What a Music Festival Taught Me About Running a Business
Every year since 2014, my best friend and I have gone to Hillside Music Festival together. It's our version of Christmas. Same location, same crowd of strangers becoming familiar, same ritual we protect on our calendars no matter what else is going on.
This year I moved through the weekend with my entrepreneurial goggles on, whether I meant to or not. A few things kept showing up, in different musicians, different sets, different moments, until I couldn't ignore the pattern. Here are three lessons from live music that I'm still carrying into how I think about business.
You Don't Always See the Impact You're Having
A musician walked onstage on the last day looking tired in that specific way you get after pouring yourself out to strangers all weekend, wondering if anyone actually cares.
Partway through the set, something shifted in them. They found one person singing along in the front row. "I can't stop looking at the person who is singing along with me," they said. "That's amazing." Tears were welling up in their eyes, and you could watch the passion come back into their body in real time.
By the end of the set it wasn't just one person. It was many. My best friend was one of them, belting out the words to a song that had carried her through some of the hardest years of her life. A song written by someone she has never met, who had no idea what that song meant to her, standing twenty feet away.
This is one of the harder truths of doing meaningful work. You rarely get to see the full weight of your impact. You put something into the world, and most of the time it lands quietly, off camera, in someone else's life you'll never hear about. If you're an entrepreneur, this is worth sitting with on the days it feels like you're shouting into the void. The impact is very likely there. You just don't always get the front row seat to it.
It's also worth remembering as a customer or client. Telling a business owner what their work has meant to you costs you almost nothing, and for them it can be the difference between doubting the work and recommitting to it.
The Business Side Isn't Optional
Standing in line at the merch tent, I noticed something else. A few musicians joked, a little cynically, about hauling merch around or being bad at the business side of things. I empathize with that feeling. But I also got tired of hearing it, and if I'm honest, it didn't make me want to buy anything.
The band I did buy from was the one that focused on their craft and let it show. They seemed proud of their music without being precious about it. They created such a good experience that by the time their set ended, I already wanted to take a piece of it home with me.
It made me think about my own slow seasons, and the seasons I see in the entrepreneurs I work with. They almost always trace back to the same three questions. What am I doing to inspire the people I want to reach? Am I connecting with them honestly? Am I proud of the work I'm putting into the world? Get good at those three things, and you'll be good at business. The business side isn't separate from the craft. It's downstream of it.
Business Is a Practice of Staying in Relationship
The musicians who stayed with me longest after the festival ended were the ones who made eye contact. Who told a story between songs instead of rushing to the next one. They let the crowd see them, and they made a visible effort to see the crowd back.
That's easy to overlook if you'd rather just do the work quietly and never have to be seen doing it. I understand that instinct. But on the other side of your business are the actual people receiving your work. What energy are you bringing into those relationships? How are you engaging with, caring for, and nurturing the people you serve, not just transacting with them?
Three Things I'm Still Contemplating
The impact of our work is often invisible to us, but it's there.
Connection and pride in our work matter more than we tend to give them credit for.
Business might really just be a practice of staying in relationship.
Business is always evolving and adapting so I don’t imagine any of us will ever have it all figured out. But if any of these observations landed for you, I'd love to hear which one. Send me a note, or reply to this post. I do my best to personally reply to each one.
