Today we’d like to introduce you to Jaclyn May.
Hi Jaclyn, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I’m originally from Virginia, and early in my career I made a defining decision: I sold nearly everything I owned and moved halfway across the country to pursue a role in medical device sales. It was a leap of faith, but one that taught me invaluable lessons about resilience, adaptability, and building something from the ground up. In that world, I learned how to manage relationships, drive results, lead with integrity, and operate at a high level in competitive, high-pressure environments.
Photography began during that season as a creative outlet—something that allowed me to slow down and connect with people in a more personal way. What started organically quickly gained momentum as friends, families, and eventually clients sought out not just images, but an experience and a story they could hold onto. I realized that the same skills that made me successful in sales—strategy, branding, communication, and trust—were the very tools needed to build a meaningful creative business.
I approached photography with an entrepreneurial mindset from day one, intentionally building a brand that values connection, excellence, and experience. Today, my photography business serves families, high school seniors, and brands who care deeply about storytelling and legacy. Beyond photography, I’ve been able to leverage my background to build and grow digital platforms, create strategic partnerships, and mentor others who are pursuing both creative and professional success.
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?
Not at all—and I don’t think it’s supposed to be.
There were seasons of real uncertainty, especially early on. Building something of my own meant navigating wearing every hat, and constantly proving my value in a saturated industry. Starting over in a new state without an established network forced me to build relationships from scratch and earn trust one client at a time.
One of the biggest challenges was learning how to scale without losing the heart of why I started. Growth brings pressure—more demand, higher expectations, and the temptation to say yes to everything. I had to learn when to pivot, when to say no, and how to build systems that supported both excellence and sustainability.
There were also personal seasons that stretched me deeply—balancing ambition with family, especially as a mom of 2 little ones (2.5 and 10 months old), navigating change, and trusting myself during moments when the path forward wasn’t clear. Those challenges forced me to refine my priorities, strengthen my boundaries, and define success on my own terms.
Looking back, none of the struggle was wasted. Each obstacle sharpened my leadership, clarified my values, and ultimately shaped a business that’s more resilient, intentional, and aligned. The road wasn’t smooth—but it was necessary.
Appreciate you sharing that. What else should we know about what you do?
I specialize in experience-driven photography for high school seniors and families, with a focus on connection, confidence, and storytelling. My work is known for vibrant, polished imagery paired with a highly personalized client experience that makes people feel seen and celebrated.
What sets me apart is my relationship-first approach. I don’t view photography as a one-time transaction—I build long-term connections, and many of my clients return year after year and refer others. I’m especially proud of the impact beyond the images, including mentoring young women through my senior programs and creating experiences that build confidence during pivotal seasons of life.
My background in leadership and sales allows me to blend creative vision with strong business strategy, resulting in a brand that feels elevated, intentional, and deeply personal.
We’d love to hear about how you think about risk taking?
I view risk as a necessary part of growth, but not something taken blindly. The biggest risk I took was selling nearly everything I owned and moving halfway across the country to pursue a career in medical device sales without guarantees. That decision required betting on my work ethic and ability to adapt, and it became the foundation for everything that followed.
Entrepreneurship brought a different kind of risk—building a business while working full time, investing time and resources before results were visible, and eventually trusting myself enough to go all in on something I built from the ground up. For me, risk isn’t about chasing uncertainty; it’s about being willing to step forward when the path isn’t fully clear but the purpose is.
I think the most meaningful risks are calculated and values-driven. When your decisions align with who you are and where you’re going, risk becomes less about fear and more about forward momentum.
Contact Info:
- Website: https://jaclynmay.com
- Instagram: https://www.instagram.com/jaclynmayphotos/
- Facebook: https://www.facebook.com/jaclynmayphotos/
Image Credits
Jaclyn May Photography
