We were lucky to catch up with Kaleb Jackson recently and have shared our conversation below.

Hi Kaleb, thanks for joining us today. Growth is exciting, but from what we’ve seen across thousands of conversations with entrepreneurs it’s also dangerous if costs aren’t watched closely – sometimes costs can grow out of control outpacing revenue growth and putting the viability of the entire business at risk. How have you managed to keep costs under control?

Due to the majority of my client base being comprised of performers who are seldom paid for their work–and when they are, it’s not a living wage–it is very important to me to maintain an aspect of affordability in my products. Often I find clients are more inclined to pay more for headshots the more expensive they are since that communicates a guarantee of quality, but I remember when I was unable to afford headshots and felt so discouraged by the insurmountable obstacle that was rising costs. That memory keeps me from raising prices, even if it’s not the smartest business move. As a photographer amidst the community that my client base is comprised of, I find my work to be an act of service in addition to a business. I never want my clients to feel the need to choose between a session with me and paying for their rent that month. 2024 has created an economy that makes it evermore difficult to afford being an artist, and if I can ease that conflict in any way, I will do so. I offer packages with the most affordable being $100 for one edited headshot, as most performers in my community only need one headshot anyway. To be completely transparent about finances, in that scenario it would take me at least three sessions to see profit after the cost of renting my studio, but it means so much to me when a client books a session with me that it’s quite difficult for me to logic charging more in today’s economic climate.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My dad is a gadget guy, I always saw him with a new gizmo he was fixated on. As a child, I remember him to always be the family’s resident photographer, never leaving home without his Olympus point and shoot in a trusty orange turtle shell zip up case. Whenever he left it unattended, I’d play around with it pretending to be him. When I was in high school, my father purchased a digital camera, a Canon EOS Rebel T5. He had so much excitement for his shiny new toy, but quickly realized technology had progressed too quickly for him to keep up. He mad me a promise that if I learned how to use and take care of the camera, that it was mine. Overjoyed, I accepted the challenge and spent the next week teaching myself all there was to know about photography and how to use this model. Being my father’s child, my camera became my plus 1, never leaving my side. I constantly asked my friends if I could shoot them, seeing the most pedestrian locations as an immaculate impromptu backdrop. College was no different and soon I realized that I was quite good at my new craft. Being an acting major, I started taking my friends’ headshots for fun and word got out pretty quickly about a headshot photographer on campus who didn’t charge anything for a decent product. I became the resident photographer on campus and my clients demanded that I start charging for my services. Due to my immense imposter syndrome, even the idea gave me so much guilt. Who was I to charge for headshots when I had no formal training, no studio and no equipment outside of my camera? After a while, I reluctantly gave in and started charging $100 for 10 headshots, unlimited wardrobe changes and as many locations as we could fit in under an hour. My business boomed, I was able to quit my campus job and just focus on portraiture and classes. Upon moving to Chicago I became immersed in the comedy scene. Improvising multiple nights a week, seeing countless shows and making beautiful friendships, it felt quite similar to college. Comedians became my first clients in the city and still today remain the bulk of my client base. I began to see an issue in the industry that did begin to frustrate me as a person who believes what I do is inherently a labor of service. Many of the headshots I saw of BIPOC clients in other photographers portfolios were just off. While the headshots from their white clients looked gorgeous, those of BIPOC clients had edited skin that looked overworked, lighting that was far too bright and made their clients look dull. Knowing that many of our first cameras were not made with People of Color in mind, as a Black person I know that care has to go into shooting BIPOC clients to counteract this design biases. Because of this, I take great care with how I set up all of my shots and especially those with clients of color. It’s important for me to do an intake of their undertones, light their afrotextured hair to make it pop and do my work in the editing room to make their skin look real and beautiful. It’s my pride that I am doing all I can to uplift performers of color with my work.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

I have definitely had to (and still do) unlearn the lesson that there is perfection in the creative process. Being self-taught, there is a constant nagging that I’m not doing my job right, but there is no correct way to make art. What further pushes this narrative is that people are paying for my services, so I have to get it right, but they booked with me because they’ve seen my portfolio and know the quality of my product. Some of the most satisfying shoots have been the times when I let go of a need to achieve perfection and just had fun with the creative dance the photography and the model engage with. Although headshots have more rigidity than creative portraiture, I’ve tried to invite that energy into my headshot sessions and it’s greatly aided my anxiety in the room.

For you, what’s the most rewarding aspect of being a creative?

I’m an interdisciplinary artist, so different disciplines have garnered different rewards. In the scope of photography, the most rewarding aspect is seeing a client’s reaction to a finished product. I grew up a person who had great insecurities in terms of my appearance, and remember the relief and joy I got from seeing a photo of myself where I looked…good. The most rewarding part of this process is seeing that feeling wash over my client. The phrase “I look like that?” is like music to my ears. As portraiture photographers, we have the gift to illuminate the beauty people hold but can’t see for themselves. The thought that my clients can march into an audition room bolstered with confidence in their headshot gives me immense fulfillment.

Contact Info:

• Website: https://kalebjackson.framer.website
• Instagram: @jacksograph