A vital dispute within the art community still demands our consideration: whether theatre or film is the leading medium that communicates to many audiences and triggers people to reflect on their own lives. Theatre is considered to be the foundation of all drama, and developed what we know as dramatic structure and acting of various forms. It also establishes an intimate connection with the audience through the live action performances and the arrangement of the set (proscenium, arena, black box, etc). On the other hand, film goes beyond the barriers of the stage and uses a range of equipment from shotgun mics to prosumer cameras to create a sequence of shots in order to tell a story. The intimacy is gained through a multitude of camera angles and close-ups to make up for the loss of direct connection with the audience. However, neither medium can be picked as ideal, because they have unique advantages and disadvantages as they pursue different creative paths to create the final product. For my project, I directed Martha Norman’s play ‘Night, Mother as a theatre production and adapted a portion of the play for a film production. From my experience of these projects, I created an educational video that will discuss how I directed the play within two different mediums, and highlight the comparisons and contrasts I’ve encountered on my director’s journey.