1. In the opening chapter, the turbulent times in which John Bunyan lived are described. Can you think of other times when Christians have lived amidst violence and persecution? How do they compare to the times in which Bunyan lived?
2. As a young man, John Bunyan's time in school was rather limited. Yet, like Abraham Lincoln (who also had little formal education), Bunyan went on to do great things. Can you think of other important people who have overcome obstacles like this in their lives? What does this say about them?
3. John Bunyan appears to have been drafted into the army when he was barely beyond his mid-teens. Can you think of other people whose early life experiences were shaped by war? How did these experiences affect them? How do you think John Bunyan's wartime experiences affected him?
4. After his time as a soldier, Bunyan was a restless young man who sowed some wild oats and gave little thought to spiritual things. What are some of the challenges of helping young people to give serious thought to matters of the heart and soul? How do we come alongside them to help them discover their life's purpose?
5. Evidence suggests that John Bunyan struggled with depression at times in his life. Churchill also wrote of moments when he wrestled with depression, calling it his "black dog." How important do you think it is to deal honestly with such challenges? What are some ways to seek healing and recovery from depression?
6. John Bunyan had a great friend in John Gifford, a man who had fought on the opposing side during the English Civil War in which Bunyan fought. What does this say about the power of grace to bridge seemingly insurmountable differences?
7. John Bunyan wrote The Pilgrim's Progress while in prison. Many other Christians have written important books or documents while in prison--one thinks of Martin Luther King Jr's Letter from Birmingham Jail. What does this tell you about the ways in which faith can shine amidst suffering?
8. Many books and many writers describe life as a journey. What books and writers do you think of when you think of life as a journey? How have they made you think? Do you think it is important to see life in this way?
9. Women were an important guiding influence at key moments in Bunyan's life. Lord Shaftesbury, the great English social reformer, said that he owed his conversion to his childhood governess, Maria Milles. Many other leaders, Christian and non-Christian alike, owed a great debt to the women in their lives. Who are some that you are familiar with? What does this teach us about the ways that kindness and love, in subtle or perhaps in more profound ways, shape the lives of those around us?
10. Many famous writers, including C.S. Lewis, have spoken with great appreciation for the ways in which The Pilgrim's Progress is an high adventure story. Does The Pilgrim's Progress speak to you in this way? If so, how?
11. The Pilgrim's Progress has added many famous phrases to the language--"the slough of despond" and "Vanity Fair" to name two. What are some of the names, phrases or places in this allegory that stand out in your memory?
12. John Bunyan often displayed great courage in his life. Who are some leaders and writers that make you think of courage when you think of them?
13. The Pilgrim's Progress influenced Abraham Lincoln's development as a writer. Can you think of other works of literature that had shaped the life of an important person? What books are they? Who did they influence?
14. Bunyan's deep appreciation of nature shines through in his writings. This can be said of many other writers. What writers come to mind when you think about this? What do you like best about the ways nature is described in The Pilgrim's Progress? What about other writers and their books?
15. Often, a great work of literature makes us think about things we had never considered before? What has The Pilgrim's Progress made you think about that you had never considered before?
16. The Pilgrim's Progress has proved an inspiration for many down through the centuries. What things about John Bunyan and his great book have inspired you?