I Hope This Finds You Well Summary, Characters and Themes
I Hope This Finds You Well by Natalie Sue is a 2024 debut novel blending humor and heart in a quirky office romance. The story centers on Jolene Smith, a disgruntled admin worker who, after a mishap, gains access to her coworkers’ private emails.
Armed with this unintended knowledge, Jolene navigates office politics, impending layoffs, and her complicated feelings for the HR guy overseeing her punishment. Along the way, she uncovers unexpected insights into her colleagues’ lives, forcing her to confront her own loneliness and vulnerabilities. This witty and heartfelt novel touches on workplace dynamics, love, and personal growth.
Summary
Jolene Smith works as an administrative assistant in a Calgary branch of Supershops, Inc., a regional retail company. On her 33rd birthday, her career takes a sudden turn when her boss, Gregory, reprimands her for sending an insulting email to a colleague. He assigns her to mandatory anti-harassment training, led by the company’s new HR analyst, Cliff Redmond.
While installing monitoring software on her computer, Cliff accidentally grants her administrative access to all department emails and private messages.
Initially hesitant but curious, Jolene begins snooping through her coworkers’ messages and soon learns that layoffs are imminent.
With her job on the line, she devises a plan to manipulate the situation to her advantage, using the sensitive information she finds in the emails. Meanwhile, outside of work, Jolene’s personal life is in shambles.
She drinks alone most evenings and is haunted by guilt over the death of her best friend, Ellie, in high school—an event Jolene feels partly responsible for.
Her strained relationship with her parents only adds to her sense of isolation, and she avoids their probing questions by pretending her life is more successful than it actually is.
As Jolene’s email snooping deepens, she begins to understand her coworkers on a more personal level.
Armin, a young colleague who often appears uninterested, has a terminally ill mother. Rhonda, nearing retirement, is estranged from her son. Caitlin, whom Jolene has always seen as a rival, turns out to be emotionally fragile.
Armin, in a desperate attempt to cheer up his ailing mother, has told her that he and Jolene are engaged. Jolene, surprised by the situation, goes along with the lie when Armin’s parents come to visit.
Jolene and Cliff grow closer during their shared car rides to work and casual outings, but their budding romance is complicated by Jolene’s deceit and the professional boundaries Cliff insists on maintaining.
Tension peaks when Jolene discovers Caitlin’s fiancé is Kyle, a former bully from Jolene’s high school days. After an awkward encounter at Caitlin’s engagement party, Cliff comforts Jolene, and they share a brief, charged kiss before pulling back due to workplace ethics.
As Jolene continues reading emails, she stumbles upon Gregory’s affair with a woman named Sheila.
Gregory offers Jolene job security in exchange for her silence. However, her snooping ultimately catches up with her when Caitlin, Gregory, and Cliff discover what she’s been doing. Jolene is fired and spirals into a low point, but eventually, with support from her parents and therapy, she begins rebuilding her life.
A year later, Jolene and Cliff, now in a healthy relationship, attend a retirement party for Rhonda. Jolene has a fresh start as a youth counselor, finding fulfillment in her career and friendships, with a hopeful outlook for the future.
Characters
Jolene Smith
Jolene is the protagonist of I Hope This Finds You Well, and her character serves as the emotional heart of the novel. At 33, she finds herself disillusioned with her life, stuck in a dead-end administrative job at Supershops, Inc., and harboring deep-seated loneliness.
Jolene is sharp-witted and often sarcastic, but this exterior hides a vulnerable, guilt-ridden core. She is still haunted by the death of her best friend, Ellie, which occurred during their teenage years—a tragedy Jolene blames herself for.
Her guilt and feelings of failure are compounded by a strained relationship with her parents, which only adds to her sense of isolation. Jolene’s snooping into her colleagues’ emails represents both her curiosity and her desire to control a world that seems uncontrollable.
Her journey from being a bitter, cynical employee to someone capable of real empathy and self-awareness is the novel’s emotional arc. By the end of the story, she begins to accept her imperfections, seek help, and forge more honest relationships, indicating real personal growth.
