Independent Contractor Spotlight — Photographer

Fashion and Commercial Photographer Steven Conway talks about his years behind the lens

Milwaukee, Wisconsin-based photographer Steven Conway has been freelancing for 25 years and has navigated the industry’s change from film to digital. After studying photography at the School of the Art Institute of Chicago and getting a master’s degree in theater lighting at DePaul University, Conway interned as a photographer for Playboy magazine, where he eventually took on a full-time position. After several years on staff, Conway branched out on his own to shoot fashion and commercial photography.

What were the challenges of working in photography while the industry went through huge changes in technology?

The only thing that has been consistent is my vision, my eye. I always embraced technology, but it hadn’t really changed when I started, and it wasn’t really changing very quickly. Then when digital came, it started to accelerate. But when it first started, we kind of laughed at the quality of the imagery as being totally unacceptable. I determined that when the quality of digital equaled what I was used to doing with film, then I would make that transition.

The advent of digital then altered client demand for photography. How did your work processes change?

Things sped up. You could look at an image and know that you got it. With film, you had to trust that you were getting it. But there was always that little bit of uncertainty that there was something wrong or something could happen in the processing of the film that could ruin it. With digital, clients demanded it faster because you no longer had to send it to the lab and go through each image on a lightbox. Then I had to develop a skillset using Photoshop. When I started shooting commercially, I had to nail that exposure, but I could just hand in a piece of film. What else could I do with the film? Then all of sudden I had this digital image where I could make the sky a different color…so clients started demanding more perfect images.

What do you like most about being an independent contractor?

I like that my time is my own. Through the good or bad, I’m responsible for my time. I’m not having to punch a clock. It’s about having a sense of freedom and deciding when I’m going to work. Another thing is that the people whom I either work with or work for change. Generally, I will work with those people again at some point. But it’s not every day. It’s kind of good to see people again after you’ve worked with them and then you don’t for a while, and then another project comes up that they’re on. I like that the pool of people changes, as opposed to going into a place of work where it’s exactly the same people.

What is the biggest challenge of being an independent contractor?

When I first started being independent, I felt like I always had to be busy. But it’s okay not to be busy all the time. Instead, I’m more strategic with my time.

Do you have any words of wisdom for aspiring entrepreneurs?

Whatever business you’re in, make sure you have a good skillset and develop that, either through school or working with someone else who is really good in your field. The other thing that’s really important is communication skills. Take public speaking and learn to be personable. I think people who do well can speak well in front of a group or communicate what they do.