HerStories is a podcast series hosted by The Chicago Network (TCN), an organization focused on empowering women leaders in Chicagoland. In 2023, TCN interviewed Ann for a feature called “Designing a Better Future for Women” in which she told the story of her unexpected rise from middle school English teacher to one of America’s leading businesswomen and the founder of multiple organizations committed to advancing women’s leadership.

In this lively conversation with host Maria Doughty, CEO of TCN, Ann explains how, at different choice points in her life, she found the courage, the mentors, and the pathways to leave behind what was safe and familiar and instead pursue what felt most true to her—and how, as she did, doors opened.

“It was hard all the time,” admits Ann. She credits her father for giving her the grit, integrity, and love of life to see many challenges through. And today? “I think my dad would be blown away. He would just be amazed, and he would be right there with me, trying to build something new and great.”

Treat yourself to an engaging and inspiring hour with Ann Drake by clicking here.