We were lucky to catch up with Cary Pennington recently and have shared our conversation below.
Cary , looking forward to hearing all of your stories today. Are you able to earn a full-time living from your creative work? If so, can you walk us through your journey and how you made it happen?
Yes, I’ve been fortunate to earn a full-time living from my photography, but it’s definitely been a journey with a few twists along the way.
In 2005, I took the leap and left my 9–5 job to pursue photography full time as a wedding photographer. That first year, I actually tripled my salary — which was both exciting and a huge confirmation that I was on the right path and wished I had done it sooner. The years that followed showed steady growth as I continued to build my reputation and client base.
Then the 2008 recession hit, and by 2009 my business took a big hit. 2010 was all about rebuilding and making up for those losses, and over the next few years I gradually found my footing again. Just when things felt strong and steady, Covid came along and hit the reset button for many of us in the creative industry.
Coming out of Covid, I used that time to really refocus my direction. In 2020, I shifted away from weddings and started specializing in headshots and personal branding — and it’s been like a roller coaster heading back up ever since. That pivot not only reignited my passion, but it also created a much more consistent, balanced business model.
If I could have sped up the process, I’d say it would’ve been by learning to pivot sooner — adapting to market changes and trusting my instincts instead of waiting for things to stabilize. Every challenge taught me something though, and looking back, each season built the experience and resilience that shaped the business I have today.
Cary , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I’m a professional photographer based in Carlsbad, just north of San Diego, and I’ve been behind the camera professionally since 2005. What started as a creative passion quickly turned into a full-time career when I left my 9–5 job that same year to photograph weddings — and I actually tripled my salary in my first year. That early success showed me that photography wasn’t just something I loved; it was something I was meant to do.
Over the years, I’ve experienced the full ride of being a creative business owner — steady growth, economic recessions, rebuilding, and of course, the curveball of Covid. Each season shaped me in a new way and taught me how to adapt, stay grounded, and evolve my art.
In 2020, I made a big shift and stepped away from weddings to focus on headshots and personal branding photography. It’s been one of the best decisions I’ve made. I found a new sense of purpose in helping people show up confidently — whether it’s professionals who need strong, authentic headshots or entrepreneurs who want their brand images to truly tell their story.
What sets me apart is the way I approach photography — it’s not just about taking a flattering picture, it’s about capturing emotion, connection, and the feeling behind the image. My clients often tell me they were nervous before their session but ended up feeling comfortable, confident, and even enjoyed the process. I take pride in creating that kind of experience — one that feels personal, easygoing, and genuine.
I believe a great photo has the power to open doors — to new clients, opportunities, and confidence within yourself. That’s what I love most about what I do: helping people see themselves the way the world already sees them — strong, capable, and real.
How’d you build such a strong reputation within your market?
Honestly, I think what’s helped me build my reputation most is how personal I make the experience. From day one, I’ve treated every session like it’s more than just a job — it’s about connection, trust, and making people feel comfortable in front of the camera.
Word of mouth has been a huge part of it too. Clients can sense when you genuinely care, and that’s something you can’t fake. I always take the time to listen to what people need — whether that’s helping them feel confident during a headshot session or capturing the warmth and love in a family photo. When someone walks away saying, “That actually felt easy — and I love my photos,” that’s the best kind of marketing there is.
Consistency has also been key. I show up with the same care, professionalism, and positive energy for every client, no matter the size of the job. Over the years, that reliability — paired with images that really feel like them — is what’s helped me earn people’s trust and build a strong reputation in my market.
What do you think is the goal or mission that drives your creative journey?
Absolutely. At the heart of everything I do, my mission is to help people see themselves the way the world already sees them — confident, genuine, and full of life.
Photography, for me, has always been about more than just creating beautiful images. It’s about connection. I want my clients to feel something when they see their photos — to recognize their own strength, warmth, and authenticity.
Whether it’s a professional headshot that helps someone show up with confidence, or a family session that captures pure love and laughter, my goal is to preserve emotion in a way that feels real and timeless.
I’m driven by the idea that great photography doesn’t just show what you look like — it reflects who you are. If I can help someone feel proud of that reflection, then I’ve done my job.
Contact Info:
- Website: https://www.carypenningtonphotography.com
- Instagram: https://www.instagram.com/carypenningtonphotography
- Facebook: https://www.facebook.com/CaryPennington
- Linkedin: https://www.linkedin.com/in/carypennington/
- Twitter: https://www.twitter.com/carypennington
- Yelp: https://www.yelp.com/biz/cary-pennington-photography-carlsbad
- Other: https://www.pinterest.com/carypenningtonphotography
Image Credits
Cary Pennington Photography