This summer, I watched Gregory Alan Isakov play guitar and sing in front of the Colorado Symphony at a sold out show at Red Rocks. It was so moving I immediately became curious about the motivation behind Isakov’s poetic sound. This was the second time in three years that I’d seen him play live. This time was the most powerful. I wanted to know: What would it feel like to play songs you essentially wrote in your kitchen that were now backed up by a full symphony at one of the most famous venues in the world?

A singer, songwriter and horticulturist, Isakov, 34, started playing music at 15. Born in Johannesburg, South Africa, he spent time in Philadelphia and then became a perpetual traveler. He would write songs hanging out in his van, playing chess with his brother, or tending his garden. His songs draw on his life on the road, and he considers John Steinbeck and Bruce Springsteen among his biggest influences. He’s put out five albums to date, with an average release every two years. His latest is The Weatherman. He won Best Subtle Storm from Rolling Stone magazine for his performance at the Americana Music Fest 2014. And last month he released a unique stop-motion animation music video of “Amsterdam” on NPR.

“Saint Valentine,” from The Weatherman, starts with a character named Grace who went out for cigarettes and didn’t return. “She has come up in a lot of songs that I have,” he says over the phone from his home on a farm located 15 miles east of Boulder. “Songwriting is elusive to me. A song that starts off about someone can be about so
many people and towns. As a poet, you’re doing investigative work. Then songs feel like they take control. When you write a song you work with it, and it works with you like a relationship.”

I hear a twang of music in the background and ask if he has the radio on. He apologizes for strumming his ukulele. “I mostly write on the uke. It has just the right amount of notes and strings. You can kind of fall into a seat and play it. It’s not this weird object that you have to grab out of the case.” He laughs.

Today he’s writing music and doing work for television. He’s planning to release both a live album and new material soon but hasn’t given firm release dates. He comes off as just another guy, who like me, enjoys rock climbing, chess, and quiet time. He lives on a beautiful farm with other talented musicians.

“I’m always working on a piece of music and running back outside to the garden to do things like lay sheet mulch,” he says. He wakes early on the farm, which is nearly impossible when on tour and playing shows late into the night. Other times, “I’ll write all night and sleep during the day.”

“Some people want to get married, buy a house. I was like: ‘I want to play with the Symphony.’ Our first show was in downtown Denver. My folks were there. My brother was crying. This is a milestone. So crazy.”

He’s been performing with this band for several years and a day in the studio can be just him, though more often with Jeb and Phil, and he records solo. Later they’ll record the arrangement: “When you’re used to working with the same
people you leave them a lot of room to do what they do which works really well for us.”

“I’m cool with my career now. Once I’m in the moment and playing that’s all there is.” After the show is a different story. It makes him uncomfortable when people come up and compliment his performance. “I have a hard time being around people. I get nervous and anxious,” he says. Though he admits it’s an incredible experience to perform in front of tens of thousands of people, “it’s not my natural state.”

When asked how it feels to hear one of his songs play on the radio, he describes the time when he was in the frozen food section of his local grocery store. Upon hearing it he stopped wheeling his cart, pulled an item out of the freezer and proceeded to read the ingredients for a good five minutes until the moment passed.

Today, Isakov’s work keeps him on the road or in the sky traveling overseas but he also gets the chance to travel for relaxation, which he says is critical for his creativity. Otherwise, these days it’s hard for him to sit down and write without any distractions and having to constantly be on the move.

“My favorite type of traveling is slow, in my Volkswagen van,” he tells me. “I write a lot of songs that way — in solitude.”