On being the captain of your own ship, comfortable collaborations, and figuring out what works for you along the way

Katie: Tell me about the beginning of you writing songs and playing music. What led you there?

Jess: I was always a singer. I was the singing kid.

Katie: Me, too!

Jess: Really?

Katie: Yeah—like choir, that kind of thing.

Jess: I remember being in second grade, on the playground with my friend, and I had this moment where I figured out how to sing. I remember because it was this moment where I realized if I tried to sing kind of how I talked, it would sound better. Instead of trying to make it sound high and pretty, or something—and it clicked. Me and my friend would have little concerts on the playground for the other kids where we would sing Ace of Base songs. I was always singing, but I never learned how to play an instrument; then I went to college and studied photography and all my friends were in bands. I worked at the radio station and the newspaper writing about bands. I would interview bands that would come through and take photos of them, but I was so jealous secretly.

Katie: But you weren’t doing any of that?

Jess: No. I wanted to be, because I was a fan. Like in high school, I was a super fan of Bright Eyes and the Saddle Creek scene. I was getting into music and going to shows all the time and it was kind of my whole world, but I wasn’t a participant.

Katie: It’s so funny because I feel like you would be my ideal friend when I was in high school. [Katie’s sister] Allison [Crutchfield] and I played music and we were the only girls in our group of friends who were participating in the music-playing aspect of it. But we had so many cool girlfriends who I think felt like they wanted to but were sort of pushed out because there was… I don’t know if this was the case for you, but there was definitely an energy of the boys that would make the women feel bad or unwelcome if they put themselves out there. Allison and I, by the time we were participating, we were pretty good at playing and writing so nobody messed with us, but I remember having all of these amazing girlfriends who I could tell wanted to get in there, but never felt safe to do that. All I wanted was to be the person who would go put a guitar on my friend and just be like, “You can do it! I’ll teach you how do it.”

Jess: Totally. My friends all had bands and I would go to their shows, and my boyfriend had a band and… My biggest thing was maybe they’ll ask me to sing backup or something, which they never did. I have a memory that’s coming back to me of being at my friends’ band practice and they were all playing instruments and it was all boys, and they were like, “Why don’t you sing something?” And so I got on the microphone and was kind of just making something up and I remember my friend laughing at me!

Katie: That’s horrible.

Jess: That stuck with me all through college.

Katie: Because you were scarred?

Jess: Yeah, because I didn’t play an instrument. And then during my last year of college, I saw this guy named Ralph White play a show, a house show, in my friends basement. He plays the banjo and it blew my mind. I loved it and kind of on a whim the next day I was like, “I’m going to figure out how to play the banjo,” and I did. That was my first instrument.

Katie: Okay, we have to have a Dixie Chicks cover band now that I know that you play the banjo!

Jess: I’m down! I think for me, it was like, “Okay, everybody else has been playing guitar since they were 12, but nobody plays the banjo, so this could be my thing, where I won’t feel like I’m behind.”

Katie: Totally, and also, low-key, the banjo is so hard. It’s like if you can play that, then you know, the guitar will be easy.

Jess: It is a little harder. I need to pick it back up.

Katie: When did you start writing your own songs?

Jess: Really from the very beginning—I started writing simple songs with the banjo. Then when I finished college I moved to New York to go to Grad school for photography. Two semesters in, I had a total freak out because I was taking out all these loans and I realized, “I’m 21. What am I doing in Grad School? I just want to have a band. I just want to play music.” I left school and had a band in New York for a little while called Rattlesnake. It was just me and a friend. It was a duo thing. I played banjo and she played guitar and we both sang. And then, a few months later, I moved back to Austin to get a solo project off the ground because I had a community there. I didn’t really have that in New York.

Katie: New York is hard. That’s cool that you knew that, intuitively, that you should go back to Austin. I had a really similar trajectory where I left New York to go to Philly and it was kind of for the same reason. The early 2000’s were a beautiful time for music in New York. I really think that around 2010 was where it got too expensive, way too crowded with artists, and it just became so concentrated and difficult to breakthrough or even find community. That’s my perspective at least. The 2010’s is when things started to look a little different, at least for me. I’m sure it’s always felt overwhelming, but at the time it felt like everybody was just this tiny little dot in this giant ocean of great art.

Moving to New York was great for me because it gave me some kind of exposure to this entire other way of creative life. Coming from Alabama, it gave me an understanding of how to actually be a full-time musician. But I also worked so much that I never could go on tour and I could barely afford to live there. So it was cool to get a quick snapshot of all of it and then to go down to Philly, where I could actually have space to focus on music and find a community. Which it sounds like what you have in Austin.

Jess: Yeah. Where did you work?

