Column 141: An Uncertain Trajectory
The fantasy life of Will Sheff.

For Okkervil River’s Will Sheff, the life of a rock star is a fantasy world that he’s trying to avoid.

I’ve been covering Sheff and his band since they first rolled into Omaha in 2002 to play a poorly attended show at the long-defunct Junction on 14th & Farnam. Virtually unknown, Okkervil River had just released Don’t Fall in Love with Everyone You See on respected indie label Jagjaguwar. It was a break-out album filled with literate, intelligent, moving folk-rock songs in the vein of Will Oldham, Bill Callahan (of Smog) and Conor Oberst that has become one of my all-time favorites. Three years later, Sheff and his band played at O’Leaver’s, this time supporting Black Sheep Boy, a critically lauded follow-up featured in The New York Times, Rolling Stone and the cover of The Austin Chronicle.

Now Sheff and Co. are back again, this time playing at The Waiting Room Friday night with Damien Jurado in support of the just-released The Stage Names, yet another collection headed straight for my year-end top-10 list. Last month, the band reached a sort of indie pinnacle, performing on Late Night with Conan O’Brien. Onward and upward, right?

In reality, little has changed since that night at The Junction. Oh sure, these days Okkervil River is considered an A-list indie band with a devoted following, name-checked by the likes of Lou Reed, but the band is still making its way cross country in a van instead of a tour bus.

“I’d be lying if I said things weren’t better than the last time we talked,” Sheff said through cell-phone static somewhere on the road. “But I’d also be lying if I said we’re living high on the hog. I’m less scared than I used to be about going totally broke or about what’s going to happen to me in the next six months. But it’s not like I’m sitting back on a pile of money.

“Looking back at what’s happened to us, it’s been a slow rise. If I thought we’d be playing Letterman or selling 100,000 copies of our CD, I’d be happy. It may happen and it may not. The fact is, there is no trajectory. Everything’s uncertain, and we’re not talking about a story, we’re talking about my life. It’s sort of frightening.”

That’s not the only thing Sheff is frightened about. He’s also afraid of getting lost in the one-dimensional world found only on the road. “I’m trying hard not to identify myself too much with what I do,” he said. “If I let myself think that I’m a rock star and I’m the reason why the band is successful, I not only become an insufferable asshole, I open myself to a lot of weakness. The most important thing is friends and family and being anchored in life in an everyday way.”

But as everyone knows, life on the road is anything but “everyday.”

“It’s killed many, many relationships I’ve had,” Sheff said of the constant touring. “It’s hard to build up a stable life. This is a fantasy world, and the longer you live in it, the more you develop skills to deal with the fantasy world that don’t relate to the real world, which is what’s left when the fantasy goes away.”

In that fantasy rock star world, Sheff said, life has a militaristic simplicity. “Your concerns are, ‘Are we going to get to the club on time?’ ‘When will I get to eat?’ ‘What will I get to eat?’ ‘When can I put my stuff in the van?’ These are my possessions. This is my routine. It’s really soothing.”

But when the tour is over, Sheff describes a let-down similar to that suffered by newly paroled convicts who don’t know what to do with their newfound freedom. “Oftentimes when I get home, I get extremely depressed,” he said. “I either go hide in my house or room of wherever I’m staying with the door closed for three or four days straight, or I get into a fight with whoever I’m in a relationship with. Life on the road is nothing like an ordinary life. Ordinary life seems so weightless.”

OK, I know what you’re thinking. No, Sheff isn’t a basket case or a whiner. He was quick to clarify that yes, he’s having a great time, that he loves his life playing music. But at the same time, he struggles with security issues. “I don’t want to sound ungrateful,” he said, “but the uncertainty of it all will really do a number on your brain.”

At 31, Sheff said he’s openly jealous of his friends back home in Austin who he feels live more satisfying lives. “I think they’re more run-of-the-mill, but there’s a depth to their lives that my life doesn’t have,” he said. “They’re not traveling around the world, but they get to have deep relationships with their friends and family.

“I know lots of older musicians who are great at being charming and cool, but aren’t good at being functioning, happy people who know how to live a normal life.”

But sometimes just living a normal life may be too much to ask for, especially from the back of a van.