On reconfiguring what success means

It’s been almost a decade since you last released a proper solo album. Why such a long time?

Yeah. That’s so weird. I had that little Dottie’s Charms record, which was more of a concept album, out in 2014 and I’ve been working on musicals, but I’ve procrastinated so long on making another solo record of new songs. It’s funny, I think maybe LA just got to me. I also think I had a little bit of a depression and I kind of got spooked. You know, the last record didn’t do so well and you just get a little crestfallen. It also coincided with going through a bad breakup. For whatever reason, I needed a break. I needed to start loving music again. I needed to start listening to older stuff, to newer stuff. Eventually I started writing again. It also coincided with getting a couple of theater projects that I had to write for. When you’re on your own and you don’t have a record company saying, “We need that record,” it gets harder. I think about a band like the Beatles, who had people saying to them, “We need another new record in three months!” When you don’t have someone pushing you, sometimes you stall. The good thing is that I was writing for other projects. Being forced to write for my musical projects, having to be a part of a collaborative community, it all nudged me back into writing again. I started loving it. Also, there’s something great for me about being back in New York, where I go out and see music all the time. In LA it just feels so hard to get in your car and drive for 40 minutes. It feels easier here.

You were famously one of the first people to use a crowdfunding platform to raise money to make your own record. This was back in 2008, before things like Kickstarter. Now it’s such a common thing to do. So many artists now even question if they need a label at all, or whether it’s easier to just do everything yourself.

Well, here’s the thing. When I did my jillsnextrecord.com no one really knew if it would work or not. I came up with the various pledging levels over the course of a drunken night with a friend. The donation levels ranged from polished rock to weapons-grade plutonium. Somehow CNN got hold of the story and the whole thing started going totally gangbusters, mostly because there wasn’t anything else like that yet. Eventually I stopped it after raising nearly 100,000 dollars because Perez Hilton—you remember that horrible man?—wrote about greedy Jill Sobule asking fans to give her money. So, I freaked out. Then a few months later everyone is doing projects this way. I remember having meetings with the people from Kickstarter, telling them about what had worked for me and what hadn’t.

So, all these years later I used Kickstarter to make my new record. I was afraid it might fail because nowadays there are so many people asking everyone else to donate to things, but in the end I did it and it worked and it was great. Still, I procrastinated forever before doing it. I just finally had to come to a point of thinking: I want to do a record. I’m not gonna get a record deal or an advance, so I’m gonna have to do this on my own. It was out of necessity, really. I had no choice.

It’s an easier thing to do if you already have an existing fanbase, but it’s still hard. You have to be really tenacious about promoting it and coming up with good rewards for people. I think crowdfunding can be hard for people because it still involves asking for help on some level, which can be a hard thing to do.

The way I look at it, you just have to make sure you are giving something back in return. It’s an exchange. You’re not begging people. My recent Kickstarter met its goal times three, and it had done really well within the first two weeks. I was completely taken aback. Some of the levels of sponsorship we created were really just like jokes, things I thought nobody would ever actually do. For 10 grand you will be my personal lord and savior. Very funny, right? Somebody bought it! Joss Whedon bought it. So on my record he gets listed as my personal lord and savior. I also did things like offer to write people their own personal theme song. That was a big ticket item that a lot of people actually went for. So now I’m writing people their theme songs, as promised.

People might now realize how many different kinds of things you’ve done over the years, other than releasing solo records. Did you find that having these outside projects—writing a musical, for example—let you come back to your solo work with renewed energy or a different perspective?

Oh, completely! How boring would it be to just do this? On one hand, with the music industry changing and being so terrible, I mean, who makes a living doing this now? It’s the one percent who actually make a living doing only this. I’m really a part of the other 99%. There used to be such a thing as a middle-class working musician, but now? I mean, we used to complain about the stupidest stuff, and how the record labels were ripping us off, but now? Shit. I’d love an advance, you know? I actually had something called a “tour bus” for a couple of years that we toured in, with all of this nice airbrushing on the side. I will never get that again. I had to explore other options, take on other kinds of projects and collaborations.

I know you worked with Ben Lee on Nostalgia Kills. When you are doing things on your own terms with your own money, do you set up certain parameters for yourself? Did you give yourself specific deadlines?

Not really. Actually, I had written a bunch of songs over the last few years here and there and just kind of stuck them aside. I basically gave everything to Ben and asked him to pick out the songs we should work on, which was a little overwhelming for him because I think there were over 50 songs there. He definitely gravitated towards the songs that were kind of melancholy. I was really interested and surprised by the things he chose, but it also felt nice to hand that part of the process off to a friend who I also trusted. There was definitely a kind of running theme in the songs he picked that might not have been there if I had chosen them. I also wrote some new songs during the process, which felt good.

Everyone’s career has peaks and valleys. Big tours and small tours, hits and misses, going from playing big rooms back to clubs. How do you keep all of that stuff from creeping into the art you make? Was there ever a time when you were sort of like, “Screw this, I’m gonna do something else instead?”

