Michaela Anne found healing and comfort in her new album ‘Oh to Be That Free’

In the middle of making her newest record, Michaela Anne’s life went through a series of life altering changes. She became pregnant with and gave birth to her first child and her mother experienced a major hemorrhagic stroke.

She spent the second half of her pregnancy, sitting by her mom’s bedside in Michigan, playing these new songs for her. They became a source of comfort, introspection and healing during a moment fraught with anxiety and unknowing.

As fate would have it, Michaela Anne’s new album, “Oh To Be That Free,” is filled with songs that examine the things that make us human. The flaws that we learn to love in ourselves, the ways that we must learn to love others the way that they need to be loved. As she watched her mom recover and her daughter’s first months in the world, Michaela had written the album she needed to hear. This week on the Reckon Interview, I sit down with the Nashville-based singer-songwriter to talk about her upcoming album.

Below is a transcript of the episode, edited for length and clarity.

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Reckon: We are here to talk about your new album, “Oh To Be That Free,” which is coming out in June 10th. And you released your last album “Desert Dove” in 2019. It was your most critically acclaimed album to date. It was one of Rolling Stone’s picks for best country album of the year. This was your big breakthrough album. And then things kind of started to fall apart. Obviously on a global scale, they were unraveling with the COVID-19 pandemic, but also for you on a personal scale. Can you tell me a little bit about what you were going through after that last album?

Michaela Anne: Yeah. Leading up to the pandemic, things were feeling really good. It felt like, oh, my career was finally starting. You know, all the ducks were in a row. Things were finally starting to line up and it was really feeling like that. Like, all the hard work is paying off and my dreams are coming true.

And then obviously everything was taken away and stopped. And then I think a year into the pandemic, I started making a new record. Then I got pregnant, but that was intentional. Life didn’t fall apart with that, it was wonderful. But it presents more challenges with having a career. But then in the middle of my pregnancy, my mom, who I’m very close to, suffered a hemorrhagic stroke.

And it was a pretty massive stroke where she was in a coma. And lost her entire right side and her ability to speak. So a year and a month past the stroke, and she’s still not fully recovered. Recovery is still full-time. It has consumed, obviously, her and my dad’s life. Thank God, my parents are still together.

And my dad is a really devoted partner and his whole life has changed. He’s become her 24/7 caretaker, but obviously that just waylaid my life completely. So, I spent the whole second half of my pregnancy in Michigan, at the hospital with my mom. And gave birth to my first daughter without my mom ever being able to come to visit, being able to help in any way.

So it’s been a really traumatic year that I think anytime you go through something really life altering and life-threatening, it kind of changes your perspective on everything. And also becoming a parent changes your perspective on everything. So my whole emotional relationship to my career and to music has really changed since I put Desert Dove out. But yeah, that’s kind of in a nutshell, what has been going on the past year in my personal life.

Reckon: Let’s talk about the timeline of it a little bit, cause you were pregnant when you started writing and recording this album and you had already recorded most of the songs by the time your mom went into the hospital, is that right?

Michaela Anne: Yeah, we had recorded everything and I made this record with my husband, Aaron Shafer-Haiss. He was first a drummer and then has evolved into a really talented multi-instrumentalist and producer. So we produced it together and we had finished recording and it was in the mixing process when my mom had her stroke.

So I was all done with it, but I was still really living with the songs and then listening to mixing rounds throughout that experience.

Reckon: And so much of this album is about the ways that we’re all connected with each other and loving each other for who we are, not who we want each other to be, surrendering yourself to forces beyond your control. Which sounds like it was the album that you maybe needed in that moment. How did your relationship to the songs change while you were bedside with your mom?

Michaela Anne: I mean, leading up to writing this record, I had gone through some tumultuous stuff in my personal life and my relationship. And writing these songs was kind of the aftermath of that. And trying to get healthy myself and then going through an experience of one, you know, becoming pregnant and growing child, and then sitting at a hospital bed where my mom is unconscious and in a coma, and we have no idea if she’s going to survive. Or, if she does survive, if she’ll ever speak or move again, that, like, I feel like the English language doesn’t have like sufficient words to really describe what those experiences are like. The songs for me just grew in depth so much, songs like “Who You Are,” which is about trying to see the people that we love for who they need to be.

