2x Emmy Award Winner

Global
Business
Leader

Survivor

Pivot Coach

TEDx
Speaker

Hi There, It's

I’ve had a career marked by firsts. 

I was the first female president and CEO of the Chicago Urban League, where I led one of the most transformational periods of growth in its history. As the communications director for the Governor of Illinois, I was the first woman and African American to serve in that role in the state’s history. I’ve been a C-suite executive at a global aviation company and a candidate for the United States Senate. I’ve held senior level positions at Amtrak and NPR. 

Today, I am the CEO of MyOwnDoctor, a groundbreaking telehealth company.

In a career spanning  international business, healthcare, civil rights, politics, government, not-for-profit, and the media, there was always one common thread. I had to learn how to convert the obstacles and challenges that women everywhere face into wins for the company—and for my own career success. 


As the founder of Grit and Grace, The Movement, I help advance the ambition of women through coaching, conferences, community, and content designed to inspire and empower. In my intimate TEDx Talk, “Grit and Grace,” I validate the career trajectories of go-getters like me, but also preach the need for women to self-advocate and to practice grace and self-compassion. Grit and grace is the only sustainable model for success.

“While you’re out there slaying dragons, saving the world, fighting for everybody, don’t forget to activate your superpower: Grace.”

Cheryle Jackson, Grit and Grace

TEDx WillowCreek

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Latest Blog Posts

How to Make Successful Career Changes: The 5 W’s

In the current job market, who hasn’t at least thought about switching jobs, companies, or careers? Or taking the leap into entrepreneurship? As it turns out, most of us have been thinking about it. According to a recent Fast Company-Harris Poll, 52 percent of U.S. workers are considering a job change in 2022. Done right, […]

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Procrastination vs. Decision Fatigue: Which Is It? How to Overcome It.

Procrastination is a fact of life. We all do it at some point. Sometimes we even procrastinate on things we know we want to do! But procrastination can also be a symptom of something more serious—decision fatigue. According to the American Medical Association, decision fatigue is “a state of mental overload that can impede a […]

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How to Succeed Quickly in a New Role

According to Gartner surveys, 49 percent of people promoted within their own companies are underperforming up to 18 months later. McKinsey reports that 27 to 46 percent of executives who transition to new roles are seen as failures or disappointments two years later.  Their companies saw fit to promote them. They had the right skills […]

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Book Cheryle for your next
speaking engagement.

Book Cheryle for your next speaking engagement.

If you’re looking to provide your audience with:

Words of wisdom from a trailblazer who has been “The First” woman and/or African American

The inspiration and motivation to overcome obstacles and perform at their highest level

An honest conversation about the impacts of high-stress living and the need for self-care.

FOLLOW ME ON INSTAGRAM @cherylejackson.