Connect
To Top

An Inspired Chat with Sarah Bailey

Sarah Bailey shared their story and experiences with us recently and you can find our conversation below.

Sarah, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What are you most proud of building — that nobody sees?
What I’m most proud of building that no one sees is my future empire—powered by student loan debt and a flat iron. I’m currently putting myself through cosmetology school full-time, which means I spend my days learning how to make other people look fabulous while running on caffeine and prayer. Most people see me telling jokes on stage, but behind the scenes, I’m juggling mannequins, textbooks, and trying not to glue my fingers together during lash practice. It’s a lot—but I’m working hard to turn my passion for beauty (and sarcasm) into something really meaningful.

Can you briefly introduce yourself and share what makes you or your brand unique?
Hey there! I’m a stand-up comedian who’s been telling jokes professionally for 8 years—and collecting life experience like it’s a competitive sport. I spent 15 years in musical theatre (so yes, I can hit a high note while crying dramatically), and for the past 7 years, I’ve also worked as an adult entertainer at a club. Somewhere along the way, I proudly coined the name “The Stripper Comic”—because why pick one hustle when you can absolutely crush both?! Basically, if there’s a stage and questionable lighting, I’ve probably performed on it.
What makes my comedy unique is that I bring my story to the mic—no filters, no shame, and definitely no shortage of material. I talk about the parts of womanhood and work that people don’t usually hear onstage, and I do it with humor, heart, and just the right amount of glitter. I care deeply about women’s rights, breaking stigma, and making people laugh so hard they forget they were ever uncomfortable.
My brand is all about honesty, empowerment, and saying the things other people are afraid to say—loudly, into a microphone, usually while wearing lashes.

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. Who taught you the most about work?
My mom taught me everything I know about work ethic—mainly by out-working everyone around her and still managing to look good doing it. She’s my role model, the strongest woman I know, and I watched her build an insurance empire from scratch… which, as a kid, I assumed meant she was just really obsessed with paperwork. But now I realize she was running a business, raising a family, and somehow never losing a fight with a printer.
She taught me that success doesn’t come from luck—it comes from showing up, putting in the work, and not crying until you get home. I definitely got my hustle from her. I just apply it in slightly different ways—like with punchlines and pasties.

What have been the defining wounds of your life—and how have you healed them?
One of the defining wounds of my life was losing my best friend, Nathan, who helped me gain the confidence for the first five minutes of my stand-up routine. We’d been best friends since I was 16, so losing him was like someone hitting pause on the soundtrack of my life—and not the good part where the beat drops.
It’s been incredibly hard, but comedy has been my way of healing. Every time I get on stage, I feel like I’m having a conversation with him, turning grief into punchlines. Sometimes it’s messy and awkward—kind of like grief itself—but laughter has helped me peel back the layers and keep moving forward, one joke at a time.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. What are the biggest lies your industry tells itself?
The biggest lie the adult entertainment industry tells itself—and that the world loves to believe—is that we’re just twirling around for fun with zero ambition. Like, sure, we’re definitely not working toward anything serious—except maybe that elusive perfect split or the world record for fastest dollar bill folding.
But here’s the truth: most of us are juggling school, kids, side hustles—you name it. Me? I’m putting myself through cosmetology school full-time while shaking it on stage. Spoiler alert: multitasking is a real skill in this industry.
So no, we’re not just “partying for a paycheck.” We’re grinding hard, building futures, and hustling harder than anyone expects—often in six-inch heels. The myth that this is just a fun hobby? Please! We’re ninjas in 8in stilettos— snapping necks and cashing checks.

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. Could you give everything your best, even if no one ever praised you for it?
Could I give everything my best, even if no one ever praised me? Absolutely. Honestly, I don’t need a parade or a standing ovation—because the only person I’m really competing with is myself. And let me tell you, I’m a ruthless opponent. I’m constantly trying to outdo yesterday’s version of me… which usually just means fewer awkward moments and better punchlines. Praise is great, but beating my own high score? That’s the real win.

Contact Info:

Suggest a Story: VoyageJacksonville is built on recommendations from the community; it’s how we uncover hidden gems, so if you or someone you know deserves recognition please let us know here.

Leave a Reply

Your email address will not be published. Required fields are marked *

More in Local Stories