Success Leaves Clues: Empowering Chicago Women in Business

April’s Heels & Handshakes Monthly Meeting hit new heights—literally. With stunning penthouse views and a room full of driven women, this month’s theme, Penthouse Views & Success Leaves Clues, set the stage for an evening full of real talk, powerful insights, and major inspiration.

Our speakers didn’t hold back. They opened up about the highs and lows of building something from the ground up—sharing everything from launching businesses at a young age to facing bias and burnout. One speaker talked about a tough investor conversation that could’ve broken her spirit—but instead, it made her stronger. Another spoke on pivoting her career after a serious health challenge, proving that resilience always pays off.

Some standout lessons we walked away with:

• Protect your time—say no to things that don’t move you forward.

• Prioritize your mental health—you can’t pour from an empty cup.

• Get organized—Google Calendar and habit stacking = productivity gold.

• Show up as your future self—"be it until you become it."

We ended on a high note with our signature “struts,” where members shared personal wins—big or small. From hitting new fitness goals to launching new services, every strut was proof that success isn’t just about big moments—it’s built through consistent, intentional action.

Here’s what’s coming up next:

• 💻 May 6: Don’t miss The Competent CEO virtual workshop—get the legal basics to protect your business.

• 🥋 May 15: Join our Ready Set Chicago self-defense class—it’s all about confidence, safety, and strength.

This month’s meeting was a powerful reminder that when women share their stories, they help others climb higher. Success leaves clues—and at Heels & Handshakes, we’re all about learning from each other, lifting each other, and building our dreams together.

If you would like to attend another meeting, you can find all of our programs for the Chicago Chapter here.

See you at the next one! 👠✨