Discussion Questions

In the Monopoly story, Andy rejects a “dollar-for-dollar” exchange because it would cost him the chance to win the game and he wouldn’t get the benefit for two months; where do you recognize Andy’s exact logic in your own financial decisions, and what “game outcomes” feel too important to risk? JumpstartAnother way to ask: Where do you use Andy’s same thinking with your money—choosing what helps you “win” now instead of what pays off later? What results in life feel too important for you to risk?

Jesus’ offer is framed as exchanging “earthly Monopoly money for eternal money” by making “friends…by unrighteous mammon” (Luke 16:9); what does this chapter suggest God is like if He deliberately designed money to be a tool for relationships and eternity rather than mere personal security? JumpstartAnother way to ask: Luke 16:9 says money can be used to make friends for eternity. What does that say about what God is like and what He wants money to be for?

The chapter calls purchases like a $5,000 recreational motorboat “using Monopoly money to buy a plastic Monopoly object”; how does that comparison challenge the way you currently classify “needs,” “reasonable comforts,” and “harmless recreation”? JumpstartAnother way to ask: If buying a $5,000 boat is like using Monopoly money to buy a fake Monopoly item, how does that change what you call a “need,” a “reasonable comfort,” or “just for fun”?

The author lists concrete alternatives for the same $5,000—medical care, supporting an elderly widow, microloans, gospel proclamation, education; if you had to choose only one of those conversions, what would guide your decision, and what would that reveal about what you believe God values most? JumpstartAnother way to ask: If you could turn $5,000 into only one thing (medical care, helping a widow, microloans, sharing the gospel, or education), which would you pick and why? What does your choice show you think God cares about most?

Jesus’ explanation of the unjust steward is applied sharply: money and property are “little things,” and “if we can’t be faithful in such a little thing as our use of money, heaven has no place for us”; what parts of that claim feel threatening or excessive, and how do you reconcile it with your current understanding of grace and assurance? JumpstartAnother way to ask: Jesus says money is a “small thing,” and that if we aren’t faithful with it, heaven has no place for us. What about that feels too harsh, and how do you fit it with grace and assurance?

The chapter argues that all earthly assets are ultimately God’s assets—“what is another man’s”—and only faithful stewardship leads to “what is your own”; how would your daily spending and saving change if you treated every dollar as belonging to God rather than as private property? JumpstartAnother way to ask: If you truly believed every dollar you have belongs to God, what would change about how you spend, save, and give each day?

Paul’s warning (1 Cor. 13:3) is used to block the idea of “buying our way into the kingdom,” insisting that care for the poor must flow from love; what are some subtle, respectable motives for giving (image, guilt relief, control, earning) that can masquerade as love, and how would you detect them in yourself? JumpstartAnother way to ask: What “good-looking” reasons for giving (like image, guilt, control, or earning points) can pretend to be love? How could you spot those motives in yourself?

The chapter claims that “throughout most of Christian history” believers wouldn’t have imagined they were living the kingdom life without helping the poor and visiting the sick and imprisoned; what does that statement expose about modern evangelical markers of maturity (Bible knowledge, church attendance, correct doctrine), and which markers would need to be demoted or redefined? JumpstartAnother way to ask: If Christians used to see helping the poor and visiting the sick or imprisoned as part of real Christian living, what does that say about today’s signs of maturity (Bible knowledge, attendance, correct doctrine)? Which signs might need to matter less or be reworked?

Tertullian’s “compassion spends more in the streets than yours does in the temple” and Julian’s complaint that Christians support “not only their own poor, but ours as well” describe an outward-facing generosity; what would have to change in a typical church budget and in your personal budget for outsiders to notice that same kind of indiscriminate mercy? JumpstartAnother way to ask: Early Christians were known for helping everyone, even outsiders. What would need to change in your church budget and your personal budget for people outside the church to notice that kind of mercy?

John Wesley’s Oxford story ties unnecessary decoration (“pretty pictures for my wall”) directly to a poor girl’s cold and ends with, “How often have you prevented yourself from doing good by purchasing that which you did not need?”—what specific “wall-picture” purchases (or ongoing lifestyle standards) are most likely preventing you from doing good right now, and what concrete change could you make this month that would actually cost you something? JumpstartAnother way to ask: What are your “wall-picture” extras—things you don’t really need—that may be keeping you from doing good right now? What is one change you could make this month that would actually cost you something?