We recently connected with Sydney Stephan and have shared our conversation below.

Sydney, thanks for taking the time to share your stories with us today We’d love to hear the backstory behind a risk you’ve taken – whether big or small, walk us through what it was like and how it ultimately turned out.

I was lucky enough to spend a few years traveling with Holland America Line. I was the female piano vocalist that was entrusted with opening their new flagship, and traveled to over 50 countries with them. This gig became very comfortable and I knew what I was doing! I was saving money, traveling, and got to meet a lot of amazing people.
But, we all know that growth doesn’t come from staying where you are comfortable.
I knew it was time to move on and see what I could accomplish by immersing myself in the scene of New York City. I was scared! New York is expensive, big, and intimidating. The most successful talented people in the world are based in New York City. Was I ready to be in the same scene as them?

In July of 2024, I decided I was.

I “retired” at the age of 25 with these particular cruise gigs. I put my passport in my nightstand and decided to give New York a proper go. I had a side hustle job and would take any gigs that came my way.

By September, I had my first residency. At Bo Peep Cocktail Bar & Lounge- Skip Brevis gave me Monday & Tuesday nights, I was over the moon. Sure enough, I was given my second residency at Fraunces Tavern. Fraunces Tavern is one of the most historical restaurants and building in the whole city- how cool!
By December, my schedule was full. I was able to quit my side hustle job and focus on gigs and whatever else I wanted to create.

Taking a leap of faith can be so scary- essentially starting a new job, but being self-employed and having to work hard for every single gig. It’s about showing up, believing in yourself, and being persistent. You can now find me playing regularly all over the city. There are days I miss traveling at times, but life gets so much fuller with routine, growth, and seeking higher things for yourself.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

My name is Sydney Stephan, and I’m a singer, actor, musician, producer, and writer based in New York City! I grew up in the potato state- Eagle, Idaho.
I was performing before I even started school- dance classes, piano lessons, and any musical my parents could find to put me in. I made my professional debut at age 14, at Starlight Mountain Theater in Garden Valley, Idaho. I was teenager #7 in the summer stock production of Footloose- but who cares, I was getting paid to do a musical?! All through growing up I sang in many choirs, and many choirs would give me the opportunity to arrange songs for my friends and I to sing. I would craft 4-5 songs together, and direct my friends in what they’re singing. I would play piano- and they would let me be in charge. We would perform these for audiences, Erica and Keith McCauley of Cantus Youth Choirs were very influential in recognizing my ability to lead and create work.

I continued to perform all over the Boise area, and at age 17 my mom found an audition in the newspaper. It was for Idaho Shakespeare Festival’s production of The Hunchback of Notre Dame. If you know this show, you know it has an ensemble AND a full choir to really fill out the music. I went to the audition that day and listened to people 15+ years older than me sing classical songs. I went in and sang my 32 bar cut of a contemporary musical theatre song. Tom Ford, sitting behind the table, asked me to join the choir for the production AND understudy one of the ensemble women. This was major for me.
This production was so influential to me- I was seeing Keri Rene Fuller (Six, Waitress, Cats) and Corey Mach (Merrily, & Juliet, Rent) do amazing work all summer. This set such a fire in me.

I went to the University of Utah and got my BFA in Musical Theatre. I graduated in 2021- in the height of the pandemic. My last 3 semesters were spent mostly online, but my professors did their absolute best to give us as much as they could. But imagine trying to learn performance skills over zoom… it’s tough!

As I was approaching my junior year, my program was missing a very important part of a BFA Musical Theatre program- the Agent Showcase. This gives graduating seniors the chance to sign with an agent, and be able to move to a city with the possibility of getting auditions. My school didn’t have this- and myself and my classmates, deserved this opportunity. I produced the first ever Agent Showcase for my graduating class. I raised over $10,000 with the help of my classmates, all while going to school during a pandemic. We used Shorey Walker and the Growing Studio to help with our showcase- we had almost no support from our school. The following year- the school gave funding to the senior showcase. While I was “producing” work for fun my whole life- this was the first project that I billed myself as a producer. Stepping back, this was a huge project and I took it on so confidently as a 21 year old.

Shorey Walker was so impressed with my work, that she took me on as her assistant. I started working for her and The Growing Studio, and I continued to help produce other showcases. It was such a skill I had- the organization, the savviness, but also the creativity, artistry, and sensitivity it takes.

Now, I am producing work in New York City constantly. I produced a solo Green Room 42 show in 2023, and have produced 2 exceptional concerts at 54 Below. I created a concert series called Sydney & Friends, we are creating FUN and safe music in bars around the city. I love to give people the chance to sing and show their talents and skills. I play solo a lot, and any chance I get to collaborate with people and learn from others- I take. 2025 will be all about my Decade by Decade Concert Series. This is a series I’m producing at Green Room 42, the first show is on January 15 at 9:30pm featuring the 1950’s! Tickets on sale now! It’s full of amazing singers, great 50’s music, and my great friend Jae Weit is hosting.
If you’re interested in booking a show, or performing in a show of mine, send me an email: [email protected]

I’m also participating in a 365 Song Challenge this year! I’m posting 1 minute of a song on Tik Tok and Instagram (hopefully) everyday of 2025. This will occasionally include collaboration with other artists, but it’s in effort to be creative for at least 30 minutes everyday.

Is there a particular goal or mission driving your creative journey?

I think my mission is driven by the few opportunities in the musical theatre industry. I love broadway, I love musical theatre, but it’s a really tough place to make a career. This industry is full of amazing, talented, kind, lovely people in my circle and there are people I’ve yet to meet that deserve to be showcased. I love CARVING space for talent, I love COLLABORATING, and I love DREAMING with people.
My friend Sabina Demidovich, is also a multi-hyphenate. She’s a writer, producer, actor, and singer. And she said something to me once, “why don’t we book ourselves?” Why don’t we!! And while I’m at it, why don’t I book people I love at the same time?
Collaboration is really where my soul soars, and I’m in control with how much collaboration I have in my weekly schedule.

How can we best help foster a strong, supportive environment for artists and creatives?

Supporting live entertainment is always what the ecosystem needs. Go see musicals, concerts, plays, gigs, etc.

Follow new artists on social media. Engage in their content on Tik Tok!! We’ve seen Tik Tok skyrocket so many artists in the last 3-4 years, and social media will continue to do this for artists. Liking, commenting, and following a creator on Tik Tok takes you no money and less than 1 minute, but it could be the step they needed to join the creator fund, or the numbers they are looking to promote to a manager, etc.

Contact Info:

• Website: https://sydneystephan.com
• Instagram: @sydstephan
• Other: @sydstephan on tik tok.

Image Credits

Songbird Studio
David Rauch-Bautista
Amanda Koslosky