Meet Bailey Roberts | Photographer

We had the good fortune of connecting with Bailey Roberts and we’ve shared our conversation below.

Hi Bailey, we’d love to hear about how you approach risk and risk-taking
At some point, I realized that in order to live the life I’d chosen and built, I’d need to get comfortable within the sweet spot of risk; a state of being that is characterized by an alchemy of authenticity, hard work, consistency, and faith. By “comfortable,” I mean extremely uncomfortable all the time.

I moved to New York from Maui at 18, worked in the photo industry there, and jumped back to Hawaii a decade later to renovate a house that had been empty for 25 years. I didn’t know what lay on the other side of these choices; I just felt an itch, that I had outgrown who I was and that I needed to lean into something that felt truer to who I was becoming. I think I’m in a similar moment now—I moved to LA from Maui two years ago, knowing I was ready for the next step. I feel like I’m still mid-air on that leap, and I can’t quite see where I’m going to land.

Each day, I really try to follow my intuition, whether that leads me to a photo shoot, a road trip, a meeting, a meditation, or a jump in the ocean. I choose to believe that it’s leading me where I’m meant to go, even if my vision of that endpoint isn’t always so clear. The majority of my time is spent in a liminal space, trying to soak up the present because I can’t be sure of what’s ahead, despite any hard work or successes I’ve had thus far. Every day is a blank slate, and I think that has influenced my process a lot. So much of my work has been based on being open to life.

To be honest with you, it’s a pretty scary space to exist in day to day. People romanticize this career and the lifestyle that comes along with it, but it takes a lot of courage. Imagine quitting your job and every day for the rest of your life inventing a game plan to get a bunch of strangers to trust you and collaborate with you. No boss, no guidebook—just a lot of risk. There are many high points, but you’ve got to work for them and be patient and relentless in your pursuit. No guarantees.

That said, I believe that the discomfort that comes with risk is a sign that you’re headed in the right direction. It’s almost as though I follow that feeling. Don’t get me wrong; it’s hard, very hard, but I think that everything valuable I’ve ever built in my life is the byproduct of being willing to take a leap. In one way or another, my entire life has been shaped by my willingness to swim in the deep end and sit with the unknown.

Let’s talk shop? Tell us more about your career, what can you share with our community?
When I’m making imagery, I tend to pour my full self into my work, I can’t help it, I get fully immersed. Whether in personal projects or on commercial sets, I’m always hunting for this amorphous flow state where everyone feels super connected and reality suspends for a second. I feel like there is something special about photography this way, specifically photography of people, you can touch this deep through line of humanity through images. When you really capture it, I think that’s one of the powers of photography, it catalyzes an empathetic response in the mind that can expand our worldview. I try to prioritize this awareness as I’m making pictures and I imagine it’s one of the things that drew me to the medium in the first place. Whatever the task at hand is, we’re in it, together, fully committed to the life of what we’re making. It doesn’t always happen, but that’s the goal.

Photography gave me a convenient excuse to live curiously, to connect with people, and to celebrate them. I wanted to nourish an insatiable curiosity towards life, its simple elements, the things that slow down time; the direction of light at a certain time of day in the town you were raised, the attention of eye contact, a loud unbridled laugh. This seeking is an ongoing practice and I’m always engaged in a dance of being able to connect with that drive.

At the beginning of my time in the industry, I was living in New York and assisting. It was a really valuable education but it was also a reality check. I love that city, but it’s not who I am. I like to walk around barefoot and move slowly and deliberately. I’ve never been one to keep up with the Joneses so the whole who’s who of the fashion and photo world was really divergent to the smiley warmth that I had grown up with back home. I needed to connect with the parts of me that were innate and authentic, I wasn’t finding that in the scene in New York. I was really struggling there emotionally, I could feel that there was a missing piece. It’s strange because when I made that jump back to Hawaii, things really shifted for me. I started booking my own clients, shooting more work for myself, and transitioning away from assisting completely. It’s almost like that move put me in better alignment with who I was and what I was supposed to be doing.

