What Nobody Tells You About Changing Directions After Years Of Success

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.

TIMESTAMPS

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

Connect with your host, Bunny Young:

LinkedIn: https://www.linkedin.com/in/bunnysumneryoung/

Website: https://www.abetterplaceconsulting.com/

Instagram: @thebunnyyoung

Connect with Cathy Olson:

Instagram: @funnelgorgeous

Website: https://funnelgorgeous.com