Today we’d like to introduce you to Jessica Winship.
Hi Jessica, please kick things off for us with an introduction to yourself and your story.
Though I didn’t fully enter the modeling and dance industries until about four years after moving to Miami, I honestly feel like my story began the moment I arrived here. During those first few years, I built relationships and connections that would eventually shape the opportunities and career path I have today.
Around the time I landed my first post-college job, I became connected to Miami’s yacht and nightlife scene, which unexpectedly introduced me to creatives across fashion, dance, and entertainment.
A few months after that season of my life came to an end, one of the girls I had met on the boats invited me to an event. I thought it sounded fun, so I decided to stop by. As it turned out, swimwear designer Joyce Wang was there, and they had actually invited me to walk in one of her shows as a model. I had no idea that was what I was showing up for and honestly felt completely unprepared.
After that experience, I realized modeling, something I had always dreamed about, was actually within reach. From there, I started saying yes to every opportunity I could just to see where it might lead. Since then, it has opened the door to brand shoots, runway shows, New York Fashion Week, and even competing in two pageants.
My dance journey began much earlier in Dallas, my hometown. Growing up, I did dance and cheerleading recreationally, though never at a competitive level. At the time, my biggest dream was becoming a Dallas Cowboys Cheerleader.
When I moved to Miami, that dream evolved into wanting to audition for the Miami Dolphins Cheerleaders. I ended up getting cut in the semifinals and felt incredibly behind compared to many of the girls who had been training since early childhood. I auditioned again the following year, only to have similar results.
For a while, I almost let those experiences close the door on dance completely. But around that same time, I received my first modeling opportunity, and it completely shifted my perspective. I told myself that if modeling, something I had also once seen as out of reach, was possible for me, then maybe my dance dreams were too.
That mindset pushed me to train in styles I had never even heard of growing up and opened my eyes to dance from a much broader cultural and artistic perspective. Over time, my goals shifted from making a pro team to pursuing commercial and industry-focused training instead, which I realized was what I truly wanted all along.
Now, I feel incredibly grateful to be learning from and training with people who are deeply immersed in the industry. One of the biggest opportunities for me was receiving a work-study position at a local studio, where I was able to train constantly while networking with choreographers from around the world who came through for tours and jobs.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I have never experienced anything as competitive as the modeling and dance industries. One is largely based on appearance, while the other is based on both appearance and talent. Being surrounded by that level of competition can definitely take a toll on your confidence and mental health.
Although both industries are known for being highly competitive, I think the biggest challenge I’ve faced has been with myself. Since I started modeling at 23 and began training in commercial dance around 24, I often struggled with feeling behind compared to others who had been doing it much longer.
Over time, I realized how much of it is a mental game. I truly believe that if an opportunity is meant for you, it will present itself when you are ready for it, regardless of who you’re up against. The idea of being “too old” is also rooted in such an outdated mindset. I have friends in their 30s landing some of their biggest modeling jobs, and know dancers still touring professionally well into their 30s.
Of course, comparison can still creep in. Sometimes I’ll see dancers I look up to posting about turning 20 and catch myself thinking, “Wow, I really am old.” But I’ve learned that constantly comparing yourself to others is one of the fastest ways to lose confidence in your own path. I think the most important thing is staying focused on yourself, maintaining a positive mindset, and continuing to show up consistently. Everyone’s timeline looks different, and success doesn’t have an expiration date.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
The three main things I do are modeling, dancing, and graphic design, and I think each one has strengthened the others in ways I never expected. Dance has helped me move and pose more naturally while modeling. Modeling has helped me become more confident performing and being seen while dancing. Graphic design has pushed me to think more creatively and outside the box, which has even influenced the way I approach choreography and visual storytelling.