And that was a huge lesson for me with my mom, when I always had to kind of set aside, like I wanted my mom to be capable and healthy, to be there for me. Because I was pregnant and I was about to become a mom. And I always envisioned that time that my mom would be taking care of me. And the roles were dramatically reversed.

She hasn’t been able to do that for over a year. And I was, instead standing in the hospital advocating for her, like writing down all of her meds and like becoming the caretaker. And then watching my dad. They’ve been together since they were 16 years old. And it’s such an incredible thing to watch a relationship evolve where, you know, you fall in love with somebody because you think they’re attractive and then you’re drawn to different things about them.

And you never expect that one day you’re going to be– and very young too. She had only turned 63– to then all of a sudden now bathing your partner and, you know, taking them to the bathroom and dressing them and doing every single thing. That is really, really hard. You know, it’s hard to not be like, “what about me?”

And so my songs really kind of, for me, helped me. They were all little reminders. Cause I had already been ruminating on like how to be more selflessly in this world for our close relationships. But also recognizing how deeply connected we all are, even the people that we don’t want to be connected with.

I believe in that in such a massive way that, for better or worse, we all depend on each other. So those were already the themes that were brewing for me. And then my experience. It was like, okay, you were thinking about this stuff. Let me give you the most intense, you know, in depth experience to deepen these thoughts and ideas of really learning about life in a really raw form.

Reckon: I know you grew up in a military family and that you and your dad and your mom traveled around the world, lived in various places. You mentioned that they were high school sweethearts. What was y’all’s relationship like, growing up? What do you remember about your mom when you were younger?

Michaela Anne: Yeah, so my mom was a stay-at-home mom. We moved every other year. So the narrative that I always heard growing up was that my mom had been on the career path and she gave it all up to marry my dad and made the decision to not have a career because it felt too hard to move all the time. And my dad was out to sea for six months out of the year. So she didn’t want her children to grow up with two parents away.

That was the story. And I always understood that the sentiment was that she didn’t regret any of her choices in life. She believes family and parenting is the most important thing, but there was also, I think, some sorrow of not getting a life that wasn’t lived. And that’s really informed me as a woman. And just the sacrifices that traditionally women make more often.

But growing up, I wasn’t aware of any like resentment. She was the best mom. Like she was always with us. Um, so my mom and my brother and I were really a trio. I kind of felt bad for my dad sometimes cause he would come home after, like, being a commanding officer on a nuclear submarine, his little five-year-old daughter would be like, “you can tell me what to do.” But also, I loved my dad. There’s videos of me as a three-year old, like not letting my mom do anything and saying “no, only dad.” so I have really fond memories of both my parents. I’ve always been very close to both of them.

Reckon: You mentioned your mom having potentially some bittersweet regrets about being a stay-at-home mom. In a statement that you put out for this new album, you talked about chasing other people’s definitions of success, because you didn’t feel like you could trust your own. Is that tied into that? You know, this need to quote unquote succeed in the music business because of that relationship with your mom, you think?

Michaela Anne: Yeah. Maybe not on a super conscious level, but I definitely came up– and I don’t even know if it was her intent– but I kind of internalized a message of, “as a woman, I’m going to put my career first.” And I need to be established before I can start a family. And I need to be independent and I’m not going to be a stay-at-home mom and, you know, have a relationship where I’m second fiddle to my husband, that type of thing. So it’s taken me a long time, I think, to work through. There is nuance and balance that you have to discover and design for yourself and with your partner. But, yeah, my ideas of success and what success looks like have definitely changed, especially in the music business, which honestly can be very toxic, very hard to navigate, like very fickle.

So I noticed the ways that putting so much focus on these numbers that we all have been trained to value, whether it’s our social media numbers, our streaming numbers, our ticket sale numbers, whatever, that was leading me to have an unhealthy relationship with myself and music and not have a happy life or make good decisions. My priorities have definitely shifted in that regard.

Reckon: We had our first child not long after you had yours. I think they’re a few months apart. And yeah, I can certainly relate to the idea of constantly chasing numbers, whether it’s podcasts downloads or page views or things like that in this field. And then all of a sudden you’re a caretaker and your priorities change because the time that you have in the day changes.

And I can’t imagine that experience of taking care of both a newborn daughter as well as your mom and both of them being in different stages of life. Have you been able to find some joy in those moments? You know, the first laugh that your daughter has or, you know, your mom successfully doing something that she maybe hadn’t been able to do.

