The Art of Music and Life: An interview with Jason Anderson

Jason Anderson is smaller than I remember. He’s so full of energy and passion in his recordings and live shows that it’s easy to forget that he’s a skinny guy with a slender face and a graying beard — or it feels like it’s graying. He looks worn and tattered, like the old trainer hoppers in cartoons. But unlike those caricatures, Anderson has a warm and inviting smile. His personality and positivity are infectious. He’s warm and welcoming and when you talk to him he really listens.

We meet in August only hours before he is set to go on stage. We sit at a small table at T.T. The Bears, a small bar down an alleyway in Cambridge, Mass. behind the more well-known and frequented nightclub and live-music venue the Middle East. It’s an unremarkable bar that feels like any dive bar in any big city with over-priced drinks. We can see the smokers standing outside through the window.

The first time I heard Jason Anderson was at a party at my first apartment in college. One of my roommates played “Movin’ to the City.” It was the perfect song for the moment. It was a cold and quiet night — we lived far from campus so people had to really trek out to visit us — and we had just begun drinking and singing in our living room. The song spoke so perfectly of the moment.

“Tumbleweeds and Joshua Trees/ This place feels like whiskey whiskers/ Rattlesnakes and scorpions/ Jagged Dr. Seuss landscapes and gila monsters / That’s alright for me and my baby.”

Anderson’s music felt new at the time. His album “Tonight” stuck out in the crowded world of Indie music. It was heartfelt, positive and upbeat. It had life and emotion. It went out of its way to avoid the tired cliches of the struggling indie artist. Anderson sounded like he was having fun and that all he wanted was you to join him. Whenever “Tonight” clicks on, my mind jumps to parties and sing-a-longs and happier times. That is epitomized in his live shows, where he wants everyone to have fun and let loose, no matter if it’s a crowd of 15 people at a bowling area in the basement of a decrepit building in a small western Massachusetts town (this happened, I was there) — or at a sold-out show. And whenever you see him, no matter the place or time (including via email), Anderson is a positive force. He’s pushing through the dreariness of everyday life with a smile and an upbeat attitude. He’s infectious.

Anderson has been touring on and off for years now. He’s been trying to piece together a music career one step at a time. We sat down before his show to talk because I wanted to know what pushes someone to keep going even when the dream seems to be so unattainable in this world of mass-marketed, iTunes and auto-tuned world.

I remember a few years ago you were doing a lot of touring.

It was about five years of straight touring.

Does that include now?

No. I took some time off to live in New York City and teach there and then I took a year to get my master’s in education and I’ve since graduated and put teaching sort of on the backburner to really focus on music. Those five years of touring were great, but it was as much a wandering Jack Kerouac odyssey as it was musical enterprise.

I think taking the break after that half-decade of adventuring — which I wouldn’t trade for anything, it was amazing — but taking a break, settling down and teaching and now coming back to music, I feel a lot more focused and driven.

When you say Kerouac adventuring, what does that mean?

For me, and I don’t think this has changed, but I’ve always felt that tour is so much more than playing shows. That’s a couple hours out of the night of course, but then you have the rest of the day and the rest of the evening to explore your surroundings.

I felt so lucky to be untethered with very few responsibilities. It was me and my guitar and car and sometimes a couple friends and so the tours were as much visiting National Parks and swimming holes, visiting friends and family, just sort of exploring the country and the world really.

When you’re doing that — I’ve seen you before and your shows aren’t your typical show—are you expecting great things are happening? In the back of your mind someone is going to be here to see me play; the whole dream. Is that there?

In order for it to be pure it can’t be there. But I think anyone who makes anything that is always in the back of your head, will this ultimately be financially sustainable? Because I think in a way that is sort of the dream.

Whether or not you’re an artist you want to do what you love and be able to do that for your living. If you love it then it’s not “work.” Obviously, I think that can also become complicated because what was your passionate hobby now becomes your job. That can easily become fraught.

I don’t focus on that or even count on it. To be honest, I am just happy when people turn out at the shows.

How did you become a teacher?

My father is a teacher. My mom worked at the high school. My sister is a teacher. I love education. I love working with kids. I love being an eternal student myself. I think music and performing and then teaching [go hand-in-hand].