Cliff Redmond
Cliff, the new human resources analyst at Supershops, plays a pivotal role in Jolene’s story. He is affable, patient, and empathetic, acting as a foil to Jolene’s initially jaded and defensive demeanor.
His role in the novel isn’t merely as Jolene’s love interest; Cliff also represents a moral compass for her. He is the one who installs the software that accidentally gives Jolene access to her coworkers’ emails, indirectly catalyzing her journey toward understanding and growth.
Cliff’s friendly, laid-back nature makes him approachable, yet he is also bound by professional ethics, which complicates his evolving relationship with Jolene. As their feelings for one another grow, Cliff’s internal conflict about workplace boundaries reflects his integrity.
His connection with his family, especially his grandmother and sister, hints at his deep sense of loyalty and groundedness, traits that draw Jolene toward him. Their relationship begins awkwardly, and they face several misunderstandings and professional complications, but Cliff’s gentle persistence and Jolene’s increasing openness lead them to a satisfying reconciliation by the end of the novel.
Armin Habib
Armin is one of Jolene’s coworkers and someone she initially dismisses as lazy and disengaged. However, through her clandestine reading of his emails, Jolene learns that Armin is coping with his mother’s terminal illness—a revelation that makes her reconsider her initial judgment.
Armin’s character represents how little we often know about the struggles of those around us. His relationship with Jolene takes an unexpected turn when he falsely claims they are engaged to comfort his dying mother.
Despite the absurdity of the situation, Jolene agrees to play along, and this shared secret fosters an unlikely bond between them. Armin is a character caught between personal grief and the pressures of maintaining a facade for his family.
His vulnerabilities ultimately help Jolene see beyond surface-level impressions and recognize that everyone is dealing with their own issues. In a way, Armin’s emotional honesty, even through his lie about the engagement, helps push Jolene toward her own truths.
Rhonda Staples
Rhonda, nearing retirement, is another of Jolene’s coworkers. On the surface, she appears to be a well-meaning, if somewhat old-fashioned, employee who leads the party-planning committee and takes her work seriously.
However, Rhonda’s personal life is more complicated than Jolene initially assumes. Jolene learns through her email snooping that Rhonda is estranged from her adult son, Carl, a detail that exposes Rhonda’s deeper emotional struggles.
Despite this, Rhonda maintains a facade of normalcy, throwing herself into work activities and office culture. Rhonda represents a generational divide in the office, often clashing with the younger employees on matters of technology and workplace expectations.
As Jolene begins to help her with basic technical tasks, their relationship softens. Rhonda comes to embody the hidden pains and resilience of older workers nearing the end of their careers.
Her eventual friendship with Miley, Jolene’s young neighbor, shows how Rhonda seeks meaningful connections despite her strained relationship with her own son.
Caitlin Joffrey
Caitlin is Jolene’s workplace rival, a woman who outwardly appears confident, successful, and emotionally secure. She represents the polished, professional ideal that Jolene resents but also envies.
However, Jolene’s snooping reveals that Caitlin’s perfect facade hides insecurities and darker personal issues. Caitlin’s engagement to Kyle, a man who tormented Jolene in high school, becomes a pivotal plot point.
As Jolene learns more about Caitlin, including her emotionally abusive relationship with Kyle, she begins to empathize with her. Jolene even intervenes, encouraging Caitlin to leave Kyle.
Caitlin’s storyline highlights the novel’s theme of judgment versus empathy, as Jolene’s initial disdain for her gives way to genuine concern. Caitlin, like Jolene, is struggling to maintain control over her life, and her vulnerabilities reveal how much of professional success is often a performance.
By the novel’s end, Jolene’s relationship with Caitlin shifts from rivalry to one of mutual understanding.
Gregory Hall
Gregory, Jolene’s boss at Supershops, is a pragmatic but morally questionable figure in the novel. He represents the bureaucratic face of corporate culture, often concerned more with maintaining appearances than with genuine human connections.
Gregory’s affair with a woman named Sheila—discovered by Jolene through her snooping—shows his duplicity, both professionally and personally. He offers Jolene job security in exchange for her silence about the affair, embodying the ethical compromises that often underpin corporate life.
