The Curious Career of Amy Stroup


Eight year old Amy Stroup sat down at the piano bench, palms sweaty, nerves on high-alert. Four cross-looking judges sat nearby in hard chairs, hair pulled back in a tight buns, faces sporting thick glasses and even thicker frowns. Stroup’s heart began to beat fast, the words “just breathe,” echoing through her mind. She slid her fingers onto the keys and began to play.

Over twenty years later, Stroup, a singer-songwriter, performer, and designer, is still telling herself the same advice. “So many times people have [told me] ‘just breathe,’ but it never helped. Most of my life I’d been focusing on inhaling huge gulps of air versus that nice, long, slow release,” Stroup told me in our conversation, reflecting on an adventure experience she’d just had in Arizona, but also on her life as a performer. “Lately, a big take away for me that I’ve been applying to my life is that — yes, I am scared — but just breathing can do a lot.” 

Stroup refused to let her childhood experiences of stage fright at classical piano competitions stifle the spark inside of her — a spark of spunk, curiosity, and unrelenting creativity. She learned to manage her fears and discovered music to be a place to connect, not compete. These would be invaluable lessons to learn as Stroup’s future unfolded and music became part of her story.

* * *

Raised in cities that helped shape the career she’s chosen — Boston, MA, Florence, AL, and Memphis, TN — Stroup grew up in places where music was part of the local scene. The Cars, Bob Dylan and Etta James, and Elvis Presley called Boston, Florence, and Memphis home, respectively, and so did Stroup. It only makes sense that music would become a huge part of Stroup’s story, too. What also became a huge part of Stroup’s narrative was the role of change; her childhood included multiple moves and eight new schools. “It keeps on you on your toes,” Stroup said of her upbringing. 

Stroup is one of only a handful of people from her high school’s graduating class that didn’t stay in what she refers to as her hometown of Abilene, Texas. As graduation loomed and Stroup’s interest in songwriting grew, she decided it was time to move...again. “I remember watching CMT and hearing stories about how people wrote songs. There was a Loretta Lynn documentary and I was fascinated by it. I was interested in how people did what they did. I wanted to figure it out... I knew that I need to try this Nashville thing.”

It was almost nine years to the day that I was able to quit my side jobs and do music full time. I think we live in an instant gratification society that says: ‘Put me on the stage of American Idol and make me a huge celebrity right now!’
— Stroup, on patience in the music industry

Having grown up in music towns, it’s fitting that Stroup would settle in Music City. Shortly after moving there, she went to a Johnny Cash photography exhibit and had an encounter with Marty Stuart, an American country music singer-songwriter and Grand Ol’ Opry member. When Stroup told Stuart her plans to become a songwriter too, he asked her a question that would be daunting to anyone chasing a dream. Stuart, who began his music career when he was thirteen, asked Stroup: “Do you have nine years in you?

The question carried weight — Stuart won a Grammy in 1993, twenty-seven years after he first began pursuing music professionally. If anyone knows the patience a career in Nashville requires, it’s Marty Stuart. Stroup reflected on the encounter:

“[Marty] was right. He was saying to me: ‘Be patient. A good career doesn't happen overnight.’ It was almost nine years to the day that I was able to quit my side jobs and do music full time. I think we live in an instant gratification society that says: ‘Put me on the stage of American Idol and make me a huge celebrity right now!’ From what I have seen in industry peers, the quicker the rise the quicker the decline. Slow and steady is a good pace to build a sustainable career and let your soul catch up to the excitement of success and the maturity it needs to lead well.”

Stroup had plenty of instances in her early twenties where these principles were challenged. During college, she was introduced by some of her bandmates to Nathan Chapman, a country music producer who was working with another young artist named Taylor Swift. Chapman went on to produce Taylor Swift, Fearless, Speak Now, Red and 1989. Every album went platinum, but you already knew that. To some, this might sound like the missed opportunity of a lifetime — a reason for Stroup to have great regret. But Stroup sees it differently.

Stroup climbs one rung at a time. At the start of her career, she collected emails from clipboard sign-up sheet at a gig to build her fan base, and worked on small graphic design projects her sister would send her to gain practical branding experience. In these more seasoned years, Stroup focuses on the relationships she has with people, and emphasizes the value of just showing up. This method of life and business can be risky; sometimes you show up and magic happens, other times you flop. But Stroup’s risks over the years have paid off. As Woody Allen is credited in saying, “Eighty percent of success in just showing up.”

If Stroup wouldn’t have shown up — to tiny gigs, to that Johnny Cash photography exhibit where she met Marty Stuart — Stroup wouldn’t be where she is today. She wouldn’t be writing songs and launching brands with her current business partner and creative collaborator, Mary Hooper. She wouldn’t be running her company Milkglass Creative, and working with clients like Andrew Belle and Chris Stapleton. Neither would she have joined the music collective Ten out of Tenn and met her touring and recording partner, Trent Dabbs, whom she performs with in the band “Sugar and the Hi-Lows.” She might not even be singing still at all. By just showing up, Stroup’s life and career progressed to what it is today: a busy mix of music, creativity, and collaboration.

With her next LP Helen of Memphis, due out later this year, Stroup is showing that a career like hers, a sound like hers, a life like hers — is a process. Marty Stuart would be proud; Stroup stuck with it. So while Stroup didn’t become the next Taylor Swift, she did become a person unafraid to share her story and sing her song. 

