Call me Chessi

I am a multitalented, resourceful, and naturally charismatic teacher, wife of a scientist, and mother of two energetic boys, The JAG Brothers.

When I am not teaching, I am most likely singing, crafting, gardening or cooking up a storm for my family.

Meet Chesand Gregory
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My personable and communicative nature lets me easily captivate young minds by engaging them in fun and exciting ways to achieve learning without their awareness. One of my goals is to continue moulding the leaders of tomorrow by writing stories that foster their growth and development while also promoting diversity and inclusivity.

In 2021, my first book, “Did Santa Wear A Mask? A Christmas Adventure With The JAG Brothers”, won the prestigious Mom’s Choice Gold Award, as well as the Parent Tested Parent Approved Award.


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Before writing my first book, I featured as a lifestyle model and depicted Melody’s mother in the American Girl® Doll Company’s book, Melody - No Ordinary Sound.

Singing has been another of my passions since I was four years old.

I have performed as a soloist in music competitions and a cabaret and won medals from the Jamaica Cultural Development Commission.

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Working with Mompreneurs

As a mompreneur, I provide strategic consultations and create customized solutions to maintain family life and balance raising children and business.