"The first time I heard Gregory sing was through a friend’s iPhone recording of a house show he went to. I instantly knew that there must be something special to his music if my friend was completely convinced that I would be floored, even with just a speakerphone recording. He was right. It was rich. It was haunting. It was, to be honest, a bit like hearing some of those old found recordings from early in the career of some of the masters. Dylan, Springstein, Young. Gregory is a modern legend in the making.

Gregory stopped by for a session while on a recent tour, and we must admit, it was something quite special. He was only with us for 20 minutes, performing just a handful of takes before heading out to the night's venue. We think you'll agree that the honesty, the skill, and the sincerity of his performance speaks for itself.

We've been listening ever since and we think you will too.

Ryan then sat down to talk with him about the peculiarity of making music a profession, chasing down ideas, and how wonderful giant post it notes can be for the writing process."

- Patrick Dodd, Executive Producer

Ryan Booth: I’ll let you take this where you want, but from you, more than others, I’d love to ask, “why music?”

Gregory Isakov: I was an horticulture major in college and have had a really crazy love affair with plants for quite awhile. But music has always been part of my day, even when I’m working on something else. I’m always after a line or a melody. It’s felt like something that I have to do. I don’t think I would be doing music right now if I didn't feel that way because it’s kind of a pain in the ass career (laughter). Though, of course, I feel lucky that I get to do it for a living right now.

RB: How did that transition happen? Was there a moment for you that you can remember specifically deciding you wanted to make a career out of music?

GI: I don't know if there really was just one moment, you know? I think I’m still there, asking the question, “Is this really working?” I managed a farm for seven years throughout college and a little afterwards. I took care of most of the food production and I would tour in the winters when we were off. The people I worked with were really great and they didn’t charge me rent while I was gone. I loved traveling and I thought music could be a cool way to get to travel for free, so I’d book a show in Whitefish, Montana or something just so I could go camp afterwards. At first, I was very shy about playing out, so I would do very short runs. Actually, I guess it’s really taken a while to get over that.

I loved traveling and I thought music could be a cool way to get to travel for free, so I’d book a show in Whitefish, Montana or something just so I could go camp afterwards

RB: Did you find the writing part to be the part you favored most? Because there is the “making stuff” part of music where it’s just you and a few collaborators, and then there is the “sharing stuff” part of music where you have to go out and play in front of people. Did you ever wish you could just do the making stuff part?

GI: I’ve learned to really love both. Performing was something I just didn’t understand for a long time. I honestly couldn’t get why people would want to listen to me just play a song. I would think to myself, "Guys, I made this record, maybe you should just go listen to that.” But over time I began to realize that there is something quite amazing that happens when you perform your music for people; it’s an opportunity to be genuine and real and I've found that it's only very rarely that you are allowed to be so publicly honest. Besides, when I was a gardener, it was probably one of the loneliest jobs I’d ever had. I’d work by myself mostly, and I’d work out stuff in my head a lot. So, getting to travel with other people and play music with my friends is just amazing. And the fact that people take time out of their day to come listen is crazy to me. It’s such an honor.

RB: What is it like to be up on stage and really see a crowd begin to take ownership of a song that you’ve written…to watch it morph and change right in front of you?

GI: It’s amazing. I only ever feel like I’m working with a song during the creation of it, when I have this really close connection to it. Even when I'm writing, I don’t feel like I own the song, but more like the song owns me. And then after I put it out in the wild, it honestly feels like I’m just covering it. I don’t even feel like the song is mine anymore.

RB: When does that happen?

GI: Meaning, when do I start realizing it?

RB: Yeah, at what point in the process of writing do you feel like that transfer happens? That you’ll move from the author of the song to the guy covering a song that someone else wrote? When is the switch?

I only ever feel like I’m working with a song during the creation of it, when I have this really close connection to it. Even when I'm writing, I don’t feel like I own the song, but more like the song owns me.

GI: I think it must be after I record it. Or even sometimes after I finish a song. I write a lot at home using these giant post-it notes. Seriously, they’re huge poster sized post-its. I put them all over the walls, and I’m always cutting and pasting and I’m always staring at these bits and pieces. I’m obsessed with finding the spark of the song, the feeling of the song that exits before I try and work on it. The rest is a literary process of sorts, trying to find the right words to draw that original feeling out. That’s when I feel like the song owns me for a while. But then I record it and there is the this strange feeling, as if I don’t know who that is that just made that thing. It’s hard to explain. It’s honestly a mystery to me— I think that’s why I really like it a lot.

RB: Has it always been like that? How has that process evolved over time? Does it still feel fundamentally the same over time?

GI: It’s always been about protecting that original feeling. In the studio we’ll work really hard on arrangements for a few months and then we’ll step back and create some space. Then we’ll re-visit the work a few weeks later and sometimes, after we listen back, we’ll throw the song out if I’m not feeling anything anymore. But if it’s still there, if it was a good idea, then we’ll take the song on the road and play it live. It may be messy and fucked up in parts. It won’t be perfect, but there will be something to it. But it always starts with a feeling.

