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In CO+nversation: Andrea Maddox

If you look at the day-to-day of Andrea Maddox, you’d see a portrait of someone whose life is saturated with and built around music.

She started learning piano in early childhood and has been writing and performing music for as long as she can remember. 

Today she’s a singer and songwriter who fronts several bands and also teaches piano and voice to about 30 students per week. During the pandemic, she reignited her passion for musical theater and produced a summer music camp for kids, which culminated with the production of an original musical. What started as a lark (and, she jokes, a way to keep her kids occupied) has now been running for three seasons – in August, the group finished up a production of Madame Clementine’s Extraordinaire at Rosekill Art Farm in August.

Photo credit: Noel McGrath

Andrea plays in many bands, but her main squeeze is the five-piece Country/Americana group Andrea Maddox and the Hey Y’alls, who also played at the 2022 O+ Festival. Even though she’d been to the festival many times as an attendee (and a fixture of the opening night parade), now as an alumnus, she found an even deeper connection to community and care. 

“It was so much fun…You walk into the clinic and everyone is just like, ‘How can I help you? What do you need?’ That was great,” she says. “It just felt really special. One of my bandmates went to the dentist for the first time in years and was like, ‘Oh my god, that was amazing’.” 

She says that receiving care in the clinic, sharing meals with other festival participants, and getting to see other performers offered a truly unique experience.

“It was so nice to see fellow musicians I’ve been playing with for years performing and attending. My entire family came and we listened to all kinds of music,” she says. “It was so nice to be part of a really caring community and feel all that love – to get the love as a performer and go and see all these other musicians doing the same thing. It just had this really warm, wonderful feeling.”

Andrea knows well the push-and-pull between making a career as an artist and making ends meet, and it’s taken her a lot of trial and error to get to a place where she can sustain herself – spiritually and financially – as an artist. 

“For musicians and artists, you’re constantly having to have another job to pay for healthcare or food or rent,” she says. “Many times in my life I’ve had to quit just trying to gig and sort of do the 9-5 so I could get health insurance and actually go to a doctor or a dentist instead of just going to a clinic.”

She says those years oscillating back and forth between gigging and working a series of “regular” full-time jobs was a constant game of trade-offs. On the one hand, there was more consistent income and health insurance; she recalls one job where, once her health benefits kicked in, she spent an entire year catching up on all of the preventive care she couldn’t access before. 

On the other hand, she was miserable. 

“I felt like I was having to sacrifice the time that I could be working on my music to be drained at a day job,” she says.  “As a creative person, I feel like there’s always a choice: you can choose not to do the work, and then there are consequences…because you choose not to follow the thing that is deep inside you and crying to get out.”

For Andrea, sacrificing that creative time meant ignoring her heart’s calling, and taking away a crucial part of her own healing and coping process. Music – composing, playing, performing – gives her a way to work through her experiences and emotions and helps her find a way forward. Without that conduit, she says, her mental health suffers. 

Walking away from her steady job with benefits wasn’t easy, and she recognizes that it’s not always an option that’s available to everyone. But it was a bet on herself that she needed to make. 

“I think the older I get, the more confidence I have. And I think I also understand that we don’t have a lot of time – what we have is this time right now.”

Still, other factors, like relatively good health, improved access to care under the Affordable Care Act, and encouragement from mentors, helped her to take the leap to pursue music full-time – and keep taking it, every day. 

“I’ve had a lot of my mentors say things like, “You don’t have to do it, nobody has to do it. But it’s hard, and that’s why most people quit.’ And that voice has been in my head so much in my life because I thought, you know what? I can do hard things.”

Andrea Maddox and The Hey Y’alls recently finished their latest album, Long Drive Home, which you can stream on all the major services or hear live at their EP release show on Friday, December 15th, 2023 at The Colony in Woodstock, along with other O+ Alums The Kondrat Sisters and Yard Sale. Get your tix here. 

You can also find them online on Instagram, YouTube, and Bandcamp