Katie: I worked at a coffee shop in Gramercy Park. Very fancy. I had a roommate who managed this café and she was like yeah, “I can get you a job.” It’s funny, I remember I made my first album, American Weekend, and I didn’t put the album out for a year and a half. Like, I made the album, didn’t give it to anyone except for Allison, and I sat on it for a year and a half before it ever got released. I remember in that in-between time is when I worked at that coffee shop and I would sometimes, just to test the waters, I’d put the album on in the café and see how people reacted to it. I remember cool people would come in there sometimes, like Adam Green would come in or, you know, just different cool people and when they would come in, I would always put it on…

Jess: Did anyone ever say anything?

Katie: I feel like maybe once or maybe twice. But, not really. My coworkers were always just rolling their eyes. Really? This again? But I would just want to see, because it was my first solo thing. I had been in bands for years before, but that was my first serious solo project and I was so protective of it and so excited about it and I felt like it was the most vulnerable I’d ever been on anything and I was just scared. And then eventually I put it out and it was fine. But I was just constantly like, can I share this with people? Maybe, like, this will be very anonymous if I just put it on to see how people would react.

Jess: What did that look like when you made the first record and what happened in that year?

Katie: It’s funny. It’s like stuff about myself that I still see all the time in little moments, things that led me to realize I had to do a solo project, which is that I’m just such an annoying control freak about everything regarding how I present and music. I just drove everyone insane. I was in the Ackleys and even then, I mean, that was my band when I was literally like 17, 18-years old … the Ackleys were a popular band in town… I’ll tell the quick version of this story.

The Ackley’s were, locally, a beloved band. We could fill up rooms and were these teenage stars in town. People loved us. But when we would go on tour, no one cared. It was kind of sad and it made us discouraged. Then we started P.S. Eliot when we were 19—it was really a reaction to the Ackleys. P.S. Eliot was sort of like us going back to our musical origin of lo-fi and punk. That was in the height of cool, lo-fi bands in New York and stuff like Vivian Girls and No Age. So we were going to do our version of that and people didn’t get into it in Birmingham. But we started to tour a little, and people really liked it.

So anyways, the whole time in that band, I just struggled. I was struggling to work within that group dynamic of a creative democracy. Because I was writing all the music, I was just sort of like “this is my thing” and was constantly having unpleasant dynamics in that setting.

From there we went in waves of not getting along and stuff and toward the end of the band is when I recorded the first Waxahatchee thing and it was in the back of my head that this is just going to be more suitable for me, to have total aesthetic and creative control over a project. I made that record right before we moved to New York.

Jess: I really relate to what you said about needing to be the boss, basically. I only was in one band, Rattlesnake, before I started doing the solo thing. It was short-lived, but for the same reasons. I realized that I need to be solo because for me, this is all I want to do. This is my life. This is my career. I’m super ambitious. This isn’t a side thing for me and nobody is going to take this as seriously as me and I don’t really want it to be a democracy!

Katie: I know! It’s so interesting. I talk about this a lot because I think it’s very relatable for anybody who’s been in a band. There are interesting power dynamics where different personality types will naturally want to be the leader even if they aren’t the one with the big creative vision and that’s really what I struggled with. It’s weird, these personal dynamics that you have to navigate. I will say, sometimes creative democracy within a band setting can lead to great stuff. I do think it can kind of go either way. I just often see bands be so much more functional when there is, sort of, a creative leader or those roles are more transparent and communicated and everyone’s comfortable with it.

Jess: Someone has to be steering the ship.

Katie: Someone has to be steering the ship.

Jess: And similarly, if everyone’s expected to steer the ship, but only one person really is, then you feel held back by that. I think the solo artist model is nice because the roles are all clearly defined. It’s like this is this one person’s project and you’re coming on to support that and it’s all clear. The first couple years it was hard for me because I needed other musicians to play with me, and there wasn’t really any money. They were part of a project called Jess Williamson and getting paid almost nothing. I would always give all of the show money to my band, but $100 split three or four ways doesn’t go very far.

And there were hurt feelings. People felt like they were in the band and they were irreplaceable and then they felt like they were owed a lot—and they were owed a lot—but it became blurry. I had an experience of being on a tour where someone that was on tour with me, midway through, had this crisis where they were like, “What am I doing here? Why am I even doing this tour for free? It’s your thing. What am I even getting out of this?” And that was intense for me because we’re half way through this tour and I’m like, “Yeah, I know! I’m sorry!”

Katie: You know, I’ve said it before and I’ll say it forever, that being in a band is truly like being in a big polyamorous relationship and it is delicate and tricky to navigate, no matter what. I feel like the older we get, and the more experience that we have, the better we get at knowing how to treat people and how to choose people who are right for us.

