Apprenticed for eight years to drummers Brandon Douglas and Rob LaRose, Kevin released a poetry debut hailed as "among the most promising poetic projects to come out of Canada in recent years" (Johnstone), a "sublime poetic debut" (Lockhart) "read with admiration" (Coetzee), "at times ... minimal ... at others ... encyclopaedic" (Crymble), "bursting from the pages in an oceanic radicalization of empathy, grief and utter fucking joy in livingness and language" (Bennett) "no poetry lover should be without" (Paré). 

      Kevin arrived to port, with scholarships, to study "Ship-building" and "Navigating by Constellation" to find the courses being taught by bearded barnacles. Before hoisting sail, he was fortunate to organize and host five years' worth of community arts events, LOMP and 42 x 81; workshop with novelist Larry Garber and poet Madeline Bassnett; dialogue with scholars Joel Faflak and Kate Stanley; interview poets Canisia Lubrin, Susan Elmslie, Roxanna Bennett, David White, Karen Houle and local artists like Angie Quick, and Derek Boswell; train intensively with the late Ian Watson, a fine actor; and play lead parts written by Sophocles, Shakespeare, and David Ives on local stages.

      With support from the London Arts Council, Ontario Arts Council, and Canada Council for the Arts, Kevin installed one group and three duo art exhibitions (with The Arts Project, McIntosh Gallery, Westland Gallery, and Centre [3]); directed and produced thirteen short films; and published poetry, dialogue, and criticism with dozens of outlets, most notably The Fiddlehead, The Devil's Artisan, and Centred Magazine. During this period, he lived in Serbia, Finland, France, Denmark, Brazil, and Japan. ​​

       As an editor and workshop leader, Kevin has supported dozens of prominent Canadian writers for the page, stage, and screen, including screenwriter and playwright Jack Copland—"working with Kevin has undoubtably made me a better writer"—academic and poet David Janzen—"Kevin Heslop is a master in the art of the workshop"—second-career therapist and poet Shannon Arntfield—"because Kevin's mind and work are expansive, so was the process; because he is skilled, incisive, and compassionate, so was his feedback."—novelist Erica McKeen—"Kevin senses intuitively where your work is going and provides suggestions that feel like they came straight out of your own head"—poet and academic Shelly Harder—"the possibilities Kevin sees in my work open up space for me to play in, and my writing becomes both more precise and more expansive in response to his unwaveringly detailed, sensitive, and thoughtful feedback"—and emerging leaders in industry like Peter Francis, CEO of Revolve Surgical—"as chief executive of a medical robotics company, I know that storytelling is fundamental. I chose to work with Kevin because I know that when the stakes are highest, you want a human in the driver's seat. I recommend his services every chance I get."

      In 2025, Heslop made his home in São Paulo, Brazil, training under Mateus Filellini of Rolling Jiu-Jitsu Academy and Mário Henrique of the Maharishi European Research University while in residency with Teat(r)o Oficina. He returned to Canada in September to represent Canadian publishers and authors at TIFF and tour his next book along with author Joanna Cockerline. Here is coverage of their tour.

     Kevin's current creative work includes two miniseries, Death Doctor and White Ribbon; a sophomore poetry collection, here lies the refugee breather who drank a bowl of elsewhere (ed. Dominique Béchard, Biblioasis, 2027); a sophomore non-fiction collection, Craft, Consciousness: Dialogues about the Arts (ed. Michael Mirolla, Guernica Editions, vol. 1 2027); a debut feature film (with Teat(r)o Oficina); a September 2026 Canadian tour of his next book, The Writing on the Wind's Wall: Dialogues about 'Medical Assistance in Dying'; and translating from the Danish the extant oeuvre of his ancestor, lyric poet Ambrosius Stub.