[1][3][4] After graduating from the New York Institute of Technology, Connare began working as a photographer for the Worcester Telegram in Massachusetts and helped establish a Cherokee-language newspaper.

[5] After completing his studies at the University of Reading, he joined Dalton Maag, a typeface design company located in Brixton, London, in 2001.

[5] While working at Dalton Maag, Connare created the Magpie font and designed a font for an update of the Ministry of Sound logo which was originally designed by the artist Chemical X[7] When Microsoft launched Windows 1995, it featured a new program, Microsoft Bob, that included a cartoon that would talk with speech bubbles, and text presented in Times New Roman.

Soon after Connare created Comic Sans, the font was adopted by many notable companies including Apple, BMW, and Burberry.

[9] Comic Sans has been used in multiple applications ranging from newspapers titles and store signs, to the Spanish Copa del Rey trophy and the Pope's photo album at the Vatican.