Growing up in a military family, music became a constant to which Nashville singer-songwriter Michaela Anne could anchor herself as she moved to many different places. While studying jazz at the New School, Anne discovered the bluegrass industry in New York City, and along came her debut album To Know Where. Three years later, she began receiving national recognition as her second album, the old-time country set Ease My Mind, garnered rave reviews and held the number five spot on the Village Voice's ranking of the year's top country albums. 2016's Bright Lights and the Fame continued to earn the singer praise, with Vice hailing her as "the answer to bro country" and "our saving grace, our angel, the person who will help usher us into a new age," and 2019's Desert Dove was her most successful album thus far; Rolling Stone placed the record at number 10 on their list of the year's best Americana and country albums and lauded it as "a shimmering sonic statement of purpose".

Seeing your career grow and having your work recognized must be rewarding, but is that the source of true happiness? In an interview with AllMusic, Anne explored this question and more as she chatted about her newest single "Does It Ever Break Your Heart" and upcoming album Oh To Be That Free, a rich eleven-song set that delicately delves into tender, vulnerable themes like motherhood, self-sabotage, and gratitude.

AllMusic: "Does It Ever Break Your Heart" has been described as an anti-love song that chronicles the conflict between bliss and self-destruction. Was this what you had in mind when you were writing it? What were your goals for the single?

Michaela Anne: Yeah, as a songwriter and as a person, I'm really interested in the dynamics of relationships, and that song in particular was reflecting on how we can confuse such strong emotions like lust and love and toxic qualities that can feel enticing, in a way that that emotional dynamic between people can seem really positive and quickly turn negative and be destructive. That's what "Does It Ever Break Your Heart" is about. It's about trying to get out of something that you realize isn't good for you and building that strength and recognizing the manipulation and toxic behavior traits for what they are, when in the process you might have confused them with attention and affection.

AllMusic: You mentioned in an interview with Reckon South that the song "just fell out" and "just kind of appeared." I was wondering, does this mean that the single was somewhat spontaneous in nature?

Anne: This song definitely was something that, I didn't have to labor over it. Some songs take me a long time to finish, but I remember that that chorus just kind of appeared, and then the verses really fell out. Just telling the story. The ending of the song has these vocal harmony layers that build and weave over each other, and when I wrote this song, that whole part kind of came out as well. That wasn't something that happened in production. It did feel formed in a lot of ways, which was really fun. It's always nice as a songwriter when that happens, because it feels like a breath of fresh air that wasn't hard or labored over.

AllMusic: A few days ago, I was able to watch the music video, which I loved by the way. It was amazing. In the music video, there's a lot of contemplative and tranquil imagery; there's soft waves and the distant horizon. I just wanted to ask, how does this complement the song's lyrics and meaning?

Anne: The foundation of the song is the narrator coming to a place on their own. So I felt like the imagery of being alone and trying to find the inner strength to walk away and not get pulled back in, and then also the metaphor of seeing the waves, all of that fed into the narrative for me of having enough solitude and independence to decide and understand where you are and what's healthy for you. Not feeling that gravitational pull from this person that can be very magnetic and enticing but ultimately, the journey of the song is understanding, "This isn't good."

AllMusic: And now moving on to the album as a whole, I know you wrote the songs on Oh To Be That Free in the wake of some personal struggles. How did this difficult period influence your songwriting?

Anne: Writing songs for me is definitely therapeutic. I'm an overthinker, so I think and examine everything in life, including why I write songs. Do I write songs as a way to build a career? Am I writing for other people? I always come back to, I'm a songwriter that writes because I'm processing and examining my life, my relationships, what I observe in others, the world. It's a practice for me, a therapeutic or spiritual practice.

I'm not someone who can really write while I'm in the midst of stuff happening. I write to process and look back at what's happening. I wrote when I was in a place of reconciliation and healing and out of the depths of the hard stuff that I had been going through. It was very helpful to me to work through what I'd been thinking about through all that. Songs really present themselves when you need them. I was in a good space when I was writing and thinking back on some stuff that I had worked really hard to get through. The songs ended up serving future struggles, which, one thing I've thought a lot about is that you can't get through life unscathed. We're all going to go through hard stuff at any given time. These songs really have been helpers for me.

AllMusic: I also understand that in the midst of producing the album, you experienced some big life changes, with the onset of the pandemic, your first child, and your mother's severe stroke. How did these changes change the way you approached or saw the songs on the album?

