Life & Work with John Jennings

Today we’d like to introduce you to John Jennings.

Hi John, we’d love for you to start by introducing yourself. 
My name is John Jennings. I’m a photographer who has been working for the last several years based in Chicago. I had a very indirect path into photography. I had gone to school to pursue acting, and during my 3rd year of the program, I bought a used DSLR from a friend to take with me on a study abroad trip. I began obsessing over taking photos, and I found myself spending all of my time learning and practicing photography instead of concentrating on my actual coursework. After a few months, I upgraded my camera to a model that shot video (which at the time was a big deal), and I dove headfirst into creating videos in addition to photos. I would shoot short films and acting auditions with my classmates, and through all of that effort I got very comfortable with shooting and editing video. 

After my graduation, I moved to Chicago and wanted to start pursuing a career as an actor. I had two ideas for how I could make money to subsidize my acting career: shoot actors’ headshots or find a video editing job. Headshots were slow to materialize since I had a relatively small portfolio, so I leaned into finding video editing work. After some hunting for video editing jobs, I had two promising leads: one with an online TV station that specialized in animal-centric workout videos and an opening for an internship with a commercial photographer who shot lots of videos and had a full editing suite in their studio. I didn’t land the animal workout video job (who knows where I would be now had I gotten the job!) and decided to take the internship at the commercial photography studio. 

The internship opened my eyes to a whole world I was unaware of: Professional commercial photography. It turned out that the photographer did not, in fact, shoot lots of video, but I was able to see what it took to be a successful photographer. They would shoot large advertising campaigns one day and then a small editorial the next. The size of the job would change, but their artistic approach and eye was being honed and utilized the same regardless the budget. 

Several months into the internship, I took a full-time job in that same studio and took over for the departing 1st assistant and digital tech. This role was the photographer’s right-hand person. I was in charge of maintaining the gear, hiring new interns and assistants for photoshoots, maintaining their body of work and archive, and I was there on every shoot setting up lights, handling the photos in the computer, and making sure the photographer was able to do their job well. It was an amazing opportunity to learn about lighting, composition, and workflow from someone who was at the top of their game. They also allowed me to use the studio and all the equipment in my free time to shoot my own work and develop my portfolio. It was a challenging few years that I worked there that really pushed me to grow as quickly as I could. Since I didn’t have any formal training in photography, I was always pushing myself to learn new software, equipment, and techniques to up my game and make up for my initial knowledge gap. 

After a few years working in the studio, I left my position and went freelance as a photographer and digital tech. That’s how I’ve spent the last few years getting me to where I am now. I’m transitioning from shooting mostly portraits and headshots to more commercial lifestyle work, and I still fill in my time between projects working as a digital tech. I never would have guessed 10 years ago when I was buying my first camera where I would end up, but that’s what makes life fun. Following opportunities and passions and keeping yourself open to the unexpected turns in the road. 

Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
One of the main challenges I find as a person in a creative profession is navigating the unknown of what comes next, in both the near term and the long term. It’s not a career that offers linear progression and clear upward mobility, and I think it’s a never-ending process of coming to terms with that. That’s true for many creative professions, and even though it’s not unique to me, it’s a very real part of our chosen paths. 

One lesson I learned the hard way was when I first went freelance. The very first job I took was for some editing and postproduction work for a photographer. I had never met them before, but they got my name through a mutual acquaintance. I did a few days of work for them and sent them back their final product along with my invoice for my services. 

Now, I was aware that most invoices are on “30-day payment terms”, but I wasn’t prepared for that not to be honored. I sat patiently, waiting for payment to come in the mail. As I got closer to 30 days, I started to feel the pressure a bit more of not having my usual paycheck every 2 weeks, but I had saved and prepared for a slow beginning and assured myself that it would be okay. 30 days came and past, and I politely followed up inquiring as to whether payment had been sent out. I was assured that the check was in the mail and there was nothing to worry about. 45 days, and still no check. I politely follow up again. The photographer assures me that they mailed out the check but would verify to make sure it hadn’t been stolen and deposited by someone else. 60 days and nothing. I reach out again and am promised that a new check was on the way! 90 days, and I’m no longer getting a response from them. 120 days, and all hope is lost. I finally reach out to the acquaintance who connected us to ask whether this person was actually trustworthy or if I had been scammed. The acquaintance reached out to the photographer, and I don’t know what they said, but I had a direct deposit in my account the next day. 

I was fortunate to ever get the money, and I was grateful for it when it showed up, but it woke me up to the challenges I may face as a freelancer. I had other gigs in the 4 months waiting for that first paycheck, which kept me afloat, but they were also on 30-day payment terms, and even the best clients rarely pay much earlier than 30 days. I had saved in anticipation of my first few months as a freelancer, but working and watching your account getting lower and lower hoping a check comes in the mail is a stressful way to start a career. 

Appreciate you sharing that. What else should we know about what you do?
I am a lifestyle and portrait photographer based in Chicago. I work with businesses, brands, and corporations to create imagery that reflects their mission and marketing goals. My work is bold, bright, and energy-filled. I love working on location and in studio, crafting the mood with light, color, and interesting composition. I’m drawn to projects that allow me to showcase the human element in a brand or corporate identity. I’m always striving to bring out the true personal experience or feeling behind the image and highlight the best, most honest attributes of what I’m capturing. I reside in Chicago, but I work wherever projects take me. 

Are there any apps, books, podcasts, blogs, or other resources you think our readers should check out?
I’ll listen to podcasts in the car on my way to or from set if the drive is long enough, and I’m always drawn towards lighthearted comedy. For me, it’s a time to disassociate from the stress and pressures of the job and just relax a bit and get out of my head. 

I love the Smartness podcast, Conon O’Brien Needs a Friend, The Always Sunny Podcast, Life is Short with Justin Long. 

These are my go-to’s for lighthearted, easy listening. There are some very good photo/creative-centric podcasts which I do listen to and which are hugely valuable: 

Dear Art Producer and Photo Dump. 

There are others which I have listened to and enjoyed over the years, but all the ones listed above are my most recurring listens. 

Contact Info:

• Website: www.johnjenningsphoto.com
• Instagram: @jenningsjohn
• Linkedin: https://www.linkedin.com/in/john-jennings-photo/

Image Credits
Gadi Solis
John Jennings Photography