Rakoffs grandparents fled to the turn of the century when Jews from Latvia and Lithuania and settled in South Africa. The family left the country in 1961 and moved to Montreal. 1967 the family moved to Toronto.
Rakoff graduated in 1982 with high school graduation at Forest Hill Collegiate Institute. In the same year he moved to New York City and began to study at Columbia University, East Asian Studies and Dance. Rakoff spent a year abroad at the School of Oriental and African Studies in London, and received his degree in 1986. In Japan Rakoff worked as a translator; after four months, at the age of 22, he was diagnosed with Hodgkin 's lymphoma. In Toronto he underwent eighteen months long treatment.
In the early 1990s he received a green card, which he made about one of his first newspaper articles. In 2003 he received in addition to its Canadian and US - American citizenship.
2010, while he was writing Half Empty, a malignant tumor was discovered behind his collarbone in Rakoff and he began chemotherapy. He died on 9 August 2012.