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In this Messy Middle Moment, host Amy P Wilkins shares a deeply personal journey through professional challenges. With a history as a leadership coach and former media executive, Amy unravels a story many women encounter: a dramatic career transition that shook her confidence. The episode sheds light on the toll of toxic work environments and the slow erosion of self-belief, culminating in a profound session with an industrial psychologist. The conversation evokes a reflection on the values of resilience, validation, and self-awareness in overcoming professional setbacks and finding one’s true path.

The narrative continues with Amy’s strategic career pivot, choosing a seemingly smaller role that prioritized her mental well-being and self-healing. This decision defies conventional wisdom but highlights the importance of safety and groundedness in rebuilding confidence. Amy eloquently articulates the necessity of grieving career losses and how processing these emotions is crucial to thriving in new opportunities. Her insights cater to women leaders facing transitions, encouraging them to pause, reflect, and embrace the winding road to leadership. Through compelling storytelling and actionable advice, the episode resonates with those navigating their messy middle while striving for growth and authenticity.

Key Takeaways
  • Toxic work environments can significantly undermine self-worth and confidence, often without immediate realization.
  • Validation from external observers can act as a catalyst for self-reflection and change.
  • Embracing career transitions, even if they seem like a step back, can offer a crucial space for healing and personal growth.
  • Grieving the loss of a professional identity or role is essential, even when the departure was beneficial.
  • Leadership is a winding path, demanding pauses and reflection to truly thrive in uncertain times.
Quotes

Thriving isn’t about having it all figured out. It’s about learning how to grow, lead, and move forward, even when things feel messy.
You’ve just described a morally bankrupt organization. You need to ask yourself why you’re still here.
Whenever something ends, even something that needed to end, there is still a loss.
Not a straight line forward, but moments where something ends, and you’re asked to pause, process, and begin again.
You rebuild it by honoring what was.

Thriving in the Messy Middle Podcast Mentioned In This Episode
A Redirection: The Truth About the Right Path for You, with featured guest Adrienne Valencia Garcia, a lawyer and transformational career coach. 

About Amy P Wilkins

Amy P Wilkins is a leadership coach, former media executive, and the founder of Choose Awe—a coaching practice devoted to helping women leaders navigate transitions with clarity, courage, and self-trust. After decades in senior leadership roles, Amy now empowers women to lead with purpose and thrive through the “messy middle” seasons of life and leadership.

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