Cheryle Jackson Empowers Women With Grit and Grace.

Cheryle Jackson has enjoyed a career that has been marked by many firsts, spanning healthcare, international business, civil rights, politics, government, not-for-profit, and the media. In 2020, Cheryle became CEO of MyOwnDoctor and Black Telehealth, a tech healthcare company committed to helping people claim their right to good health. For nearly 10 years until 2019, she served as Senior Vice President of Global Business Development and President of AAR Africa for AAR, a global aviation services company.

Cheryle Jackson Chicago DefenderJackson is the founder of Grit+Grace, The Movement, a women’s empowerment, coaching, and media company that is dedicated to helping women to achieve success and reach their full potential.

Tammy Gibson (TG): Looking back at your many accomplishments, what are you most proud of?

Cheryle Jackson (CJ): I am proud of what I was able to accomplish at the Chicago Urban League. But, I’m most proud of the courage it took to run for the U.S. Senate.

TG: What was one of your most challenging moments, and how did you overcome it.

Cheryle Jackson: One of my most challenging moments was battling breast cancer and a divorce at the same time. That was a challenge. How I overcame it, was by practicing something that wasn’t first nature for me. I have a successful career in part because of my tenacity, determination, and ability to withstand a lot and push through. I wore that as a badge of courage.

The revelation is what inspired my TEDx Talk “Grit+Grace.” I had relied on my Grit for my career, but it was the ability to offer myself Grace that really was the thing that brought me back to me after this tremendous battle with breast cancer and divorce.

It was learning how to practice grace with myself and the power of that practice in my performance.  My success moving forward is very different than my past.  It was my most challenging moment, and that’s how I got through to the other side.

I talk a lot about that with the women that I coach. I help women be unapologetic about pursuing their highest ambitions, learning how to practice grace, offering themselves grace in the process, and achieving stratospheric success that can be sustained.

TG: Who inspires you to live your best life and gave you the drive and determination to be successful?

Cheryle Jackson: There are quite a few people that have and continue to be an inspiration in my life.

Strong black women like Oprah and most recently watched Michelle Obama go through what she went through and to see her come out on top.

My original inspiration would have to be my mother.  She has taught me the power of individualism, re-invention, and the secret to living your best life. It’s to always have a goal and a project in front of you. My father taught me resilience. My father was forced into entrepreneurship in the 1960s because of racism and Jim Crow in Memphis, TN while raising a family. My father had a lot of resilience.

TG: What made you want to be a motivational speaker and what motivational talk did you feel the audience connected?

Cheryle Jackson: I wasn’t looking to be a motivational speaker. My background was in communications and public relations. I had worked as a spokesperson in many of the jobs that I had, but that is different from being a motivational speaker.

The catalyst for me stepping into being a motivational speaker was sharing my story of overcoming breast cancer and divorce as a hard-charging career-minded woman. When I did get on the other side of my long journey with breast cancer and divorce, I had an epiphany about Grit+Grace. That one won’t let you give up, and the other makes it okay to let go. When I had that epiphany, I knew it was something I wanted to share with other women and the need to practice Grit+Grace. The understanding of living out your dreams and pursuing your highest ambitions.

When I got invited to give a TEDx Talk, I knew exactly what I wanted to say. It was very intimate. I shared my life, my soul. In my TEDx Talk, I believe, I connected with many people because everyone is going through something. Oftentimes, we are taught about how to be strong, fight, persevere, and power through.

But we never receive accolades or acknowledgment for taking care of ourselves. It was my TEDx Talk that resonated with a lot of people.

TG: Where do you see yourself in the next five years in your career?

Cheryle Jackson: I’m working on a project now. I can’t announce it just yet. Let’s just say my passion and work for advocating and helping people isn’t over. When I can, I will go public with it, but I’m excited about the opportunity that is in front of me.

TG: What would be your advice for young women who are starting their careers?

Cheryle Jackson: I have three things:

  1. Adopt a practice of grace with yourself. That is very important.
  2. Be fully responsible for your own career. I created and teach a course called “Career Free Agent.” For young women starting out, become a Career-Free Agent. You are in complete control of your career, and you decide to call the shots of where you go next. To be a Career Free Agent, it must be anchored in your passion, natural gifts, talents, and abilities. Be clear about what your natural talents are, focus on those strengths and align that with your passion and purpose. Put yourself in environments where you can bring your passion and gifts where they are recognized and valued. That’s how you become successful is when you can operate from your most authentic self from your seat of your power.
  3. The best time to have a coach is when you are not in crisis. It’s maintenance on how you go from good to great. When you are in crisis, you have to pull yourself out of a hole to get to the good.

Beyonce made history by receiving her 28th Grammy. That comes from perfecting your craft, not salvaging yourself from a crisis. To perfect your craft, you have to be in an environment that supports who you are, your talents, gifts, and passion. While you are in those good places, invest in your future career move and a coach so that you can really go further faster.

To learn more about Cheryle Jackson, go to


Tammy Gibson is a travel historian and author. Find her at Facebook, Instagram @SankofaTravelher, and Twitter @SankofaTravelHr













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