How Cheryl Grace Built Her Dream Life And How You Can Too

It’s a Tuesday evening, around 5:30 pm when Cheryl Grace joins our Zoom meeting.

I immediately take in her green & black sweater, pink lipstick, and auburn hair – she’s stylish.

Moreover, her presence has illuminated the virtual room. She smiles, politely greets me, and makes playful banter before we get to business. She’s exactly how the media and those who follow her, describe her.

Cheryl Grace is a highly sought-after executive coach and speaker committed to helping women achieve their dreams unapologetically at work, in love, and at home.

“[these areas] go hand in hand,” she says.

Her ability to coach on home, love, and work comes from personal experiences and 25+ years in corporate America where she was regarded as a powerhouse and a pioneer, who shifted the way the nation regarded Black America’s spending power and cultural influence.

I’m interviewing Cheryl today to learn about her journey in building her dream life, which she refers to as a life of ‘fabulosity’, and to gather some tips that any woman can use to follow in her footsteps.

While Cheryl eventually got it all – a great career, a great husband, and a few other items on her vision board like a cottage by the water; her life hasn’t been perfect.

Like most people, she’s had up and downs in love and her career, but she’s mastered the art of pulling through to get the life she desires.

Here’s how she’s done it and how you can too.

Recognizing Her Power

Cheryl shares that some of the low points in her life include a divorce from her ‘starter husband’ and moments when corporate America stole some of her confidence.

Both experiences, however, taught her important lessons like remembering who she is, and recognizing her power – tools that have helped her get ahead.

“While we were going through the divorce, [my starter husband] would send very negative emails,” Cheryl says. “Every time I read one, I didn’t feel good about myself. Then I thought, okay, I can control what I read. So, I stopped reading his emails.”

At that time, Cheryl realized that she also needed to change her mindset. “Instead of focusing on what I didn’t have, I started focusing on who I was at my core, which was type A personality, and a high achiever.”

With those simple actions, Cheryl was able to begin her journey to getting the life she wanted.

If you’re struggling to recognize your power, Cheryl says to banish naysayers to naysayers’-land and begin writing a list of all your achievements.

“Make a list of everything that you have accomplished in the last month or the last year, or since you got out of college, etc. This gives you the confidence to know what you can do. Show yourself evidence.”

Cheryl stresses that recognizing your power is foundational to getting the life you dream of.

“As women, we tend to talk ourselves out of things before anybody else does. That’s why managing negative internal chatter is important. When you’re operating from a point of internal power, you’re not afraid to ask for what you’re worth. You’re not afraid to go after what you say you want.”

Moving Boldly

When I ask Cheryl how she got into corporate America she replies, “I got bold.”

She tells me that she was working for an NGO when she heard about a position at a television station in Chicago, a community affairs position that rarely came about.

She wanted the job. She says she knew she would be perfect for it. However, by the time she found out about the role, it had been out for months. Realizing that the position would be filled soon she sent a fax to the station in all caps that read:

STOP! DON’T MAKE ANY HIRING DECISIONS ABOUT THE DIRECTOR OF STATION RELATIONS POSITION BECAUSE I’M THE PERFECT PERSON FOR THE JOB AND YOU HAVEN’T TALKED TO ME YET.

Cheryl laughs thinking about it.

The fax was received, and Cheryl was invited to have a quick chat with the general manager who warned her, that two candidates had already been short-listed and the final decision was to be made soon.

Still, Cheryl was determined to put her best efforts forward. She quickly strategized a way to sway the decision in her favour. She spent the days before her meeting preparing a presentation comparing the radio station to its competitors to show what she was capable of.

Her strategy worked. After her meeting, she was offered the job, and that was her start in corporate America.

“I got that job because I got bold. When you have nothing to lose, go for it,” she advises readers.

Leaning into Fear/Discomfort

Moving up in corporate America was not as painless as moving into it for Cheryl.

Cheryl shares that after working for the television station she eventually moved to Nielsen, where she entered as a VP. As she performed well, several positions opened, and her boss encouraged her to apply.

At first, Cheryl declined. The more senior positions were in other cities and after going through her divorce, Cheryl did not want to uproot her son and move to a place where she did not have support.

What’s more, Cheryl had some fears related to these positions.

However, there came a point when her boss told her if she kept passing on opportunities they would stop coming, so Cheryl bit the bullet and took a Senior VP position that was out of her comfort zone.

“I didn’t feel like I was a good fit,” she says about the job. “I didn’t feel like I fit in.”

To be successful in the position, Cheryl learned to manage her lack of confidence by identifying where it was coming from. She realized that she feared not understanding the new space she would be working in. She also feared not fitting in, and that she wouldn’t be as smart as her colleagues who had been in the space for a long time.

When fear is holding you back from an opportunity, Cheryl advises making a list of the things that scare you and then instead of running away, recognize what you have to do to overcome those fears.

“Buy books or sit down and have informational interviews with people who know the space, and who can fill in knowledge gaps if that’s what it’s going to take to make you a little bit more comfortable,” she says.

While she did not feel comfortable in that role, she does say that it was the position she learned the most in. In the end, she was glad that she leaned into the discomfort.

“As women, in particular Black women, we tend to stop ourselves before we even try. I didn’t feel comfortable. So, I wasn’t going to try for it. But it worked out to be one of the best things I’ve done. If I hadn’t had [that role], I never would have started the series of reports on multicultural consumers that is the legacy that I left at Nielsen. So, have faith in yourself.”

While Cheryl is glad for the experience, she also wasn’t afraid to walk away from the role when she felt it was time to move on.

She adds that it’s important to speak up when something’s not working for you, “If the company values you, they’ll find something for you. You just have to make sure that you’re over-delivering.”

Being Intentional

From working at an NGO to moving up at Nielsen, Cheryl says she was intentional about every step of her path.

“I made a pact with myself that every four years, I would either move up or out. So, I would either move up at the organization or the company that I was in, or I would go and find someone who wanted to promote me to the next level [somewhere else]. I was very intentional about that. When you get comfortable, that’s when you should be most worried because that’s probably when you are growing the least.”

For Cheryl, being intentional means planning and taking action to achieve your goals. During our interview, she waves a diary filled with notes at me.

“I’m the vision board queen,” she says.

Cheryl creates monthly vision boards that tie back to her annual vision board. Once her vision boards are done, she sets goals to achieve her life of fabulosity. She says when she gets intentional – putting action behind her goals, that’s when things click. Setting deadlines for her goals is a tactic that has helped her push forward when some visions are falling behind.

She recommends using vision boarding and goal-setting to help you achieve your dream life too.

Throughout her life, Cheryl has felt that there were times that she needed help reaching her goals but often struggled to find it.

Wanting to be the resource she wished she had when she was working her way up, Cheryl has left corporate America and is now working as an executive coach.

When I ask her how coaching makes her feel she tilts her head back and grins.

“It feels amazing. I can’t stop smiling. When my clients, from entry-level up to EVP and beyond, have success, I feel like I’ve had success. Watching them transition from whatever their confidence gaps or knowledge gaps are, is fulfilling. I don’t feel like I’m working anymore.”

Cheryl’s coaching focuses on identifying what’s holding her clients back and then working with them to overcome those barriers to achieve their dream life.

When I ask Cheryl if there’s an ideal client for her program she replies, “Anybody willing to do the work, because it does take work, fabulosity doesn’t happen overnight.”