This episode features a conversation between Jennifer and writer and speaker Jocelyn K. Glei about navigating personal and professional transitions in uncertain times. They explore the discomfort of liminal spaces, the challenges of letting go of established identities, and the importance of acknowledging both achievements and losses. Jocelyn offers insights on embracing "generative discomfort," moving from expertise to experimentation, and remembering our inherent wisdom during periods of change. As they discuss the metaphor of caterpillar-to-butterfly transformation, Jennifer and Jocelyn reflect on how periods of uncertainty can be powerful training grounds for creativity and renewal, particularly relevant as they navigate political shifts and professional transformations in 2025.