You’re performing in front of kids.

Yeah, they’ve been sort of two-sides of the same coin. I’m passionate about both. I think they sort of inform each other.

I know that after five years of touring I was really excited to take a break and live in one place. It was great to live in Brooklyn and having the consistency of the same job — getting to know the students, the staff, the families, the community — but then, after four years of doing that and then a year of doing graduate school, I was ready to put that aside and focus more on music and traveling again.

Where did you go to graduate school?

At Smith College in Northampton.

I didn’t know they allowed men in at Smith.

Little known fact is that the grad school is co-ed. Great school. I am very much a proud Smithian.

I went to UMass and I love that area.

So you know. The Pioneer Valley is such a bucolic, awe-inspiring place. I was sad that my program at Smith was only a year. It was great living in Northampton.

A little slice of heaven.

The Montague Bookmill. We could go on and on.

I used to go there to read a lot of poetry.

Such a dreamy spot.

Thats a hike to get from Northampton to the Montague Bookmill [which is not in Northampton, but in Montague, Mass.].

Yeah, but worth it.

You must have gone to a lot of shows at the Calvin and other venues in Northampton.

Being in a one year masters program is really intense. I feel like a lot of the time was spent studying. I was student teaching, taking graduate course work and doing a fellowship. I was working with high school kids in the north end of Springfield doing a program called Project Coach, it was really a six in the morning until nine at night schedule.

It points to the fact that I think after that year and the four years of being settled in New York I was ready to get back into music full on.

You’ve taken on some interesting projects like the song-a-day project, which was great but is hard.

That is when I was in New York and it was nice because I wasn’t traveling or playing shows and I was working as a teacher. It was nice to have that outlet where everyday I would get to create and write a song or two or three.

And now you’re touring again. Is there something new coming up?

Yeah, this band is new. This record is new. I’m just so excited about the songs, the lyrics, the melodies, the group I’m playing with. I feel like, again, that those five years I spent touring, it was great, but I was just figuring out what I wanted and how to do it.

I’m sure you’ve seen me play in different configurations, some shows I would just play on a folding chair with an acoustic guitar leading everyone in sing-a-longs a la the Pied Piper. Some shows would be with a big seven piece band with a horn section and would have more of a 70s Van Morrison, Bruce Springsteen vibe. Other shows I would just sit down at a piano in church and play. I enjoyed all those configurations, but right now I am excited to inject a little consistency into the presentation, to have a consistent band.

This is our third show. We’ve rehearsed eight or nine times and every time we sit down to play it gets better and better. Playing with the same guys over and over, everyone is bringing things to the table, people are coming up with parts, people are singing harmonies, and I’ve never experienced that. I’ve always done the sort of rolling thunder [thing where] I get to town if my friend’s band is opening up I’ll say, “hey do you guys want to stay up there and back me up and I’ll yell the chord changes at you like ‘Back to the Future.’ Hey, this one’s in G, let’s do it!” There’s a great energy that comes out of that—this sort of the heat of the moment, one night only, carpe diem expression.

Right now, I am sort of excited to take things to the next level. I really believe in these new songs and I think they deserve to be taken more seriously with more intentionality.

Have you picked that vibe, that moment in time and style you like now?

The thing that I like about it is that it kind of feels like me. I think when I had bands in the past it would be more of a sort of an E Street Band party rock feel to it. With this it feels more straight-ahead, direct. I think it suits the songs and the lyrics because they’re so direct and it’s feeling really good. I’m really excited for you to check it out tonight.

Do you have a permanent base now? Are you a troubadour now?

I haven’t had a full-time place since leaving my apartment in Northampton when I graduated from Smith. And especially now I feel like I’ve been so many places working on this new project.

I recorded the new album in Austin, Texas and I’m getting ready to fly down there in September to mix it. The band lives in New York, so I’ve been down there rehearsing with them. I feel like I’ve been bopping around so much that the idea of having a lease and paying rent—it doesn’t make sense when I’m not in place longer than two or three weeks at a time.

Are you living with your parents again?

