Rewriting Your Money Story with Winnie da Silva

What if the reason you're not earning what you're worth has nothing to do with your skills — and everything to do with the stories you believe about money? Are you showing up like someone who knows their value… or playing it small to keep the peace? Let’s be real — money is messy. It brings up all kinds of emotions, expectations, and unspoken rules. In this solo episode, I’m sharing something personal: my own journey around money, self-worth, and what it’s taken for me to finally feel comfortable asking for what I deserve.

This episode kicks off a new theme we’re exploring this month: Leadership & Money Mindset. If you’ve ever hesitated to ask for a raise, felt weird quoting your rates, or second-guessed your worth, this one’s for you. I’m talking through the mindset shifts I had to make (and am still making!) to move from discomfort and doubt to clarity and confidence — and how you can do the same.

You’ll hear me discuss:

• What happens when you don’t value yourself. I used to feel weird asking to be paid — like it somehow made me less sincere. But I’ve learned that when I don’t own my value, other people don’t either. That had to change.
• The early money messages that shaped me. I grew up in the Midwest, where the rule was: don’t make anyone uncomfortable — especially with money talk. That silence stuck with me for years. Maybe you can relate?
• A simple framework that helps uncover limiting beliefs. I share the Story → Behavior → Result model I use with clients to break down what's really driving your actions — and how to shift it.
• Three powerful client stories — Annie, Eleanor, and Zoe. These are women who faced real turning points in their careers — promotions, negotiations, job changes — and had to totally reframe how they saw their own value. Their courage might give you the nudge you need.
• The bigger forces that make this harder, especially for women. We’ll touch on why this issue isn’t just personal — it’s also systemic. From unpaid labor to leadership stereotypes, there’s a lot working under the surface.
• A surprisingly fun tool to explore your money mindset. I’ll introduce you to the Money Type Personality Assessment (yep, it’s free!) and share what I learned about myself as a “Visionary” with a close second of “Nurturer.”
• Five big takeaways to help you shift your mindset now. These are practical, real-world ideas you can apply — whether you're pricing a project, negotiating a role, or simply trying to stop shrinking yourself at work.

Resources

Money Type Personality Test

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