It’s interesting from all sides, the leaders, the players, I see every side of it at this point. I feel like I could write a whole book about all the crazy experiences I’ve had with my different band mates.

Jess: I felt bad that there wasn’t enough money or any money or whatever and so because of that, I was like, “Well, I guess how I can make up for that is make sure that you’re having a great time. And so, I can’t ask too much from you because I’m not paying you enough and it should just be really fun for you.” So I would bend over backwards and do so much of the heavy lifting and even having experiences where it’s like, it doesn’t matter if I can’t hear myself singing, as long as you’re having fun playing your instrument, that is equally as important as me being able to hear myself sing because I’m not paying you enough. That was honestly my mindset at a certain point in time.

Katie: I know. Honestly, same. And having bad boundaries with that stuff and not taking care of myself and then also being overly generous or having an inflated sense of responsibility. A lot of things stem from bad working dynamics. It becomes really toxic, really fast. It also reflects my personal relationships so perfectly. The journey that I’ve been on with my close, personal relationships—like my romantic relationships and my close friend relationships—follows parallel to my band relationships. I’ve just learned so much from the experience.

Jess: Yeah, it is a learning thing. There’s this Rumi quote that I love which is “What you seek is seeking you.” With this Sorceress album cycle and with these upcoming tours, which at this point, who knows when they’re going to happen, but I was like, “Okay. I’m going to have a whole new band. I want good players but I want the right vibe and I know it’s a tall order, but I think that those people are out there and they’re looking for me, too.” So I sent out an email that basically explained I’m looking for strong players and I’m looking for, most importantly, the right vibe and I want this to be fun and a celebration of life and music and good experiences and part of that for me is having a healthy relationship with substances.

I led with that where I’m like, “I’m not saying that it needs to be a dry tour at all, that’s not what I’m looking for, but I can’t do a party band. I can’t do people hung over at the 10:00 AM radio session. That’s just not my style. My style is let’s make tea after sound check. Let’s go on a walk. I want to find AirB&B’s with a hot tub,” you know? And I just really nicely wrote that in these emails and the people that responded were like “THANK YOU!!”.

Katie: Of course! I mean, honestly, it’s interesting we got this far in this conversation and didn’t bring up the fact that a lot of my issues in the past have everything to do with bad relationships with substances. With this new phase of the project, I was exactly the same as you. With Saint Cloud, I wanted to prioritize finding people who will make me, as a newly sober person, feel comfortable on the road. I cannot do the sad, hungover, next morning anymore. I can’t do the we’re all going out after the show. I was the one leading that charge for so long. I do find that through trial and error you find your people and that is really, really beautiful and important. And also everyone takes so much more pride in the reason that we’re all there is to perform and play music and have a beautiful experience on stage. I feel like for so long, because I was just in a bad way with alcohol, I feel like I didn’t really care about the way the show went. It was like, “I wrote these songs. I’m a songwriter. I’m not really a performer. I don’t really care about sounding good, or whatever. I’m just going to go out there and just be myself and do my thing and have a bunch of drinks and then just go out. That’s why I’m here.” And now, my perspective has just shifted so dramatically.

Jess: It is this kind of punk attitude that I think I had, too, when I was younger and just trying to play shows and thinking it doesn’t matter what I wear because I’m not a performer. As if that’s selling out or something.

Katie: Same! 100%. It’s so dumb! I know! It’s so dumb.

Jess: It is dumb!

Katie: And I feel like now, I’m like no! It’s self-respect. I need to love myself enough to go out and hone some power for a second and put it out into the world. Earlier on I was just like, “I’ll just stumble out on stage and kind of mumble my songs into the microphone and then stumble off and go out with my friends. That’s what’s actually important to me.” It’s shifted so much, and now, here I am.

Jess: And now, here we are!

Katie: Here we are! Yeah. I’m just trying to sustain that excitement for as long as I can until finally we all get to do our thing again.

Jess: That is kind of one of the big lessons of the quarantine, for me, is it is making me appreciate playing live music like never before.

Katie: I know. It’s interesting because for someone like Kevin [Morby], he has just done a full album cycles worth of touring so it’s a good time for him, he’s tired. He’s ready to take a break and it’s an interesting scenario for me because I had just taken such a conscious break. I was like, “I am going away. I’m going away for a few years and then I’m going to come back and I will have missed playing music so much that by the time I’m playing again, I’ll be so grateful for it.”

I had really run myself into the ground to the point that I got sick of it and that was kind of all happening right when I got sober and I was so excited and ready and now I’m like, “Okay, I’m just going to have to wait a little bit longer.” And, that’s okay.

