Jo-Ann Oosterman is a graduate of The Humber School for Writers where she studied under the mentorship of David Adams Richards and received a Letter of Distinction for "superior writing merit" after completing the first draft of Tom's Story. She is also a graduate of the Adult Enrichment Program at the University of Ottawa.

The author has written and produced two documentary films about homeless people who chose life on the streets rather than staying in the shelters. She left the world of graphic design to study addictions and psychology, partly because her youngest brother died of an overdose. As the result of her study and work, she felt drawn to, and most comfortable with, people who were marginalized due to addictions, HIV, homelessness, mental illness, childhood trauma and abuse. She wrote Tom's Story over a sixteen-year period from 1998 to 2014 when she had a close and often complicated friendship with Tom Hogan. Tom was an Ojibwa man who was a self-described chronic alcoholic. He was perpetually homeless, could tell a story like nobody's business, and he could paint as well as Norval Morrisseau. Sitting on street corners bearing witness to Tom's life and stories helped Oosterman find meaning in her own life