Singer-songwriter Sara Bareilles clearly remembers her first tour. It wasn't pretty. The guys in Maroon 5, who were friends of hers, invited her to accompany them on an East Coast tour.
"I had no idea what I was doing," she says via phone from her New York home. "I rented a RV instead of a van. I made so many poor business decisions and lost my ass financially on that tour. I was just a kid figuring it out. I have a lot of fond and nostalgic memories about that period of my life because so much of it was unknown. It's actually a cool thing to have built off. "
Bareilles has certainly "built off" that initial experience. To date, she's been nominated for five Grammys and appeared as a celebrity judge on The Sing-Off. She's played herself on shows such as 30 Rock and Bucket & Skinner's Epic Adventures. Her most recent album, last year's The Blessed Unrest, is an introspective affair that has become a massive hit thanks to the anthemic single "Brave," a song that's constantly played on commercial radio.
While Bareilles had a hit early in her career with "Love Song," a tune from 2007's Little Voice, her major label debut, she took an organic approach to launching her career and has always had a road warrior's mentality.
"Touring was a priority to me and my first manager that I worked with for 10 years," she says. "It's the idea of grassroots and building a fan base by being accessible. The thing that's equally important is that you get to know yourself as a performer. You can't fake it. You have to put the time in. I feel like I've had an amazing ten years of self discovery and seeing who I am as a performer and what makes me tick and what I'm good at and what I'm not so good at. It's been a good time of self-exploration."
By playing the small coffeehouses near UCLA, the place where she attended college, Bareilles built what she calls a "natural foundation" of fans.
"I have to tip my hat to the UCLA community," she says. "As I was going to school there, a natural foundation to build on developed. We had a couple of spots that I played at frequently that were close to campus. I cut my teeth there and went out from there."
The success of Little Voice, however, took her off guard. When it came time to write the follow-up album, she suffered a serious case of writer's block.
"More than anything else, it was the fear of the sophomore slump," she says. "I was so grateful for the success I experienced with the first album and with 'Love Song.' Believe me, from label to management to myself, we were all shocked. I got stage fright about it. I didn't want to disappoint people and I was doubting my own abilities. Some great friends and collaborators encouraged me. You just have to write what you know. And you do the best you can. You just want to write something that feels honest and that's how I got through that moment of fear."
Then, when it came time to record The Blessed Unrest, she experienced a different set of anxieties. Frustrated by a lack of progress in her life, she ditched her long-time band and moved from L.A. to New York as she set out to make a more personal record about all the change and upheaval she was experiencing.
"This record was a real transition point in my life in general and also in my career," she says. "I was really trying to break out of my own patterns on a personal level and professionally. I took a look around at my life and felt less inspired than I wanted to. That manifested itself in a lot of changes. It was the ending of long-term relationships. It was moving from Los Angeles to New York. It was taking a look at my health. It was a lot of things in my life that had to come into closer alignment. Some of it was taking more control and taking a larger role in driving the ship. It's been a process of discovery and something really important that I needed to go through at this time."
Sounds like the textbook example of a mid-life crisis. But isn't Bareilles, 34, too young for that kind of thing?
"I'm not that young," she says with a laugh. "At the end of the day, I feel like it was necessary, but I don't want to say a necessary evil. It was a hard year. It was very emotional and dark. I'm ultimately glad I faced some of my own fears and got to know myself better. It's chronicled there in the music. That's how I process my world. I put it into music. Everything in my life that changed is on this record."
The album's opening track, "Brave," is a tune she wrote with Fun.s's Jack Antonoff. While it's explicitly meant to encourage a friend to come out of the closet, the song, which starts with a bit of electronic percussion and slowly buildings into a full-blown rock number, isn't so explicit that it only appeals to someone struggling with his or her sexuality.
"That song is essentially a love song to a dear friend of mine who was struggling to come out as an adult," she says. "I worked with Jack and we are both passionate about human rights and particularly how it pertains to gay rights. At the time we met up, it was in the ether. There was a lot of gay marriage and issues on ballots and just in conversation. It was something we were talking about a lot. That song came very quickly. The first time we sat down together, that's what came out. It's been a cool thing to watch develop as the song's been out for a longer period of time as people have become familiar with it. I've seen it incorporated into all different people's lives. What I'm finding is that people are feeling so courageous with their vulnerability. They're sharing stories that are so intimate and private and I think that's such a beautiful sentiment."
Between the awards, the TV appearances and the constant touring, Bareilles has been on one helluva ride since launching her career ten years ago.
"You know, it's been quite a rollercoaster," she says, adding that she's currently writing a book and working on music for a musical. "I think that sometimes I feel like I'm catching up with it emotionally. It's been an amazing journey for me. I didn't truly expect it. There have been a lot of surreal moments in my life, stuff that I feel really blessed for. Getting to work in your passion is a huge gift and I don't take it for granted. It is a lot of work but it's the best work in the world. To make music for people is incredible. I feel grateful that this gets to be my life and I continue to dig deep and be an honest performer. It's a good problem to have. It's a good thing to try to wrap your brain around."
Sara Bareilles with Emily King and Hannah Georges
7:30 p.m. Friday, July 11, Jacobs Pavilion at Nautica, 2014 Sycamore St., 216-861-4080. Tickets: $35-$55, livenation.com.
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