Meet Winterlyn Stebner

We caught up with the brilliant and insightful Winterlyn Stebner a few weeks ago and have shared our conversation below.

Hi Winterlyn, thanks for sharing your insights with our community today. Part of your success, no doubt, is due to your work ethic and so we’d love if you could open up about where you got your work ethic from?

I honestly believe I was born with my work ethic. It’s just part of who I am. But it was really shaped and strengthened by the women who raised me. I come from a line of incredibly strong, independent women who worked for everything they had. Nothing was ever handed to them, and they still managed to accomplish so much without formal education or prior experience in their fields. Just pure drive and determination.

Watching my mother, especially as a single parent, showed me what real perseverance looks like. She never let sickness, exhaustion, or even physical pain stop her from providing for us. Seeing that kind of resilience up close taught me that hard work isn’t optional—it’s a way of life. I carry that same mindset into everything I do, whether it’s my business, my art, or the way I show up for my clients.

Thanks, so before we move on maybe you can share a bit more about yourself?

I’m a Chicago-based wedding photographer and the owner of Winterlyn Photography. For more than eleven years, I’ve had the honor of documenting love stories across Chicago and the Midwest. Capturing everything from intimate elopements to full wedding weekends. My approach has always been about more than just taking beautiful photos; it’s about creating an experience where my couples feel seen, valued, and completely at ease in front of the camera.

What I find most exciting about what I do is the connection. Every couple brings a new story, a different energy, and I get to translate that into timeless, artful imagery that becomes part of their legacy. There’s something so powerful about freezing those fleeting moments. The tearful glances, the laughter, the quiet in-betweens—and knowing they’ll be cherished for generations.

What makes my brand special is how personal the experience is. From the first consultation to the final gallery delivery, everything is customized for each couple. I only take on a limited number of weddings per season so I can give every client the attention and care they deserve. My work is driven by storytelling, emotion, and an editorial eye that blends elegance with authenticity.

Professionally, I’m in an exciting season of growth. I’ve expanded my collections to include an assistant on every wedding day to ensure an even smoother, more elevated client experience. I’m also developing new branded video content and behind-the-scenes features that highlight what it’s like to work with my team. My goal is to continue evolving my brand into one that not only represents luxury and craftsmanship but also heart because at the core of everything I do is the belief that love stories deserve to be told beautifully and truthfully.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

Looking back, I’d say the three qualities that have had the biggest impact on my journey are resilience, connection, and consistency.

Resilience has been everything. Building a business from the ground up, especially in a creative field, means hearing “no” more times than you can count. It means late nights, slow seasons, and moments of doubt. But every setback taught me something and pushed me to grow stronger. Not just as a photographer, but as a businesswoman and a person. My advice for anyone starting out is: don’t be afraid of the hard days. They shape you in ways success never could.

Connection is at the heart of my work. Photography, to me, has always been about people. Their stories, their emotions, their energy. The more I connect with my couples, the more meaningful and authentic the images become. For those early in their journey, focus on listening and understanding before you pick up your camera or start your craft. Your relationships will become the foundation of everything you build.

And finally, consistency. It’s not about being perfect—it’s about showing up every day with purpose. Whether that’s refining your skills, marketing your brand, or providing an incredible experience for your clients, consistency builds trust and momentum. My advice: do one small thing every day that moves you forward. Over time, that’s what creates longevity and success.

Who is your ideal client or what sort of characteristics would make someone an ideal client for you?

My ideal clients are couples who value art, emotion, and experience as much as the final photographs. They’re intentional about every part of their wedding day and care deeply about the story being told, not just how things look, but how they feel.

They trust my creative process and understand that when they hire me, they’re not just hiring someone to take pictures; they’re inviting an artist to document one of the most meaningful days of their lives. My couples appreciate timeless, editorial imagery but also want their gallery to reflect who they truly are. The laughter, the tears, the quiet in-between moments.

They’re often busy professionals who care about quality and craftsmanship. They respect good communication, love collaborating on vision and details, and believe in surrounding themselves with vendors who bring calm, positive energy to the day. Above all, they value connection. They’re kind, grounded, and excited to celebrate not just a wedding but the beginning of their marriage.

Those are my people. They trust me fully, they let me guide them through the process, and together we create something that feels personal, effortless, and unforgettable.

Contact Info:

Image Credits

Winterlyn Photography

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