Cheris Monique | Sharing The Blueprint On Confidence

Confidence doesn’t come easy. It’s something you learn to build, piece by piece, through experience, intention, and grace. For Cheris Monique, a certified Family Life Educator, confidence coach, and entrepreneur, that process has become both her life story and her life’s work.

As the owner and director of Jumping Jacks Learning Center, a Wilmington, Delaware institution that’s served families for more than three decades, Cheris has built more than just a business, she’s built a legacy. Through her company Rebuild Your Life, she helps women and entrepreneurs rediscover their power, shift their mindset, and create the life they truly deserve. It doesn't stop there. She empowers young women , 7-13, through her mentorship program Ram Role Models Society.

Cheris confirms her many titles and adds, "So when we say rebuild your life, that's real life to me in real time."

The Rebuild Starts Within

Cheris’s journey began with something simple but powerful: a journal. The Rebuild Your Life Journal and Planner wasn’t originally part of her plan. It evolved as she reinvented herself and wanted to create a tool that could help others as journaling had helped her. She began by coaching young girls on self-confidence and realized they needed structure, not just motivation.

The journal combines affirmations, goal-setting, and accountability exercises. It’s undated, so users can pause and resume anytime. Inside are her core pillars (mindset, confidence, and identity), which she says are the foundation for personal growth.

“You have to get rid of the stinking thinking,” she explained. “You have to get rid of the self-sabotage energy."

Each page of her journal and planner is designed to help users find focus, stay organized, and hold themselves accountable.

From Modeling Dreams to Mentorship

Long before she became a confidence coach, Cheris was in front of the camera. She appeared on television in Law & Order, One Life to Live, and even walked the runways of New York Fashion Week, sharing the stage with America’s Next Top Model winner Eva Marcille.

But when life shifted, she didn’t stop dreaming. She pivoted. She says her relationship with God keeps her grounded and guides her through tough times. She takes pride in being the same person “online and offline,” emphasizing the importance of authenticity and integrity.

Even though the Ram Role Models Society is not actively a part of her current structure, she continues to mentor young women on a one-on-one basis.

"You tell them to believe in themselves and build up confidence, (but) they need tools and strategies too."

Steel Toes to Stilettos: A Movement

When Cheris couldn’t find a space that fit her vision, she built one. Her YouTube talk show, Steel Toes to Stilettos, brings together women who share stories of perseverance, purpose, and personal transformation.

The title holds deep meaning. She explains that the name reflects both her personal and professional journey; wearing steel-toe boots during her time in construction and stilettos as a symbol of empowerment and grace. Cheris uses her show to pour into others, helping women see that confidence isn’t about perfection; it’s about persistence.

It also represents a metaphor for life: women must “lace up their boots and put on their hard hats” to face challenges. Cheris hopes to one day evolve Steel Toes to Stilettos into a full talk show or coaching platform.

A Confident Woman Knows Her Worth

Cheris defines confidence not by image, but by intention. She celebrates women who keep showing up for themselves and their families despite challenges, reminding them to give themselves grace and acknowledgment for their efforts.

“A confident woman is a woman who knows her worth. A confident woman is going to go get the job done, regardless of what it looks like."

At 48, Cheris continues to prove that reinvention has no expiration date. She’s currently growing her brand, coaching clients, and developing a Rebuild Your Life app (a digital extension of her planner) that will deliver daily motivation and structure to users worldwide. She also plans to continue growing her podcast and expanding her reach in media and commercial spaces.

The Blueprint on Confidence

Through every season, Cheris Monique has shown that rebuilding isn’t about what you’ve lost, it’s about what you’re becoming. Her story is a guide for every woman who’s ever doubted her next step, proof that faith and focus can take you farther than fear ever will.

Her message is simple, but powerful enough to live by:

“Do not let your circumstances dictate your destiny.”

Because when you learn to rebuild from within, you don’t just find confidence.

You become the blueprint for it.

Check out the complete interview on our YouTube channel.