Stop Climbing the Ladder. Do This Instead.

Midlife reinvention does not have to mean starting from scratch; it means building on what you have already learned. Actress and filmmaker Leonora Pitts joins us to discuss how to navigate the unexpected shifts in a creative career. What happens when the career you imagined takes a completely different path? Leonora Pitts joins Deborah Read on Over 50 Shades of Great for an honest, funny conversation about midlife reinvention, women in Hollywood, and creating your own opportunities. Leonora opens up about rejection, imposter syndrome, motherhood, and the community that helps her keep going. From a spectacular Broadway audition disaster to an unexpected invitation to teach at the American Film Institute, her story is a reminder that a setback doesn’t have to be the end of your creative life. We also go behind the scenes of I Hate Myself and Want to Die, the dark comedy she produced and appears in, written and directed by J. Davis. Out now. Leonora shares what she learns from working with Jay and Mark Duplass, how motherhood shapes her approach to producing, and why she still believes in the future of independent film. Whether you’re navigating a career change, finding your creative confidence, or wondering what comes next in midlife, this episode offers a refreshing perspective on building a meaningful life—and finding people to share it with. IN THIS EPISODE: • Career reinvention and creating opportunities in midlife • Women in film, ageism in Hollywood, and changing acting opportunities • Imposter syndrome and learning to recognize your own abilities • Independent filmmaking, producing, and working with the Duplass brothers • Motherhood, loneliness, and building a supportive community • Returning to school and finding an unexpected path to teaching at AFI • Writing, directing, and developing her feature film, Stranger Light • Self-tape auditions, AI actors, and our “Shade or Great?” game CHAPTERS: 00:00 Welcome and meeting Leonora Pitts 02:11 Behind the scenes of independent filmmaking 06:56 The Duplass brothers and imposter syndrome 09:23 How motherhood translates to producing 14:04 Exploring the film’s dark comedy and emotional themes 21:09 Hope for the future of independent cinema 35:11 From New York theater to Los Angeles 43:19 Creating your own work and rebuilding confidence 47:56 Finding community and starting a mothers’ group 49:42 Returning to school and developing Stranger Light 57:29 Rejection, persistence, and the unexpected AFI opportunity 1:09:15 Why showing up matters 1:11:39 Shade or Great: aging, Hollywood, auditions, and AI 1:23:41 Claiming her next creative chapter 💬 What opportunity are you ready to create for yourself? Tell us in the comments. 🎙️ Subscribe to Over 50 Shades of Great with Deborah Read for honest conversations about life after 50, career reinvention, relationships, creativity, and discovering what’s possible next. Content note: This conversation includes discussion of depression and suicide in connection with the film and Leonora’s personal experiences. @hatemyselffilm now available to rent on ‪@AppleTV‬ ‪@PrimeVideo‬ @fandangostream and ‪@YouTube‬ A Written and directed by J. Davis #LeonoraPitts #Over50ShadesOfGreat #MidlifeReinvention #WomenInFilm #independentfilm #moviemaking #careeradvice #careergrowth