 Jessup has stated in numerous interviews that his intention is to work in the film industry beyond acting, as a director and filmmaker.In an interview with the " Toronto Star", Jessup said that directing "is where my mind and heart [are] at the moment".In 2014, Jessup starred in the short film "Fragments", and in 2015, Jessup's short film "Boy," which he wrote and directed, and was funded by bravoFACT, premiered at the 2015 Toronto International Film Festival.