Lessons From the Road: A Hundred Dollar Encounter

Stories for Anyone Learning to Stay Open

A while back, I wrote about how a childhood fear followed me into adulthood. On a solo journey through the Sierra Nevada mountains to the Mojave Desert, I unpacked 40 years of coping—examining where fear had shaped me and where it still held on.

Something cracked open inside me. The result was The Road to Joshua Tree and the Voice Fear Tried to Silence.

Lessons from the Road is a companion to that piece—short reflections that zoom in on key moments from the journey. By breaking them into small, digestible parts, I’m able to explore not just what happened, but why it mattered and how it might guide the way forward.

In this installment, I share an encounter with another solo traveler, reflect on what it revealed, and leave you with a question of your own.

At this point of the journey, I’ve been on the road for four days. I was beginning to trace the roots of my personal fears and slowly, through conversations and connections with others, turning that fear into curiosity. But in this moment, I slipped back into old patterns.

“My last stop before meeting them is a campground in the San Bernardino State Forest. After a long day of heavy traffic, I arrive drained — frustrated, tired, mentally foggy.

As I pull into my site, a fellow camper approaches. He looks like a solo traveler too. “This is going to sound weird,” he says, “but do you have change for a hundred?”

Immediately, fear takes the wheel. I scoff, instinctively suspicious. A hundred-dollar bill? This guy must be trying to scam me. I brush him off without a second thought.

But the truth is — I did have the change. And this was a cash-only campground, just $15 a night. He wasn’t lying. He just needed help.

All trip, I’ve been working to quiet that fearful voice, to choose connection over retreat. But that night, I let my exhaustion do the talking.

By morning, he was gone. I stood by his empty site, staring quietly.
Once again, fear had taken something from me. Another moment. Another chance.”

What does this show me about the voice of fear? For me, it’s strong—and it’s been my MO for many years.

This moment reminds me that we don’t get to choose when chance encounters show up—we just have to be open when they do.

In my youth, I avoided deep connection. I didn’t know how to sit with those feelings, let alone express them.

It wasn’t until many years later and a bad breakup that I began to understand the value of real connection. To unlearn my old ways, I had to set clear boundaries around who I allowed into my inner circle.

Making this shift—choosing to engage in meaningful relationships—profoundly impacted how I moved through the world.

In the past, I’d stay on the surface—now I try and stay curious. When opportunities arise, I lean in and try to connect. Because when fear takes the wheel, it often robs me of something small—but potentially life-altering: a new perspective that could shift everything.

What’s the most transformational relationship you’ve ever had? How did it change you—not who you are, but how you move through the world?