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Cautiously Pessimistic
An intimate and enlightening no-holds-barred memoir that uncovers the many unexpected details of dying, Cautiously Pessimistic is one woman’s personal account of her husband’s death and what it means to die in the public eye.
Cautiously Pessimistic is both deeply moving and funny, as it recounts McGee’s husband’s diagnosis of brain cancer and the eight months leading up to his death. It is told in the first person and through posts from Facebook and Twitter, text exchanges, and email. Alternating chapters tell the story of McGee and her husband’s tumultuous early relationship, through the use of excerpts from journals and letters. Throughout the narrative the presence of the tightly knit St. John’s arts community is strongly felt. The etiquette of offering condolences on social media is examined in an afterword by the author.
Cautiously Pessimistic is both deeply moving and funny, as it recounts McGee’s husband’s diagnosis of brain cancer and the eight months leading up to his death. It is told in the first person and through posts from Facebook and Twitter, text exchanges, and email. Alternating chapters tell the story of McGee and her husband’s tumultuous early relationship, through the use of excerpts from journals and letters. Throughout the narrative the presence of the tightly knit St. John’s arts community is strongly felt. The etiquette of offering condolences on social media is examined in an afterword by the author.
- GenresMemoir
216 pages, Paperback
Published June 10, 2025
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Displaying 1 - 4 of 4 reviews
March 16, 2026
5★
I read this book last year, but as it was announced today that Cautiously Pessimistic is one of the finalists for the 2026 Winterset Award, I wanted to come back and say how beautiful this memoir was. I’ve found myself thinking about it multiple times since I first read it. It is actually still on my nightstand as I haven't wanted to put it to rest on my shelf just yet.
Debbie McGee recounts the story of meeting her husband, Gerry Porter, as young arts workers in St. John’s in the 1980s. That story is told alongside the story of his diagnosis and later death from brain cancer in 2016. The memoir moves back and forth between these two periods gracefully.
McGee draws on personal journals, emails, and online posts to tell the story of the eight months following her husband's diagnosis. It’s one of the most moving things I have ever read. Her telling is unflinching. She shares the good, the bad, and everything in between with the reader. I will say that the same honesty that makes this memoir so touching may also make it difficult reading for those who have had loved ones with serious illnesses.
The backdrop of the St. John’s arts community adds another layer to the memoir. As someone who knows many artists and arts workers, I am familiar with that community. While I do not live in St John's, it was fascinating to see both the similarities and the differences compared with today.
Community now exists both in person and online, and this memoir also shows the complicated side of that. Well meaning people online can feel a closeness to a situation that sometimes overwhelms the family actually living through the grief. It has made me reaccess how I have interacted with the internet.
This is a deeply generous book. Honest, painful, and beautiful. I’m very glad to see it recognized.
I read this book last year, but as it was announced today that Cautiously Pessimistic is one of the finalists for the 2026 Winterset Award, I wanted to come back and say how beautiful this memoir was. I’ve found myself thinking about it multiple times since I first read it. It is actually still on my nightstand as I haven't wanted to put it to rest on my shelf just yet.
Debbie McGee recounts the story of meeting her husband, Gerry Porter, as young arts workers in St. John’s in the 1980s. That story is told alongside the story of his diagnosis and later death from brain cancer in 2016. The memoir moves back and forth between these two periods gracefully.
McGee draws on personal journals, emails, and online posts to tell the story of the eight months following her husband's diagnosis. It’s one of the most moving things I have ever read. Her telling is unflinching. She shares the good, the bad, and everything in between with the reader. I will say that the same honesty that makes this memoir so touching may also make it difficult reading for those who have had loved ones with serious illnesses.
The backdrop of the St. John’s arts community adds another layer to the memoir. As someone who knows many artists and arts workers, I am familiar with that community. While I do not live in St John's, it was fascinating to see both the similarities and the differences compared with today.
Community now exists both in person and online, and this memoir also shows the complicated side of that. Well meaning people online can feel a closeness to a situation that sometimes overwhelms the family actually living through the grief. It has made me reaccess how I have interacted with the internet.
This is a deeply generous book. Honest, painful, and beautiful. I’m very glad to see it recognized.
November 23, 2025
Gut wrenching and illuminating. Anyone who has lost someone will connect with this book and will learn from it.
July 1, 2026
Every year, I pick up copies of the three finalists for the BMO Winterset Awards, attending the event, held at the Rooms, where the authors read aloud from their books. I choose which one to read first based on which book speaks to me the most from the readings.
I was greatly interested in reading about the St. John's arts scene in the 1980s and the way that Debbie read from her book with great enthusiasm had me hooked.
St. John's is indeed a small place, as I was reading I realized I knew a few people that were close in Debbie's inner circle.
I thought this book was a beautiful book.
I compare reading this book to having recently digitized a friend's family VHS collection. A friend whose father had passed the same year as Gerry, and she had never seen what was on those tapes. It was such a vulnerable experience that I was grateful to have gone through. I, not knowing anything about the family and their dynamics, experience their life through multiple years. It was raw, and it was honest. It was beautiful, and sad.
Lastly, the book was great to reflect on the fragility of life and grief.
I was greatly interested in reading about the St. John's arts scene in the 1980s and the way that Debbie read from her book with great enthusiasm had me hooked.
St. John's is indeed a small place, as I was reading I realized I knew a few people that were close in Debbie's inner circle.
I thought this book was a beautiful book.
I compare reading this book to having recently digitized a friend's family VHS collection. A friend whose father had passed the same year as Gerry, and she had never seen what was on those tapes. It was such a vulnerable experience that I was grateful to have gone through. I, not knowing anything about the family and their dynamics, experience their life through multiple years. It was raw, and it was honest. It was beautiful, and sad.
Lastly, the book was great to reflect on the fragility of life and grief.
June 29, 2026
Newfoundland-based author remembers her husband, recounts their history and his passing from cancer. She includes some social media posts
Displaying 1 - 4 of 4 reviews