Molly O’Leary has written a courageous record.
The 26-year old singer/songwriter has crafted “Holding Space,” a 13-track album addressing serious themes and challenging experiences that have touched her and those around her. Drawing comparisons to Alanis Morrissette and Phoebe Bridgers, the New Bedford resident will perform the album in its entirety with her four-piece band this Sunday, August 29th at the Heron in Westport. Doors will open for the free outdoor show at 3 p.m. and music will start at 4 p.m. with a performance by Hooly J. Chan. Described as “family friendly,” guests can bring their own food. Rain date for the event is Sunday, September 12th.
“It’s cathartic and empowering to write and perform these songs,” O’Leary says. “It was initially scary to speak about these things but getting over that was a big step. It’s all worth it when you can reach someone whose had a similar experience.”
The experiences on “Holding Space” include O’Leary’s battle with an eating disorder, the addiction of a loved one, and the lives of the socially marginalized. But while the themes may be heavy, O’Leary describes the album as being “positive,” a collection of songs that is ultimately about “healing” and“overcoming.”
“People may feel isolated in what they’re going through and that they’re the only ones going through these emotions,” she says. “But once I started playing them out people were saying that they’d had similar experiences. A light bulb went off that if we talk about these things we can connect and get through it together, which is much better than facing it alone.”

“I was blown away by her vocals,” Mailloux says. “Usually vocal tracks are the last thing recorded on an album, but Molly nailed them on the first take. They were so good that we kept almost all of the original performances. The emotion was there from the start. It’s very unusual for the original vocal tracks to be keepers.
Much of O’Leary’s lyrical inspirations come from the non-musical sides of her life. With a Master’s Degree in Social Work, she is a Yoga Instructor at the Heron, and a Student Adjustment Counsellor at the Rodman Elementary School in New Bedford.
The title “Holding Space” is adapted from her yoga meditation.
“I used to push away negative emotions that were difficult,and constantly feeling pressured to put on a happy face,” she says. “Holding space is for emotions that are more difficult such as sadness, anxiety or anger. Instead I’ll let them exist and I’llfeel them out. For me, there have been lessons and songs that have come from that.”
“Holding Space” contains songs about systematic oppression and injustices, including “Our Little School,” a song about some of the students that she works with at Rodman.
“I wrote that song while I was thinking about all of the societal structures and forces that are against them,” she says. “I wanted to write about the system and let them know that our school can be a pocket of change and that we care about them a lot.”
And writing about the addiction of someone close to her,she says that “I wanted to write a song that let them know that I will always be there for them.”
All but one of the songs on “Holding Space” were written during the COVID-19 pandemic. The album was recorded at Bongo Beach Productions in Westport with John Maillouxproducing, engineering, mixing and mastering. Recording began in February of this year.
O’Leary’s studio performance caught Mailloux by surprise.
“I was blown away by her vocals,” Mailloux says. “Usually vocal tracks are the last thing recorded on an album, but Molly nailed them on the first take. They were so good that we kept almost all of the original performances. The emotion was there from the start. It’s very unusual for the original vocal tracks to be keepers.
“The first time Molly played her songs for me I gravitated to them,” Mailloux says. “I recognized her talent and that her writing was pretty deep as well.”
“Holding Space” will be released on CD in mid-September. It was funded entirely through Kickstarter. The album features performances by guitarist John Fernandes, bassist Rob Massoud, drummer Tom O’Leary (Molly’s brother) and Brianne Vieirawho contributes violin, viola, and cello to the record.
In addition to playing with the full band she also performs her songs solo and in a duo with Fernandes.
“Molly has a beautiful voice, it draws you in right away,” Fernandes says. “Her lyrics are personal and a listener can sense the honesty. She uses dynamics very well – there are influences but the way she sings with her inflections and guitar playing isher own style, she’s her own musician for sure.”
In addition to Morrissette and Bridgers, O’Leary cites the influences of Alicia Keyes, Claud, Billie Eilish, Laura Jane Grace, and Natalia Lafourcade.
O’Leary began guitar lessons at the age of 11, studying with Rochester native Rebecca Corriea. Now a singer/songwriter living in Nashville, Correia is not entirely surprised by the positive reactions O’Leary is receiving for her music.
“I knew she was a natural from the beginning,” Correia says. “I would give her something to work on and she would return for the next lesson having it down times ten.
“The things she’s singing about are touching to hear. To see her living her truth and telling her story is awesome. I think she’s going to make a lot of waves and help a lot of people. The combination of being an artist and a teacher gives her the ability to reach a lot of people and affect a lot of lives. Young women can benefit from her messages and the stories she’s telling.”
“I think we captured the emotions Molly was expressing,” Mailloux says. “She has a lot to say, she’s very empathetic and that comes out in her writing. There’s some beautiful, ambient-sounding stuff, but there’s also some rock-and-roll and some aggression on some of the tracks.”
O’Leary has spared no expense in creating “Holding Space.” In addition to printing the entire set of lyrics, the album is accompanied by illustrations for each of the 13 songs, designed by her friend Frida Garcia, who she met while studying Spanish in Puebla, Mexico in 2017. The cover is a photo image of an embroidered design created by Garcia.
“The process of writing this album has fueled a fire in me,” O’Leary says. “I’ve realized that I love being a counsellor for the students I work with, but at the same time I also love being a songwriter and I want to tour more playing my original songs.”
The Heron concert will include Chan playing songs from her latest album, “Make Believe.”
Directions to the Heron include setting a GPS for 333 Sanford Rd. in Westport, and taking Legacy Lane between houses 333 and 337, taking a dirt path and following event signs for “Parking.”
O’Leary will also be performing with Fernandes on Saturday, September 11th as part of the Stoveboat Concertsseries. Sharing the bill with North Carolina’s Juliana Finch, the concert will take place at the New Bedford home of nationally-celebrated songwriter Sarah Donner, at 63 Thomas St. Starting at 7 p.m., there is a $10 suggested donation.
