Watching Holcombe Waller ‘98, a former Duke’s Man and singer-songwriter, perform his traveling folk festival “Into the Dark Unknown” at the Yale Cabaret might have been the highlight of your week. WEEKEND sat down with Waller to discuss incorporating art and music, his move into a more electronic sound and whether Yalies should trade Goldman for a guitar.

Q. How do you think the Yale environment shaped you as a musician?

A. The singing groups are a wonderful and rich Yale tradition; a cappella was one of the things that actually attracted me to Yale. What I liked about the singing groups was their interpretation of popular music — take, for instance, the Duke’s Men’s cover of “Carolina in My Mind” by James Taylor. Singing with the Duke’s Men was my formative experience in terms of learning how to sing before an audience.

Q. So, was going from a cappella to indie folk weird?

A. I felt like it was a logical progression, at least for me. I learned guitar largely through osmosis, living with a good friend right here on Park Street. He practiced 10 hours a day, so I just picked it up. When I went back home to San Francisco, I just brought the guitar and started playing coffeehouses.

Q. The indie festival you’re currently touring with does incorporate some art, like video installations, though — how did your art major play into your musical career?

A. I did sculpture and focused on video installations. When I was about 29 or 30, I sort of stumbled into theater and really caught the bug a bit late in life. I was already playing concerts a lot, so I decided to create a show that incorporated theatrical elements and video installations — I wanted to integrate that into my life again. I also still did freelance video production [post-Yale.]

Q. What has your work in film been like?

A. I’ve edited my own videos and made some short art films, and now I generate media and video for live shows. So I’ve changed my focus a bit professionally, which has meant whole new worlds of organizations and venues that take an interest in such interdisciplinary work. It’s opened a lot of doors. The realm of performing arts has really become one of convergence.

Q. What about the development of your musical style?

A. My first record, “Extravagant Gesture,” was fairly poppy and produced. “Triple Times” was my next record — with it, I took a really big step towards a much more spare, spacious and kind of almost spiritual-political bent. I was in a Saturn-y phase, questioning a lot of things, and also responding to the post-9/11 Bush years which I found, and still find, troubling. I think that record really opened the door to what I’m doing now, which is really pretty straight-up folk; it’s American folk revival-inspired work. But my style is really always changing. I’m getting more involved with electronics again — that’s where it all started for me in high school.

Q. What do you think of the new popularity of folk music? What’s it like to be a folk musician post-Bon Iver?

A. I feel like I missed the boat or the boat missed me. I’m kind of moving on myself now. He really hit the nail in the head with “For Emma,” which felt like a post-grunge American neo-folk record. I’m looking forward to not really identifying as folk anymore, with my interest in electronics. I enjoy the economy of producing music with a laptop. Also, I have access to larger venues at this point, and, with that, something that’s nice is to really play with the full range of sonic dynamic. One way to do this is with electronic instruments, as opposed to having drummers or something.

Q. As an artist transitioning his sound, what do you think of attempts to label and categorize musicians?

A. One of the things I enjoy most when I read reviews of me is that writers make really good reference comparisons, and a few people go on to say that I have something that’s pretty much uniquely Holcombe Waller. I actually am creating a type of music that’s a bit in a vacuum. I don’t really have a scene. And I think that’s my goal as an artist, to pursue and investigate my own voice — how it’s like other voices but also how it’s unique.

Q. You were an art major; now you’re a musician. What do you have to add to the ongoing debate on Yale’s campus about students choosing lucrative financial sector jobs instead of fields that may be their true passions?

A. You know, I did [conform] and I didn’t. It took a lot of investigating to figure out what I want to do. And a big part of that was taking a corporate IT job that paid me really well and established a level of savings that floated me for years while I kind of explored the type of things I’m doing now. That job really sucked, but I learned a lot about corporations, about people — it’s not all bad.

Working in IT at a telecom company, I didn’t feel like I was harming anyone. My friends who are working in finance — I don’t necessarily feel like they’re harming anyone individually. It’s if you step back, you see a lot of deplorable stuff that needs to be reformed. Yalies going into that sector need to be aware of this important debate. They need to have a broad perspective on the world and not just their own benefit.

My new record actually dwells a lot on socioeconomic stratification. It’s obviously something that’s really interesting for a lot of people: the division between the serving and the gentry class that exists here and that we don’t necessarily even recognize. Now, people are actually finding themselves moving to a level below, over a boundary they didn’t know existed. It’s enlightening, and it’s opening people’s eyes; that’s a lot of what’s fueling Occupy. I was really happy to see the tents on the Green are still up; they’ve gone down everywhere I’ve been for the last two months.

Q. Do you generally have a political bent to your music?

A. My most recent record was very political. I was a bit politically burned out last year, and I spent a lot of the year angry about it, writing about it, singing about it. “Into the Dark Unknown” has a lot of political undertones, but it’s pretty broadly existential.

Q. What words of wisdom do you have for Yalies that want to be musicians?

A. I honestly don’t know. I wouldn’t recommend my path to anyone: I fell sideways into it; it was never my goal, it happened out of necessity. But I would say that if you’re ready to work extremely hard, be strategic and take care of yourself enough to maintain your bearing through pretty rough stuff, you can do anything.

It’s also always good to sail a little bit in the direction the wind’s going, especially in the arts. It’s a process you’re participating in but not necessarily in control of. If you don’t let the world shape your creative direction, you’re going to be fighting an uphill battle. I’m not saying sell out, but recognize this.

Music is not the industry it has been; yet it’s still so many things. The arts are all profoundly important, now more than ever; culture’s especially important, as things get rough. I applaud anyone who wants to pursue that path.

Q. Do they have to be in a cappella?

A. Oh no. Definitely not.