Gregory’s character, while not central to Jolene’s emotional journey, serves as a catalyst for her realization that the workplace is rife with hidden motives, manipulations, and moral grey areas. He is emblematic of the toxic aspects of workplace dynamics that Jolene ultimately tries to escape from.
Jolene’s Parents
Jolene’s relationship with her parents is fraught with tension, reflecting her internal struggles with self-worth and guilt. Her mother is overbearing, often showing up unannounced and asking intrusive questions about Jolene’s life.
Jolene’s interactions with her mother are marked by defensiveness, as she lies about her life to avoid judgment. Her father, on the other hand, is emotionally distant, contributing to Jolene’s sense of alienation.
However, her parents’ visit after she loses her job reveals their underlying care for her, even if their way of expressing it is imperfect. This reconciliation helps Jolene begin to mend her relationship with them, and it marks a turning point in her journey toward self-acceptance.
Their acceptance of her, despite her flaws and setbacks, is a crucial step in Jolene’s healing process.
Miley
Miley, Jolene’s young preteen neighbor, serves as a reflection of Jolene’s younger self. Lonely and somewhat neglected, Miley reaches out to Jolene, and the two form a tentative friendship.
Miley represents the vulnerability and innocence that Jolene has lost over the years but also the potential for emotional connection and growth. As Jolene mentors Miley and sees echoes of her own struggles in the girl, she begins to soften and open up, showing Jolene’s capacity for empathy and care.
By the end of the novel, Miley’s friendship with Rhonda, facilitated by Jolene, suggests a sense of continuity and intergenerational support. In the context of the novel’s exploration of workplace alienation and personal growth, Miley’s character serves as a reminder of the importance of community and human connection beyond the confines of the office.
Themes
The Ethical Complexities of Digital Surveillance and Privacy in the Workplace
“I Hope This Finds You Well” explores the deeply entangled ethical dilemmas that arise from the misuse of technological oversight in a professional setting. Jolene’s unauthorized access to her colleagues’ private emails and direct messages delves into the moral grey areas surrounding digital privacy, data access, and workplace boundaries.
While Jolene initially uses this accidental access for self-preservation, the novel gradually exposes the inherent dangers of surveilling others without consent. As Jolene becomes increasingly enmeshed in her colleagues’ personal lives, her actions raise questions about the responsibility of holding private knowledge and the consequences of exploiting it for personal gain.
The novel illustrates how modern office culture, with its reliance on technology, creates opportunities for both transparency and invasive surveillance, pushing the boundaries of ethical behavior and corporate loyalty.
The Social Alienation and Emotional Disconnect of Modern Office Culture
At the heart of the novel lies a critique of the isolation and loneliness often embedded in contemporary office environments. Jolene’s experience is not just that of a disgruntled worker, but also of someone deeply disconnected from the human connections that office settings claim to foster.
Her coworkers exist more as annoyances or rivals than companions, which is reinforced by her habit of writing hidden email postscripts to vent her frustrations.
This emotional alienation is juxtaposed with her growing reliance on reading her colleagues’ personal correspondence, which, paradoxically, helps her understand and empathize with their struggles.
The novel subtly critiques the superficiality of professional relationships, showing how even when individuals work in close proximity, meaningful connections are stifled by corporate hierarchies, competition, and the impersonal nature of digital communication.
Through Jolene’s journey, the novel asks whether genuine connection can ever be achieved in an environment so governed by pretense and professional expectations.
The Intersection of Personal Trauma and Professional Identity in Shaping Self-Worth
Jolene’s personal history—particularly the traumatic loss of her best friend Ellie—profoundly shapes her present behavior and professional life.
The novel skillfully intertwines Jolene’s unresolved guilt over Ellie’s death with her disillusionment at work, suggesting that the weight of personal trauma can hinder one’s ability to find meaning and fulfillment in a professional setting.
Jolene’s reclusive lifestyle, her drinking habits, and her reluctance to forge meaningful connections with her coworkers all stem from this unresolved grief, and her isolation within the workplace mirrors her emotional isolation.
