Kenway received his JD from Osgoode Hall Law School. He works in the field of personal injury law in North York. He has an interest in Entertainment Law and volunteers with the St. Clair Art Walk which aims to engage, inspire and transform the community by showcasing local artists and performers.

Kenway is also an accomplished Improv Comedy performer and continues to take classes with Second City, the Bad Dog Theatre and the Impatient Theatre. He performs in shows at least twice a month."