HOW TO: Process and Embrace the Assistant Position (w/ Grace Guy)

This week, we sit down with writer and comedian Grace Guy to unpack the complicated, often unspoken dynamics of assistant culture in the entertainment industry. Drawing from her own experience as a former assistant, Grace shares the inspiration behind her deeply personal play Deckhand—a sharp, emotionally charged story about a boss and assistant trapped together on a boat. We dive into the love/hate tension that defines so many of these relationships, and the uncomfortable truth that while assistants are often told their proximity to power will lead to opportunity, that promise rarely materializes. Grace also opens up about recognizing when it’s time to leave a job, the importance of self-care and building a real support system, and the danger of tying your dreams to someone else’s success. The conversation then shifts to her creative process—how she approaches writing “forced proximity” stories, and the journey of developing Deckhand, including testing it in front of audiences ahead of its Edinburgh run.  TIX FOR 50/50 COMEDY FESTIVAL MAY 3RD!! Grace's Insta (see upcoming show dates & more!) DECKHAND SHOW Books Mentioned: Artist's Way, Rick Rubin's Book, Anne Lamont (Bird by Bird, Good Writing)