We’re excited to introduce you to the always interesting and insightful Ashley Jordan. We hope you’ll enjoy our conversation with Ashley below.
Ashley, thanks for joining us, excited to have you contributing your stories and insights. When did you first know you wanted to pursue a creative/artistic path professionally?
I’ve known since I was very young, probably around age 11, that I wanted to pursue my career as an artist and musician. I’m sure that sounds like a very “dreamer/head in the clouds” type of statement to most, but to other creatives like me…when you know, you just know. I was perhaps a little too intense about it, but I don’t really know any other way. I’m all in or I’m all out, as they say. Music helped me get through some pretty unimaginable times growing up and being in the public school system. I think being so sure of my passion, purpose, and goals turned off other kids my age because they couldn’t understand it (or me). I’ll admit I’m a decently quirky person as well so I’m sure that didn’t help! One day on a whim, I decided to enter to perform at my 6th grade talent show, without my family’s prior knowledge. I secretly rehearsed and sang all the time but was very, very shy about it with my family, so I never really let on what I was up to. I finally told my mom and dad that I was going to be in the show and I’m pretty sure I recall my dad saying …”What are you going to do…hoola hoop?” haha….because at this point they really didn’t know! I performed the day of the show and remember looking out into the crowd to see the very shocked looks on their faces as I sang. That was truly a fun memory. The next day, the local paper printed front page news with the headline “NEXT TEEN IDOL?” with a close-up photo of me singing on stage for the talent show! I guess that’s probably when things started to take off for me in pursuing music!
After that point, I was always off working on my music in some way or another: performing, writing, recording, traveling, etc. I started to street perform in Boston around the age of 12 so by the time I was 13, I believe I had begun to professionally pursue my music career. I loved to street perform wherever people would listen to me – and Harvard Square in Cambridge was one of my main areas (as well as in the subways). I also made great money as a street performer, believe it or not! From there, that love and passion just grew and grew – I was traveling all over the state and country playing shows for captivated audiences. Being able to share my stories and original music with strangers wasn’t scary to me because I felt very much at home. I grew up watching and listening to my late grandfather play and sing his traditional country music, and thus country music still pulls at the strings of my heart. I have very nostalgic memories there, as my grandpa definitely passed down that love and overwhelming emotion I feel when I play and hear certain types of music. It’s difficult to fully put that into words here.

Ashley, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
When I was a child, school and traditional learning was so difficult for me. I was the proverbial square peg in a round hole… never felt like I fit in and I struggled on a daily basis. I was identified as having “leaning disabilities”- namely ADHD and a specific learning issue called “dyscalculia”. With dyscalculia – numbers and math are like a foreign language that can’t be interpreted. Numbers made no sense, time was a mystery… it was very difficult. Though I excelled at language/reading and creative endeavors, everything else was a struggle. In all, my learning difficulties played a huge impact on my life and my self esteem.
The one thing that did make sense to me was music. I discovered this secret talent but kept it to myself until the day at age 11 when I stepped out on a stage and shared my voice and realized the impact I could make. I immediately wanted to learn to play the guitar, then began to write songs from the heart – and proved early on that I knew exactly what I wanted to be doing. After street performing and going to open mics for years as a pre-teen, I graduated to recording several albums and performing on all sorts of stages and venues.
Music was a healer for me, but it also separated me from my peers. Growing up in a community where there really wasn’t an outlet for music made me seek alternative locations so I moved on from my peers and did my own thing. The problem with that is- teens can be cruel and don’t necessarily support those who don’t fit the norm or do what everyone else is doing. I paid a high price for being different – and my teen years were pretty brutal. But I survived because I had a way to vent (music!) and I just wrote songs to carry me through the darkness.
My early music was very emotional and true to who I was as a person. But as I found my way through the music community, I began to have a bit of an identity crisis. I don’t know if all musicians experience this- but for me there came a time that I believed I needed to make changes in what I was doing so I could be more mainstreamed. Hit more audiences – I don’t know…. Maybe I was trying to fit in again. Translation: I was playing more covers, building a mainstreamed band, creating an image that wasn’t authentically me. In time, this lack of authenticity and burnout was brutal. It wasn’t what I wanted at all.
Only when I let myself regroup and find my way back to the authentic me was I able to find my voice again. I moved to Nashville and started over from scratch in a strange new land (lol). It was the scariest and best thing ever. Just me and my guitar. Lots of heartfelt songwriting and lots of letting go and starting anew.
We’d love to hear a story of resilience from your journey.
I built my music, band, shows, professional music career in Massachusetts for many, many years. It would have been a very safe option at the time to just maintain that and continue on at my home base where I was comfortable and had experienced such great momentum, success, and milestones (which I never could have dreamed I could reach). But there was that little voice in my head that could envision more. I think an important part of developing as a person and as an artist especially, is learning to be comfortable with shaking things up, finding new inspirations, reaching for new heights and finding new goals to chase. So, I pushed all my fears aside, and with the help of my new husband, we packed up everything we owned into cardboard boxes and moved to Nashville a year and a half ago. We left all our family and friends, connections and relationships behind. Personally, I had no idea what I would do next – and I knew very few people and had zero representation. It was a definite leap of faith and I can’t tell you how many tears were shed. I’m proud of myself for it because although it’s a very scary feeling, there is something super freeing about it. I guess I’m doing what I always set out to do.
It feels daunting at times, growth isn’t pretty, it’s mostly what I would describe as uncomfortable and in some cases awkward and lonely too. I have found that mental toughness is key, and man it took me a lot to get to a place where I could embody that. One of the hardest parts about growth is that our brains seem to want us to stay in the safe zone, for obvious reasons. So you spend a lot of time fighting against that feeling, fighting to free yourself from that doubt, struggling to believe in yourself no matter the trials and tribulations along the way.
What’s the most rewarding aspect of being a creative in your experience?
I think for me, the most rewarding part about being an artist is being able to tap into the part of my Neurodivergent brain that really knows how to do its job – if that makes sense? Music always triggers the part of my brain that feels connected, that feels confident, excited, reassured, smooth – like a road you’ve driven on since you were a young kid and you recognize every single bend and turn. For some reason I’m always happy to feel that connection, to live it and see it, to experience it again and again. It’s almost like a really powerful deja-vu that hits you when you least expect it. For me, being an artist and performing my music feels like I’m coming home to my truest self, and I can be fully myself there. This happens on the good and bad days – and trust me there are bad days every now and again! But I always come back to that feeling of being at home in the music and all the memories and joy that lives there with me.
My added reward is that my personal connection to my music then allows me to more deeply connect with my listeners. I think that when I’m in this “zone” of being true to myself with everything “clicking” or happening naturally – then I truly hit some kind of sweet spot that resonates with my listeners as well.
Contact Info:
- Website: https://www.AshleyJordanMusic.com
- Instagram: https://www.instagram.com/ashleyjmusic/
- Facebook: https://www.facebook.com/AshleyJordanMusic/
- Youtube: https://www.youtube.com/ashleyjordanmusic
- Other: Spotify: https://open.spotify.com/artist/7wxOVBmNgYIPgIplnxGgQO?si=Yap_htxaTHSTVpnRn8YjzA
Image Credits
2nd (close up)-indoor shot, by Tommy Colbert Photography: https://tommycolbert.com/

