Description

What happens when the very thing you spent years building successfully starts asking you to become someone new?

In this episode of Yes, And! Bunny chats with long-time creative collaborator and tech founder Cathy Olson to unpack the often uncomfortable evolution that happens inside a business when it grows out of its original container.

This conversation moves past surface-level marketing advice to land in the emotional landscape of entrepreneurship. Cathy shares open, vulnerable reflections on shifting her business model, navigating massive identity transitions alongside a long-term partner, and the vulnerable process of staying grounded when the structures around you are in constant motion.

Underneath the logistics of funnels, platforms, and programs is a much deeper work that needs to be done, and it's about trusting your intuition and finding the permission to let your identity change as your vision expands.

Chapters

00:00 Intro Yes, And!
04:15 Feeling the identity shift friction
10:30 Navigating systemic business changes
16:45 When partnerships face new structures
23:10 Nervous system cost of adaptation
31:15 Trusting the slow evolution process
39:40 Balancing alignment with scaling needs
48:20 Mid-transition business vulnerability
54:10 Creativity bringing us back home
54:10 Finding comfort in the strange, beautiful ways creativity brings us back to ourselves