We recently had the chance to connect with Sydney Stephan and have shared our conversation below.
Good morning Sydney, it’s such a great way to kick off the day – I think our readers will love hearing your stories, experiences and about how you think about life and work. Let’s jump right in? What is a normal day like for you right now?
A day in my life normally varies day by day, keeping my world exciting!!
Today, I have the day off! I’m home doing admin and prep on my computer in the morning. Around 12, I’ll probably shower and run a few errands. Tonight, I’m attending my first opening night on Broadway! My best friend Jae West invited me to see the opening of Marjorie Prime.
Tomorrow, I have 2 exciting gigs in a row. I’m doing dueling pianos for Felix and Fingers at a holiday party in Morristown, NJ from 11am-3pm. Felix and Fingers is the premiere dueling piano company for private events and parties around the country. Then, I’m playing one of my resident gigs, Bo Peep Cocktail Lounge, from 8:30pm-11pm. Bo Peep was recently ranked the #1 bar in all of midtown Manhattan!
Then the next day is very different as well, as I’m producing a show at The Green Room 42. My company Productions by Stephan has a signature concert almost every month, and that show is set to be fantastic! For every show I produce, I run a tech rehearsal and then at the show, I ensure the artist and the venue have a fabulous, smooth evening!
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Sydney Stephan and I’m an artist & producer in New York City! I have an entertainment company called Productions by Stephan that brings live entertainment all over the city and nearby regions. Everything I do is very women-centered, and performer focused. I like to give performers in NYC great experiences, that are paid when possible, and provide safe and fun spaces for performers to be artists!
I’m also a performer, I sing and play piano all over the city, averaging about 7 gigs/week. I am based in Manhattan, but occasionally perform for Howl at the Moon all over the world. Howl at the Moon is a live music company based in Chicago, that serves entertainment to Norwegian Cruise Line and Armed Forces Entertainment. Howl at the Moon has allowed me to travel to 7+ countries just this year, and I have more contracts signed with them for 2026. My biggest solo concert of my career is coming up this January at 54 Below. 54 Below is a famous Broadway supper club in NYC, located beneath the former Studio 54, known as “Broadway’s Living Room,” offering live cabaret, dining, and drinks, a hub for theatre stars and fans. On the 6th of January at 9:30, my show ‘Songbirds of the 70s’ premieres! There will be a full band + guest singers, Sabina Demidovich & Eric Byers. The set list includes artists like Carole King, Fleetwood Mac, Janis Joplin, Roberta Flack, Linda Ronstadt – all women of the 70’s (my favorite decade of music!!)
Tickets are on sale now, and they are going fast! You can purchase tickets here: https://54below.my.salesforce-sites.com/ticket/#/instances/a0FUY000007eo6v2AA
Amazing, so let’s take a moment to go back in time. Who saw you clearly before you could see yourself?
I am so lucky to have gained incredible knowledge and influence from a lot of mentors who have always believed in me. From choir directors and vocal coaches to school teachers and family, I’ve been fortunate to have a lot of support around me. My parents have always had my back and encouraged me to pursue everything I dreamed of. My mom would drive me from dance class to choir rehearsal, eating dinner in the back seat of the car while I changed out of ballet tights and reviewed my Alto 1 line! My parents still support me wholeheartedly, and both make trips to NYC at least twice a year- sometimes more.
I’m especially grateful to the adults and mentors in my life that aren’t artists – the people that know the importance of the arts and have showed me endless support since day one! My family from around the country that livestream my shows, my friends that buy tickets to everything I am involved in, even when life in NYC is expensive and hectic, and my partner who takes the time to help and support me everyday of the week. I’m so grateful to my community!
If you could say one kind thing to your younger self, what would it be?
I’d tell her to keep taking piano lessons!!
I was always been a go-getter, and have always created opportunities for myself. I do wish I had double majored, or gotten a minor in something business related. Now that I’m a business owner, and self-employed, having a business degree would maybe give me a little more confidence!
I would absolutely give her a lot of love. I would tell her how talented she is, and that she should trust in that. Some people grew up being told they were a prodigy- imagine the confidence someone has if they were told that! My parents are realists and they knew I had talent but they also knew that a lot of the industry is networking, money, longevity, and luck.
But most importantly, I would love to tell my younger self that she can do it. I’d get to tell her that she is going to premiere her new solo show at 54 below, where she’ll share a night at Broadway’s Living Room with Matthew Morrison! While she’s 26 years old! That’s crazy!
Sure, so let’s go deeper into your values and how you think. Is the public version of you the real you?
Yes, absolutely!
I’m very authentic and real with people and audiences. I’m not going to be fake with people, that’s not fun. I think audiences appreciate my sense of humor, how comfortable I am on stage, and how genuinely I enjoy performing for them.
I do think that the persona that so many artists share on social media isn’t always 100% genuine. We have to promote shows, events, releases, and many other things constantly- and it doesn’t always feel natural to me. Promoting sometimes feels like the most unreal thing about the public image that I have, as it feels awkward to promote things as frequently as I have to. But, the public version of me is very real.
Speaking of needing to shamelessly promote… I was recently nominated for 8 BroadwayWorld awards. 2 nominations were in the Piano Bar Entertainer category, I think this is a testament to who I am for audiences and how beloved my shows are around New York City. Voting is open until December 31st! You can vote at this link: https://www.broadwayworld.com/cabaret/awards/ And while I’m at it, you can catch me performing all around New York City at Bo Peep Cocktail Lounge, The Ivy Room, Fraunces Tavern, Prohibition, The Russian Samovar, Peck Slip Social, and more. My schedule is on my instagram- I would love to see you at a gig soon!
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. Are you doing what you were born to do—or what you were told to do?
Definitely what I was born to do! No question there.
However I am grateful that in my case, I haven’t had a lot of people tell me that I should be doing things differently. I am meant to be an artist and a producer, and I believe that with every piece of me! Everyday I wake up grateful to spend my time doing what I love. I’m even more grateful that I can make a living while doing that as well. This month marks 12 months of officially being self employed. Being a self-employed artist in NYC is not easy, some days are amazing and some days are frustrating, but I’m so thankful to have the opportunity to do so.
Thank you so much for having me and taking the time to share my story. If readers want to learn more, they can follow me on Instagram and TikTok: @sydstephan. And follow my company: @productionsbystephan.
Contact Info:
- Website: https://sydneystephan.com
- Instagram: https://www.instagram.com/sydstephan/?hl=en
- Other: https://www.tiktok.com/@sydstephan?lang=en
Image Credits
David Rauch-Bautista
LoneAce Design
VickyJ Visuals
Annie Brown
Amanda K Photography
Jake Carter
so if you or someone you know deserves recognition please let us know here.
