Heather Maloney Makes Her Own Breaks

The name of Heather Maloney‘s alluring 2015 album is Making Me Break, but it just as easily could have been titled Making Me Breakthrough.

Comfortably enjoying the ride while staying in cruise control, the contemplative singer-songwriter from Northampton, Massachusetts, got a career jump-start in 2012 when she signed with Signature Sounds. Her first album for the prestigious New England label, released  in March 2013, ranked high on my best of the year list.

With her follow-up out since April, Maloney is finally making her move. Embarking this September on one of the most ambitious tours of her career — 40 shows in 40 cities over six weeks, stretching from the East Coast to the West — she’ll turn around to work her way back home before Thanksgiving.

“I just love performing,” Maloney said, catching up while relaxing on a couch inside an artist hospitality area during a rainstorm at the Rocky Mountain Folks Festival this summer. A couple of hours earlier, she endured the dog-days-of-summer heat over a noontime set. “It’s what I’m kind of thinking about when I go out with a new record. I’m so into the actual time onstage  and connecting that I’m not … I feel like if I went out and was like — ‘What are people gonna think of this (new album)?’ — it would make it not as fun for me.”

Though she didn’t start seriously writing songs until 2009, while contemplating leaving her job at a meditation center in central Massachusetts called the Insight Meditation Society, some critics might wonder why Maloney isn’t in more of a hurry to get where she’s going.

As a number of musicians have stated about their profession, it’s a marathon, not a sprint. Breaking big before reaching the big 3-0 doesn’t necessarily have to happen, unless you want to be a major league athlete. Besides, she’s already dealt with more difficult challenges.

“I feel very encouraged because [my career] hasn’t done anything but grown,” she says. “There hasn’t been a plateau or a dip. It’s just a steady, slow climb in a way. And to me that’s more than I can ever dream of or ask for in this business. So I feel very grateful.”

That mantra hasn’t changed a bit from our first interview in February 2013, ahead of her Heather Maloney release, when she said, “I feel encouraged enough by the momentum and sort of what’s been built to continue. And it feels like it’s just growing. If I felt like it was diminishing [laughs] I might not be so excited about continuing. But it feels like — musically and on a business level — it feels like it’s a growing thing.”

Maybe it’s all the hard work she did to reach this point that makes Maloney seem content with her progress. The one-time aspiring opera singer has a very easygoing stage presence. She smiles broadly, delivering cheesy puns and constantly addresses the audience as “friends,” while delving into emotional material from her past, such as “Linger Longer,” “Making Me Break,” and “Day With You.”

She wrote the latter in the summer of 2014 while she was teaching at the Sisters Folk Festival near Bend, Oregon, and missing her boyfriend, artist/photographer Kevin Hill, whose images of Maloney appear on the Making Me Break cover and throughout the accompanying booklet.  

If there was any visible post-set anxiety from Maloney on this August afternoon, it had to do with Hill’s participation in his men’s baseball league championship game. Getting a couple of updates via text messages from a friend, she said proudly, “He does shortstop and sometimes third base. Sometimes they put him in the outfield, too. … He loves it. He’s really good, too.”

To keep calm during moments like these, either onstage or off, Maloney said she still practices meditation and stays “connected to that community” in Barre, where she previously worked.

“Meditation for me has become very mobile,” she adds. “You know it used to be such a routine. But I don’t have any routine now because I’m always (dealing with) different hours, different places, different cities and whatever. So it almost becomes something that’s very kind of woven into my day. I’ll stop for a few minutes and do a little meditating. I’ll stop for a few minutes and do some conscious breaths, but it’s smaller increments throughout my day.”

That practice not only keeps her grounded, but she maintained, “I actually need it. I need it onstage, I need it on the road. I need that to be connected to my body, to the moment. I’ll get worn out if I’m not. … I need to pause, I need to take a breath. I need to stop because I’ll just run myself ragged.”

It also allows Maloney to stretch herself as an artist, drawing from her past to write personal songs that bring back upsetting memories.

“A lot of times you have to go through a breakdown to get to the breakthrough and I felt like a lot of the songs in this sort of era of my life were from that, going through a lot of hard stuff,” she said.

Asked if she could share an example, Maloney hesitated, then opened up.

“It ends up sounding so cliche when you talk about it,” said the only daughter among three children who were raised in the northern New Jersey town of Hamburg and watched her parents go through a divorce.

