Chicago area entrepreneurs plant seeds in photography, fashion

Wake up at 5 a.m. Shower, eat a small breakfast (if there’s time), then drive to O’hare International Airport to start a 7:30 a.m. shift. Clock out at 2 p.m., drive home for shower number two then change clothes and head to Verizon Wireless. Work a few hours, clock out and go to class. Get home by 11 p.m. Sleep. Repeat.

For Brian Flynn, 32, this is a typical Monday. A part-time digital photography student at Harrington College of Design (where he also works in the equipment cage), Flynn juggles three part-time jobs, school and his true passion, capturing images.

Photo Credit: Brian Flynn, B Flynn Photography

“[The challenge is] having enough energy to keep up with doing everything that I do, said Flynn in a phone interview. “I’m probably a very crazy individual at this point because I do so much, and there’s simply not enough time in the day to accomplish everything.”

If he has the weekend off from his ramp services job at United Airlines, Flynn starts his Saturday around 9 a.m. with a photo shoot or editing in his shared studio space. In his last semester at Harrington, Flynn said he is ready to focus more on his company, B Flynn Photography. Still, he is nervous about putting himself out there as a full-time photographer.

“It’s a little scary because there are so many ups and downs between how often I have paying clients,” he said. “I still need to work, still need a steady paycheck.”

Laid off from Blue Cross Blue Shield last November, Kylisha Alsberry, aspiring fashion designer and creator of online boutique Haute Sheek, knows this fear all too well. Though given the option to stay at her company, she said she opted for a severance package and invested nearly $5,000 in her own business.

“When I finally decided to step out and call my own shots…there’s nothing like it,” Alsberry said. “I was meant to be a boss; I have to be a boss.”