"I think people think that I feel underappreciated," Sara Bareilles said to me, just days before the drop of her new album, Amidst the Chaos. "I just get a lot of people who comment at me and say that I'm underrated. It sounds like a weird thing to say, but... I really am so cool with where things are at," she laughed. "I don't wish for anything else. I am really, truly contented."

And Bareilles has plenty to be content with. Her career has been illustrious, in a sometimes blissfully quiet kind of way; there's no controversy or drama that have trailed Bareilles around as she's forged her own path. And that's not because she stays hidden in the wings, or avoids taking a stand about what matters. Rather, Bareilles is plenty outspoken—her new album is her most political yet—but she uses her platform and voices her opinions with an ineffable poise and specificity that provokes admiration rather than consternation.

Despite all her achievements, though (including nominations for Emmys, Grammys, and Tonys), Bareilles said, "I'm a work in progress like everybody else is." Whether it's through her music or via engagement with activism, she's dedicated to trying to be better all the time. "I think it's really dangerous to pretend that we don't make mistakes," Bareilles said. "I hate when people act like they've got their shit together—I'm such a flaming pile of mess."

"I think it's really dangerous to pretend that we don't make mistakes… I hate when people act like they've got their shit together; I'm such a flaming pile of mess."

Bettering herself is an ongoing process for Bareilles, one she's very open about; she told me, "I am in therapy once a week, I have been for eight years. No signs of stopping soon. I have good days and bad days." She laughed: "I'm in a fucking fetal position half the time." And it's this particular kind of all-too-common personal messiness and growth that she explores on her new album; she explained to me, "I stopped trying to hide the mistakes."

Amidst the Chaos is, therefore, filled with "mistakes," the kind of raw moments that aren't polished over, so you have more to sink your teeth into. The album feels representative of her process of finding delight in her own imperfections, and taking the empathy she gives to herself and extending it to the very messy, very raw world around us. It's political because it's personal, and vice versa.

"One of the major catalysts that made me want to start writing again was the election," Bareilles said. "I think sometimes I catch myself falling into the trap of thinking this is all brand-new, but life is chaotic—it has been since the dawn of time, and it will be forever. So, I take the pen and paper and piano and try to make sense of it; it's about how do we cope and exist and keep living and choosing love amidst the madness."

And while Bareilles still won't write you a love song, she did write a couple of them for the Obamas and throw them onto her record. This doesn't mean there's any name-dropping on the album, it's far more subtle than that, she explained: "Love comes in so many forms, and I just happened to be a big believer and big supporter [of the Obamas]. In their absence, in a more formalized way, I found myself with a lot of gratitude that I got a chance to get to see an example of leadership with so much grace. What great teachers we got for a minute."

Bareilles is using those lessons imparted to share some wisdom of her own and shed light on some of the horrible things happening in our country. She told me how her song "A Safe Place to Land" was inspired by hearing about children who had been ripped from their families at the U.S.-Mexico border. She said, "[Songwriter Lori McKenna and I] were catatonic, sitting in a studio feeling completely helpless." Bareilles said they found themselves wondering, "Can't we find the compassion to offer safe harbor to each other? Can't we just remember the humanity at the base of this? That someone doesn't put their babies in their arms and walk 1,000 miles because it's good at home?"

"Can't we find the compassion to offer safe harbor to each other?"

Bareilles knew John Legend was the perfect duet partner for this song, and joked to me, "He'll always be my Jesus," referencing her time starring opposite him in Jesus Christ Superstar; continuing: "I really look up to him and how he seamlessly moves from artist to activist to advocate. He lends his voice to projects he believes in, he's not afraid to piss people off." And with this song, they both do it again, with all proceeds benefiting the ACLU.

Bareilles collaborated with more people than ever before on Amidst the Chaos; in the past, she told me, collaborations left her feeling "distanced" from the final product, but this time, she found a certain cohesion and place to pour out her heart, and ruminate on love. She refers to her relationship with songwriter Lori McKenna as having a sort of "seamless chemistry" that helped her ease into some of her most personal work yet.

