I Hope This Finds You Well

1. General Impressions

Gather initial thoughts and broad opinions about the book.

• What were your favorite and least favorite aspects of Jolene Smith’s character? In what ways was she relatable and/or unrelatable?
• What other workplace romances does I Hope This Finds You Well remind you of? How does Sue’s novel compare to these works?
• What were your favorite and least favorite scenes in the novel? What emotional reactions did these scenes elicit, and why?

2. Personal Reflection and Connection

Encourage readers to connect the book’s themes and characters with their personal experiences.

• The novel explores themes of empathy and judgment. Which facets of Jolene’s interpersonal relationships surprised you? Did you relate to how she sees her friends and coworkers?
• Jolene and Cliff become involved even though they’re coworkers. Did this raise any ethical or practical concerns for you? Would you ever pursue a relationship in a workplace setting?
• I Hope This Finds You Well explores alienation, particularly in the context of the workplace. How did Jolene’s vocational experience resonate with your own? 
• The novel explores complex parent-child relationships. Which characters’ familial situation resonated most with you, and why? Did you find some family dynamics more believable than others?
• I Hope This Finds You Well explores notions of integrity and privacy. What moral and ethical questions does Jolene’s accidental email access raise? How did her decision not to reveal the truth about the emails alter your impression of her character? Do you think she should have been fired?

3. Societal and Cultural Context

Examine the book’s relevance to societal issues, historical events, or cultural themes.

• Discussions surrounding mental health, alienation, and isolation in the workplace have become more prevalent since the 2020 COVID-19 pandemic. How do you see Jolene’s experience and the Supershops climate engaging with these sociocultural issues? What answers is Sue providing to questions about work-life balance?
• What critique (if any) does the novel offer of companies’ motivations for adopting anti-harassment initiatives and similar programs? 

4. Literary Analysis

Objective: Dive into the book’s structure, characters, themes, and symbolism.

• How does the Supershops setting develop the novel’s explorations of honesty, alienation, and empathy? How do characters including Jolene, Gregory Hall, Rhonda Staples, Cliff Redmond, Armin Habib, and Caitlin Joffrey each relate to this environment?
• In what ways do the characters’ encounters with hardship connect them? What wider commentary about the human experience is Sue making via these parallels between the characters’ personal lives?
• What is the symbolic significance of Joey the Fern? How is Sue using the fern to further her explorations of interpersonal relationships and workplace culture?
• Compare and contrast the characters’ use of digital and analog communication. What do their emails and sticky notes convey about their characters? How is Sue using these contrasting modes of note-writing to comment on communication broadly?
• Jolene and Armin’s relationship is an example of the “fake dating” trope. What is the thematic and narrative effect of this device in the context of I Hope This Finds You Well?

5. Creative Engagement

Encourage imaginative and creative connections to the book.

• Baked goods are a prominent motif in the novel. If you were going to bake something that captures the spirit of the novel, what would it be, and why?
• Using print magazines and/or newspapers, create a collage that represents the workplace atmosphere and interpersonal dynamics central to I Hope This Finds You Well. Consider how the characters relate to Supershops and each other, as well as how these dynamics relate to digital, analog, and in-person communication. 

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