Making HERstory: Bold. Brave. Feral AF Stories from Female CEOs

Making HERstory: The Journey from 9 to 5 to Freedom Part 1 with Jenna Boyer

Ashley Crabb Season 1 Episode 4

What happens when you finally bet on yourself. In this first half of the conversation, Ashley Crabb sits down with brand photographer and community builder Jenna Boyer to talk about leaving a 9 to 5, following intuition, and stepping into the unknown. Together they explore what it really means to trade “safe” for self-made and how that decision can rewrite everything about motherhood, business, and identity.
If you’ve ever wondered what freedom could look like on the other side of fear, this episode is your proof.

This Episode Is For You If:

  • You’re standing on the edge of change and need the courage to jump.
  • You’re craving a story that feels real, not polished.
  • You’re ready to believe that motherhood and ambition can coexist.

About This Episode:
Jenna shares the emotional side of quitting, the tears, the doubt, and the moment she knew she couldn’t stay small anymore. Ashley and Jenna talk through the first steps toward freedom and how letting go of “shoulds” can open more doors than any strategy.

  • The emotional goodbye that started it all
  • Why “safe” can be the most dangerous place to stay
  • What it feels like to choose yourself and mean it

Available now on Apple, Spotify, and YouTube.
If you’re ready to stay feral, hit subscribe so you don’t miss Part 2. Leave a 5-star review for the one that hits you hardest, and share this podcast with the women who need it most. Tag @itsashleycrabb so I can hype you up and keep this fire going.