Cheryle Jackson’s history-making career has been marked by her ability to break barriers as a Black woman. She has served as a C-suite executive at a global aviation company, CEO of the Chicago Urban League, a candidate for the U.S. Senate seat vacated by President Obama, communications director for an Illinois Governor, and a vice president at National Public Radio. In 2020, she became CEO of MyOwnDoctor, a telehealth company that offers culturally specific care with platforms Black Telehealth and LatinX Telehealth.

In 2018, Cheryle founded Grit and Grace, The Movement, a women’s empowerment, coaching and media company. In her intimate TEDx Talk “Grit and Grace,” Cheryle validates the career trajectories of go-getters but also implores women to place self-compassion on par with ambition as a lasting model for success.

Cheryle also co-hosts When Magic Happens, a podcast by WBEZ Chicago, where intergenerational conversations of love, life and laughter collide. Three Black women. Three generations. No filters.