Yeah. We’re very close and I will often stop by there and spend a couple days with them, but it’s really been this summer I spent a month out in Michigan hanging around Detroit. I spent sometime in Portsmouth (New Hampshire) house sitting, been down in Brooklyn, was up in Portsmouth again for another week.

How do you pay for all of this?

I did a tour early in the year. Every time I tour I will make a little bit of money that will get me through the next couple of months. I always have freelance music things, I just did a children’s gig at the ICA [Institute of Contemporary Art] in South Boston, which was really nice. Next week I am teaching a songwriting workshop out on Star Island, off the coast of New Hampshire, for four days. In October I am playing music at a wedding. There are little gigs that will come up that keep me solvent. I’m certainly not flush with cash, but it’s enough to get by.

It’s piecing together a life until you can figure it all out.

Ideally the dream is to finish this record, land it on a label, start touring and see some not only artistic consistency, but see the band get to a place where we can feel comfortable doing what we do and not having to scrape by so much.

There’s an interesting documentary about the band The Snake the Cross The Crown and their second album and how they were at the point where they’re at that point where they’re semi-popular but they don’t make enough money to live off of this journey, so what do we do next? When does this become a dream and when does it become a crushed dream?

I feel like as much as I have worked in the past, five years is a long time to push it, I don’t feel like I have reached my potential yet and that’s what excites me. I feel like the albums I’ve put out in the past, for example this album that I am making in Austin it’s been in a real studio, it’s been recorded over weeks and months. With everything in the past it’s been alright, you have one day to do this in someone’s living room. Or you have enough money to get a studio for two days and you have to record and mix it in 48 hours. I’ve never gotten to work in this way and I’ve never been 100 percent satisfied with anything I have recorded or released because I have always known I have something more in me. With this album I feel like I am finally stepping up to the plate in a way I know I have always been able to, but have never either because of financial or logistical, never been able to get there. Also, performance wise, yeah I spent five years pushing but I don’t think I had it straight in my head what I wanted to do.

Now, having this band I can see it a lot more clearly. Your question is valid, maybe we put out this record and push it for a year or two and it still doesn’t feel like it’s reaching a larger audience. You know, I’ll always be writing songs. I’ll always be playing shows even if there are just 10 people there and giving it 110 percent. I’ve never been concerned with turnout or financial reward, but at that point does it become more of a hobby and I go back to teaching or maybe go back to grad school, absolutely.

Would you go back to teaching?

Absolutely. It’s nice that I now have the master’s degree and have that in the backpocket. Because it’s such a twin passion it doesn’t feel like a consolation prize. The idea of teaching and maybe going on a few tours over summer break, that sounds pretty dreamy. In a short answer, in a way I still feel like I am ascending especially because those five years I spent touring I was just sort of figuring out the DIY scene, playing houses, basements, kitchens, backyards. It was such a learning experience. I guess I’m just excited for the next year.

Jumping back, what gave you the idea to start playing music? By idea, I mean there is a moment people don’t like to talk about but it’s there where they decide to pick up an instrument or a pen or something.

I’ve always felt like a bit of a performer. When I was little, my brother, sister and I would always — and this is a tradition we do today and I’m glad we stuck with it—every Christmas we write a play for our parents and we make them sit in the living room and we perform for them. My brother and I used to put on Beach Boys tapes and wear sunglasses and play tennis rackets and play these “concerts” for our parents. I grew up going to summer theater camp. I always enjoyed performing and entertaining people and the connection that comes with that.

Obviously when you’re younger you’re not analyzing it or thinking I like this because it’s an exchange of humanity or I like this because it’s a centering thing where we’re all in the moment for a half an hour vibing on it. It was just fun. I enjoyed it. Maybe I even just enjoyed the attention a little bit. There’s that performance piece: my grandmother teaching me the piano when I was in third grade and then getting into guitar in sixth grade and switching to electric guitar and getting to play guitar in the jazz band in high school. There was that element of being really intrigued by instruments and music. And then you combine that with a personality that is pretty gregarious and I enjoy connecting with people and making them laugh and having fun. It seems like it was always something that was sort of metastasizing with me.

