Book Review: I Hope This Finds You Well by Jessie Chaffee
It’s not every day that a book’s title feels like a personal affront, yet I Hope This Finds You Well had me intrigued from the moment I flipped open its pages. Jessie Chaffee captures a modern workplace dynamic with humor and poignancy, offering a satirical lens on office politics and interpersonal conflicts. However, as I dove deeper, it became apparent that my enthusiasm was misplaced, mainly due to the insufferable protagonist, Jolene.
The premise of the novel, which revolves around the unfurling of a young woman’s life through the lens of everyone’s communications at her workplace, initially piqued my curiosity. Imagine having access to all the whispered gossip, unnoticed tensions, and unfiltered truths that swirl around the cubicles—what a deliciously chaotic concept! I wanted to dive right in and uncover everyone’s dirty little secrets. Alas, the execution fell flat for me, primarily because of Jolene, who is, without a doubt, the most grating character I’ve encountered in quite some time.
Let me be blunt: I cannot imagine a character more deeply oblivious to her own shortcomings and the ramifications of her behavior. Jolene is perpetually self-centered, tactless, and emotionally stunted. Her interactions with her coworkers and neighbors were eye-stabbingly painful to witness. Whether it was her cruel dismissal of a colleague in grief or her utter disregard for a vulnerable young neighbor, every page left me grimacing. There’s a profound lack of accountability in Jolene—which is frustratingly frustrating! Despite sporadic moments of self-awareness, she continually shirks the responsibility of her actions while wallowing in self-pity.
Chaffee’s writing often oscillates between sharp wit and earnest sentiment, though this juxtaposition did little to soften my growing disdain for Jolene. The pacing, while occasionally snappy, often lingered on Jolene’s spiraling bad decisions, making it difficult to empathize with her plight. The moments where she could have shone through—like attempting to help Caitlin escape her toxic boyfriend—were overshadowed by her consistent failures to act decently toward those who genuinely cared for her.
As for subplots and character development, they felt somewhat unsatisfying. I found myself yearning to learn more about Ellie, a character whose death haunts Jolene throughout the story. Instead, Ellie serves more as a tool to propel Jolene’s narrative, leaving me emotionally uninvested. Understanding the depth of their friendship could have enriched the story significantly, but it remained frustratingly superficial—a missed opportunity that only deepened my disappointment.
In full honesty, my initial two-star rating dropped to one as I closed the book, mainly due to my growing frustrations. The bizarre grace everyone else extended to Jolene felt unfounded, rendering her a problematic character.
Despite my vehement dislike for Jolene, I acknowledge that readers who enjoy introspective character studies and nuanced takes on personal accountability might find merit in Chaffee’s narrative. However, if you’re looking for a relatable protagonist or even a redemptive arc, you may want to tread carefully here.
Ultimately, I Hope This Finds You Well will leave you with mixed feelings about human nature—if you can tolerate Jolene’s relentless failings long enough to ponder them. This reading experience, while challenging, sparked passionate reflections on growth and empathy, even if its protagonist was unforgivably flawed. So, if you’re up for a bit of a literary endurance test, perhaps give it a go—just don’t say I didn’t warn you about Jolene!
Discover more about I Hope This Finds You Well on GoodReads >>






