Few things leave me pining for words — trying to articulate the resonance of Terra Naomi’s voice and talent is among those few things.

Her voice could be described as powerful, raw, or having great range, and still there is something that these adjectives lack. Her lyrics are personal, impassioned, sometimes sad, always relatable. Again though, adjectives. Listen to her catalogue and you will understand — it is as if Terra knows the location of a secret reservoir of emotion, which she has been given permission to draw from with beautiful cause and delicate expression.

Preparing for this interview meant clicking through a library of YouTube content spanning the better part of a decade. Revisiting these older pieces of content one thing is clearly consistent — Terra’s voice — a voice that supersedes the quality restraints of low-resolution video. (Take for example, this 2010 performance of ‘I’m Happy’ and/or this 2008 performance of ‘Suffer for Her Sins’.)

It has been ten years since Terra won the first-ever Youtube award for “Best Music Video” with her release of “Say It’s Possible.” Her singing and songwriting skills have only grown since then. Skills she has demonstrated numerous times, including the 2012 release of her Live & Unplugged album, which features acoustic renditions of songs from her first album and other points in her career, as well as haunting covers of Bridge Over Troubled Water, Billie Jean, and Hallelujah.

This interview comes on the heels of her successful Help You Fly Indiegogo campaign, which she dubbed as her “2016 Reboot.” The initial goal of the campaign was a modest $35k, which was surpassed when the campaign closed on April 21 with funding just over $50k. The money raised in this effort will help her fund what she calls, “A melodic album full of emotional honesty, showing what’s possible when we believe & never give up!”

Reading this lead-in to our interview can not aptly underscore what it is to witness Terra Naomi perform live (read: command a dagger of emotion through your chest), that is something we advise you seek out and experience for yourself.

This article is not simply about a powerhouse singer-songwriter so much as it is about highlighting a person coming to terms with her own doubts and taking on the sexism, ageism, and standards of an entire industry in pursuit of her talents.

Meet Terra Naomi

Terra-Naomi-Nick-Holmes-Nude-HairPhoto by Nick Holmes

[we asked Terra to fill in the blanks] My name is Terra Naomi, I am a singer, songwriter, musician, person. I am 50% dreamer and 50% doer. I would describe myself as cautiously optimistic and I am most inspired by life. I dream of building a lifelong career in music and I will do that by putting one foot in front of the other.

Dreamers & Doers: Can you tell us a bit about how you came to be a musician? What was the first instrument you played, how many instruments can you play, and how old were you when you wrote your first song?

Terra Naomi: I sang from a really young age — like before I was one year old — and my parents were always very supportive and encouraging of my musical pursuits. I started playing piano when I was 4, then French horn at age 8. I sang in choir, started voice lessons at 16. If I’d known about Berklee School of Music, I would have gone there, but I came from a small town and didn’t know much about how to become a singer/songwriter (this was in the days before Google), so I went to college for opera and voice performance. I moved to NYC after graduation, taught myself to play guitar, and started writing songs.

Prior to 2006 what were your expectations if any about having a career in music and what did it mean to you at the time to win the first-ever Youtube award for “Best Music Video”?

I recorded my first CD in 2002 and used it to book a tour of small clubs and coffee houses. On that tour, I met a producer who told me he’d work with me if I moved to LA, so I did. I honestly didn’t know anything about the music business, didn’t even know what to expect, and he was the first person to pay me any real attention, so I signed with him. I learned most of my lessons the hard way, and wish I could have had access to more information, the way we do now, with everything and everyone online. I guess I thought I would move to LA, keep touring the US, build my following, sign a record deal, release some albums… I felt like I was at the mercy of the people running the record labels at that time. Some artists were recording and touring independently, but aside from Ani Difranco, I didn’t really know of any who had sustainable careers. It was very hard and required a lot of money, so most of us who weren’t independently wealthy focused on getting record deals.

Myspace and YouTube changed everything for independent artists. Even before YouTube, I was able to build a decent following on Myspace — I could suddenly tour and play to 40-50 people each night, in cities around the US. I still wanted to sign a record deal, but it seemed possible to build a career without one.

Winning the YouTube Award changed everything in an even bigger way, but it was such a new space, and no one really knew what that YouTube exposure would or wouldn’t do for musicians. We didn’t know if those millions of “likes” and “views” could be monetized. I wanted to believe it was possible to build a great career online and control every aspect of it, but I was the first person in the position to give it a try, and it was too scary and uncertain for me. I had all these major record labels reaching out to me, offering me a lot of money, and I was broke and in debt, and didn’t feel like I could afford to turn them down.

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Obviously a lot has changed since then, what have you learned in the last ten years and how have you grown as a person and as an artist?

Haha — that’s kind of a massive question. What haven’t I learned?! The biggest lesson has been in trusting myself and my own intuition, coming to understand that no one cares about me or my career as much as I do, so I can never hand it over to other people the way I did back in 2006.

It is empowering to watch someone like yourself decide not to give up on your pursuits and to take a chance on doing it your way, can you tell us about the process that led up to launching ‘Help You Fly’ and your 2016 reboot?

I reached a point where I had basically given up on myself, decided it was too late, that the mistakes I’d made (signing with Island Records and releasing an album I didn’t like, etc.) were too big and too damaging. I’d watched so many promising artists go down that path — watched them start out so full of talent and hope, only to be crushed by their experiences in the business. It can be a treacherous journey for some artists, and it definitely was for me. And some people don’t make it out of that. I thought that might be my fate, and I had a few lousy, depressing years, and then… I don’t know, something changed. Something told me to stop listening to those voices in my head, telling me I had failed… something told me to get up and create the life I wanted to live. So I decided to try.

