How to Zip Line

There’s something magical about being tucked away in the mountains of Chile, surrounded by friends both old & new. We were there for a wedding celebration—a group of thirty people, brought together for a week. With barely any cellular reception or WiFi, the usual distractions faded away. We were present in the truest sense, and the sense of connection was refreshing given the fast paced life we all live.

One morning, our hosts handed out a sign-up sheet for activities: hiking, white-water rafting, horseback riding, or zip lining. My eyes stopped at zip lining, and a memory from nearly ten years ago surfaced. I was in Costa Rica then, standing on a zip-lining platform for the first time, heart pounding, legs trembling. But I still remember the thrill of that leap, the way it felt to fight a fear of heights and soar inside and out. That day had been about leaning into adventure. I felt called to do it again.

As we hiked up to the first platform, the forest came alive around us. The trees seemed endless. The air smelled crisp and earthy, and the sounds of rustling leaves and distant birds were all around. But as we approached the first line, my stomach churned. My palms were sweaty, and every glance down at the ground below made the distance seem even greater.

Yet being surrounded by friends was grounding. Their laughter cut through my nerves, their encouragement softened the edges of my fear. We were in this together, the energy building as each person prepared to leap.

When my turn came, I stepped forward, was clipped in, and took a deep breath. The guide smiled and said, “Lean back, trust the line.” With one final inhale, I pushed off.

It was over in seconds, but it left a mark—a mix of exhilaration and disbelief. I’d done it. Again. 

The second line came easier, the fear loosening its grip. By the third, I was grinning. A few lines later, I was volunteering to go first, laughing as I jumped into the void. Each time, I felt a feeling of sadness when the line ended, like waking up from a dream I didn’t want to end.

What struck me most wasn’t just the thrill of the zip line. It was the way the experience awakened something childlike in me—a joy that felt pure and unburdened. It reminded me of summer camp, of days spent outdoors with friends, trying new things, and simply being in the moment. There’s something about pushing through fear that makes the fun on the other side feel so much sweeter.

And then there was the four-year-old in our group. She stepped up to the platform with a calm confidence that took my breath away. After her first line, she didn’t just want to go—she wanted to go first. Watching her was humbling. She didn’t carry the weight of fear that we adults do. It reminded me of when I started my first company at 20, bold enough to jump into the unknown simply because I didn’t know any better. That kind of untested bravery can be a gift.

What made the day unforgettable wasn’t just my own transformation, it was seeing everyone else overcome their fears, cheering them on, and feeling their excitement as if it were my own. 

I thought about the difference between joy and enjoyment I had once heard. Joy is what you feel in your own heart—private, personal. Enjoyment is when joy is shared with others. It amplifies everything. It’s what made this day more than just a series of zip lines. It was a shared connection and experience between all of us. Similar to sport, music, food and even work. 

I can see how my zip lining experience mirrors life. It’s an adventure that requires trust, courage, and the willingness to step into the unknown. It’s scary and thrilling and beautiful all at once. And the best moments aren’t just about what I experience—they’re about who I share them with. Even though the journey is fleeting, the connections we make along the way are what stay with us.

And that is how I learned to zip line.

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