Gregory Alan Isakov is a lot of things—a songwriter, a performer, a farmer, and even a Grammy-nominated artist. He’s an introvert that enjoys journaling and taking pictures. But above all, he’s someone who’s simply trying to figure life out. 

There’s a saying that says: ‘Do what you love and you’ll never work a day in your life.’ Following your passion is, in many ways, key to a full life—and it’s a truth that every artist, including Isakov, knows well. 

“I’ve thought so many times over the years of why I feel like this is an important thing for me to do because it is so challenging [to tour]. And I feel really grateful for it, but I always keep coming back to that answer: I need to play; I need to create (…). And I love that because I don’t understand why anyone would do it if they didn’t feel that way,” says Isakov. “That incessant need and draw to create, and to put yourself out there on that scale which can feel completely against the grain of your personality.” 

The need to create and share his music has always been with Isakov. As an artist, he began touring with a band in Philadelphia when he was only 16. And during his earlier years, he often shuffled from coffee shop to coffee shop, playing small gigs and attempting to sell his CDs.

Now, Isakov plays sold-out shows around the world—from his native Johannesburg, South Africa, to his current hometown of Boulder, Colorado. 

Given how draining constantly being on tour and away from home can be on an artist, Isakov has had to find practical ways to ensure he’s still looking out for his own wellbeing in the craze of it all.

“I write a lot of poems… I have a comic; I draw comics a lot. I take photos, too,” he says. “My bandmates always make fun of me because every night after the show when everyone is going out I’m always in my bunk,” he adds with a laugh. “They’ll just be like ‘Hey guys, Gregory is in his bunk again.” 

Beyond tapping into other creative spaces, the Grammy-nominated musician has also found solace in another unique (albeit unexpected) passion: farming. 

“For the most part I tour during the shoulder seasons and in the winter,” says Isakov. “So I’m home from around March 15th, which is when I start most of my crops, until about mid-September.” 

Isakov’s interest in horticulture began when he was a young boy—so much so that this ever-evolving interest led him to pursue and earn a degree in horticulture from Naropa University in Boulder in 2003. He also obtained first-hand experience working on several different farms, and now spends half the year working on his own 4-acre lot in Colorado. 

“I also do a lot of crop planning while I’m touring,” he says while laughing. “So it gives me time away from the farm to plan on how to have a better season.” 

“So, even when you’re not farming, you’re farming?” I ask. 

He laughs. “I know, it’s ridiculous.” 

Isakov’s dedication to creating folk music all while attempting to live out an authentic folk life inevitably keeps him pretty busy—though he doesn’t necessarily mind, as “even in his work he finds rest,” often making sure to compartmentalize his passions into particular seasons.

“I’ve noticed that I’ve had to say ‘no’ a lot more than I expected. There’ll be some opportunities that will come up during the summer and will get me excited, but it’ll be impossible for me to do both (…). And I’ve realized over the years that farming is pretty imperative for my health and even my balance of income.” 

But what might have started as a passion project for Isakov, has since evolved into a full-fledged farm that’s supported by a solid team of people who tend to the lot’s duties while he’s on the road.

Isakov’s farm provides produce to about 20 different local restaurants and chefs, and includes vegetables like broccoli, cabbage, carrots, turnips, beets, and kale, among others. 

“We grow near 100 varieties of mixed vegetables, but I think the salad mix and the tomatoes are probably our most popular (..). Today I even planted some greenhouse tomatoes and some lettuce.”  

While Isakov spends a great deal of time on the farm, his music is still at the forefront of his creative pursuits—and oftentimes, the two actually go hand-in-hand.

“When I’m home, about two to three days a week I’m in the studio,” says Isakov. By studio, he’s referring to the 800-square-foot, soundproof recording studio space he built into his barn. “And once the big bulk of the season starts and we’re packing orders, we’ll have set days for that and I’ll work in the studio during the other days.” 

Oddly enough, his otherwise opposite passions seem to balance each other out.

“Being a grower gives me time while I’m doing repetitive actions to digest and master ideas that I’m working with in music. Sometimes I’ll be sitting on one line of lyrics for about a week, and [I’ve learned] that if you try to force an idea it’s not going to work out.” 

Isakov believes that engaging in relaxing farming work is more beneficial to his songwriting than sitting in a studio waiting for inspiration to come to him. The lines will usually “come on their own,” and before he knows it, he’ll be creating an entirely new song. 

The truth, however, is that songwriting isn’t easy. It requires hard-work, time, and full dedication. “It’s probably the hardest thing I’ve ever tried to do,” says Isakov. “And it’s one of those things I will never master (…).” 

His songwriting process towards creating a new album is centered on creation; on letting songs be written without fear of what they’ll be or whether they’ll be good or bad—it requires soulful work and a thoughtful selection. The grander scope of writing for all writers, says Isakov, is always more than some may believe it to be. 

“You need to be cool with writing stuff that isn’t up to par, so that when the good stuff comes, you’re ready for it.” 

This is a sentiment likely shared by most artists because art itself is not about perfection, but about putting yourself into your work. Creating it requires giving it your all to formulate something that speaks from the innermost part of yourself. The result, oftentimes, isn’t going to be perfect nor near it. 

And this same thought is one of the main principles that guides Isakov in his life. 

“[A mantra] I repeat to myself often is ‘It ain’t perfect, but it’s mine.’ That might be a song or a planting that didn’t quite work out perfectly (…). This kind of frees me from the idea that there’s a goal [I need to reach].” 

Gregory Alan believes it can be easy to get stuck on wanting to create perfection, so it’s important to not let oneself get tangled into that. A person’s imperfection is what allows them to create such genuine pieces. 

“I love how messy we are,” says Isakov with a laugh. “I think we should really own it (…) instead of letting shame or embarrassment take over (…). It really is amazing how much artistic material there is in just noticing how extremely imperfect we are.” 

Authenticity and vulnerability are important qualities to develop. And Isakov’s authenticity can be found time and again in his songwriting and albums. 

He’s currently working on a follow-up to his grammy-nominated 2018 album, Evening Machines. So as he continues to farm and to write, and as we eagerly await his new music,  let us take more time to reflect on the people behind the art we enjoy—the people behind these passions. 

“I think [it can be dangerous] to identify as a writer or a musician or anything. When I’m writing and making music, it’s about life and the world, but if all of my existence is [centered around] being a musician, then I don’t really know what I’m reflecting on.” 

It’s important to be real, to be human, and to lean wholeheartedly into all of our passions—just as Isakov has. If we do that, everything else will follow.

For more information on Gregory Alan Isakov or his farm, visit www.starlingfarmproduce.com.

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