RB: It can be a frightening feeling to want to communicate something but to not exactly know what that feeling is. Almost like it’s floating in the ether a bit. It seems like some people panic and can get very literal and feel the need to explain everything. Maybe it’s just a way to cope with their own fear of the unknown, essentially. But that “unknown” is fundamental to the creative process.

GI: Yeah, for sure.

RB: That’s interesting to start with wanting a song to feel a certain way and then beginning to construct it in a way that brings that feeling to life.

GI: We recently had a week off of tour, right before you and I met, and my house flooded. We came back from the West Coast tour and found quite a bit of my stuff ruined, though mostly replaceable things. Except, I have kept all of my writing since high school, and it all got trashed, really soaked, and I was really bummed about it. I set everything out to dry, hundreds of journals that had I kept throughout high school. They were all spread out all over the place. And I reread them while they were drying. It’s interesting to see how I felt like I needed to try really hard to express something in words in a very literal way. It felt very high school to me. So maybe that is “growth,” to be able to express things in a non-literal way. To have a feeling and bring it to life. It’s actually the way that I experience things in my life as well. It’s not in words or phrases or full sentences, or you know, but more like scenes or snapshots. I guess that is how you would make a film.

RB: I do sense that correlation for sure. I feel like that to like to really create a moment for people, you have to create a framework that allows people to bring their own thoughts and experiences to it in a way that fills in the gaps. Almost like the song isn’t really done until people listen to it and respond to it. Only then is it a finished thought. You know?

GI: Yeah, exactly. That’s exactly right for me. I think one of the reasons why my band works so well together is cause they just have such a great respect for the spaces in the music. And I mean they’re badass players, but you almost would never know it because they are serving the space in the music. I think we’re trying to create these pockets for people to dream up things.

RB: Interesting. so the live show is an integral part of what you do then. It would have to be, in that context.

I had really felt like as a songwriter, it was my job to work for months and months and months until everything was perfect. But something has shifted and I am finding the imperfections to be beautiful now.

GI: It definitely is. I’m even beginning to bridge that gap with our records too. The record we just put out was recorded mostly live, whereas the records before this one were really slick and assembled. With Empty Northern, if something didn’t feel right, I would take the song and work on it for weeks, muting tracks and digging for sounds. I wouldn’t stop until it was right. That was a really cool process for me. But this record, if something wasn’t feeling right, we’d just start over and try and capture it all at once.

RB: I can’t quite put my finger on it other than it seems like that that process of tracking live and really simplifying production is a theme I’m hearing come up with a lot of people right now. I wonder what that is.

GI: Maybe I’m just feeling the collective on that for a second, because it was uncomfortable for me at first to work that way. I had really felt like as a songwriter, it was my job to work for months and months and months until everything was perfect. But something has shifted and I am finding the imperfections to be beautiful now. That comes from the live show too, where nothing will ever be perfect. You’re just trying to create a space for the listener. I think another reason I’ve changed my approach is that when you’re the artist, there is a very small window of time where you can have a fresh perspective. But soon, you’ve been sitting with the songs for months, and you just don’t know if they’re good anymore. So we work quickly to try and stay inside that window of time.

RB: That’s an interesting way to think about it. Basically, you need to get the big chunks of it done as quickly as possible, just so that you can work faster than you can think.

GI: Yeah, and then you can clean it up a little later if you want to, but…

RB: But you may not be able to fundamentally change the structure of the thing if you’ve gotten it done in those broad passes. Interesting. Basically, you’re trying to take yourself out of the equation.

GI: As much as you can, yeah. You know for me, I feel like I’m five years old in all of it, I feel like I’ve just been trying different things and I don’t really know if I’m better than I used to be. It’s art and you’re just trying to be present. Maybe I’ve gotten better at a few things like being uncomfortable and being present, but I don’t think songwriting is something that I can master.

RB: Do you feel like that are you somebody that worries about the idea of making progress, whatever that may be?

GI: I don’t think I do anymore. I think I maybe used to feel that way. But I think a lot of artists go through that, you know? When I started, I never thought anyone would hear my songs. But then you work hard and put out a record that people hear and you’re like, “Oh fuck. Now I have to make something better.” I think that feeling comes up for everybody, and you just have to kick that to the curb as soon as possible because I mean that’s the opposite space of feeling creative. That feeling can be what most people would describe as “progress.”

RB: So, if not progress, what about goals? Would you say there is a direction you’re heading?

GI: I think about that all the time. I don’t have a goal. It’s funny, I actually still feel like I’m just trying this whole music thing on. There was a high school kid who came up to me after a show the other day. He’s a musician and just starting his career and he came to ask me some advice. I just told him, "my goal is not really really having one. You should really try to be fully invested in the song and not worry about Facebook or Twitter or all that crap." Honestly, I feel like it’s a weird thing to take art and make it into your career. I’ve never really worried about it because I’m a gardener by trade, and so I’m always going to do that in addition to music.

