We’re excited to introduce you to the always interesting and insightful Jay Shifman. We hope you’ll enjoy our conversation with Jay below.

Jay, appreciate you joining us today. What’s been the best thing you’ve ever seen (or done yourself) to show a customer that you appreciate them?

Whenever I work with someone, I always make sure they leave the interaction with more than just their photos. I want clients to have a wonderful experience each time. Anyone can take photos, you know? With cameras on our phones, more and more people are able to do what I do. So I recognize that I need to create an experience.

One thing I do is make sure I never center the payment. I want my clients to know I’m working with them for the love, for the happiness, for the desire to give them what they want, and not just because I’m looking to get paid. One of my core client bases is writers here in Philadelphia. As a writer myself, I get what they need. But more than that, I get that it’s not a career that’s making anyone (except maybe the top .01 percent) rich. So for young writers, I often give them their first author shots for free. For those with more means, I almost always give major discounts in exchange for actions they are likely to do anyway. Like posting about our shoot on social media, or shouting me out in the book. That kind of thing. It helps me, and it helps them keep money in their pocket, which we all need right now!

I always like to hang out with the person first. That we can chat and I can learn about what they like, what they don’t like, what they are confident in and less so. It helps me shoot exactly what they are looking for and give them the best experience I can!

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

My main day to day is photography. I sort of split my business in half; the artistic work and the client work.

For clients, I do everything from author bio pics and promotional pictures to engagement photos and the like. Pretty much the only thing I don’t do is weddings.

The artistic work is much more my own. Much of it is politically focused. Others tell their own message through the art. I describe my artistic photos as marked by stark contrasts and bright colors. I’ve said before that I seek to show what I sometimes fear is how I, alone, see the world. Bright and colorful, and stark all the same.

I came to this after a few different careers. I spent over a decade in nonprofit and political fundraising and campaign management. Then I went on to run my own business, Choose Your Struggle, focused on education and advocacy around the issues of mental health, substance misuse and recovery, and drug use and misuse.

After all that I said, to be honest, I just need to follow my passions and launched myself full time into my photography and writing. So that’s what I do now!

In early 2025 my wife and I opened a gallery and community space called Flashpoint. Unfortunately, we lost our physical space recently, in early November. But we are currently looking for a new location. So fingers crossed. Stay tuned!

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

Ugh I hate to say this but I sort of had to unlearn the idea that I shouldn’t follow my passions. I have a lot of privilege. But for a long time I let a few loud voices tell me I shouldn’t focus on my passions and instead should focus on making money. “Stack your paper!” That kind of thing. Eventually I came to the realization that as long as I have enough to keep the roof over my head and food on the table, I’m good. And sadly, that isn’t something enough people can say. I think about this quote from Billy Beane in Moneyball (I’ll be honest, I don’t know if he really said this or if it was made up for the book/movie) but he said “I made one decision in my life based on money and I swore I would never do it again.” Not everyone has that privilege. But I do. Now, I follow my passions. And you know what? I’m thriving. I feel immensely richer than I did before. I surround myself with other artists and passionate people who are doing incredible things. I couldn’t be happier.

What else should we know about how you took your side hustle and scaled it up into what it is today?

When I sunset my business Choose Your Struggle and decided to focus full time on my passions, it was a real struggle for me. I have to shout out my therapist at that time, because she was instrumental in helping me dispel some unhealthy ideas and truly listen to myself and my intuitions. But once I launched myself full time in this, I started by simply taking my camera whenever I went to the events I was already going to. As a poet, I’d shoot the open mics and readings I went to, then share those pictures with the other poets and writers. They’d tag me on Instagram and people would inevitably hit me up to get some shots. I feel like the best advice there is I didn’t take myself so seriously, you know? I was doing this for the love. So I was happy to share the pics with people and it still makes me happy to see pictures I took at these events used by people on their flyers, websites, social media etc. I just love seeing these other creatives happy.

Contact Info:

• Website: https://www.JayShifman.com
• Instagram: @SouthPhillyJays

Image Credits

All the photos were taken by me except for the one of me with my camera, which was taken by Georgiana Constantinescu.

The model in the blue headdress is Rachael Hannah. The model on top of the car is Maia Brown-Jackson. The model in the wedding dress is Ariel Monroe.