I spent a solid five years traveling from Hawaii to LA and New York, shooting in all three places and frankly having a blast. It felt great, I was living my truth. During that era, I spent most of my time shooting outdoors, facing the elements, and shooting with water housing out in the middle of the ocean. I truly integrated my physicality into my work; I integrated a whole other level of myself into my practice as a photographer. I wasn’t shooting for major fashion houses or debuting solo shows but I was free diving and jumping off sailboats and photographing some of the top ocean athletes in the world. There were moments where it was totally crazy but looking back on that time I really reflect on what a special moment of becoming that was.

I’m very connected to my home in Hawaii and when I was in New York trying to “make it” I was really denying a critical part of myself. When I invited that part back in, something started to click. That chapter helped me get clear on my voice, my perspective, and what I have to offer. I carry that with me everywhere I go now and even though I’m based in LA, that Maui girl is still at the core of me. I’m really proud of that. I think we each have our own version of that authenticity and I think it’s a very important element of aligning with success. If you’re faking it or doing something that’s unnatural for you, you’ll burn out. This career is a marathon so you gotta really align with the things that will allow you to ride the highs and lows.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
This is a tricky question for me because even though I’ve been here for two years, I still feel pretty fresh to LA. I wanna be the guest on someone else’s version of this week-long trip.

That said, my best friend is my favorite surf buddy so I’d probably pick up a sandwich and snacks at Bay Cities and drive up to Leo Carillo to spend a day surfing and hanging at the beach. We’d go hike and swim at Malibu Creek state park then go visit our friend who lives in Point Dume for a sunset beach walk. I’d take her to Found Oyster to have Pet Nat and Oysters followed up by dinner at Saffy’s. I’d make a day of the Rose Bowl, York Street and dinner at Joy, Shrimp Wontons are a must. I’d rally a crew of friends for a sunset fire at Dockweiler. Maybe we’d day trip up to Ojai, swim in Matilija canyon river, hang by the pool at the Capri Hotel and eat dinner at Rory’s place. We’d definitely have to spend a morning being California girlies at a farmers market and maybe finish our day with a breath work class at Open. I realize I’m skipping over entire Los Angeles universes but I’m truly still getting my bearings and am open to suggestions.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
This is an interesting follow-up question after contemplating the idea of risk. While I’m out there in the ether, riding the undulation of uncertainty, you better believe there was a solid cohort of folks ready to catch me when the downside hit a little too hard.

Most notably, my parents and family have always had my back. I was lucky that way, having a mom, dad, step-dad, and sister who encouraged me to follow my passions, celebrated every win, and helped me shake off the losses. They were open to me being an artist. They never tried to talk me out of it. I think my mom deserves a special thank you because she tends to be the one I call with tears, spiraling anxiety, worries, or just plain boredom. She’s an exceptionally patient and loving woman.

I also have an incredible boyfriend who is a steady and solid force in my life. He carries an atmosphere of calm regardless of what happens and really helps me tackle hurdles pragmatically with optimism. I’m very thankful for his influence on my life.

I have been supported by some pretty incredible mentors: Carrie Levy, Keith Kandell, and Pamela Hanson. Each of these people offered extraordinary guidance and support, providing perspective on this hurricane of an industry, and boosting me up in moments when I probably got pretty close to throwing in the towel. Mentors are huge; their lives intersect with yours, and they model for you a way of moving through the world. They show you what’s possible and if you’re lucky they’ll give you a glimpse of the hurdles of humanness they stumbled over on their path. I cherish the people in my life who have sat in this role.

Lastly, I’ve got some incredible friends; people who have been through adversity and aren’t afraid to walk through it with you. They all believe in me more than I believe in myself, and they have brought so much richness to my life. You know who you are, and I’m thankful for you.

Website: www.baileyrebeccaroberts.com

Instagram: @baileyrebeccaroberts

Linkedin: https://www.linkedin.com/in/bailey-roberts-a66a6515/

Image Credits
All images © 2023 Bailey Rebecca Roberts