After a successful modeling and construction careers, Cheris Monique evolved into a certified Family Life Educator, confidence coach, and serial entrepreneur who has spent over a decade helping individuals shift from self-doubt to self-belief. She is the owner and director of Jumping Jacks Learning Center, Delaware’s STARS-certified early childhood program. With a family-first approach, the center fosters confidence, creativity, and academic excellence, proudly serving its community for more than 30 years. In recognition of its impact, Jumping Jacks has been honored by the Wilmington City Council for its commitment to children and families.
Cheris is also the founder of Rebuild Your Life (RBYL)—a transformational platform empowering women and entrepreneurs to pivot, grow, and thrive. Through sold-out workshops that blend personal development with practical business strategy, RBYL equips individuals to rebuild their lives with purpose and power.
A two-time author and the host of Steel Toes to Stilettos on YouTube, Cheris engages a growing online community of over 20,000, reaching millions with her motivational, down-to-earth content.
Her journey into fashion began early, sparked by a love for the camera and a dream of seeing herself in magazines, on runways, and on TV. Inspired by a cousin’s success in the modeling world, she pursued her own path—landing roles in One Life to Live and Law & Order, walking in New York Fashion Week (including a show with America’s Next Top Model winner Eva Pigford), and appearing in music videos and print campaigns.
As her modeling career evolved, so did her passion for mentorship. Cheris founded the Ram Role Models Society, a dynamic program for girls ages 7–13 that uses workshops, photo shoots, and fashion shows to build self-esteem through creative expression. This passion for uplifting others now fuels her work as a confidence coach—guiding clients to rebuild their lives with clarity, courage, and consistent action.
Deeply influenced by her mother and inspired by everyday women—especially the real, hardworking moms she follows online—Cheris is a fierce believer that it’s never too late to start over. She is focused on expanding the RBYL community, elevating her work as a confidence coach, and growing her presence as a podcast host and media personality.
Ask anyone who’s worked with her, and they’ll tell you the same thing: Cheris Monique is the real deal. She’s an authentic force—proof that big dreams are possible, that genuine people still exist, and that with the right encouragement, anyone can live their truth boldly and confidently–from the runway to the construction site.