Michaela Anne: Completely. I’ve thought about this a lot in that the past year of my mom having a stroke was by far the most painful year of my life. But what I didn’t understand was just the extreme joy that also comes with experiencing deep pain, when the joy does return. And obviously having a little new baby, there’s so much joy in a baby and watching them develop. It’s been so extreme, just the laughter of like seeing your baby laugh for the first time or recognize things for the first time. And yes, with my mom, I was actually just writing about this the other day, especially in the beginning, the small little things felt like such massive miracles. I’ll never forget the day that she moved her thumb for the first time. She had just kind of started to begin speaking again. And they wouldn’t let you stay overnight at the hospital. So I was leaving at the end of the night and I was always leaving after the visitation time was done and I kept like saying goodbye to her. And I saw her little thumb move and I was like, “mom, did you just move your thumb?”

And my mom is not one to celebrate herself. You know, she’s a very behind the scenes, like don’t fluff over me. And she just looked at me and was like, “yeah.” And I was like, “Mom! You moved your thumb!” So yes, I’ve learned with deep heartache comes great joy when it returns.

Reckon: Taking care of a child full-time and taking care of your mother, at least part-time, if not full-time, can drain a lot out of you. So how are you taking care of yourself?

Michaela Anne: Well, I’m lucky that I have an incredibly supportive partner. He is very focused on that type of stuff and wanting to make sure that I… he reminds me all the time, “if we don’t care for ourselves, then there’s really nothing left.” And I have to say, you know, the last several months since my daughter was born, I haven’t been able to go be with my family as much. I go like every other month and try to help out. But I don’t want to take away from my dad and my brother and my mom’s siblings, it’s been such a larger family effort to help her. And I have a lot of guilt about that as well, but when I am there, I help out as much as I can. But yeah, I think selfcare… it’s been, again, a lesson of even a few minutes actually does make a difference.

Just walking around the block for 10 minutes can really shift perspective. So those are the things, some exercise, a bath, you know, I’m obsessed with Tara Brach, who’s a mindfulness [leader], has a podcast and a Western Buddhist teacher, listening to her. Those little things really help rejuvenate me.

Reckon: What did you learn about yourself while working on this album? I know that you deliberately chose your close friends and your husband to work together with you on the production. It’s very intimate, very introspective. And it’s interesting to hear you talk about all of this that you’ve gone through since writing the album and producing it, because so much of what you write about and sing about relates to these experiences. But I’m curious what you learned in the process of creating it?

Michaela Anne: I had a big realization, which was surprising to me because, honestly, I kind of always thought of myself as a confident person in my abilities, but I realized I’ve spent a lot of times seeking outside validation. And seeking outside producers, outside writers, to basically tell me like, “okay, yeah, what you’re doing is good enough,” or “I’ll make this good enough.”

And I realized I started dating my husband when we were 20, 21 years old. So I realized I had kind of enveloped him into my insecurities. He didn’t count as an outside person. So working with him musically was really scary to me because I thought, well, who’s going to make this good? Who is it going to tell us? Like you don’t count because you’re just an extension of me. You know, when I shared this with him, he was like, “okay, that kind of sucks. But at the same time, like, I’m glad you’re working through this.”

So, you know, it was a leap of faith of really understanding that about myself. This whole kind of time period has been a lot about identifying and embracing the things that I would maybe think of as negative about myself, because I think that there’s so much growth and strength in owning everything about ourselves, even when we could put it in the box of negative characteristics or character flaws. And that makes me feel so much more confident in the process.

So that was a big learning lesson through this. And it’s kind of been over and over again, this strength in, do what you can with what you have. You don’t need to go try to find the best whatever person to tell me that I’m good or the best, you know, videographer. It’s been a lot of like, “Hey, we’re creators. This is good because it’s true.” That’s been a lot of the lessons through this time.

Reckon: Well, and the lead single off of the album, “I’m Only Human” on first listen, it sounds like you’re being very hard on yourself, but you’re also kind of giving yourself permission and kind of the grace to love yourself despite, in your words– and I don’t know if you’re writing this as you or if you’re writing this as a character– but “I’m selfish and unstable, I’m emotional and mild, I’m hateful,” but you know, you end it with “I’m only human” and it sounds like you’re talking to a partner in this one.

