Conversations with Jessica Holman

Today we’d like to introduce you to Jessica Holman

Jessica, we appreciate you taking the time to share your story with us today. Where does your story begin?
I started my career working at PR agencies fresh out of college. This was great for learning the ins and outs of storytelling and personal branding. After a while, I couldn’t shake the feeling that I wanted to do something a little bit different – something that really made an impact, even on a personal level.

As a slightly lost twenty-something, I was fortunate enough to book a one way plane ticket out of Nashville to figure out what I truly wanted to do in life. That time away gave me a lot of perspective (and some pretty cool photos!).

I realized that I’ve always loved capturing moments and telling stories, but doing so through a camera lens felt like the perfect mix of creativity and purpose. Since then, I’ve been building my photography business from the ground up. It hasn’t always been easy, but I wouldn’t trade it for anything. I’m excited to see where this adventure takes me next!

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Leaving a full-time job with benefits to jump into self-employment was honestly terrifying. There was no safety net, no steady paycheck, and definitely no handbook on how to make it all work. From finding new clients to figuring out the finances, building a business no matter the size takes trial and error.

There were times when I seriously questioned if I’d made the right choice, especially during the slower months when bookings were scarce – but the transition has pushed me out of my comfort zone in the best way!

It’s been a rollercoaster, but each challenge has made me more resilient and even more passionate about what I do. I wouldn’t change a thing about the journey, bumps and all!

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
I started out in graduation portraiture, which always makes me laugh because I’ve never really loved being in front of the camera myself. That’s exactly what drew me to it, knowing how vulnerable it can feel. I wanted to help others feel beautiful and confident in their own skin. There’s nothing more rewarding than showing someone a photo of themselves and seeing their face light up.

Right now, I’m in the process of transitioning to something I’m really excited about: destination engagements, elopements and micro-weddings. I love the intimacy and authenticity of these moments. Capturing love stories in meaningful places feels like the perfect evolution of my work.

Personally, I’m proud of my focus on making people feel comfortable and confident, no matter how camera-shy they might be. I strive to create an experience where my clients can just be themselves and I can’t wait to see where this new journey into destination photography leads!

We love surprises, fun facts and unexpected stories. Is there something you can share that might surprise us?
Something surprising that most people don’t know about my brand is that I struggle with posting online even though it’s such a big part of running a photography business! You’d think capturing beautiful moments would make it easy, but I’m my own worst critic. I often overthink captions or wonder if a post is “good enough,” which can lead to a lot of second-guessing (and more drafts than I’d like to admit).

It’s a work in progress, but I’ve learned to let go of perfectionism and just share more authentically. I remind myself that the most important thing is connecting with people and telling real stories, even if it’s not perfectly curated.

Contact Info:

• Website: https://www.jessicaannephoto.com/
• Instagram: @jessholman_photo