Unless you’re going to come right out and ask it bluntly, the question is a tricky one, especially when dealing with an artist who has little time for bullshit.

In the case of Jolie Holland, it has everything to do with where she finds herself in 2014, which is to say playing the same-size rooms as on past tours for critically adored records like Springtime Can Kill You and The Living and the Dead.

At first, the Georgia Straight tries to phrase the question delicately, which is another way of saying not very clearly. When the Texas-born, currently New York–based singer makes it obvious that she doesn’t understand the query, a second attempt yields an instant response. Basically, Holland is asked if she’s disappointed that the size of her audience doesn’t match the mountain of glowing press that she has accumulated over the course of her decade-long career.

The answer, as the singer gets set to hit the road for her sixth and latest solo album, Wine Dark Sea, is a definitive no, with the 38-year-old stating emphatically that there’s nothing disappointing about playing clubs instead of plush soft-seaters.

“This is important to note: I don’t like playing theatres,” Holland says with a wry laugh, on the line from the Big Apple. “I don’t consider what I do music for theatres, in a way. And I don’t design it for that kind of experience. I have friends and I’ll hear them say ‘I’ve always wanted to play that venue, and I’m really excited that I’m going to get to play there.’ But that’s not how I relate to being a musician. I basically don’t care about any short-term goals—like, zero.

“I have played Carnegie Hall, but it was never on my list of things to do,” she continues. “I’ve played Radio City Music Hall, but it was never on my list of things to do. All I want to do is just, you know, maintain honesty in the work, and be a better bandleader and a better musician.”

Those missions are admirably accomplished on the stellar and uncompromising Wine Dark Sea. Long-time fans looking for the sepia-toned jazz and slurred country stylings of her past outings won’t be disappointed this time out, the singer delivering more of what’s made her a cult folk hero. Whether it’s the smoky sax-powered R&B of “All the Love” or the raw-and-scratchy Americana of “I Thought It Was the Moon”, Holland again seems like an artist from a different place.

But she’s also pulled something of a career reinvention this time out. From the cacophonous kickoff track, “On and On”, to the ghostly “Dark Days”, Wine Dark Sea is scattered with spectacular guitar violence. The assumption might be that Holland enlisted some of New York’s most respected six-string innovators—including Adam Brisbin and Indigo Street—and then told them to let loose on songs like “On and On” once the tape was rolling. The singer is, however, quick to shoot that idea down.

“I wrote everything on ‘On and On’,” she says. “Even, like, the guitars on the drum solo. I wrote everything. It’s really impolite to great musicians to ask them to basically write things for a work that’s not their own, for a work that they are not going to be properly attributed or compensated. So, as much as possible, I try to compose everything so that I’m not putting someone in that position.”

Funnily enough, while Holland is worried about others being properly compensated and recognized for their work, that’s obviously not a big concern of her own. As she notes, she’s in it for the long haul, not for a marquee appearance at the Orpheum.

“Like it says on the record, most of my heroes died in the gutter,” she says. “I think for people who are doing really good work, there’s often a 30-year lag time before anyone appreciates or understands what you are doing. And by that time, you could be dead. That’s what it’s like when you’re not Céline Dion playing softball with your audience.”

Jolie Holland plays the Biltmore Cabaret on Monday (June 16).