Jess: I know. I just keep thinking everything is going to work out how it needs to. I’m learning a lot. It’s funny. I announced my tour dates, which are in June, which … you know, as of now, they’re still on. I just want to wait until the last possible second before canceling. But even when I announced the tour dates, which was before the quarantine, I had this panicky feeling where I was excited but I had this feeling of dread almost because at that point, I didn’t have a new band yet. I hadn’t figured out who was going to be in my band so I was announcing tour dates not knowing how I was going to pull this off.

Katie: Right.

Jess: It gave me a lot of anxiety. And then I put my band together, which brought some relief but I was still nervous. But now the threat that the tour might not happen has made me appreciate it so much, and made me realize what a gift it is that people want to go on this tour with me and be in my band and people want to come to these shows and how lucky am I to get to do this? I need to have no stress about this. This is nothing but a good thing and a fun thing.

Katie: Totally. I’ve honestly had the same attitude about it and, you know, I’ve had to just believe that it was always meant to happen this way and what was meant to come out of it is going to come out of it and it’s all going to be fine.

At the end of the day, I feel like we’ve both just made career high records. We made our best records yet. That’s really great and exciting and, you know, people will respond to that. Also, people need music right now. That’s really been my big thing. I was really sad about my tour because I was so excited about it. I feel like I put together this perfect family band—we had rehearsed and we’d all spent this magical weekend together and right after that was when we all basically just got stuck.

I was very bummed and I had to grieve that and I’m still kind of grieving, but I do think that a big thing I’ve learned from this whole experience is just that … Saint Cloud is my most hopeful album. I feel like if it can bring people some joy right now, then that’s great. It feels almost like it was meant to happen the way it happened. I’m happy to be releasing this new music right now, in this situation. I feel like people need it and appreciate it.

Jess: I agree. And I think we talked of this before, it becomes not about what we get out of it anymore. Because all bets are off.

Katie: Yeah. I know … Well, that’s the thing, too. When I really think about it, I’m like, “Oh my god! My tour and this and that and me, me, me…” And then I zoom out and I’m like, “Wait a minute! Beyoncé can’t even tour,” you know what I mean? “The NBA is not happening.” Everyone is in this situation. It is really not about me. Every single performer all the way up the ladder and all the way down the ladder, every single person is in this exact same situation and there’s some comfort that comes from that sort of shared feeling. We’ll all figure it out in good time and so will Beyoncé. It kind of makes me feel comfort just knowing that this is a shared thing, it’s not just my tour. It’s everyone’s tour. It’s everyone’s life.

Oh, I wanted to talk about another thing that we share, which is being an indie rock person but coming from the South and having country music as a big part of our foundation. It feels like now we’re both trying to bring it back into the fold of our own music. I feel like both of us did that on these new albums in a way that’s really interesting to me and exciting. Tell me about your relationship with country music.

Jess: I love this question and then you also have to answer. Well, I grew up with it like you did. I remember being a little girl, being like mom, I’m going to be a singer like Dolly Parton. That was my reference point. I was raised on country music in Texas and then in high school I thought it was lame. I thought country music was bad because I liked pop-punk and whatever.

Katie: To be fair. In the early 2000’s, country music was bad.

Jess: True. And then when I moved to Austin to go to college at UT, that was when I realized country music was cool because my new friends were showing me music like Townes Van Zandt.

Katie: Yeah, Texas is where so much country music is from, arguably some of the very best. How have you worked it back into your own music?

Jess: I think it had to do with just giving myself permission to lean into country sounds that I knew that I loved but for some reason it felt like that wasn’t what I was allowed to do. I don’t know why, but it’s like, “Oh, that’s not what I do, so I’m not going to do that.” I don’t know why that’s what I thought and then honestly, that Kacey Musgraves album, Golden Hour, came out..

Katie: Yeah, so good.

Jess: It is so good and it was this moment when I heard that when I realized nothing is off limits. Pop, country, indie music, are all rolling around together in the same cosmic swamp and sharing and learning from each other and we don’t have to put these arbitrary boundaries on what we’re allowed to work with.

Katie: Totally! I totally agree. For so long there was a lot of stuff I was throwing on my songs to make them sound a certain way. Because my songs at their very root are so simple and can be played a lot of different ways, on my albums I was really throwing these heavy indie rock references all over the place to sort of be dubbed indie. I had the same experience as you growing up. I loved country music. That’s how I learned how to sing. Those are my favorite songs from my most formative times as a musical person and I think with this album what I was really trying to do is something that felt more organic. It just feels more natural. I really hear that with your music, too, where it’s leaning into what is exciting and unique about you and I think something that’s really exciting and unique about you is that you are from Texas and you can in a very authentic way pull from those reference points. That’s not something everybody can do. People respond to that.

Jess: No, I think that’s such a good point. There’s almost a magical quality to just being 1000% yourself. That’s what anybody connects to. Authenticity is an almost tangible thing.