Anne: The songs are really representing this type of exploration of how I want to live my life. Up until that point, I had been very focused in my life on achievement and building my career and sacrificing my personal life for my music career. I was going through this process – I saw the ways that that mentality was actually very destructive for me. Hearing and trying to think about what makes a good life and what is joy. What is real joy and contentment? Is it through seeking validation and success, or is it through the mundane and the seemingly, sometimes boring aspects of living just a good daily life? And trying to find that joy in those moments, rather than seeking the high of feeling good about oneself because you got a good press review or you sold a bunch of tickets. That kind of process.

So then, to have such a massive upheaval in my personal life, my mom's stroke, my whole life became about her. The three months she was in the hospital, I spent there at the hospital. And everything else just kind of went to the backburner. My career, my friendships, everything was just like, this acute thing is happening, and everything else can wait. And of course, having a child, my personal life and my family became front and center. It changed my perspective on what I'm willing to give — time-wise, emotionally — to my career that has always been so important to me [and] has helped me recenter why I make music and where I want to spend my emotional and mental energy and time. Those songs were already exploring those things, and then supported this perspective [of] growth and change, of what really matters at the end of my life. Am I gonna look back and think, man, I wish I spent more time building my TikTok profile? Or will I be grateful that I centered on caring for my mom? I know that everybody's journey is different — I don't want to say it's one or the other — but for me, it's been a process of valuing these really important relationships, and the songs have served that through this time.

AllMusic: I love how you said that. I think it's really important to really focus on things that truly matter to us and not get distracted by the little things in life sometimes.

Anne: Yeah, I think in today's world it's easier than ever because we have so many distractions. I'm not on TikTok because I just refuse. I hear constantly from people and friends that oh, there's so many ways that it can grow your profile and get new fans and so many people going viral and getting music careers. But my head is spinning from what new piece of technology or platform am I supposed to now jump on board and cater my artistic life to because I've been told that that's how you're gonna do it. And I already spend enough time on all these different platforms. I want to spend more time in my life. If that means that I'm not gonna be as, quote-unquote, successful, then that's the sacrifice I'm willing to make, because I've spend a lot of time sacrificing a lot of important things because I thought the idea of, oh, you have to devote every single minute of your time to growing this career under the ways that we've been told you can grow it by getting on all of these tech apps. Maybe I'm jaded and old now, but I just don't think that that's good for our mental and emotional health, so I'm trying to make more guided decisions, especially now having a daughter. What kind of life do I want her to live and build? Do I want her to be scrolling [through] her phone constantly, or do I want her playing outside and knowing the names of trees and flowers?

AllMusic: You revealed in a statement that these songs on Oh To Be That Free turned into a lifeline for you following your mother's stroke. How do you hope the album will help listeners? What impact do you hope that it'll have?

Anne: I hope that people find connection in the songs. I think about the ways the songs have helped me, and the songs I love the most are ones that I hear and think, Oh yeah, that's how I feel. And that makes me feel less alone. Or, Oh, I didn't think about it that way, and that helps open up my mind and my world to a different perspective or triggers my empathy. That's what I hope these songs do for people, especially if they're going through something and need to understand that they're not alone in their journey. Everything I've gone through the last year, what has helped me a lot is seeking out and finding stories, whether it's through songs or memoirs or books [from] other people who are going through similar journeys. In turn, I hope that people find that in the work that I choose to share as well.

AllMusic: Finally, what aspect of the album would you say that you are most proud of?

Anne: I think the production of the record, I'm really proud of. I've been with my husband [Aaron Shafer-Haiss] for fifteen years, we met and started dating in college. We are both musicians and it's taken us a very long time to get to a place where we can work together. This record was really such a beautiful project for me because we produced it together, but he did so much of it and really listened so open-heartedly and created a record that really sounds like what I heard in my head for these songs. So I'm really proud of that collaboration and also my commitment. From the onset of this record, it was about working with what we have. I work with an indie label, we don't have massive budgets to work with video directors or fancy studios. You can spend a lot of energy wishing that you had more to make everything that you could imagine, and this record has really been about being content with what we have and working within our limits and making something beautiful out of that with just what's at our disposal. I'm really proud of that.

Oh To Be That Free is due to drop June 10th through Yep Roc Records, and you can pre-order the album here.