“For a songwriter, there’s just this well of stuff that’s still there,” she adds, “years and years and years later. … I was 6 or 7 and having [my] whole world fall apart. Yes, I’ve done the work and I’m not like struggling with it every day, but it shaped who I am. So I see it reflected in my relationships. In my relationships with friends, with my partner, with my family. Because it shaped who I am, I see it reflected in the present. That’s how something like a divorce happening when you’re 6 or 7 years old can inspire songs all these decades later.”

Maturity has its advantages, though, Maloney realized while finding lightheartedness at the end of the tunnel.

“Becoming an adult, I understand my parents more,” she said. “When you’re a kid, you’re just like … they’re heroes or they’re villains. And then they just become humans when you get older. And I think that’s another thing I’ve been going through a lot. Like in my late 20s, I’m just like, ‘Oh, I totally get it. They were winging it that whole time.’  … Plus my mom is a psychotherapist, so I tend to process and overanalyze everything anyway.” 

So with that in mind, Maloney keeps her chin up, whether she’s on tour as a headliner or supporting artists such as Willie Watson, Gary Clark Jr., or Rodrigo y Gabriela.

A relatively late bloomer as a musician — she started taking piano lessons in college before mom handed over her guitar in 2009 — Maloney has become more adventurous.

At the Folks Festival with touring members Brennan Leeds (guitars) and J.J. O’Connell (drums), she even put down her tenor guitar to go electric, playing a sky blue Fender Stratocaster on loan from Denver singer-songwriter Megan Burtt, “a real sweetheart” Maloney said she met through Zach Heckendorf, another Colorado-based musician.

Venturing west of the Mississippi River in recent years also has helped Maloney broaden her fan base while crossing paths with a wide range of entertainers.

She’s rubbed elbows with actor-comedian Cheech Marin and Heckendorf (at Boulder’s There with Care benefit in 2013) and Shakey Graves. (Go to the end of this article for the video of their bluesy collaboration on Grease‘s “You’re the One That I Want” at eTown, also in Boulder.)

Maloney’s Denver-based 7S Management team has helped to make some of these connections possible, including the enlisting of Band of Horses‘ Bill Reynolds to produce Making Me Break in Nashville.

Reynolds, who encouraged Maloney to plug in for Making Me Break, played bass and guitar on the album, too. Other featured musicians included his Horses bandmate Tyler Ramsey, My Morning Jacket’s Carl Broemel and the talented dudes from Darlingside, who toured with Maloney in support of her Woodstock EP.

Possessing a voice as precious as Joni Mitchell’s on the wondrous and respectful cover of her folk hero’s timeless classic, Maloney caught the attention of Graham Nash, whose rocking version with Crosby, Stills, Nash & Young on 1970’s Deja Vu remains a golden oldie.

Also at the top of Maloney’s musical wish list: “I’ve always wanted to sing a duet with Thom Yorke from Radiohead. I’m just such a fan of his voice.”

That anything-is-possible dream is a far cry from 2009, when Maloney self-released the first of two albums. While still learning how to write songs, those initial years were “a total struggle” that led to a period of second guessing.

“I had quit my job and just went all-in,” she said during our 2013 phone interview. “And there were times where I felt like, ‘Am I crazy to do be doing this? Am I fooling myself? Do I just need to go get a job that I hate?’ So there were times I felt sort of the desperation of that.”

Yet giving up wasn’t an option. “I’ve never had a Plan B,” Maloney added. “It’s always been in my mind that this is what I have to do.”

With sharp, versatile vocal prowess, Maloney can shift seamlessly from the stylings of Mitchell on “Flutter” to Ella era jazz (“Great Imposter”) to inspirational pop (“Oh Hope, My Tired Friend”) as quickly as it takes to shuffle a playlist. Though her sonic sensibilities differ substantially from the country-folk twang of Nashville’s Lera Lynn, they’ve taken similar career paths.

The primary difference? Producer T Bone Burnett recruited Lynn to write and record songs for the True Detective soundtrack, which led to a short but memorable recurring role for her in Season 2 of the HBO series. If fate picked Lynn to receive such a major break, Maloney doesn’t hesitate to wish her well. “I think it’s nice when an artist can be doing it for a few years and then start to have that kind of success or spotlight,” said Maloney, who plays Swallow Hill Music‘s Daniels Hall in Denver on Oct. 24 two weeks after Lynn. “I think it means that they’ll be around longer. They just won’t be a flash in the pan.”

That way of thinking should keep Maloney humming along the long and winding road. As long as her fuel supply remains, she’ll know when it’s time to turn on the afterburners.