Describe your path to what you’re doing now. Both of my parents were acting teachers and actors, and they had an acting studio in Seattle, which is where I was born. When I was five years old, they divorced and moved back to Los Angeles where they had originally met—in acting class, actually. My dad continued to teach acting, and my mom, who is kind of a Renaissance woman, worked many different jobs.
Because I grew up around actors and, frankly, saw a lot of them struggling, I understood from an early age what a difficult, heartbreaking path it could be—especially when you loved it. And I thought, no way am I going into that crazy world. I considered becoming a politician or an architect, or maybe even an astronaut. Obviously, none of those stuck.
Instead, I fell in love with music when I was 11. What I loved most about it was that, even though it terrified me, I had a stronger desire to conquer it. I didn’t want to just be good at it; I wanted to be great, and nothing was going to stop me—including not being very good at the start. And that has been my overarching motivation in life: to pursue whatever propels me toward courage. I guess I could have picked a career that didn’t scare the crap out of me, but that would be boring. (laughing)
And how did you end up getting signed as a musician? Were you submitting demos? It was crazy. I was 21, still living with my parents, fairly shy, pretty far removed from the outside world, and writing songs about forests and fish and heartbreak. I had made the rounds with quite a few labels, although I was very nervous about taking the major label route. Still, I sent my music to a bunch of people hoping I’d somehow find the right home. One day, Jason Flom, the newly appointed head of Virgin Records, heard my music and a couple of days later he was on a plane. He came to my parents’ garage, where I’d set up a small session with fellow musicians. We played, and my mom baked cookies. (laughing) I was so nervous I could barely talk. Jason signed me two weeks later. It was all pretty surreal.
“Facing the unknown is daunting. It’s so much easier to let things be, even when you know you shouldn’t. When you feel that resistance—that almost overpowering, bone-crushing force—you have to push back…that is when you really find yourself and figure out where you’re supposed to go.”
That was a few years out of high school when you had decided to focus on music and try to make something happen? Yeah. I was really determined. I had this crazy—I guess you could call it fierce—confidence, which was pretty astonishing considering how much I doubted myself on pretty much every other level. I was shy around people, but I desperately wanted to reach out. Music was the only way I really knew how to communicate. So I threw myself into it, which was equally difficult and exhilarating.
After three records, I needed a break. Putting that kind of constant pressure on the most vulnerable part of yourself requires investing an equal amount of energy in feeding yourself creatively, which I’d neglected for a long time. I felt completely hollowed out, and I needed to fix that. I wanted and needed to do something new, challenging, and collaborative. Something exciting and scary—the scarier the better.
I thought, “Fuck it! Maybe I’ll try acting after all.” And when I finally said that to myself, I realized I had always wanted to do it, but I had blocked it out because I had thought it would break my heart. Fear can be debilitating—and it’s not so much the fear of failure as it is fear of the unknown. But I was lucky. I had a lot of support from the people I love and a wonderful manager willing to take a chance on me, so I decided to try.
I took acting classes for a year before I started auditioning—and I cried after every audition. My third audition was for Transparent. Of course I didn’t think I was going to get it because no one thinks they’re going to get anything on the third audition. But I really, really admired Jill Soloway’s work. I thought that if I could do a good enough job to get a callback and meet Jill, then I’d be happy. And then I somehow got the role, which I honestly still find hard to believe. Transparent is this beautiful, society-shifting piece of work, and I got to be a part of it. I’m so proud of that.
Landing the role in Transparent gave me the confidence to do a few more auditions. Then I auditioned for Dig, a new show by the creators of Homeland and Heroes. I actually cried harder after that audition than all the others combined. I was certain I’d botched it, and I was ready to quit acting then and there. And then I got the phone call.
You’ve already talked about the risks you’ve taken along the way, but is there one that stands out? Yes. I’ve let go of A Fine Frenzy, which was a big part of my life. People have asked me, “Are you insane? What are you doing?” At a certain point, it became apparent that A Fine Frenzy was a very important chapter in my life and work, but, in order to grow, I had to close it. In doing so, I changed the team I had been with for the past eight or so years, including my label. That was crazy; it was a really difficult period full of uncertainty. I had worked with those people for a long time, and they were great, but they were part of a world that was very different from what I wanted for my future.
That was hard, but necessary. Facing the unknown is daunting. It’s so much easier to let things be, even when you know you shouldn’t. When you feel that resistance—that almost overpowering, bone-crushing force—you have to push back, even if you have to corral every little bit of life-force inside of you to do it. You’re stronger than you know. I think that is when you really find yourself and figure out where you’re supposed to go. But, man, it sucks when you’re in it.
“The sheer responsibility of seeing your dreams come to fruition is totally nuts. It’s oftentimes easier to just dream about the dream than to actually try to do the work. The work is crazy, but it makes it real and worthwhile.”
Have you read The War of Art by Steven Pressfield? Yes! I read it during the time period I just referenced. It’s such a great book.
We read it right before we started the magazine. Once you get over that initial hurdle and refuse to give in to resistance, you start to gain momentum and things start to happen. When you’re in that place and you feel that resistance, it seems like no one has felt resistance like that before. You feel like you’re never going to be able to move past it. But when you do, it’s incredibly powerful. I think that’s where true greatness is born. I wish there was an easier way, like, eat a watermelon and—BAM!—you’ve got it. (laughing)
You know when you’re not doing what you’re supposed to do in your life—your whole body knows it. And you know what you have to do to get there, but it can be overwhelming. The sheer responsibility of seeing your dreams come to fruition is totally nuts. It’s oftentimes easier to just dream about the dream than to actually try to do the work. The work is crazy, but it makes it real and worthwhile.
What advice would you give to a young person starting out? There’s no shame in starting from the bottom. In this day and age, everything moves so fast and many people want to get to the end goal without necessarily taking all of the steps. I think there’s something really valuable in humility, in admitting that you don’t know. Learn from everyone who is willing to teach you; learn from the people you admire, from the people you don’t admire. Keep your eyes open, be helpful—and go beyond what your comfort level is in order to help. You won’t necessarily find your greatest growth from your successes; you’ll find it from making mistakes and learning from them, and from being humble. Be willing to do what others aren’t and you’ll stand out.
“You won’t necessarily find your greatest growth from your successes; you’ll find it from making mistakes and learning from them, and from being humble.”