1. Winston Churchill’s parents largely ignored him when he was a child. How do you think their behavior affected his development? How did your parents’ treatment of you as a child shape your life and outlook?
2. Churchill was brilliant student when the subject interested him but struggled when he was bored. Consider the pros and cons of allowing students to study only what they enjoy.
3. Churchill said that the most miserable experience of his life was being a prisoner of war. Share some times when you have felt trapped and helpless, and what you did about it.
4. Though Churchill recognized he had a speech impediment and worked hard to overcome it, the defect never entirely disappeared. In the end it didn’t affect his popularity or his ability to communicate. How do you deal with your own perceived defects?
5. Several times Churchill insisted he did not believe in God, yet he often invoked God’s name in times of crisis. He daughter believes he was a Christian. What defines a Christian?
6. Like his father, Churchill was chronically in debt. He made a fortune as a writer but spent even more, at one point putting his home up for sale to pay his creditors. Imagine justifying to someone much wealthier than you why they ought to live more frugally.
6. For years between the world wars, Churchill was ridiculed and marginalized for warning of the dangers of German rearmament. Yet he never abandoned his position and never tired of fighting for it. Describe what keeps you going when others don’t believe in you or your vision.
7. When Churchill’s daughter Marigold died he spent little time grieving, but instead forged ahead with his schedule and traveling. Does it honor the deceased more to grieve for a season or to move ahead with a minimum of delay?
8. Churchill essentially had no private life, yet seemed not to mind. His life was the world of politics. Could he have been an attentive family man and still succeeded in his historic accomplishments? List what you believe are the keys to the right balance of family and career.
9. For the most part, Churchill’s wife stayed in the background and quietly supported him, making it her life’s work to make his life easier. How does that compare with the biblical model of a marriage?
10. Churchill was a historic wartime leader who fully knew the cost of war, yet he also said he loved war. Share your ideas about how someone could hold both of these views at the same time, and about what constitutes a just war.
11. Churchill’s son Randolph was a failure by most measures but Churchill never saw it. Was it that he didn’t see, or saw but wouldn’t admit it? Talk about a time when you or someone you know couldn’t – or didn’t – see a serious flaw in another person.
12. Bricklaying, painting, and travel were Churchill’s hobbies and he indulged in them often. How important were they to his success? Compare Churchill’s attitude about hobbies and leisure to your own.
13. Through sheer inspiration Churchill drove a nation to carry on in the face of near impossible odds. What is the nature of inspiration? The word means “God breathed;” how does God figure into Churchill’s inspiring words and deeds?
14. By most measures Churchill stayed on too long as prime minister. Like President Roosevelt, he hid the severity of his illness from the public. What was his justification for disguising his frailty? Was it justified?
15. History positions Churchill as one of the greatest heroes of all time. What one attribute or characteristic do you think was most responsible for this? What is a hero?