Do you see a parallel between where you were on YouTube in 2006 and where you are now in terms of utilizing the digital space? Do you feel like you are setting an example for other aspiring singer-songwriters?

I don’t know if I’m setting an example, but I hope I can inspire other people — not just artists — to believe in themselves. I hope I can help people feel like it’s never too late to create the lives we wish to create.

To be taking a huge step like this for your career and to see your Indiegogo campaign be supported to the tune of 143% of your initial ask, that must be an inspiring thing in and of itself, can you talk a little bit about your fans and their support from 2006 to now?

I have the most supportive group of fans — I feel lucky every day. And I’ve definitely made mistakes and lost some of them along the way, the people who believed in me as a sort of “indie poster child” back in 2006. It’s hard for people to understand why we make the choices we make sometimes. In my case, my intention was never to “sell out” — I simply had to survive. So the people who stuck with me through the Island Records years and then through the few years where I was basically MIA, and are still with me, just as excited to hear my new music as they were 10 years ago — I am making this album for these people.

Indiegogo was challenging, I’m not gonna lie. I don’t like asking for help, and I especially don’t like asking for money. It was very hard to get up every morning knowing that I was going to spend the majority of my day promoting my album campaign and asking people to support it. I didn’t want to annoy these amazing people who’ve been with me all these years! But they want to hear my new music, so they supported the campaign, and I am very grateful that I get to record this album.

Honestly, what has the process of relaunching your career been like so far? What have been the biggest challenges?

The biggest challenges continue to be my own self-doubt and criticism. I try not to regret anything in my life, but I often catch myself hanging out in the past, thinking “if only I’d done this or not done that, or worked with this person when I had the chance, or said no when I said yes…” And I have to catch myself and remind myself that everything led to this moment, when I’m writing the best songs I’ve ever written, and I’m so proud of the challenges I’ve overcome, both in my career and personal life. But it’s hard. The music industry is extremely sexist/ageist. They’re kind of the same thing, because ageism is sexism. I choose to ignore it, but I know it exists. I know it will be much harder to get my music out than it would be if I were a super attractive 20 year old girl. But I also know the impact it will have when I do; the ability I have to inspire so many more people who really need to be inspired. I know the power of what I have to say in 2016, and it’s much bigger than it was when I was in my early 20s.

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What was the writing process for ‘Help You Fly’? How much of your writing process has been inspired or affected by your experiences within the music industry?

I wrote the verses and chorus of Help You Fly in the car, on my way to a session with a producer, and then I wrote the bridge/ending a few months later. Initially I thought I would write it for another artist, and the producer created a track for the song that was not my style at all, much more pop. But then I realized that the song was for and about me, so I decided to re-record it for this album, with different production. I’ve only recorded an acoustic demo version so far, and can’t wait to see what happens in the studio, when it’s produced with other instruments. I hear a lot of percussion on that track. And strings! But to answer your question, I don’t think I write much about my experiences in the music industry anymore, because I write about life, and I don’t spend much time in and around the industry these days. I guess that will change when I release this album….

What is your overall writing process? Where do you draw inspiration from, how often do you practice, how do you know when a song is finished?

I don’t practice as often as I should — usually just when I have a show coming up. But I play my instruments whenever I write, because my process is to sit with my guitar or at the piano, and play some chords, melodies, and see what comes. I can always tell when I have something good, because it flows out effortlessly. I can also usually tell when there is a song in me that wants to be written, because I get this edgy, angsty, uncomfortable feeling. I don’t know how I know when a song is finished… I’ve never thought about that! I just know!

Your voice, your musical talents, and your songs themselves have catered immensely to intimate solo performances, can we expect more of that intimate setting with your upcoming tour?

I will always include solo performance in my shows, but I also love playing with other musicians. I played a couple of weeks ago at Hotel Cafe in LA, and had two friends with me, a percussionist and a cellist. I would love to be able to tour with them, but it all comes down to money, and whether I can afford to hire them when the time comes. I hate that so much is dependent on funding. I hate combining art and finance. It’s the worst thing about being an artist. I wish I could just create the music I want to create, without the limitations of budget. I’m definitely not a fan of capitalism’s impact on art.

Terra-Naomi-Nick-Holmes-nude-1Photo by Nick Holmes

Are there other artists you look to for inspiration?

I tend to gravitate towards artists who’ve had tricky paths, had to overcome big odds, had significant ups and downs in their careers, because that’s been my experience, and I like to see people succeeding in spite of having a rough start. It gives me hope.

What goals or dreams do you have as a musician?

I would love to play beautiful theaters every night of my tour, in different cities, 1,500-3,000 seat theaters, like The Wiltern, or Shepherd’s Bush Empire in London, or outside venues like The Greek Theater. That’s pretty much my dream at this point, to play every night in a different city, for people who love to listen to music. I’m not trying to be a buzz band at this point. I just want to make music that moves people, and perform it in venues conducive to that experience, where people can relax in their seats and just feel.

If someone reading this interview needed a crash course, quick introduction to Terra Naomi, what three songs would you recommend they listen to right now?

‘For My Last Number,’ but it’s not recorded yet!! So… ’Say It’s Possible’ is the song that kind of launched my career, on YouTube. ‘Flesh For Bones’ is one of my favorites, and the only recording I like from my Island Records album. Picking one more is so hard… So… I’ll let you choose, Frankie!

Fair enough… this is tougher than I thought. Even though I have many personal favorites, I’m settling with ‘I’ll Be Waiting’ — maybe specifically this performance:

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If you happen to live in Los Angeles or if you will be visiting soon, you can catch Terra when she performs at The Roxy with Jay Brannan on August 12. You can listen to a selection of Terra’s music on her website or on her YouTube channel, and you can follow her on Twitter.