Then you know there are a couple flashpoint moments. I was a teenager in the mid-90s when bands like Pearl Jam were breaking so it was a really exciting time to be so impressionable and coming of age when music on the Top 40 was so powerful, bands like Nirvana, Smashing Pumpkins, it’s crazy to think that these bands were played on the radio. Another was I went to undergrad out in Portland (Oregon) at Lewis and Clark College and when I was 18 I got to see Elliott Smith play a solo acoustic show when he was just getting started at a coffee shop to probably 30 or 40 people and at the time I had never heard of him. My friends dragged me there and I was absolutely blown away.

And you know, living in the pacific Northwest when bands like Modest Mouse, Built to Spill, Death Cab For Cutie, were all forming and starting to play their early shows I was kind of in the right place at the right time. At the time when you’re living, and at the time I don’t think you’re analytical, but looking back now I can sort of point out little mile markers when I thought, hey, I’d like to do that too or this is really inspiring me.

What was the first show you played then?

The first show was really funny. I had this band called Vivid Colors with Derek Swenson and Bryant Stockwell. I was in ninth grade and they were in eighth grade and we played a show in Derek’s parents’ barn and we invited three girls to watch us play. We were so embarrassed to be performing that we didn’t sing and we insisted on hanging a bed sheet between us and the girls so these poor, patient high school girls they were sitting on folding chairs staring at a white bed sheet while these three dorks behind it were playing instrumental songs because they were too sheepish to sing.

Were you suppose to sing?

I don’t know if we had a lead vocalist at the time. Probably either me or Brian. I don’t know if that really counts. We played some battle of the bands in high school and then when I was in college I started playing solo acoustic shows at the student coffee shop. That kind of felt like the first real shows, I was writing my own songs.

When you started out were you the nervous type or were just as you are now, full of energy?

Definitely nervous. I mean it’s developed. That’s another thing, not to go back to those five years spent on the road, but I wouldn’t trade it for anything because aside from all the adventures, meeting new friends and seeing so many amazing places and learning about America and beyond, I just really learned about performing and it definitely wasn’t as, I don’t want to say effortless, I feel comfortable and I feel a lot more adept at reading audiences and comfortable communicating with people. I was just figuring it out year after year.

When you started out what is the one thing you really learned?

With performing, I definitely learned to listen more and be more flexible. I used to sort of be combative in the sense that it came from a good place, I really believe that live music can be a lot more than a crowd of people just staring at a performer on stage. And so I have always been one to encourage participation, at least try to reach out an open hand to the audience, but I think in the past I was a little more heavy handed of like “We should all sing along!” But more not realizing that not everybody in the audience is going to respond to that. Some people just enjoy standing there, letting it wash over them and that can be an emotional transcendent experience. That you don’t have to have your fist in the air, you don’t have to sing along, you don’t have to be right up front. You don’t have to be crowdsurfing. There are many ways to find transcendence and catharsis in music. That is something that I learned and it’s been really humbling to me, if that makes sense.

That does because I am the person who stands in the back and leans against the wall and just enjoys being there.

I think part of that is my maturation has dovetailed with that. I think people have loosened up a bit at Indie Rock shows especially because when I started there was a lot of arms crossed, staring at your shoes, distance. It was very serious in that way and I wanted to push back against that a little bit and remind people what about bands like Springsteen or U2 or bands that could make you feel like you just went to the Church of Rock N’ Roll, like can’t we feel something again. It came from a good place but I was young and I was just figuring it out, so I think it was a bit over eager, “everyone come up front, everyone get in a circle, everyone put your hands in the air, lets do it! Let’s be alive tonight!” You can lose people that way. As many people who saw that as being refreshing and invigorating and galvanizing there were people who probably thought, “dude, chill out, we just want to enjoy your tunes.”

When you go to teaching do you take these lessons with you? I feel like they’re so similar, each kid is different.

You have to listen. There is no one cookie-cutter lesson plan. You have to be willing to throw your lesson plan out if someone asks a question five minutes in and you realize, whoa, we got to backtrack.

Did you teach music?

I did in New York, but I got my master’s to be an elementary school classroom teacher, so gen. ed., math science, social studies.

Where would you want to do that? Would you want to go back to New York?

I loved being out in the Pioneer Valley. I student taught in Northampton. I often daydream of ending up back in Amherst or Shutesbury or somewhere like that.