We caught up with the brilliant and insightful Orel Chollette a few weeks ago and have shared our conversation below.
Alright, Orel thanks for taking the time to share your stories and insights with us today. Earning a full time living from one’s creative career can be incredibly difficult. Have you been able to do so and if so, can you share some of the key parts of your journey and any important advice or lessons that might help creatives who haven’t been able to yet?
After graduating from college in 2017, and once my family had flown back to Virginia, reality hit me hard. Unlike many of my peers who were applying for jobs in the industry, I chose to pursue freelancing under my own brand. I remember staring at my schedule, seeing nothing but blank weeks and the inevitable “rent due” on the 1st. That pressure really pushed me to figure this out. Every day, I worked on something different to market myself in Chicago. I created flyers, sent cold emails, DMed people to collaborate with, and read books on freelancing.
Growing a freelance business is not that easy. To me it’s all about doing an excellent job for one person, and they will tell others. This principle applies both online and offline. You want to be the go-to person for what you do. After working with a lot of people, I slowly built a reputation for my work. More and more people started sharing my work, leading to a steady stream of bookings.
Beyond the fun creative work, I had to learn how to run a business—a challenge where many people struggle. If you don’t know how to confidently name your price and back it up, you risk being seen as unprofessional, or worse, the “cheap guy.” The numbers, contracts, and the admin work aren’t very fun but it’s so important. Doing good work, being fun to be around, and understanding how to run as a business led to me being able to support myself as a full-time artist.
However, if I could do anything differently, it would be to pitch myself to brands I wanted to work with. I have a bad habit of just taking the projects that come to me. I’m terrible at going out and securing the work I’d prefer to do. I believe that if I had been more confident in doing that, I would have advanced further earlier in my career.
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
I am a full-time filmmaker and photographer, dedicated to elevating brands through my visuals. I work with many artists, creating music videos, cover art, and promotional content. I love taking a variety of ideas and giving them a life through visuals. I’m even more fulfilled when clients seek out my unique style and nothing else. There’s no better feeling than someone wanting to collaborate with you in the way you want to create art.
Recently, I reached the 10-year mark in this career, and I’m proud when I look back on my journey. At this point, I’ve developed a new passion for teaching others how to do what I did. I learned many lessons the hard way throughout my freelancing career. It’s incredibly fulfilling to share my knowledge, helping others accelerate their growth and avoid the mistakes I made. I’ve turned to YouTube and workshops to reach those just starting out.
What do you find most rewarding about being a creative?
A question I like to ask myself and others is, “What would you do if you didn’t need to earn money?” So many of our life choices revolve around the quest for money and survival. But what would we do with our time if that wasn’t a concern? If I rewind my adult life and go back to my childhood, I can often find the answer.
For me, when I got home from school, I would teach myself how to create videos on my laptop. I’d make stop-motion videos, gaming content, little music videos, and spec commercials. This is what I did in my free time. It was always what I would rather be doing. I didn’t make any money from it, didn’t have to show anyone, and didn’t seek outside validation. I created visuals simply because it brought me joy and confidence.
Now, as a full-time filmmaker and photographer, I feel like I’m keeping my childhood dreams alive. I know that I would still be doing this if I didn’t need to earn money anymore. It’s challenging at times, but at the end of the day, there’s nothing else I’d rather do with my life.
Well actually being in a rock band would be cool. But I’ll take pics for now.
Can you tell us about a time you’ve had to pivot?
After freelancing in Chicago for almost eight years, I started to hit a wall. I was making great money, it felt like the whole city knew me, and I was one of the top go-to people for visuals. I had reached a place I had worked so hard to get to, but something was missing. I was losing my passion for art.
One day, I looked back at the work I used to create when I first picked up a camera. Im talking about work from the first two years. Even though I knew less about the craft back then, my work was more creative and ambitious than it had been recently. I felt disappointed in myself. The money and the reputation weren’t enough to satisfy me as an artist—I wanted to create work I was genuinely proud of. I realized I had been shooting on autopilot, taking on projects that didn’t even interest me. I remember being on one of the many shoots that I dreaded and telling myself, ” This is not the reason you picked up a camera”.
The pandemic was a very important opportunity for me to sit and rethink my world. I decided it was time for a change, so I left Chicago to start fresh in a new city. In 2021, I moved to Los Angeles. The city initially intimidated me a lot. I knew there was so much talent out here and I was new trying to break in. I also heard a lot of negative stories from others who had moved there and left. Despite, I wanted to create my own story in LA. When I arrived, I immediately started studying new styles, reaching out to new people, and slowly started to create work that reflected my ideas.
As a freelancer, you simply don’t survive unless a lot of people know you and admire your work. I felt immense pressure to build my name and make money in a place that costs far more than Chicago. It was stressful and still can be, but I feel the drive I had been missing for so many years. I remember studying my craft and trying new things like I did when I started. I was watching my favorite movies and consuming a LOT on pinterest to spark inspiration. I fell in love with my camera again and the desire to share my work with new people. Now, I feel far more creative and excited about my work. I’ve gotten a good rhythm in LA by being on various sets and projects. This move to LA truly saved my passion for visuals and I’m so glad I did it.
Contact Info:
- Website: https://www.chollette.com
- Instagram: @chollette
- Youtube: https://www.youtube.com/@Chollette
Image Credits
All photos by Orel Chollette @Chollette