1. Freedom is a central theme of this book. Describe the different ways Jack and Essie express longings for freedom. Do they find it? What does freedom mean for the busy mom struggling to balance priorities? Or the restless husband, still wild-at-heart but committed to his family?
2. Have you, like Essie, ever been overwhelmed with parental responsibilities? Humor can be the best medicine. Music can also lift the spirit. What are some other healthy coping mechanisms for our “mid-life crises”?
3. Do you think Essie should continue to work outside the home? Why or why not?
4. Does Essie resemble the Proverbs 31 woman? Why or why not? How can a 21st century woman fit this description?
5. Ham is living proof that money isn’t everything --- and may not even be in the top five! How does the pursuit of wealth and the accumulation of possessions fail to deliver happiness for Ham? For Jack?
6. How does Hamilton’s pursuit of love and strength, and his ultimate rise to hero, parallel that of his grandson, Cole? In what ways do both characters attempt the improbable, risking life and limb to prove he is a man of noble character?
7. At its heart, Essie in Progress is the story of man’s deep desire, whether young or old, to be found strong --- to be the hero --- and a woman’s longing to be found beautiful --- a princess --- and the artistry of our Creator who reveals the truth of these identities to us as we grow in His likeness. How does John 10:10 summarize this idea? What other verses reflect the heart of this story?
8. Discuss the use of symbols to build imagery of royalty and heroism throughout this book. For Essie and Juliet? For Hamilton, Jack and Cole?
9. What is the nature of the conflict between Ham and Jack? Essie and Pearl? Compare and contrast the reconciliation between Jack and his father and Essie and her mother. How does forgiveness and restoration impact all three generations in the Wells’ family?
10. How does God use family and friends to draw Essie into a closer relationship with her heavenly father? Discuss the role of Ada and Emily in Essie’s spiritual growth.
11. What need did Ham and Ada fulfill in each other’s lives? How can we recognize true love amid so many counterfeits in our culture? Is it ever too late to search for true love?
12. God’s providence is the central theme of the book of Esther, yet direct acknowledgment of God as the book’s true hero is conspicuously absent in the text. In what similar ways is God’s hand actively at work behind the scenes as the real hero in this story as well?
13. This book describes the endless spin of a working mother, homemaker, wife, lover and friend in today’s fast-paced lifestyle. In what way does the book also suggest a Grand Design at work? How does God weave a beautiful tapestry out of the seeming chaos?
14. In a conversation with God over her children’s nativity scene, Essie discovers a “truer identity”. What is it? In what way is every believer a child of royalty?