Tillman grew up the oldest of four siblings in Rockville, Maryland, a remote suburb of Washington, D.C. His father worked in sales for Hewlett-Packard, and his mother was a homemaker who sang in the church choir. Both were devout Christians who ensured their house was “bursting at the seams with religious product” including family and faith-oriented music like Bullfrogs and Butterflies and Psalty the Singing Songbook. Forced to attend a number of religious schools, Tillman says he felt skeptical and embattled from the beginning. “I have this really vivid memory of my first day of Sunday School,” he says. “I asked the teacher, ‘Who made God?’ and she said, ‘Well, God’s just always been.’ I remember thinking, ‘Well, I don’t know about that.’”

As an adolescent, he found himself unable to relate to classmates speaking in tongues, or play along when teachers attempted to expel their demons—“mine would never come out,” he says. “All of that caused me to withdraw deeper and deeper into my own worldview, like, ‘I just need to put my head down until I’m fucking out of here and I can finally breathe.’” Though he grew up wanting to be a cartoonist (“‘The Far Side’ and ‘Calvin and Hobbes’ are my two biggest influences”) Tillman’s constant, nervous tapping on whatever was available led his parents to buy him a drumset in exchange for quiet and calm, at the suggestion of some concerned teachers.

Years later, after being forced to attend a Christian college in Upstate New York, he left school and the East Coast without saying a word to his family or professors. The destination was Seattle, where he slept on floors, sold plasma to make money, and distributed self-recorded demos to bartenders all over town. Throughout his 20s, he’d record a number of deliberately difficult and downcast folk albums under his own name, J. Tillman, many of which were disregarded outside of Seattle and Europe—particularly by his parents, who told him, “We don’t support this choice. Do not send us your music.” They wouldn’t speak again for nearly a decade.

But in 2008, as local folk-rock outfit Fleet Foxes quickly gained national renown, Tillman, a fan, was asked to join the band as a drummer. The transition—from installing acoustic paneling for a few dollars an hour one week to sitting in front of thousands at a festival the next—provided its own sort of culture shock. “How could you not think, like, ‘I’m saved?’” he says. “When I joined that band, I dreamed that if I could just play music for a living, I could be happy. But I really have to watch my miraculous thinking, because I was so disillusioned that it didn’t end up being this version of it that I had in my head. I didn’t feel enlarged by that experience. I felt diminished.”

What happened next is now the actual stuff of legend. On a solo trip along the Californian coast, Tillman linked up with a French-Canadian shaman and a course-altering dose of ayahuasca near Big Sur. He found himself naked, hallucinating in a large oak tree on a cliff overlooking the Pacific, and experiencing what he now describes as the first clear glimpse of himself—pretty good as far as rock’n’roll origin stories go.

“I started to recognize my voice coming through for the first time,” he says. “And all the conflict and the psychotic caveats and disclaimers and messy extraneous bullshit was, ironically, where all the clarity was: My spiritual gift is my skepticism and my cynicism and my sense of humor and my penchant for stirring shit up. That’s what I have to offer the world.” He resolved to pursue a creative vision based not on the prevailing archetype of how a singer/songwriter should look or sound, but one in service of a newfound sense of self: “I realized I’m the hero of my own tale.” He left Fleet Foxes, a decision that, at the time, looked like the equivalent of professional suicide, but one that has since proven to be more in line with quitting your lifeless day job to follow your bliss, a narrative most of us find tantalizing. He was awake.

Three years later, in September of 2013, Tillman married Emma in a ceremony of their own design in front of a small group of friends and family in Big Sur. The day before, he took her on the three-hour hike along the cliffs, to the same oak tree. They climbed up together and sat for a few hours, just talking. “When I was there the first time, there was nothing better in the world than being alone,” he says. “But you transform. Now, if I’m not with her, there’s something lacking. I didn’t see that one coming.”