Gather initial thoughts and broad opinions about the book.

1. How did Brown’s personal stories and vulnerability throughout the book affect your reading experience? Have you read other self-help books that employ this level of authorial disclosure, such as Brown’s later work Daring Greatly? How do their approaches compare?

2. What was your initial reaction to Brown’s definition of wholehearted living as “engaging in our lives from a place of worthiness” (2)? How did your understanding of this concept evolve as you read the book?

3. Which of the 10 guideposts resonated most strongly with you, and why?

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

1. Brown discusses how shame thrives in secrecy. Do you agree? Has there ever been a time when sharing a difficult experience helped you process shame? What made it possible for you to be vulnerable in that moment?

2. The book explores the difference between fitting in and belonging. When have you experienced this distinction in your own life? How did it shape your understanding of authentic connection?

3. Consider Brown’s discussion of creativity and comparison.