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April 25, 2025 47 mins

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This is the episode I’ve been writing in my body for years. One part closing chapter, one part initiation, this conversation brings you behind the scenes of why I’m closing The Cheetah Company®—the brand that brought me into rooms with the most brilliant female founders and allowed me to serve at the highest level in business advising, coaching, and consulting.

But this episode isn’t about a pivot in business. It’s about a deeper calling. A reclamation. A reckoning with what happens when success looks incredible on the outside but starts to quietly erode the inside.

Whether you’ve outgrown the business you built, or you’re navigating your own silent “what now?”—this is a space for your truth to breathe.

Inside This Episode:

  • Why I’m officially closing The Cheetah Company® after five beautiful years
  • The unseen addictions inside the female founder space: stress, being needed, being known
  • The silent grief that cracked me open and changed the trajectory of my life
  • What happens when ambition goes unchecked—and why so many high-achieving women are quietly asking, “Is this it?”
  • A look at one client’s journey navigating the tension between building her empire and choosing van life
  • The difference between productivity and presence, and how pleasure is often the missing ingredient

A Look at My Client Work (Then + Now):

  • Supporting multi-six and seven-figure entrepreneurs in seasons of reinvention
  • Holding space for “successful” women as they unedited their lives and quietly unraveled
  • Shifting from strategy-heavy consulting into soulful, somatic, life-based guidance
  • How I moved from helping clients build scalable businesses to helping them build spacious lives

Key Takeaways:

  1. If you feel like you’re holding it all but losing yourself in the process—you’re not alone.
  2. There’s no business strategy that can make up for a life that feels misaligned.
  3. Real harmony asks us to slow down, feel, and reorient before we build again.
  4. Sometimes your legacy lives on the other side of letting go.

This work is just beginning. If you’re in a season of softening, surrendering, or shifting, join me over at The Deep Edit — my weekly newsletter where we blend narrative, nuance, and the next evolution of leadership for high-achieving women ready to live differently.

Subscribe to The Deep Edit to receive your welcome issue and a podcast to anchor you into this next season of life.

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