Celebrating 20 Years of Transformative Leadership with Winnie da Silva

15/10/2025 32 min
Celebrating 20 Years of Transformative Leadership with Winnie da Silva

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Episode Synopsis

“Every challenge you face builds your leadership muscle for the next one.” - Winnie da SilvaWhat makes someone take a leap with no safety net - and end up building a life and career more meaningful than they ever imagined? Twenty years ago, I turned down two job offers, quit my job, and had no real plan - just an 18-month-old baby, a husband between startups, and a mortgage. Looking back now, it was one of the best (and scariest) decisions I’ve ever made.In this episode, I open up about that journey. How I went from social work to corporate consulting to entrepreneurship and what I’ve learned about leadership, growth, and trusting yourself when the path ahead is anything but clear.You’ll hear me discuss:Why great leadership always starts on the inside and how real change begins with ourselvesThe pivotal moment that pushed me to walk away from “safe” and build something on my own termsWhat it really took to transition from social work to business consulting (and why theater skills helped!)How saying “no” to the wrong opportunities can open the door to the right onesThe lessons I’ve learned from launching my own podcast - imperfectly, impatiently, and all on my ownWhy learning to take the long view has shaped everything from my client relationships to my definition of successResourcesWinnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [email protected]