Michaela Anne: I wrote it with two other writers, Madi Diaz and Kate York. And Madi is a really close friend of mine. I had only really, I had only met Kate on that session. Madi, and a bunch of my other girlfriends, we all talk about the same stuff all the time. And it is like struggling with all of those feelings, depending on the day, I am jealous and jaded and hateful and whatever at different times. But that doesn’t mean I am those things. I feel those things. I had a therapist, years ago, who I remember I was going through, like right out of college, struggling with feeling jealous and not knowing what to do with myself and then feeling so guilty for feeling those things. Feeling so bad about myself for feeling jealous of a friend.

And I remember the therapist being like, “okay, everybody feels those things. It’s what you do with that feeling. So let yourself feel it, honor it, and then let it go.” If then you’re, like, mean to that person because you’re jealous, like, then there’s the issue. I think honoring that we all struggle with so many of these same feelings, we’re not bad for it, it has been a big process.

Reckon: One of my favorite songs off of this album, “Who You Are,” we talked about it a little bit earlier with your mom, but it’s about loving people for who they are and not who you want them to be. That’s a beautiful idea. It seems very hard to put into practice. You know, do you have any advice for how to do that?

Michaela Anne: As I mentioned earlier, this changed a lot of meaning through the experience with my mom, but when I wrote it, I wrote it thinking about my partner. But also even with strangers because this was, I’m trying to remember… I started writing it in 2018. So for me, my experience, the Trump era, it was just like the beginning of so much division that was also like tearing families apart and it’s just progressed and gotten deeper and things have gotten crazier. And I think a lot about how to have positive change in the world to feel more inclusive, I don’t think that happens through screaming at each other. So part of that story for me was also like, how can I see strangers who I violently disagree with on certain topics and think that, how am I supposed to be tolerant of their intolerance and their beliefs that are trying to hurt other people? How can I still find a way to love them because they are humans on this earth? And we have to cooperate with each other. This isn’t giving any advice on how to do that… [Laughs]

Reckon: Are there limits to that? You know, what if the way that somebody needs to be loved involves you having to kind of sublimate part of yourself or subordinate part of yourself? You know, you’re talking about like being tolerant of other people’s intolerance.

Michaela Anne: Yeah, I believe more than ever in boundaries. Setting boundaries. And I think you can love people from afar. I do think that you can decide, like, I really disagree with somebody, or I think this person is damaging or their beliefs are damaging and I’m going to fight to change these things or whatever. But I want, always, to strive for it to come from a place of love and to still love those people. And for instance, like what I’m specifically thinking of are people who are working so hard to pass laws that hurt trans kids and people who are homophobic and people attacking women’s rights and that’s stuff, honestly enrages me. But the thing that I ultimately want to do is I want those people’s minds to change to have more compassion and empathy and not be fearful of something in other people that they don’t understand, therefore not want to spend their lives, creating laws that endanger others. And how am I ever going to do that if I just am filled with rage and hatred towards them? These are goals. Cause I don’t know how to do those things. That’s why I write songs

Reckon: You have a new single that’s coming out in a few days. It’s called, “Does It Ever Break Your Heart? What can you tell us about this song?

Michaela Anne: Yeah, this song was one of those songs that kind of just fell out which is nice when that happens. It just kind of appeared and including at the end, there’s this kind of vocal part that overlaps and kind of creates what in my mind feels like, I dunno, like a musical tornado in a sense. A cyclone feeling.

Yeah, and it kind of plays like a little movie in my head of being in a relationship that you know is not good for you and getting to a place where you have the strength and confidence to finally walk away. But that tension and that push and pull that can be so enticing but toxic, is really kind of what this song is about. And ultimately deciding like, kind of referencing what we were talking about, somebody who you need to set a boundary with and you can love them from afar and not be up close.

Reckon: The title of the album “Oh To Be That Free” comes from one of the songs on the album, which is sort of reminiscing about how carefree we are as children and this idea of living in the moment. It’s beautiful because it seems to have three generations of women in that song. And it’s a nice kind of bow on that relationship with you and your daughter and your mom. Tell us about that one and why you chose it as the title of the album.

