59 pages • 1-hour read
We Can Do Hard Things: Answers to Life's 20 Questions
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Discussion Questions
General Impressions
Content Warning: This section of the guide includes discussion of gender discrimination and racism.
Gather initial thoughts and broad opinions about the book.
1. How does the authorial approach of We Can Do Hard Things compare to single-author self-help books you’ve encountered—for example, Elizabeth Gilbert’s Big Magic? What advantages or disadvantages do you see in having multiple perspectives woven throughout?
2. The authors deliberately avoid prescriptive “steps” in favor of ongoing questions and practices. How does this approach affect your engagement with the material compared to more structured self-help frameworks, such as Russ Harris’s The Happiness Trap?
3. What surprised you most about the book’s tone or content? Did any aspects challenge your expectations about what a book on “hard things” would contain?
Personal Reflection and Connection
Encourage readers to reflect on how the book relates to their own life or work and how its lessons could help them.
1. The authors describe authenticity as “excavation” rather than “acquisition.” Reflect on a time when you discovered something about yourself by removing external expectations. How did this process unfold?
2. Which of the book’s 20 central questions (identified in the chapter titles) resonated most deeply with your current life circumstances? What made that particular question feel urgent or relevant to you right now?
3. The book suggests that the closest relationships often require the most forgiveness and conflict navigation. How does this idea sit with you based on your own relationship experiences?
4. Consider the authors’ distinction between “flaccid safety” and “dynamic safety” in relationships. Can you identify examples of each in your own life? What prevents you from moving toward more dynamic safety?
5. The book presents anger as information rather than a character flaw. Reflect on a recent experience of anger: What might it have been trying to communicate about your needs or boundaries?
6. How do you currently respond to the “stab of joy” (452)—those moments when beauty and impermanence collide? Do you tend to numb this bittersweet awareness or lean into it?
Real-World Relevance
Prompt readers to explore how the book fits into today’s professional or social landscape.
1. The authors frequently critique systems like capitalism, patriarchy, and white supremacy as sources of disconnection from authentic self. How does this systemic analysis enhance or complicate traditional self-help approaches that focus primarily on individual change?
2. Consider the book’s publication in 2025 alongside cultural conversations about mental health, work-life balance, and authentic living. Why might the authors have felt the moment was ripe for discussions about “doing hard things”?
3. How might the book’s emphasis on collective well-being and interdependence challenge or support current workplace cultures and professional development approaches?
Practical Applications
Encourage readers to share and consider how the book’s lessons could be applied to their personal/professional lives.
1. The authors suggest creating personal “Touch Trees”—anchoring practices that help you return to yourself. What specific practices or truths could serve as your Touch Trees, and how will you integrate them into your daily routine?
2. Based on the book’s approach to embodied decision-making, identify a decision you’re facing and describe how you might apply the practice of paying attention to physical sensations rather than seeking external consensus.
3. The book advocates for “carefrontations” rather than conflict avoidance. Choose one relationship and outline how you might initiate a caring but honest conversation about an underlying issue.
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