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When Passion Meets Persistence, Empowerment Begins

Cheryle Jackson

An Interview with Cheryle Jackson, Sr Vice President of Global Business Development, AAR Global Aviation Services Company

Cheryle Jackson is the visionary founder of a movement called Grit+Grace, designed to support and advance women in developing their leadership skills. Cheryl believes that it’s not only important to have some fight in you, but that you’re also walking with grace—for yourself and for others. I spoke with her about her remarkable career journey and the lessons she’s learned along the way and wanted to share some of that with you today.

WeInspireWe: Great to talk to you today! Why don’t you tell us a little about yourself?

Cheryle Jackson: My name is Cheryle Robinson Jackson and I am the Senior Vice President of Global Business Development for AAR Global Aviation Services Company. In this role, I travel the world, helping the company break into new markets. I’ve been with AAR for 8 years. It’s been a phenomenal growth opportunity for me.

That’s what I do for my 9 to 5, but for my 24/7, I am an advocate for women and girls. I’m particularly focused on helping women tap into their full potential.

WIW: Nice! Tell us a little bit more about that personal passion, your 24/7.

CJ: I coach women who are very accomplished but still feel like they need permission to embrace their success, to promote themselves and to celebrate their accomplishments.

When people know about your talents, abilities, and successes, the further you’ll go. Not only will you advance in your personal career, more women will get to see your successes. They’ll learn about and be empowered by them—and be what they see. So, I help to encourage accomplished women to own and leverage their power and influence that they’ve amassed.

For women who are more in a building mode—whether they’re in the workforce, or as entrepreneurs, or women who are transitioning—I’m able see their potential before they realize it themselves. I see what they can’t see. I help them to look at themselves with new eyes. I coach them and connect them to resources that can help them advance their potential.

Another sacred space that I find myself holding is that intersection of the personal life and the professional life. The two are so intertwined for everyone, but so much more so for women. I help women reconcile their personal lives and development in concert with their professional lives and advancement.

This is my 24/7 because this kind of support is something that I’ve yearned for. Coming up in my career, I encountered a lot of obstacles, a lot of adversity, and a lot of isolation. I had to figure it out on my own and struggle alone, so that’s my motivation. You want to give what you didn’t receive. I want to give it in abundance.

WIW: That’s fascinating. We’d love to hear more about your path that’s gotten you to where you are, professionally as well as this “giving back” mentality that you have to support other women around you.

CJ: My path, I think, is different. Unique. First, I began without a clue about what I really wanted to do. My undergraduate degree has nothing to do with where I am today or anything that I’ve done in my career. And every opportunity I’ve had seemingly on the surface looks disconnected from the other. I didn’t stay within an industry. I didn’t even stay within one skillset. I was just different all the way around.

My undergrad degree was in painting and drawing. I loved to paint, and I was very creative when I was growing up. I was always taking painting classes and enjoyed doing artistic things. I wanted to go into graphic design and eventually went to graduate school thinking maybe I would become a professor of graphic design. But that opportunity didn’t work out.

And then I encountered a health crisis—Grave’s disease—and it just shifted my whole perspective. When I got better, I no longer wanted to teach so I started working. I was an Art Director at a local PBS/NPR station in Memphis, Tennessee and had a short stint as the Manager of Publications for a college in Memphis too.

Then I got married and moved to D.C., where I worked for NPR as an art director. And it was at NPR that I had the most dramatic professional growth. I went from an Art Director to Director of Corporate Identity and Marketing to Vice President of Corporate Communications and Marketing—where I was the first African American in that position, as well as one of their youngest (I was 32 at the time).

Not long after I became Vice President, my then husband wanted to return to Chicago, so we moved. I became the Regional Vice President for Amtrak where I was the first African American in that role too. That job was absolutely the best thing for me, even though it was a tough environment.

From there, I was tapped to be the Communications Director and Press Secretary to the Governor of Illinois—Rod Blagojevich, where I was the first woman and first African American in that role as well.

I left the Governor’s office in 2006 and became the President and CEO of the Chicago Urban League. I became the first woman CEO in the 93-year history of the organization. It was an incredibly intense experience.

In 2009, I took a leave of absence and ran for U.S. Senate in the Democratic primary, for the seat that President Barack Obama vacated. President Obama had a shortlist of six people he wanted to take his seat and I was one of the six. It was such a vote of confidence and a shot in the arm.

Even though the President’s endorsement was a wonderful thing, what really prompted me to run was that times were so tough, particularly for the constituency that I was representing as President of the Chicago Urban League (CUL). I wanted to make a difference and I believed in my ideas, so I ran.

After I didn’t win the Senate race, I received a challenge from a board member of CUL, the chairman and CEO of AAR: “If you really want to help your community, you need more experience beyond the Southside of Chicago” and that was my eureka moment—here’s an opportunity to learn the world. He offered me an opportunity to work at AAR, where I work now, even though aviation was the furthest thing from my mind.

WIW: Wow, what a journey! It definitely is a unique one, with so many big life changes. When did your personal passion for advocating for women really begin to blossom for you?