Michaela Anne: So the song is, “Oh To Be That Free Again,” but the record is “Oh To Be That Free.” and the song is a true story. I mention in the song, the little girl being called from the porch. Her name is Tiger rose and Tiger Rose is a real person. My husband is from Maine and his cousins are farmers. And their little girl’s named Tiger Rose. And every time I go up there, I’m just kind of enamored. She’s just like a little wild farm girl that’s so comfortable with the animals and I didn’t grow up that way. So one summer she was running around half naked and her grandmother was standing next to me and said, “oh, to be that free again.” And it felt like, you know, a bolt of light came through me and I was like, that’s a song.

So I started it. And then when the pandemic happened, it was the first time… we had lived in our house for a couple of years, but I had never seen spring here because I was always on tour. So it was the first year that I was like seeing what blooms in April and May in my backyard. And I was really sinking into and embracing that beauty. And I finished the song and, again, like the song just carries so much more meaning for me having a little girl of my own now. And anytime I think about the way that I live my life, I think, how do I want to raise my daughter? What kind of life do I want her to aspire to have? And what kind of things do I want her to value? Do I want her to value scrolling Instagram all the time? You know, looking at how many likes she got? Or do I want her to feel like the freedom of running around in the backyard and knowing how to identify trees and flowers and that’s my ideal. Again, these are all kind of like blueprints for like when I get very easily caught up in the things that I don’t think are ultimately good, which is very easy to do in modern life, a lot of these songs on the record are reminders for me of how I want to live within my value system and integrity.

Reckon: You’re about to tour again, would that be the first time you’ve toured since before the pandemic? Or have you been touring?

Michaela Anne: Yeah, so I think when this comes out, I will have just finished a two week tour with the Milk Carton Kids, which I’m very excited about. So I’m sure if it was post-Milk Carton Kids, I’m sure I’d say, oh, it was wonderful.

Reckon: This’ll be your first tour as a mom or as a parent, I guess, I should say, I know people always ask that question just to women. But this’ll be your first tour as a parent, how are you feeling about it? Will your daughter be able to go with you? Will you be apart for two weeks?

Michaela Anne: No, we’re bringing her with me. And I do think, you know, I’ve known a lot of men who tour who have kids and, for the most part, they don’t bring their kids with them. So it is valid. It is really different for a mom, especially when they’re very young babies, especially if you’re breastfeeding. It’s just so much harder to be away from them. So I think that’s valid. Gender does come into play in different contexts. She’ll come with us. I’ve done like a three-day run in the past where I took her, but this time my husband’s coming with us, thankfully. And he’s coming just as dad and taking care of her. And that feels very comforting, but, yeah, it’s different. It’s so much more exhausting. I’m like excited, but also like, oh wow two weeks with, I think, there’s only one day off. So I pray she sleeps but she’s a great traveler. But yeah, it’s just there’s so much more.

I have a lot of friends who I really admire who are moms who’ve given so much guidance and Leyla McCalla who is based out of New Orleans, Aoife O’Donovan, you know, all of the tips of like, what time do you do bedtime? Do you do it at the venue? You know all these logistics. Like, do you pump? Do you breastfeed? Like it’s just so much more energy and time that I really do feel like my goal is—and my friend, Laura Cortese, has talked about this, that she wants to talk about this stuff publicly. Because she doesn’t want young girls to grow up and think, oh, I want to do that but then I couldn’t have kids, or I want to have kids so I can’t have that career.

It’s not set up for us, but I think there’s a lot of us who want to create culture to do that because I want to see and hear and consume more art by women. So, I want a culture that supports them to be able to have the time and the energy to create beyond just their family life.

Reckon: Just one last question. I think this is a record that a lot of people are going to find a lot of comfort in in terms of the themes that you’re talking about. What are some words of advice or comfort that you would offer to them or even that you would offer to yourself when you were writing it three years ago?

Michaela Anne: I think one of the biggest things I try and emulate is– and I think a lot of what I’ve been working through with the themes of this record– is that it’s so easy to feel alone in our experiences, but so many of us experience so many of the same things. So finding ways to connect with others and find those who can see us or empathize, that’s what I want to nurture and offer that. Like, that’s my whole purpose in being a musician. It’s not necessarily to entertain people, but to create spaces where I’m vulnerable and honest in my sharing. Because when I witness that, it gives me the permission and the comfort to be that as well. Trying to offer spaces telling people it’s okay to feel the things that they feel and share.

Michaela Anne’s album “Oh to Be That Free” from Yep Roc Records is out June 10.

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