We were lucky to catch up with Jeannie Caryn recently and have shared our conversation below.
Alright, Jeannie thanks for taking the time to share your stories and insights with us today. Let’s jump back to the first dollar you earned as a creative? What can you share with us about how it happened?
I didn’t grow up playing music — Unfortunately, I had been given a guitar at 14, but since I wanted to play piano, I only fiddled with it briefly. Silly kid! But later in life, the guitar found me when I needed it most.
During my divorce, when my kids were just 4 and 6, the house would suddenly become extremely quiet when they were spending time with their dad. That silence could have been heavy, but instead, I filled it with music. I picked up a guitar and started teaching myself how to play — learning songs I loved, figuring out chords by ear, writing my own songs, and playing for hours with no audience but myself.
For a long time, playing music was just mine. A way through stress, anxiety, and grief.
Then one night, a friend convinced me to go to an open mic.
There were maybe three or four people in the room — but to me, it felt electric. For the first time, I wasn’t just playing for me… I was sharing something. I sat on a bar stool with a microphone and my guitar and performed for about an hour since there were no other players that night.
I was hooked.
The very next night, I pushed myself even further and went to a packed open mic at Hemmingway’s on Marietta Square. The stage was narrow but raised high above the crowd, and the room was full. I remember feeling more confident than I should but having taught high school for fifteen years by this time, I wasn’t as nervous as I had imagined I’d be. I closed my eyes and just started playing.
Song after song, the energy kept building. I was playing my favorite covers, and they seemed to be everyone’s favorites too. People were cheering, singing along… and I could feel something shifting in real time.
Then, right in the middle of it, the bar owner walked up, looked up at me, slapped a $20 bill at my feet and said, “I want to hire you for a gig.” The crowd roared!
That moment changed everything.
That $20 wasn’t just money — it was permission. Proof that something I had turned to for healing could become something I shared with the world. It made me feel like finally, I was where I belonged.
I used that $20 to buy a large metallic sun for my garden, and I still have it today. Every time I see it, I’m reminded of that night — the moment I stepped up to the big stage and on to a path I had only dreamed of but never planned.
Nearly two decades later, that path has grown into a full music career — performing, writing, and creating spaces for others to step into their own light. Through my company, MUSIC SPEAKS, I now get to offer that same first moment — that same courage, connection, and spark — to other artists finding their voice.
And it all started with a quiet house… and a $20 bill
Jeannie, 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?
What sets me apart is that everything I create comes from a deeply personal place — whether it’s my original music, my writing, or the experiences I build for others.
At my core, I’m a storyteller. My original songs are rooted in real life — love, loss, resilience, and growth — and I bring that same heart into my children’s book, THE ADVENTURES OF HUGO THE ROUND PUG (Amazon), which was inspired by one of my own dogs. That project, in particular, represents a different side of my creativity — playful, heartfelt, and centered around connection in a completely different way. The goal with that project is didactic- teaching people about pet safety and nutrition – there are five books in the series with Book 2 coming out later this year.
I’m most proud that I didn’t take a traditional path into any of this. I started later, built everything from the ground up, and allowed my creative life to evolve naturally — which is why it’s so multifaceted today.
I’ve been performing live music since 2010, building a music career that has grown organically over time. What started as playing covers evolved performing my own original songs — each one reflecting lived experiences and moments that shaped me. Over the years, I’ve performed across a wide range of venues and settings, developing not just as a musician, but as a performer who connects deeply with an audience. That evolution — from learning in private to sharing original work publicly — is something I carry with me every time I step on stage.
From there, MUSIC SPEAKS grew as an extension of who I am.
It’s not just a brand — it’s a community. It’s where music becomes something people don’t just watch, but step into. Through open mics, songwriter showcases, karaoke, and live events, I’ve created spaces where people at all levels — from first timers to seasoned performers — can show up, be supported, and find their voice.
What I offer now spans both performance and experience: original and cover performances (solo, duo, or full band), live music events, curated showcases, and creative platforms for other artists to grow. But no matter the format, the goal is always the same — connection.
What I want people to know about my work is that it’s not about fitting into one lane. It’s about creating meaningful, memorable experiences — whether that’s through a song, a story, or a stage.
Because at the end of the day, music — and creativity as a whole — isn’t just something we consume. It’s something that brings us back to ourselves and to each other.
Is there a particular goal or mission driving your creative journey?
With MUSIC SPEAKS, my mission is to create spaces where people feel safe to express themselves, connect with others, and share their voices.
Music has always helped me in my life when I needed healing, and it gave me a way to process, grow, and move forward. Because of that, I don’t take creativity lightly — I’ve experienced firsthand how powerful it can be. That’s what drives everything I do.
Through my original music, I aim to tell honest stories that people can see themselves in — songs that make someone feel understood, or maybe even a little less alone.
Through my book, THE ADVENTURES OF HUGO THE ROUND PUG (Amazon), I get to bring joy, imagination, and heart to a different audience, creating connection in a lighter, more playful way.
And through MUSIC SPEAKS, that mission expands even further. It’s about breaking down the invisible barriers that keep people from stepping onto a stage or sharing their voice. I want to make music feel accessible — not just for professionals, but for anyone who feels that pull to express themselves.
If there’s one thing driving my journey with MUSIC SPEAKS, it’s this: creating moments where people feel seen, heard, and inspired to take that next step — whether that’s writing a song, singing for the first time, or simply believing they have something worth sharing.
Because when one person finds their voice, it has a ripple effect far beyond that moment — and I get to be part of that.
Recently I started a Substack to showcase the performers that grace our stages – THE MUSIC SPEAKS WEEKLY – Follow us to learn more about our events and our players!
Is there something you think non-creatives will struggle to understand about your journey as a creative?
I think one of the biggest things non-creatives may not fully understand is that a creative path rarely looks linear — and it’s almost never “stable” in the traditional sense.
From the outside, it can look like a series of disconnected projects or ideas. But from the inside, it’s actually very intentional. Every song, every event, every new direction is part of an evolving process of growth, expression, and connection.
There’s also this assumption that if you’re not doing one thing full-time, you’re somehow not fully committed. But for many creatives — myself included — building something meaningful often means wearing multiple hats. I’m a musician, a writer, a performer, a host, a teacher, a business owner, and a community builder… and all of those roles feed each other.
Another piece people don’t always see is the emotional investment. Creative work isn’t just output — it’s personal. You’re sharing parts of yourself, your story, your perspective… and that takes vulnerability and resilience, especially when you’re building it from the ground up.
And finally, success in a creative life doesn’t always look the way people expect. It’s not just about fame or big moments — it’s in the smaller ones too. It’s in watching someone sing for the first time at one of my events, or hearing that a song I’ve written connected with someone in a way they needed.
If there’s any insight I can offer, it’s this: a creative journey is less about chasing a single destination and more about staying open, consistent, and willing to grow. It may not always make sense from the outside — but from within, it’s incredibly purposeful.
Contact Info:
- Website: https://www.jeanniecaryn.com
- Instagram: @jeanniecaryn
- Facebook: https://www.facebook.com/jeannie.caryn
- Linkedin: https://www.linkedin.com/in/jcaryn
- Twitter: @jeanniecaryn
- Youtube: https://www.youtube.com/channel/UCxsYuryvDBVydNV9YpG81RA
- Other: https://linktr.ee/Jeanniecaryn
Image Credits
Larry Mitchell
Keith Lawson
Christine Calvin