Book Club Guide

1. Olivia spends much of her life holding everything together for others. What early signs did you notice that she was starting to unravel?
2. How did Olivia's workplace challenges shape her understanding of her own identity and worth?
3. Which betrayal impacted you the most, and why?
4. Discuss the role motherhood plays in Olivia's decisions. How do her daughters influence her resilience?
5. How does the novel explore emotional labor and invisible responsibilities?
6. Which character's arc surprised you the most, Stephen, Brandon, or Allison?
7. What did you think of Olivia's struggle between performance and authenticity?
8. How does Olivia's relationship with Brandon differ from her relationship with Stephen?
9. What did you think of Olivia's relationship with Xavier?
10. Discuss the metaphors of the glass jar and the glass ceiling within Olivia's journey.
11. What do you consider Olivia's true turning point?
12. Which woman's journey resonated with you the most and why?
13. How did the ending reflect Olivia's emotional transformation?
14. If Olivia could speak directly to your group, what would you ask her?

1. When in your life have you stayed in a situation long after you knew it was hurting you?
2. What kept you there?
3. Which part of Olivia's story made you reflect on your own boundaries?
4. Have you ever silenced yourself to keep peace? What did that cost you emotionally?
5. What was the moment in your life when you realized you needed to choose yourself, even if others didn't understand?
6. How did Olivia's experiences mirror the invisible labor you carry at home, at work, or in relationships?
7. What is one belief about yourself that you outgrew or are currently outgrowing?
8. Which scene in the novel made you say 'I've lived that'?
9. If you could go back 10 years and give your younger self advice about love, friendship, or career, what would you say?
10. What did Olivia's healing journey teach you about your own relationship with forgiveness, release, or rebuilding?
11. What surprised you most about how much you related to Olivia, even in the moments she struggled?

These questions invite male readers to reflect on relationships, emotional labor, and the impact of male behavior in women's lives.

1. Which parts of Olivia's story challenged you to think differently about the emotional load women often carry in relationships and families?
2. How did Stephen's behavior reflect patterns you've witnessed in men you know or in your own past?
3. What moments in the novel highlighted the difference between being present physically and being present emotionally?
4. In your relationships (past or present), how have the women in your life supported you during your low points? How did you respond to that support?
5. What did Brandon's character show you about men who choose accountability, growth, and emotional availability?
6. Think of a time when a woman in your life silently struggled while still holding everything together. What signs did you miss at the time?
7. Which character made you consider the impact men have on women's confidence, careers, or mental health?
8. How does the novel influence your view on communication, transparency, and emotional responsibility in relationships?
9. What is one way you now see that men can help dismantle "glass ceilings" or reduce the "glass jar" pressure women carry?
10. If Olivia were someone in your life, a sister, partner, friend, or colleague, what advice would you want to give her and at what point in her story would you offer it?

1. How did Olivia's transformation mirror the challenges many women face while leading teams or households?
2. What moments in the book highlight the unique pressures placed on high-achieving women?
3. Have you ever experienced a "Sherman" in your career, someone who quietly undermined you? How did you respond?
4. In what ways do women in leadership often become default caregivers, even at work?
5. What did Olivia's breaking point reveal about burnout, overwhelm, and emotional labor in leadership roles?
6. How do power dynamics in the workplace affect women differently than men, especially women balancing motherhood?
7. What leadership qualities did Olivia reclaim as she rebuilt her identity?
8. How does retaliation, overt or subtle, shape women's career choices and confidence?
9. If Olivia were mentoring you, what leadership lesson do you think she would emphasize first?