Makowsky graduated from Roslyn High School and Brown University, then moved to Los Angeles to pursue a career as screenwriter. His first feature film credit was the independent dark comedy "Take Me", which was produced by the Duplass brothers and distributed by Netflix. He then wrote and produced his second film, "I Think We're Alone Now", which was helmed by Reed Morano and starred Peter Dinklage and Elle Fanning. The film screened at Sundance Film Festival in 2018.