* * *

Like Connor Dwyer, our first Dreams Go Live featured artist, Stroup is not in this business so that others will think she’s cool. Sometimes her days are spent writing with colleagues of Kendrick Lamar or providing creative direction for a Miranda Lambert music video, but other days, she’s occupied with the small stuff. Accounting and taking out the trash — the less glamorous, but required tasks. But none of these things hold Stroup back — the high or the low moments.

Strip away the stories from Stroup’s past, take away the impressive connections, turn the noise down and crank the volume up. You’ll hear something special, something that make you stop and say:

“Damn. That’s cool.”

Client work from Milkglass Creative

Stroup, particularly on her latest singles (Magic and This Is My Time), is the epitome of cool. A vintage, soulful sound laid over modern, emotionally-charged lyrics. Pulsing rhythms that make you tap your feet. As Stroup sings on a recent track, this is her brand of cool, this is her sound, this is her time.

Tell the whole world / This story is alive / And this is my time  / Gonna jump a mile high / Yea I’m feeling strong / Gotta get that word out.

Stroup didn’t always sound like this — her earlier albums boast a gentler, more folksy sound. While her talent is clear on those tracks, I think Stroup is right in saying that this is her time. Stroup agreed: “When your sound stays the same, it could be a sign of a lack of growth. I’m constantly pushing my boundaries with trying to write better lyrics and melodies… and for me pushing through certain sound ceilings. I love surprising people with freshness and them saying, ‘I didn’t think your next song would sound like that...and I like it!’”

I’m constantly pushing my boundaries with trying to write better lyrics and melodies…I love surprising people with freshness.
— Stroup, on the evolution of her sound

* * *

With a long list of impressive accomplishments in songwriting, performing, and branding, Stroup emphasized that though it may look like she has “made it,” she has not “arrived.”

You can open for Grammy award-winners Kings of Leon and Chris Stapleton on New Year’s Eve and still feel like that nervous little girl with sweaty palms at the piano bench in Florence, Alabama. You can perform in front of thousands at a sold out show at Royal Albert Hall in London and arrive at home and just need to have a good cry. You can release a slick music video wearing outfits that are as a fly as ever, and on the eve of its release "feel like you're about to run through Nissan Stadium naked."


Vulnerability, nerves, and risk are all part of Stroup’s career, and she has learned that this kind of life takes hard work. Stroup called the pursuit of success “an invisible ladder,” defining the climb as something which requires discernment to know when enough really is enough. As Stroup’s climbs on, she’s learned what it takes to keep her career (and life) going: curiosity and connection.

When I asked Stroup what was peaking her curiosity as-of-late, it didn’t take her long to answer. 

“I’ve been learning a lot about emotional intelligence recently. I love studying how to be a sharper, more kind and empathetic person and being a healthier human for myself and friends.  I love learning about how people overcome and survive all the things we as humans go through. Being human is remarkable! It’s easy to want to settle, give up, give in, just do the drugs and become complacent. It’s a hell of a lot harder to face reality and take responsibility for yourself and be a good steward of fellow humans.”

It’s no coincidence that Stroup’s curiosity compelled her to explore a topic focused on connection. It seems that Stroup’s curiosity is not a tool to influence and impress others, but a means to better express and empathize with others.

“I think disconnection is the source of all our great problems with ourselves and the world. I’m at my lowest when I’m on the road for a long time and feel disconnected from myself, friends and family,” Stroup told me, replying to my own curiosity in what truths she abides by. “Try to stay connected. Connect with your self, your God, your friends and family. As an artist, staying connected to your true self gives you a shelter in which to create from. It’s something to continually nourish and grow.”

Try to stay connected. Connect with your self, your God, your friends and family. As an artist, staying connected to your true self gives you a shelter in which to create from. It’s something to continually nourish and grow.
— Amy Stroup

When you look at her career, Stroup practices what she preaches. I asked her to describe what a normal day is like for her; the components she shared all involved connection. “I spend most days touching base with my team at our Milkglass headquarters...cowrite with an inspiring writer…finish with dinner with some good people.” In between, Stroup said she goes for trail runs, practices yoga, attends church community group, or stops for a cup of coffee—her times to refuel, reset, and connect with herself.

Both the loud parts of life...(her work with Milkglass Creative, playing to huge crowds with her band or as a solo artist) and the quiet parts of life…(having a good co-writing session with her friend Drew, making a connection with a fan) enable Stroup to take her own advice and stay connected. She’s chasing after her mantra, a quote from Madeleine L'Engle. “We can either contribute chaos to the cosmos, or cosmos to the chaos,” wrote L’Engle. “That statement guides much of what I do,” said Stroup. “As an artist I have a great responsibility to bring light and order, or else I will contribute more noise.” 

Amy Stroup

As Stroup seeks to contribute light and not noise, she will do so by doing what she’s always done: by showing up and being herself. Her past reveals that she’s not the next Taylor Swift, and her present proves that she does not need to be. Stroup isn’t afraid to push boundaries and pursue success patiently. She looks fear in the face and tells it to take a seat, and places importance in the small moments. She keeps climbing, keeps going, keeps breathing.

Stroup may be a decade deep into her career, but something tells me she’s just getting started.

So Everybody can clap along / Gonna write my story / Yea I’m singing my song.


Follow along with the rest of Amy’s story on Instagram, Twitter, and Facebook, or explore her website. Listen to her solo music on iTunes or Spotify, and be sure to check out Sugar and the Hi-Lows while you’re at it. Thanks for following along with us!