I think a lot of people watch TV and have a fundamental misunderstanding as to how music or art is made. I mean, people actually think a show like American Idol is how you fucking make music, and it’s so sad. As if you need some judges’ permission to make something.

RB: I think there’s a lot of pressure. I mean our national culture is wrapped up in buying and selling things. So, if you make anything cool, eventually someone is going to ask you, “So what’s your plan for buying and selling this thing?” I think the sub-layer to the “goal” type questions is, “What do you want,” and that is almost always phrased as an economic question. I struggle with that a lot, but I’ve found that I have made more “progress” finding my voice or vision by taking the commercial side out of the equation and doing work that doesn’t involve getting paid. I think a lot of people, especially when they’re starting out, are really focused on trying to make money doing this thing they love, and as quickly as possible. I’m not sure that is the healthiest place to start from.

GI: It’s sad right now, because I think a lot of people watch TV and have a fundamental misunderstanding as to how music or art is made. I mean, people actually think a show like American Idol is how you fucking make music, and it’s so sad. As if you need some judges’ permission to make something. I mean, for me, I’ll get my friends together in my basement and play music just having the best time of our lives. Even if it’s shitty music. Who cares! Playing music with your friends or by yourself late at night, it’s a sacred thing.

RB: Is there something that you hope people take away from bumping up into your music, whether that be live or listening to a record on their own?

GI: Yeah, definitely. It’s always on my mind, both at shows and when I’m making the records. I think they’re both such different beasts with different audiences. When I’m writing a record and recording it, figuring out what kind of instrumentations or the lack of instrumentation, I’m singing to this one person in their car. I’m “performing” for that one nameless person. But when I’m playing music live, it’s such a different energy and we’re really playing for the collective. I always like hope people walk away feeling inspired to go do their art. I also hope they walk away feeling live we’ve had a conversation about the stuff in life that’s really fucking hard. And maybe they might see that it can be beautiful too.

RB: I love that. Now, I’m sure you get asked a lot, but do you find a connection to what you did as a gardener and what you do with music? Is their overlap for you?

GI: Yeah, I think so. For me, I think any kind of work is so good for art, especially working outside. I was a roofer too, for a couple years. I don’t know, I have this huge nerdy science side of my brain that needs to be fed all the time. And gardening really does that for me. I mean, I was a soil science major, but…(laughs)…I think hard work can help you be empty when you play.

RB: Interesting, what do you mean by that?

GI: I think a lot of work is like that, it’s at the end of the day when you come home empty that you can actually create art.

RB: Like you’ve expended yourself, to the point…

GI: Yeah, you’ve had all your thoughts, your body is tired and you’re done with all those mental processes for a little bit.

RB: Do you feel like that’s a requirement to then be creative or make whatever your art is?

GI: For me, it definitely is and I do miss it when I don’t have it. I don’t feel right when we’re on a three month tour and that’s all we’ve been doing. I don’t feel like that’s a healthy, sustainable lifestyle. (laughs) I think we’re all trying to find that balance of giving and making sure that we’re taking care of ourselves in our own way.

Even to follow through on that initial stroke of inspiration takes a ton of work. I think that always gets overlooked, because I think people see artists that they admire and think maybe they were born that way or something. But then you realize people work really hard at it. It’s a constant relationship with the process.

RB: Is there a moment that wells up inside of you, a feeling like, “I have to write something.” Is there a starting point for you when you start working on new songs?

GI: Yes, definitely. In the beginning of my relationship with writing, I would go through this period of being very productive and cranking material out. Good or bad, just writing. But now, there might be big chunks of time that go by where I haven’t written anything. I used to really get worried about that, thinking, “Am I done? Is that all I got?” But now, I just trust that it’s going to come back. There will always be this time where you feel like there is something you have to dig for to find, or else you just don’t feel right. And for me, songwriting comes down to that, like kneading bread.

RB: It’s a process and that is both maddening and comforting, I think.

GI: Sometimes, someone will come up after a show and tell me how much they love my songs and that I must be such a good writer. And I just laugh and say, “nope, you’re just hearing the stuff that I decided to keep.” I think there is so much “punching the clock” type work involved in writing if you want to really see it through. Sure, inspiration may come at random times, and you try your best to grab on when it does, but even to follow through on that initial stroke of inspiration takes a ton of work. I think that always gets overlooked, because I think people see artists that they admire and think maybe they were born that way or something. But then you realize people work really hard at it. It’s a constant relationship with the process. I have this friend at home and we always talk about Leonard Cohen, and how we think this guy is such a genius. One night, we were talking about this one particular song, and I suddenly realized, no one ever sees his trash can. No one ever sees all the shit he throws away. As artists we wish it could just be easy and that it should all come at once, but that hasn’t been my experience personally.

RB: Yeah, I don’t think it’s anybody’s experience, if we are honest. Especially not if our goal make things that have kind of substance that last more than you know, a week.

GI: Yeah, I get lucky once in a while, like once in a while like a song will happen and like you know 5 or 10 minutes and then it’s done. It’s so rad when that happens. But it’s definitely not often. So, in the meantime, I keep working.