Cassie Cavallaro ’21 on turning skills into freelancing and a career path

headshot of a person smiling

As the world was sent into a spiral last March, Cassie Cavallaro found herself homeless due to unfortunate family circumstances. She was living in her friend’s storage room. Simultaneously, the Dunkin Donuts location she manages was cutting hours, slashing her source of income. So, she turned toward her best skill and passion: illustration.

She spent the last of her bank account on equipment she needed and started putting her work out on freelancing websites like and Upwork. Soon after that, she booked her first paid job.

“In the beginning, I felt full throttle fear,” said Cavallaro. “I was taking the last couple hundred dollars in my bank account and trusting that this job was going to follow through. And trust I’d make the money back and then some.”

Cassie Cavallaro’s illustration work

Cavallaro, who plans to graduate from Syracuse University in May with a bachelor’s degree in Illustration, has been freelancing ever since, netting over $10,000 in her first quarter. She has developed relationships with many clients, built a website and broadened her network online. She worked 80 hour weeks over the past year to turn freelance illustration into a self-sustaining job. Throughout, she continued to manage her Dunkin Donuts store while keeping up with full-time coursework.

“Becoming homeless and having to crawl your way back up from the very depths of darkness,” Cavallaro said, “I think it changes a person.”

It can be very intimidating to start off as a freelancer, said Cavallaro. Putting work out there to be critiqued and analyzed is scary. But she has one piece of advice: just go for it.

“If you don’t put what you have out there, you can’t see how the market will react to it,” she said.

Freelancing takes a lot of planning, said Cavallaro. At the beginning, she would take whatever job came her way with no long-term goals in mind. She found herself floundering with too many competing projects. This semester she is focusing on getting plenty of sleep while developing her portfolio. And she thinks about where she wants her freelance work to take her, the world of children’s book publishing and art licensing.

She is also in the process of finding an agent or business partner to help make connections in that industry. The creativity in children inspires the young illustrator and businesswoman, driving her towards that profession.

“To take a child’s imagination and reinvent it and transpose it, I think it is possible to remember what it’s like to be a child,” she said. “To not be afraid to create, to forgive, and to look forward to conquering tomorrow.”

 Cassie is launching a newsletter February 1, which will extrapolate on her creative process and share her illustrations. You can sign up for it through her website.

Interested in becoming Cassie’s agent/business partner? Reach out to her at:

Story by Patrick Linehan ‘21, LaunchPad Global Fellow; photo and illustration supplied by Cassie Cavallaro