“To do this job, you have to be an extraordinarily self-centered person,” Drew Kennedy says. “That’s just what it requires. I don’t want to be self-centered, but I was made to do this. A lot of artists say art comes from conflict––they talk about relationships ending or trying to overcome serious habits. Well, my conflict is this: how do I be so self-centered while being as selfless as I can?”

Kennedy is asking himself these questions as he drives through some snaking Colorado mountain roads, on his way to pick up his wife and two young sons from the airport after about a week apart. He’s missed them terribly, but it’s been such a good run: listening rooms scattered throughout Colorado, New Mexico, and West Texas, all packed with devotees anxious to hear just him and his Gibson Hummingbird tell stories. He’s doing what he loves while who he loves most is 1,000 miles away. And it’s that tension––the struggle between being the kind of man he wants to be and being the kind of artist he has to be––that keeps him up at night.

It’s also what enables Kennedy to write songs that comfort even as they break your heart.