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Conversation: Michaela Anne’s Rapturous Reality Check

Michaela Anne
Natia Cinco/N.V Photography
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In the fall of 2019, the last time I spoke with her, Nashville songwriter Michaela Anne was floating. Her album Desert Dove, full of songs of freedom and self-determination, was a new Americana hit, and she had a full calendar of good show and festival dates, the reward for years of grinding it out on the road as an emerging artist. Today she’s in a more complicated place, adjusting to events both bitter and beautiful that all seem to point to the same conclusions, that carefree youth has an expiration date and that even hard transitions come with profound rewards.

The challenges came fast. First, the Covid shutdown obliterated that carefully planned 2020 tour calendar. Anne confronted herself over her alcohol intake and what she calls a tendency toward “self sabotage.” And tragically, her mother suffered a hemorrhagic stroke that left her in a coma, followed by a painstaking rehabilitation. During the same stretch though, Michaela had her first child, a daughter, and she drew inspiration from the collision of responsibilities and blessings that came from caring for her recovering mother and growing daughter at the same time. Somehow amid all this, she worked with her husband, multi-instrumentalist and producer Aaron Shafer-Haiss, to make a pivotal album, the lush modern country project Oh To Be That Free, which arrived last Friday.

In the conversation posted here, Michaela tells me that existential musings and personal accountability were much on her mind even before her recent life events. “I was asking all those questions during the time that I was writing the songs for this record, and really rooting in my home life and contemplating starting a family and how I wanted that to look like and what my value system was,” she says. “That's what I was writing about when I wrote this record, and then (it) led into having a baby and my Mom having a massive stroke and all of our lives changing. And so the songs felt like future gifts in a way - they were helping me cope before I really knew I needed that help.”

Michaela Anne

The title track is a distilled dose of nostalgia for simpler, more childlike times, set to one of Michaela Anne’s signature melodies, which are as sweet and lofty as her voice. She cites the sweeping “Good People” as a more challenging and exposed song, one more about “being honest about our shadows.” Album opener “I’m Only Human,” written with her old friend Madi Diaz and new friend Kate York, emerged in the trio’s first songwriting session, and sets radical self-awareness and forgiveness against pillows of strings arranged and played by Nashville’s fiddle maestro Kristin Weber. The record is seductive sonically, and surely the tender “Does It Ever Break Your Heart” will take listeners to the paradise landscape settled a few years ago by Kacey Musgraves in Golden Hour.

Michaela Anne says that processing and adapting to a life newly full of hyper-adult responsibilities gets her thinking about how she was shaped growing up in a peripatetic military family, ever saying goodbye and starting over with new friends in new places. “I wonder all the time, how it'd be different because moving, you're in survival mode all the time. You just want to fit in as fast as possible,” she says. “So it's hard to know what was me? What were my interests? I experienced that a lot. I feel like I've been a chameleon for a very long time.”

When she got to choose her own destination it was New York, where she attended a jazz conservatory, got her songwriting career going and worked a day job at Nonesuch Records, offering a look at one of the most sophisticated corners of the popular music business. She chased her fascination with the music coming out of East Nashville by moving to town in 2014, where her adaptation skills served her well. Until she says she began feeling like she was over-serving herself, living too hard and drinking too much. Which led to her decision to get sober amid the kinds of life dramas that would lead others in the opposite direction.

Her music earned national acclaim with the release of her second album, Ease My Mind, in 2014. Then after moving from Brooklyn to Nashville she made Bright Lights And The Fame in 2016 with assists from Rodney Crowell and banjo master Noam Pikelny. Opportunities further expanded with 2019’s Desert Dove, a pastoral disc recorded out west with similarly minded artist Sam Outlaw as producer. Rolling Stone and others hailed it as a year’s best, while invitations to key festivals like Bonnaroo (where she’s playing her twice-delayed makeup date this weekend) poured in.

“This entire past year, this experience with my mom, sitting by her hospital bedside, I mean, I have days where I'm just like, I still can't believe that all this has happened,” she tells WMOT. She’s seeing poignant connections between her daughter’s cognitive development and her mother’s cognitive recovery. “Like my daughter learning to walk - just walking up and down the hallway back and forth. I've done that a million times with my mom this past year. And it's so surreal, but at the same time, I have to think that there's some type of magic in that experience, too.”