Late in life, Chicago songwriter Flo Estes delivers a stunning folk debut

Estes plumbed the depths of folk songwriting as a labor organizer. But it was a hobbyist guitar class where she landed an album offer.

SHARE Late in life, Chicago songwriter Flo Estes delivers a stunning folk debut
Flo Estes.

Flo Estes.

Taylor Glascock Photography

As it was for most people, Flo Estes’s life during the COVID-19 lockdown was difficult. She got depressed. She grew tired of taking her beloved songwriting class through a computer. Then, she got the virus itself.

When restrictions relaxed, she decided life must change. For her, that meant recording an album of songs she had recently started writing. Not only did Estes eventually complete the record, but “Jolly on the Inside,” her self-released debut out this month, would be stunning even for the most seasoned musician.

At 70, an age when others are settling into familiar routines or bristling at exploring untapped potential, Estes boldly reveals a part of herself she says surprised even her. “I had this feeling I’d like to share myself with the world. I was always pretty shy about doing that,” she said.

With lyrics and a sound reminiscent of Linda Thompson, Iris DeMent or Eva Cassidy, these lovely songs feel like glimpses into private thoughts that take time to reveal themselves. Estes’s quiet voice forces the listener to lean in, not the other way around, to hear their depth.

“At the Bottom of the Ocean,” the album’s opening song, could easily be about scorned love — “That’s where our love is resting/We watched it drown,” she sings. But later, it becomes evident, it was society, not the lovers themselves, that did the scorning. “I wish we’d lived in another galaxy/where people would love to see you holding hands with me,” sings Estes.

The obvious folk sensibilities in her music are rooted both in her background in labor organizing and her genes. Her family were musicians and her father, a scientist with McDonnell Douglas, an aerospace contractor for NASA, knew old gospel tunes from rural Kentucky, where he was raised. Music “was like air or water” around her, in all the places her parents moved, from Missouri to Texas and Florida.

“It was not something you thought about doing as much as just participating” in it, she said.

Flo Estes strums her guitar in her North Side home. On April 23, the 70-year old singer-songwriter will make her debut fronting a small band assembled by Chicago musician Steve Dawson of Dolly Varden. 

Flo Estes strums her guitar in her North Side home. On April 23, the 70-year old singer-songwriter will make her debut fronting a small band assembled by Chicago musician Steve Dawson of Dolly Varden.

Taylor Glascock Photography

Estes became interested in labor efforts when she joined a union in Amherst, Mass., where she worked a clerical job. She eventually earned a master’s degree in labor economics and taught at the University of Kentucky, where she received her doctorate. Textile mills, auto plants and mines dominated the region, and Estes eventually taught labor law and history to miners and factory workers. Music became part of the curriculum and songs like “Dark Like a Dungeon,” a mining song by Merle Travis, “The Aragon Mill,” by activist-songwriter Si Kahn, “The Coal Tattoo,” a traditional, and “What Side Are You On?” by Pete Seeger, were staples.

Eventually, she and her colleagues performed in union halls across the South and Midwest, the songs testifying to the universal struggles of laborers across industries and generations.

She moved to Chicago in the late 1980s and continued teaching and working for labor organizations; it was one experience, teaching English as a second language at the Howard Area Community Center in Rogers Park, that led her to the title song on her album.

An older Mexican woman needed help learning English, so Estes worked exclusively with her for six months. Over time, a familiarity developed between both women. When the woman announced one day that she felt comfortable with her English enough to join the regular class, Estes congratulated her, hugged her, then burst into tears in her car on her way home. She had discovered she would sorely miss a friendship she didn’t realize had formed.

“I was so attached to her I didn’t want to stop our teaching relationship,” she said. Out loud, to herself, she asked, “Why can’t I be jolly on the inside?”

Starting with its first chord, the song sounds like a familiar classic written decades ago, not just for its confessional warmth, but because of its universal appeal.

“When you have a profound moment, at the time it can feel like any other moment. But then you keep it inside of yourself and you realize how very special it is,” she said.

As in childhood, Estes filled her adulthood with music, but up until now singing, playing piano and guitar “were just for me,” she said. After moving to Chicago, she attended community song circles at the Old Town School of Folk Music and small open mics at coffeehouses around town, but never considered showing anyone her original songs. It wasn’t until she took an Old Town School songwriting course with Steve Dawson, the celebrated singer-songwriter and leader of Dolly Varden, that she decided to give it a try.

Prior to then, Estes had been stockpiling the songs that made her first record.

“It’s the kind of thing when she would present a song, I would not know what to say other than that song is great,” Dawson said. “I didn’t do a lot of coaching.” Estes said she didn’t expect the positive reaction from Dawson and her fellow students.

“If you’re not in the public music business, you’re a little island and you’re isolated and you may not know how other people relate to your songs,” she said. “That surprised me.”

The next surprise was Dawson’s offer to record an album at Kernel Sound Emporium, a recording studio he owns in Wicker Park. There, he recorded her at a keyboard and later he added guitar, bass and electronic strings that enhanced the songs without sacrificing their intimacy. Her voice, sometimes doubled and other times echoing, draws the listener into the world of each song.

The album’s most straightforward song, “If You Can Still Walk You Can Dance,” came from her memory of dancing with her father when he was in the last throes of his Alzheimer’s.

“Music is an amazing thing. It’s so deeply a part of you. He still remembered those old songs. Even though he didn’t remember what he did 10 minutes ago,” she said.

On April 23, Estes will make her debut with a small band Dawson assembled, including himself on guitar, bassist Tim Hoyer and singer Emily Haden Lee. “Jolly on the Inside” will be available for sale, and she is deciding if she wants to continue past this one date.

“When you reach a certain age, you don’t think of yourself as starting something new or being public. But then I started thinking, ‘Well why not? You’ve only one life and it’s pretty short,’ ” she said.

Flo Estes performs with her band at 7 p.m. April 23 at Jarvis Square Pottery, 1443 W. Jarvis Ave. Find event information here. Find her music on Bandcamp.

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