Henry attended Annotto Bay Primary school where he continued to hone his drawing skills. In these formative years, he dabbled in life drawing, focusing mostly on the figure. He then attended St. Mary’s High School where he was exposed to other areas in art, focusing on graphic art and imaginative composition.

After leaving high school, he went to Edna Manley College of the Visual and Performing Arts, where he studied Art Education and Painting. He was the top of his classes in drawing classes and ranked in the top five in Painting.

He taught at Papine High School for one year, where he founded the school's art and chess club. It was during this time that he started making comics as a result of his students’ encouragement. He taught himself about the process of making comics and graphic design so as to create his first comic book. Henry considers comic books to be the answer to many reading problems faced by young Jamaicans from the underprivileged environment as well as a useful outlet for them.

Henry spent the next 3 years teaching at Bog Walk High School trying to empower the students in his care to appreciate art. He also founded the art club in this institution. Henry left the teaching profession to pursue his dream of being a comic book artist, and has been contracted to work along with different writers as the artist for their comic books/graphic novels.

He currently owns his own comic book publishing company, with the hopes to encourage young people to draw sequential art and create creative worlds with characters that Afro-Caribbean persons can relate to.