One real through-line of this album is the idea of love, of commitment. She said to me, "I really feel this urgency to recommit to love right now. It's such a tumultuous time, and it's so easy to become hopeless… there's these distilled little moments that have so many thorns." She's very much in love in her own life right now and in a relationship with actor Joe Tipps, whom she met while working on Waitress.

Her love also extends to the immense changes that have occurred in her life since the release of her last album, Blessed Unrest, six years ago. Back then, she found herself "going through seismic shifts," and left behind her home, band, manager, and boyfriend. She named the album based on a quote credited to the dancer Martha Graham: "There is only a queer divine dissatisfaction; a blessed unrest that keeps us marching and makes us more alive than the others."

And that blessed unrest brought Bareilles to exactly where she is now, exactly where she wants to be. She told me: "I'm going to be 40 this year, and I sort of love the place that I'm at. I don't feel particularly like I have anything that I need to prove." That six-year period following her blessed unrest was filled up, after all, with the beautiful mixed up sugar, butter, and flour of her work on Broadway hit Waitress, which Bareilles referred to as "deeply nourishing," and having changed "literally everything" about her life as she knew it.

She returns back to the show regularly, whether as a guest star or as simply a guest; she was running off to a performance just after our interview. She joked that they'll never be able to get rid of her, and said that she has "an intense sense of gratitude" for the production. She explained, "It showed me so much about my own potential and my capacity for growth and stepping out as an actor, as a composer, being a teammate, not just an artist." It also led her to new opportunities, with legendary producer T Bone Burnett and filmmaker J.J. Abrams. She told me she'd do another show "in a heartbeat," in absolutely any capacity. The theater community proved to be refreshingly warm, immediately accepting, and unlike what she'd experienced with the music industry.

With Burnett as the producer on Amidst the Chaos, Bareilles was able to let loose and return to the music she'd so passionately loved when she first independently released her debut album, Careful Confessions. There's a certain jazzy element to the new work, everything is much more relaxed and unholstered. It's not necessarily made within the framework of appealing to pop radio but doesn't entirely throw the idea out the window. Bareilles said that Burnett was able to pass on "his complete lack of interest in perfection" to her while recording, and it's left her with a newfound sense of ease. "In a society where things are getting retouched and refined and slicked over and repolished and surgeried, there's such an intense emphasis on this false god of perfection that doesn't actually exist," Bareilles said. "We've been tricked in some way."

It's clear, as she pivoted conversationally, that this disinterest with perfection is much bigger than just sitting down in the studio; it's the execution of a life lesson that has taken her years to come to terms with on her own. She referred back to a book of essays she wrote, Sounds Like Me: My Life (So Far) in Song, in which she began writing letters to herself. "When I could step back and be the more compassionate part of myself," she said, "I saw that I was always doing the best I could… It's so powerful to learn to be your own friend."

"When I could step back and be the more compassionate part of myself, I saw that I was always doing the best I could… It's so powerful to learn to be your own friend."

Though her own compassion can't be sent back to her younger self, it's a welcome companion to Bareilles now, especially as she works on her new TV series with J.J. Abrams. The show, called Little Voice ("to tip the hat to that period in my life") follows "the life of a young artist, at that juicy time where you're being told you're an adult by everyone, but you feel like a fucking mess all the time… I guess you never grow out of that."

Though that's an awkward period for most (if not all) of us, Bareilles explained, "It was such a fertile time for me as a writer, because I was just pouring out everything into these new little song seeds… just those first steps you're taking into finding yourself."

Of course, we all know that "yourself" is sometimes the hardest thing to discover, especially amidst the chaos of life. But, Bareilles said, "Ever since I was a little girl, I had a great sense of faith about all that. I really trust the universe, god, whatever you want to call it… I trust that everything happens for a reason."

Video: Dani Okon + Charlotte Prager

Production: Alexandra Hsie