It’s been really interesting seeing how all three worlds overlap with one another. I recently started doing graphic design work for Orfun Magazine, which was co-founded by a model friend I met through the industry. The first issue actually just came out, and I was really excited to finally see some of my spreads printed physically for the first time. One of the articles, “We Won’t Be Erased,” is definitely one of the designs I’m most proud of because of how much work it took to get to the final version. I also got to create a spread for Offset Crew, a dance group based in South Florida, which felt like a really cool full-circle moment since dance is such a huge part of my life as well.
As I’ve grown in each field, I’ve slowly started figuring out where I fit creatively. In the beginning, I said yes to almost every opportunity simply to gain experience and figure out what I genuinely connected with. Over time, certain strengths naturally started revealing themselves. Within graphic design, I’ve found that complex layouts like magazines and websites are my strong suit. In modeling, I tend to work most successfully within commercial, beauty, and hair campaigns. Within dance, I’ve established commercial heels as my strongest style, though I still admire and enjoy exploring many others.
At the same time, I never want to limit myself creatively or become too comfortable staying in one lane. Almost every opportunity I’ve received has come through random connections, unexpected conversations, or experiences I never originally planned for. I think shutting yourself off from certain opportunities because they don’t immediately seem beneficial can sometimes block you from the things that end up changing your life the most.
All in all, I think what sets me apart most within each field is my relentlessness. No matter how I’m feeling, what challenges I’m facing financially or emotionally, or how out of place I may sometimes feel, I continue showing up to the best of my ability. I think it’s very easy to let external circumstances affect your confidence or motivation, especially within creative industries that can feel incredibly unpredictable and competitive. But over time, I’ve learned that consistency, resilience, and genuinely loving what you do are what keep you moving forward.
Networking and finding a mentor can have such a positive impact on one’s life and career. Any advice?
Finding the right mentor can completely change the trajectory of your growth because they can help you learn lessons you may not discover on your own for years. At the same time, I think it’s important to pay attention to both what you’re learning and who you’re learning from. Is this person in a position you would want to be in? Do they align with the way you approach life and your goals?
I think those questions matter because the wrong mentor can sometimes do more harm than having no mentor at all. Some people operate from a place of tough love, while others lead with softness and encouragement. Neither approach is necessarily wrong, but not every dynamic works for every person.
I once had a mentor whose personality and approach were very different from mine, which eventually created tension and led to the relationship falling apart. There were a lot of factors involved, but I think much of it came down to differences in communication, especially surrounding constructive criticism, as well as different beliefs about what could realistically be accomplished starting later in the industry.
Now, I have a mentor whose personality and work ethic align much more closely with my own, and he has become one of the most positive influences in my life. Since meeting him, the growth I’ve experienced not only within modeling and dance, but also within myself, has been exponential.
On top of that, I think it’s important to have mentors in different areas of your life, and it’s completely okay to have more than one. They also don’t necessarily have to know they are your mentor. Sometimes mentorship simply comes from observing the way someone carries themselves, approaches their work, or handles challenges in life.
As far as networking goes, the best thing you can do is consistently show up in spaces that genuinely make sense for you and treat every person with the same level of respect, regardless of their status or where they are in their journey. You never know who someone is, who they know, or what opportunities can come from a simple interaction.
Within every industry, there’s often an unspoken hierarchy that influences the way people treat one another. My current mentor, who works with dancers at levels far above mine, once told me he remembered me walking into a class and saying hi to every single person in the room, regardless of whether they were beginners or currently on tour. At the time, I didn’t think much of it because I genuinely knew all of them from working the front desk at the dance studio for so long. But to him, it spoke to my character, and he remembered it more than a year later.
Contact Info:
- Website: https://www.instagram.com/designsby.jessica
- Instagram: https://www.instagram.com/jessicaawinship
Image Credits
Image 1 (Personal): Stanislav Kozub, Image 2: Jesse Warner, Image 3: BP Dre (@bpdrephotography), Image 4: @redlightphotos, Image 5: N/A, Image 6: Anton Guzman (@antonguzmanportraits)
