A Chance Conversation in East Tennessee That Changed How I See Regret
A story about how an unexpected conversation in East Tennessee turned into a powerful reflection on regret, time, and what truly matters.
“That’s my biggest regret,” he said. “And now it’s too late for me,” he continued, “but you have your whole life ahead of you. Don’t make the same mistakes I did.”
Those words came from a man I'd just met at a campground in East Tennessee. I could tell he shared them to encourage me. At the same time, it felt like a confession—a release of the guilt he'd been carrying for the mistakes he'd made. His encouragement stuck with me, and I've thought about that conversation many times since. I hope it brought him some peace, too.
Chasing Waterfalls and Sunrises Through Southern Appalachia
This spring, I had the opportunity to chase waterfalls, wildflowers, and sunrises through southern Appalachia—mostly unplanned and totally unexpected. It became one of the most unforgettable adventures of my life.
I’d wake up hours before dawn, drive up quiet mountain roads in the dark, and hike miles on the Appalachian Trail to meet the sun with only my headlamp lighting the way. I saw every color of trillium, rare orchids, and savored the rich scents of Appalachian spring in full bloom. I also relished early mornings in solitude at the base of some of Georgia and Tennessee’s most majestic waterfalls. It was truly the experience of a lifetime.
But as I’ve written many times before, the gifts I gain while traveling go far beyond nature’s breathtaking beauty and solitude. The people I meet along the way are what make the experience truly memorable.
Sunrise over the Blue Ridge Mountains in eastern Tennessee
The Camp Neighbor
One evening, after I'd set up camp, an older gentleman walked by with his shih tzu and stopped to chat.
"That's a really cool setup," he said.
"Thanks, we've had a lot of fun adventures with it," I replied, not in the mood to chat after a long day of travel and errands.
"Sorry to intrude," he said. "I've just never seen anything like that."
"No worries," I said. "It's one of a kind."
"How does it work?" he asked.
I told him about the adventure rig my husband had built over the course of a summer a few years ago.
The next day, after a much-needed, extra-long hike, and getting caught up on email and laundry, our paths crossed again.
Regret and the American Dream
“Are you one of those remote workers?” he asked.
“Kind of?” I replied sheepishly, not entirely sure how to explain my life.
He asked what I did, and I told him about what I’ve been up to during the last decade of my life and what brought me to southern Appalachia.
“Wow, that’s incredible,” he said. “Good for you. Keep doing what you’re doing and don’t stop chasing your dreams. Because when you’re my age, the only things you’ll regret are the things you didn’t do.”
Then his tone shifted.
"Looking back," he said sadly, "I would have done it all differently. I worked so much to provide the best for my family, but now I see that we didn't need bigger homes and the latest vehicles. I worked so hard to keep up with the Joneses and buy all the best things. And now all that stuff is gone, and it feels like a waste."
“But what I really lost out on, working all those hours, was time with my family. I never got to know my kids, and now it’s too late. We’ll never be close, and that’s my biggest regret. I wasted my entire life chasing the American Dream and missed out on what truly matters.”
If you know me, you know I love deep conversations—even when they make me uncomfortable because I don’t always know how to respond.
I responded with what felt true in the moment: “as long as we’re still kickin’, it’s never too late.”
Then I shared a few of my own regrets—moments I'd spent too much time chasing the wrong things, or staying too long in situations that didn't serve me.
“But you know what I realized?” I asked. “Even though those were awful experiences and I wish they had never happened, the truth is that if we could go back and change one thing about our past, we’d change everything. And there’s so much in my life today that I wouldn’t want to give up. My past — the good, the bad, and the ugly — brought me here and made me who I am today.”
Perking up a little, maybe even with a twinkle in his eye, he said, “I think you might be right.”
Sun rising over the Appalachian Mountains in Tennessee
Finding Meaning
This encounter stirred something in me, and I hope it does the same for you. I think the message lands differently for each of us, depending on our life experiences. But here’s how it lands for me: one of the most important things we can do on this short adventure called life is to live in a way that feels true to us.
That means choosing more of what brings meaning into our lives and less of what we think society expects from us. One way to check whether we're living authentically is by asking ourselves:
If no one saw this, would I still buy it, do it, say it, or write it?
I understand that we all need to work and do plenty of things we don't want to. That's part of life—we can't escape it. But it's also important to understand that everything is a trade-off. At some point, we need to decide what matters most and what we're willing to trade for it.
If I asked you to name three to five things you value most in your life today, what would you say? And how does the life you're living align with what you value? Are you moving toward more of what is meaningful, or further away from it?
If you don’t like your answers, remember what I told my new friend in Tennessee: "As long as we're still kickin', it's never too late."
Morning magic in the mountains
Coming Full Circle
As I wrapped up my time in southern Appalachia and drove across the great state of Georgia to my next big adventure, a song popped up in Apple Music that caught my attention.
The song, called "John," by bluegrass band Wood and Wire, is about their buddy who lives an unconventional life that looks very different from his friends, who are all pulling in big paychecks in their suits and ties. The song honors both lifestyles, but in the end, they conclude that:
“Livin’ ain’t easy when you don’t have money, but money means nothin’ when you ain’t livin’ free.”
It was the perfect line to sum up what this stranger had told me—and a fitting reminder of the questions I keep coming back to.
Like most things, regret isn’t all bad. Although a little regret can be healthy when it pushes us to grow, we must remember that it’s impossible to change the past. So instead of fixating on what you might regret someday, ask yourself:
What will you not regret?
If you’re craving more reflections about slowing down, reconnecting with nature, and living a more meaningful life, subscribe to my newsletter for monthly inspiration, exclusive content, and practical tips for living a more adventurous and intentional life. Then check out my Substack for even more stories and photography.
