in me couldn’t ignore the itch: Go paragliding.
I’d seen ads for paragliding off a nearby mountain, but I didn’t want to go alone.

So I turned to the Yes Theory online world-wide community, a group known for embracing spontaneous adventures, and posted a shot-in-the-dark message:
"Anyone around Medellín want to go paragliding this weekend?"

Five minutes later, a stranger named Juan replied: I'm in.

But why stop at two strangers?

I couldn’t believe my luck that someone said yes so quickly. I secretly hoped someone else would say yes so that I didn’t have to go alone with this stranger. Plus, the mountain was about two hours away by car, so I was thinking it would be a bit sketchy to go alone with a guy I’d never met.

That’s when the lightbulb came on. The day before, I’d taken an Uber and had a great conversation with the driver, Diana. It’s not every day you get a woman Uber driver, so I had gotten her cell phone number before she dropped me off, in case I ever needed a ride again.

While Juan and I were figuring out our transport to the paragliding place, I texted Diana to see if she was available to take us. She was.

Wait! “Juan, what do you think if we ask Diana to actually paraglide WITH us, not just drive us?” He thought it was a great idea.

"Want to come actually paraglide with us?" I texted Diana.

She said yes without hesitation.

(left to right) Juan, Diana, and myself

The Courage to Say Yes

In the car, Diana later told us she was terrified of heights, but she was determined not to let fear rule her life anymore. She shared with us she told her kids that a stranger (me) had invited her paragliding, and she half expected them to be against the idea. But she was surprised to find her kids actually supported the idea and encouraged her.

Diana told us had recently lost her father, brother, and husband all within the span of a year. She’d started driving for Uber not just to make ends meet, but to talk to people, to feel life around her again.

Saying yes to paragliding, to a stranger’s invitation, was her way of choosing to face her fears and also to feel courage again.

Juan’s story was different but carried the same spirit. He’d traveled the world then came back home and was living with his parents while he studied bond trading. He rarely checked the Yes Theory group but felt pulled to look that day. He told me later, "When I saw your post, it felt like a sign." Turns out we didn’t just watch the same Youtube channel, we enjoyed the same books, had similar tattoos, enjoy traveling, and are both runners.

From Strangers to Something More

The three of us — a bond trader, an Uber driver, and myself (a restless digital nomad adventurer), drove two hours out of the city, talking the entire way like old friends catching up.

We skipped the small talk and went straight into life: grief, dreams, books, travel, tattoos, running, politics, the hard and beautiful parts of being human.

At some point, I looked around the car and thought, This is it. This is what life is all about.

Not the paragliding. Not work.
This.
Three people, completely different paths, sharing one wild, unrepeatable afternoon.

Flying and Letting Go

When we finally ran off the cliff and into the sky, I watched as Diana soared, and with her, the weight she carried seemed to lift too.

Later, we all got coffee on the mountain and teary-eyed, she told me, "For the first time in a long time, I felt free."

That day wasn’t just about the adrenaline. It was about remembering that every connection, every leap, literal or not, has the power to heal and to unite people.

The Takeaway

The world is full of future friends we haven’t met yet. Sometimes we catch ourselves by surprise at the people we meet, but most times it is in our power to go out and try to meet them.

We don’t always have to wait for adventure to find us. Sometimes, it’s up to us to create it.

So next time you feel that tug to do something spontaneous, don’t hesitate. Invite others in. You never know whose life you’ll impact, or how they’ll impact yours.

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