Yeah, absolutely because it can be heartbreaking. It can all be so wonderful and then also just so crushing. There was a time when I just didn’t want to listen to music. At all. Not just mine. I don’t know if listening to music just reminded me of my own regrets or failures or what, but I just couldn’t do it. At some point I also realized that I have no marketable skills doing anything else. I have a friend who is a very talented artist and musician, but she also has a law degree and a real job and can be organized. Her thing was always, “If I wasn’t a lawyer and didn’t have this job, maybe I could have made it in the arts.” Jane Siberry has a song that’s called something like, “I’d probably be famous now if I wasn’t such a good waitress.” I basically have no skills to do anything else. Sometimes that feels like a curse, but it could also be a kind of blessing. There was nothing else I could do but this.

How has your definition of success changed over the years?

Oh yeah. What is success? I hate how it’s always like you have to be at the very top or somehow you are meaningless. Like, if LeBron James is the greatest of all-time that somehow means Michael Jordan is now a loser. Like, what are you talking about? Does it mean that I’m a loser if I’m not playing Madison Square Garden or if I’m not even selling out the Bowery? I always get people coming up to me and saying things like, “Oh, I loved you! Why aren’t you bigger? Why aren’t you more famous?” I know they mean well and that they mean that as a compliment, but damn. It’s hard to hear things like that over and over. Like, yeah, why aren’t I? I don’t know. But when that happens I have to remind myself of things like… you know, last week I played a show at someone’s house and I was singing, “I Kissed A Girl” in between Lily Tomlin and Jane Wagner, who were singing along with me at a party that I was hired to play. In that moment I’m like, you know what? I’m a fucking success. We’re all so fucked up about what success means now.

For people who are artists or entertainers, there’s always something to measure yourself against that’s unfair or unrealistic. It’s very easy for your mind to get warped by those things.

Oh my God. I befriended these girls who love to write with me, Carla and Martina, and they’re in high school. I think they got the Disney song of the week or something and on their Instagram they have something like 80,000 followers. Seeing what their world is like, the way success is measured and validated, really is like that episode of Black Mirror. To be a an artist now, what does it really mean? You need to have a certain number of “likes” or a certain number of followers in order to be seen? It’s a whole other hornets nest.

But what is success? Lately I’m feeling more successful than I have in a long time, just because you change the parameters for yourself about what that means. If I’m being paid to play these house concerts or I’m playing Joe’s Pub or being asked to do a reading of something that I’ve written… that is success. If someone comes up to me and tells me how hearing “I Kissed A Girl” really helped them feel better while growing up in their backwater town… that is success.

It’s interesting you mention that song. It may seem tame by current standards, but it’s hard to underestimate what a powerful thing it was for a song about same-sex attraction to be a hit back in 1995. It may have seemed like this sweet, simple song, but if you were a queer kid living in the Midwest, that was really pretty radical.

Yes. I mean, It’s nice to hear you say that. Even though that song felt like kind of a cross to bear at times, “I Kissed A Girl” probably is my biggest success. Not because of sales and not for it being on MTV but because of what it did for people. That feels like a success. Someone told me once that the best thing you could feel as an artist is that you are providing something. You’re almost like a social worker, a social provider. That can mean a lot of different things. If I play a concert and manage to entertain someone who was maybe feeling miserable or unhappy, that is success. If I make something that someone related to or that made them feel better or made them think, that is success. Whether you are doing that for just one person or a million, it doesn’t really matter. You are successful.

It’s clearly better to have had a hit song than to never have had one, but it’s weird how a song like that—something that really ripples through the culture—can follow you around forever. It can be a mixed blessing.

Yes. I don’t resent it anymore though. I kind of took back “I Kissed A Girl” and I still play it. I’m one of those artists who feels like if someone wants to hear a fucking song and they ask for it, as long as I can remember how it goes, I’ll play it. It’s about giving. You wrote a song and someone wants to pay money to come and hear you play it? You’re lucky. How many people can say that?

Sometimes it’s also really just about getting back to that very simple spark of what you loved about doing it in the first place.

I feel better in that way as I get older. I feel more fearless now. I never have a set list. I just wing it the entire time. As I get older, I’m more in touch with what I loved about music from the very beginning. I think that maybe also after going through such stuff—the highs and lows—music right now isn’t heartbreaking anymore for me. It’s beautiful. Does that make sense? I feel like crying almost because it’s the first time I’ve kind of verbalized this. I mean, this could end tomorrow. I could be like, “Is that all there is?” But right now I love it.

That feels very real and very true. We can’t be in love with our art and our process all the time. It can’t always be 100% awesome and amazing.

Absolutely. You never know what is gonna push you into it or back out of it. For example, I was at a party in LA before I did my Kickstarter. I was at this party with a bunch of millennials and I overheard someone say, “You know, someone over 40 just can’t write good songs anymore. They’ve lost it.” Even though I was kind of nervous, I went over that person and just blurted out, “You are an idiot” and walked away. They looked at me totally appalled, like “Ugh, who is that person?” That person instantly became my new nemesis. That made me think, “Fuck you. I’m gonna go home tonight and write songs like a motherfucker.” It was a fuel that I didn’t even know I needed. I should dedicate my next record to them: To my nemesis, who doesn’t even know who I am.