How 20 Years with Leaders Changed Me

“Every challenge you face builds your leadership muscle for the next one.” - Winnie da Silva

What 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 ourselves
• The pivotal moment that pushed me to walk away from “safe” and build something on my own terms
• What 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 ones
• The lessons I’ve learned from launching my own podcast - imperfectly, impatiently, and all on my own
• Why learning to take the long view has shaped everything from my client relationships to my definition of success

Resources

Winnie da Silva on LinkedIn | On the Web | Substack | YouTube | Email - [e-mail]