As she learns more about her colleagues’ personal struggles, Jolene gradually confronts her own vulnerabilities and begins to realize that her professional identity does not need to be defined by her past.
The novel explores the complex relationship between personal trauma and professional self-worth, illustrating how healing often requires confronting deeply buried pain before one can forge a more authentic and rewarding career path.
The Gendered Dynamics of Power, Manipulation, and Workplace Competition
The novel deftly unpacks the subtle and overt ways in which gender influences power dynamics, manipulation, and competition in the workplace.
Jolene’s interactions with her male boss Gregory and her female rival Caitlin highlight how women in professional settings are often pitted against one another while male figures maintain authority and control.
Gregory’s manipulation of Jolene—offering job security in exchange for keeping his affair secret—serves as a stark example of the gendered power imbalance that allows men to exploit their positions while women are forced to navigate moral dilemmas just to keep their jobs.
Similarly, Jolene’s rivalry with Caitlin exposes the competitive undercurrent among women in the office, where professional success is often framed as a zero-sum game.
The novel suggests that this competition, fueled by a patriarchal corporate structure, limits women’s opportunities for genuine collaboration and mutual support. However, as Jolene eventually begins to empathize with Caitlin’s situation, the novel advocates for solidarity and compassion as a means of overcoming these gendered obstacles.
The Role of Corporate Sensitivity Training as a Superficial Band-Aid for Deep-Rooted Workplace Culture Problems
Cliff’s sensitivity training and the anti-harassment lessons Jolene is forced to take are presented as mechanisms meant to foster a healthier work environment. However, the novel subtly critiques these corporate initiatives as often superficial and ineffective.
Jolene’s initial resistance to the training, combined with her growing personal affection for Cliff, showcases how these programs can fail to address the deeper cultural issues within a company.
Rather than fostering genuine change, the training becomes a form of performative discipline—something the company mandates to cover its own liability, without addressing the more systemic problems such as poor communication, toxic competition, and managerial manipulation.
The novel critiques the over-reliance on such bureaucratic procedures to fix inherently flawed workplace dynamics, suggesting that true cultural change requires more than just token policies and compliance seminars. By juxtaposing Jolene’s personal growth with her experience in these training sessions, the novel questions the effectiveness of corporate HR practices when they are disconnected from genuine empathy and understanding.
The Fragile Intersection of Authenticity, Vulnerability, and Office Politics
The tension between authenticity and performance runs throughout Jolene’s journey, as she navigates the often perilous waters of office politics. The novel illustrates how individuals in professional settings are encouraged to present curated versions of themselves, hiding their insecurities, personal struggles, and true emotions behind a façade of competence and detachment.
Jolene’s initial approach to her job is rooted in emotional self-defense, where she hides her frustrations in invisible email notes and maintains a sharp, sarcastic demeanor. However, as she gains access to her colleagues’ private thoughts, she is forced to confront the fragility of her own emotional defenses.
Her gradual realization that everyone around her is also struggling with their own vulnerabilities—Armin’s anxiety about his mother’s illness, Rhonda’s estrangement from her son, and even Caitlin’s insecurities—helps Jolene shed her protective shell. By the novel’s end, the narrative suggests that vulnerability and authenticity, though often dangerous in a political work environment, are essential for building meaningful human connections and escaping the isolation that office culture can create.
The Impact of Personal and Professional Boundaries on Identity and Mental Health
One of the novel’s most significant themes revolves around the boundaries—both real and self-imposed—that define personal and professional identities. Jolene’s obsessive separation of her personal life from her work life is gradually dismantled as she learns more about her coworkers and as her interactions with Cliff blur the lines between the professional and the personal.
This collapse of boundaries forces Jolene to confront not only the emotional baggage she’s been carrying but also the detrimental effects of compartmentalizing her identity. Her mental health, which is already fragile due to her unresolved grief, worsens as her workplace environment becomes a battlefield for manipulation and secrets.
Yet, the novel also posits that the breaking down of these barriers, while painful, is necessary for growth and healing. As Jolene learns to embrace vulnerability and authenticity, she begins to merge her personal and professional identities in a healthier way, seeking a future where she can be honest with herself and those around her.