CJ: My advocacy for women really kicked in after I ran for Senate. I spent a lot of time wondering how my outcome for my race could have been different. And I came to the conclusion that to vote in a different kind of voice, someone who’s not the establishment, really requires women or young people. And I thought about how we could engage women more.

Often women are not as engaged in politics. If given the choice between supporting a non-profit or a charity or to be engaged in politics, women tend to be more inclined to make a difference in their communities through advocating for their causes and non-profits. But I feel that women are the best chance and voice to represent all of us.

When I thought about how I can engage women more, I decided that I must first help women reach their fullest potential. During the Great Recession, women were at the center of the crisis—the housing crisis, small businesses collapsing, families losing their homes, recent college grads returning home to live with mom because there were no jobs, caring for those around them, etc. It was those times that gave birth to my passion for advocating for and empowering women.

I started working on this concept called Real Like Me – helping women to gain confidence and to create a game plan to advance their professional lives.

I was ready to pull the trigger to launch this program when I was diagnosed with breast cancer. I had a mastectomy. While I was receiving treatment, I decided that I was going to push forward and launch it anyway because it was something really positive for me to focus on.

I pushed forward, only to be dealt another blow—my divorce. So, with the combination of the two, I had to push this vision aside and really fight for my own life.

Years passed, and I would think, maybe that time has passed. Maybe this wasn’t the right idea. And then I was asked to give a TED talk—and I knew what I wanted to talk about: my experiences of cancer and divorce and finding resilience and grace in the fight of my life. Grit and Grace is the result of that effort.

Before my life crises, I was focused on helping women to fight, or developing grit. After my life crises, I added grace, which I refer to as the sustainability model for success that endures, that the secret sauce to achieving success that won’t burn you out, chew you up and spit you out.

The response to Grit and Grace has been so tremendous that I decided to revisit my ideas about helping women. I’ve got some things in the works. I definitely plan to have a Grit and Grace Day in March 2019. The first half of the day will be focused on how to help women advocate for themselves, and the second half of the day will be focused on how to help women take care of themselves.

WIW: One of the things that you talked about that piqued our interest is the idea that you can't be what you can’t see. What are your tips on how to discover what kind of leader you want to be?

CJ: That’s a great question. You need to look at others who are doing great things that you admire, that resonate with you. They’re having a phenomenal, tremendous impact in the area or the work that they’re doing and this work that’s important to you.

Look at what they do, their path, their journey, what inspires them, what they read. Look at their outcomes, their pathway, and their behavior.

So how do you talk yourself into pursuing opportunities where you don’t see yourself represented in? You have to go really deep within and know that you have just as much right to an opportunity as anyone else. And you really have to believe in the power of your ideas and embrace your uniqueness.

WIW: We're curious about how you get into that headspace, that you have a right to be there and that you can be yourself? As women, we can be labeled as a b@#$& if we’re assertive or incompetent or unknowledgeable if we don’t speak up.

CJ: Attitude and belief, many times, follow behavior. Sometimes, you have to act even if you’re not there in your headspace. So how do you get past the mental baggage and limitations that are imposed on us by others and we impose on ourselves? You don’t wait for yourself to feel differently. You have to just put one foot in front of the other and move forward while even having these feelings of self-doubt and limitation. The more you begin to behave in a certain way, what you feel and believe will follow that.

It’s important to be very selective about your friends and your network, who I call your “power pack”—it matters. That energy is either going to feed into self-doubt, lack, self-limitation, or it’s going to encourage you and feed into the energy that gives you courage to move forward in the face of adversity, obstacles, self-doubt and self-limitation.

WIW: When you think about leadership and the dynamics of male vs. female leadership, what are the nuances and differences, and how can we start to break down those barriers?

CJ: I think women’s style of leadership is more inclusive. We naturally move toward win-win situations and encourage team building. I think women can better tune into multiple dynamics in workspaces and have the emotional intelligence to read a situation.

Women are only able to bring that more nurturing leadership style to the table when they feel comfortable to be themselves. You don’t get the full impact of a woman in leadership if there’s just one woman. It gets a little better with two women. But when you have three or more women, that’s the tipping point for creating a culture for women to feel comfortable enough to be themselves and bring their authentic selves to the table. Certainly, there’s a lot of pressure to conform if you’re the only woman in a work culture that is lead by mostly men.

WIW: Any words of wisdom for younger women to rise up to where they want to be?

CJ: Great question. For younger women, confidence is key and how they show up for themselves and in the workplace. I can’t overstate the need to build confidence.

We’ve all been there—you’re sitting in a room, a topic comes up and you’ve got an opinion or comment or an answer, but you never say it. You just lack the confidence. Meanwhile, the guy next to you says it and he’s brilliant!

So young women need the confidence to go for opportunities, and to advocate for themselves--particularly advocating and negotiating for promotions and a richer job experiences and assignments.

So grateful to Cheryle for sharing her phenomenal and inspirational journey with WeInspireWe. She has been able to break through multiple glass ceilings as a woman and as an African American, and definitely embodies the powerful dynamic of having both grit and grace as a leader. We wish her continued success with Grit+Grace and look forward to celebrating Grit+Grace Day on March 22nd, 2019 in Chicago!

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