Last December, Will Sheff was on the verge of a good-bye. While playing shows to promote the ten-year anniversary of Black Sheep Boy, the 2005 breakthrough album from his folk-rock band Okkervil River, Sheff had quietly begun work on an album so different from his past catalogue that it felt like a farewell to rock music itself. “I was coming to the end of some kind of engagement with playing a certain way,” Sheff says. “I’d gotten distracted from my original path of trying to write something interesting and meaningful.” All of a sudden, the songwriting process he'd relied on for years seemed more like a tired, restrictive formula. So he challenged himself to start over, writing the songs that became Away, Okkervil River's eighth studio album, out tomorrow on ATO Records.

Okkervil River began as an acoustic folk act in the late '90s, playing dreamy songs that reflected the sound of influences like Elvis Costello. Within a few years, Sheff found himself writing music that edged closer to punk, leading up to the critical triumph of Black Sheep Boy. But as the next few years went by, Sheff’s exploration of aggressive, ugly sounds, as well as some unpleasant experiences with “bad drugs,” left him unsatisfied. He noticed that both his sound and his lyrics, which had been noted for their thoughtful, literary qualities, seemed less potent — and worse, he was getting the sense that his audience felt the same way. "I started to see the limits of both the lifestyle that I was living and the kind of music that I was aspiring to,” Sheff says. “And I started to feel like all that rock and roll does, is it sort of scrapes the surface of something...I felt like it was yielding a diminishing return.”

Isolated in a friend’s cabin in the Catskills — “Not a fancy town, like Phoenicia, where it’s become sort of this hipster Brooklyn,” Sheff is quick to add — he wrote both 2013’s The Silver Gymnasium and the new album. In retrospect, he sees The Silver Gymnasium standout "Pink Slips" as his first step away from rock and back toward the free, abstract lyrics and alt-country music he’d once been immersed in. “I just remember writing that song and...feeling so much like that song was the beginning of me setting myself free,” Sheff says. “The way I used to write, I might have a really specific goal in mind, almost like writing an essay. I was trying to show that I was smart. [Now] I just find it gross.” As the title of the first single from Away, “Okkervil River R.I.P.” suggests, Sheff spends the new record symbolically ditching that hyper-intellectual style of writing — in the music video, he gives it an actual funeral, singing from a coffin.

One path to enlightenment, for Sheff, was the use of psilocybin mushrooms: While he was working on Away in the Catskills, he wrote both “Call Yourself Renee” and “Mary on a Wave” while tripping. (He mentions the teachings of traditional healer Maria Sabina as an influence.) “So much of my life has been dedicated to trying to keep my inner child engaged, and not trying to switch off my conscience and my empathy and my spirit,” Sheff says. “So when I talk about [taking mushrooms], I hope it doesn’t come across as flippant or like it’s party time. To me, those psychedelics can be a really powerful tool for really getting to someplace deep and powerful.”

The lyrics on Away float intangibly, indefinite in their imagery and significance. On “Days Spent Floating (In The Halfbetween),” Sheff sings, “To disappear between two notes in a twelve-tone scale / Floral Jesus floats in a sky of warm toast / You can only spend so much time, brother, as the world's guest.” Sheff says he would prefer someone else tell him what his songs mean — now he does his best to avoid having any specific goals when he writes. "I like to be able to write something where you can’t say what it means or what it’s about,” Sheff says. “I could talk to you about what I think it’s about, but I would hope that there’s something more than about-ness, with the record."

That said, many people listening to Away have noticed a running theme of mortality — including Sheff himself. “This record has been this wonderful, special, encouraging presence to me. I thought of it in these very positive terms, like it was glowing and friendly,” he says. “And then when I listened to all the stuff in order, I was really shocked at how much I was talking about death.” Around the time of the album’s writing and recording, some members of Okkervil River left the band to be with family or work on other projects, and Sheff's grandfather passed away.

But the album's take on death isn’t necessarily a mournful one. On “Okkervil River R.I.P,” Sheff tells his audience to “Gather, crowd around me / In the gutter where you found me” but then adds hopefully, “We’ve got a big chance coming now.” Later in the same song, he sings about several real-life deaths, including his grandfather’s, but clarifies that he didn’t “open up [his] mouth just to piss and moan” about personal losses. The song ends with a sense of wonder at the situation around him: “All the air is glitter.” “A lot of the time when people think about death, they think of it as unthinkable or a super serious thing,” Sheff tells me. "[But] I feel like there’s something very beautiful about a certain kind of death, that’s tied to a certain freedom."

Sheff rejects the idea he's seen in some press that he was "distraught" after his grandfather's death. "He was very old, and you can’t live forever,” he tells me. “The thing that really makes me sort of sad is when people call my band 'sad bastard music.' I’m not interested in being the man in black.”

Instead, he says, he wants to represent the “complicated cocktail of emotions” that allows us to both cry and laugh at the same time. He often smiles with delight when he performs, even when he's singing his saddest songs. “I just don’t think of smiling and sadness as incompatible,” Sheff tells me. “Smiling while you’re singing about something that might be a little intense — I don’t think that’s weird. A lot of times I’m just smiling because I’m happy to be alive.”