We caught up with the brilliant and insightful John Jennings a few weeks ago and have shared our conversation below.

John, thanks for joining us, excited to have you contributing your stories and insights. One of our favorite things to brainstorm about with friends who’ve built something entrepreneurial is what they would do differently if they were to start over today. Surely, there are things you’ve learned that would allow you to do it over faster, more efficiently. We’d love to hear how you would go about setting things up if you were starting over today, knowing everything that you already know.

If I were starting over today there are a few things that I would do differently. One big trap that I see many aspiring photographers get stuck in is the belief that their gear is what’s holding their photography back. This was certainly true for me. I’d think I couldn’t shoot this project without some specific piece of gear, or some big client won’t take me seriously if I don’t have this amount of equipment. Gear is a common distraction people have with photography. It’s a lot easier to think about all the amazing things you could do with a new camera body or lens, than to actually plan out and produce a photoshoot and execute it.

I remember on one of my early editorial assignments, I was sent to shoot a full body portrait of a Doctor in their exam room. I brought out all my gear I used for similar projects. A full 9′ backdrop with stands. Several lights and modifiers. Everything in my mind that I would ever need for a portrait. When I arrived at the location I was walked back to the room we were allowed to shoot in and I was shocked. It was TINY. The room was 8 feet wide by 8 feet long with 7 foot tall ceilings. Not to mention there was an exam table right in the middle of the room, along with a computer desk and chairs. I asked if there was any other space for us to do the portrait in, but since it was a functioning medical practice there was absolutely no other room we could use. The backdrop I had wouldn’t fit in the room. The light modifiers were too big to use in the room. All the stands, and accessories were all useless. But I wasn’t there to make excuses, and the Editor at the magazine wouldn’t care what obstacles I might come up upon. So I threw out the plan I had in my head and started figuring out how to deliver on the assignment. I cleared as much from the room as I could out into the hall. I cut up my seamless backdrop to a smaller size and rigged it up against the back wall. I took a single light and bounced it into the opposite wall to spread the light as much as possible. I had to put my camera up against the wall and shoot with my widest lens to fit the doctor in the frame head to toe, but I got it. I spent the few minutes the Doctor scheduled to get a few options, and I walked away knowing that I got the shot that I needed. All the gear in the world couldn’t have prepared me for that shoot. When it came down to it, it was minimal gear and creative thinking that got the shot. It was challenging, but afterwards I walked away knowing in any similar situation that I could figure out a way to get the shot I needed to.

It’s easier to blame inadequate equipment than to admit that we may not have the skills or knowledge yet to execute a concept we want to shoot. The only way to bridge that gap is to do your absolute best to bring your idea to life using what you have. You’ll figure out so many more things that you never would have thought of in the planning stage, and you’ll probably get closer to your vision than you thought you could. You’ll walk away with a huge amount of real experience which will help inform your next shoot, and build your confidence much faster to tackle those challenges.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I am a lifestyle and portrait photographer based in Chicago. I work with businesses, brands, and corporations to create work that reflects their mission and marketing goals. I’m drawn to projects that allow me to showcase the human element in a brand or corporate identity. I ground my work in the authentic experience of the subject, whether that’s in a documentary or lifestyle piece, or in an absurd conceptual driven narrative. 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.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

A major lesson I had to unlearn was that failure is bad. Failure is the single best way to learn how to do something. For every one thing you fail doing, you’ll learn several valuable lessons. You can plan and plan before you execute, but inevitably something unexpected will happen.

When I was first starting out marketing my photography business I wanted to send out a big email blast to prospective clients a promo of some of my best work. It was important to me that I did everything right, so I took several days putting everything together. I curated the photos I wanted to use, got a custom design template, wrote a really solid short pitch on my work, and then I started collecting emails of all the agencies, producers, and editors I wanted to send it to.

I was feeling confident that this was going to be an effective marketing push, so I started sending out all the emails from my email account. After a few hours of sending out promo emails I set the project aside for the day and started responding to my inbox of existing clients I had to get back to. I felt really proud of the work I did, excited for all the new opportunities that were sure to come.

A few days later I get a phone call from a client asking about my availability for a job they emailed me about. I was confused because I had responded to that email confirming my availability. I told them this and asked for them to check their spam. Nothing. We finish up our phone call and I start sending out test emails to friends. None of them are coming through. I’m in a small panic about what is happening. Why are none of my emails reaching anybody? How long has this been happening? After some frantic googling and research I discover that my email has been flagged by google as a spam account. Apparently at some point during my big marketing blast, google saw the sudden volume of email I was sending and locked my account. After jumping through some hoops I was able to unlock my account, and resume sending and receiving emails normally.

When I started working on my email promo I thought I could plan everything out for it to be successful, but something I never expected or even thought could happen ended up happening. That initial marketing effort was technically a failure because nobody ever saw it. I could have been discouraged and told myself that I’d never send out another marketing email, but instead I took everything I just experienced and turned around and used it to figure out a better way to move forward. In that failure, I learned a lot of valuable lessons about email marketing, and it made all my follow up efforts much more successful.

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

The most rewarding thing about being a creative for me is the satisfaction of seeing something you’ve imagined become a reality. It’s easy to take for granted to all the work and effort that goes into a creative production, but I’ve found that the amount of work you put in matches the reward at the end. I also feel very fortunate that I’m able to make my living creating imagery for people everyday. It’s can be challenging and lead you to very unexpected places, but that’s what makes it so exciting. Every day that I get to do this I feel extremely blessed.

Contact Info:

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

Image Credits
Headshot – Steven Glynn Photo