Discussion Questions

Clayton describes York as a “dying city” with lost manufacturing jobs and then traces a founding “spirit of rebellion” in its history; how does that way of reading a city shape what you expect God to do there, and what dangers come with assuming you can diagnose a “spirit behind every city”? JumpstartAnother way to ask: Clayton calls York a “dying city” and says it has a long “spirit of rebellion.” How does that shape what you expect God to do there, and what’s risky about saying every city has a specific “spirit” you can figure out?

When Clayton says the York settlers were “rebels” who defied William Penn’s treaty, what does this raise about how Christians should talk about local history that includes broken agreements and injustice, and how might repentance or restitution factor into “mission to a city”? JumpstartAnother way to ask: If York’s early settlers broke William Penn’s treaty, how should Christians talk about local history that includes injustice? How might repentance or making things right be part of a “mission to a city”?

Clayton’s turning point into long-term city ministry began with copying Dwight Moody—walking streets to recruit fourth graders when none showed up; what does that story reveal about God’s use of ordinary initiative rather than “originality,” and where do you resist that kind of simple, public, potentially awkward obedience? JumpstartAnother way to ask: Clayton started long-term ministry by copying Dwight Moody—walking streets to invite kids when no one showed up. What does that say about God using simple effort instead of being “original,” and where do you avoid that kind of public, awkward obedience?

Clayton repeatedly refused the school building because “we’re not going to go in debt,” then received it essentially for closing costs; what theology of God’s provision is operating here, and how would you test whether this conviction about debt is faithful discipleship or a personal scruple being turned into a rule? JumpstartAnother way to ask: Clayton wouldn’t take the school building because he didn’t want debt, and then he got it for almost nothing. What does this show about how he believes God provides, and how can you tell if avoiding debt is faithful discipleship or just his personal rule?

After 911 reportedly said, “that’s the church block,” Clayton responded by becoming more active—painting a handicap spot, adding a crosswalk, putting up a “no parking” sign; what do these choices suggest about the church’s responsibility for neighborhood order and care, and where does that collide with modern assumptions about staying in your lane? JumpstartAnother way to ask: After 911 called it “the church block,” Clayton painted a handicap spot, added a crosswalk, and put up a “no parking” sign. What do these actions say about a church caring for order and safety in the neighborhood, and why might people today say, “stay in your lane”?

Clayton observes that neighbors were happy with smiles, cleanup, and block parties, but not with street preaching and tract distribution; what does that contrast expose about what kind of “good works” our culture tolerates, and how do you decide when love requires confrontation rather than mere community improvement? JumpstartAnother way to ask: Neighbors liked smiles, cleanup, and block parties, but not street preaching and tracts. What does that show about the kind of “good works” our culture accepts, and how do you know when love means speaking hard truth instead of only improving the community?

In the arson story, Clayton chose not to lie when police asked what they saw, even though “nobody wants to be a snitch”; how should Christians weigh truth-telling, neighbor-love, fear of retaliation, and distrust of police, and what would early Christians likely have assumed about cooperating with civil authorities in a violent neighborhood? JumpstartAnother way to ask: After the arson, Clayton chose to tell police the truth even though nobody wants to be a snitch. How should Christians balance telling the truth, loving neighbors, fear of payback, and distrust of police, and how do you think early Christians viewed working with government in a violent area?

When prisoners argued “cameras are fine but you shouldn’t have called the police,” Clayton asked, “then what do we do with that information?”; what answers would you give to Clayton’s question, and what does your answer reveal about your view of justice, vengeance, reconciliation, and the role of the state? JumpstartAnother way to ask: Some prisoners said cameras were fine but calling the police was wrong, and Clayton asked, “Then what do we do with that information?” How would you answer, and what does your answer show about your view of justice, revenge, forgiveness, and the government’s role?

Clayton grounds courage in Job’s “hedge” and repeatedly says, “nothing can happen… unless God lifts the hedge,” yet he also admits praying “lift the hedge” was “stupid” after his son got hurt; how do you hold together God’s protection, suffering permitted by God, and responsible caution without sliding into either paranoia or presumption? JumpstartAnother way to ask: Clayton says God’s “hedge” protects us, but later regretted praying “lift the hedge” after his son got hurt. How do you believe God can protect people and still allow suffering, while also being wise and careful without becoming paranoid or careless?

Clayton recounts spiritual-warfare practices—singing “Peace Be Still” when approached by unknown men, praying for a “mirror” hedge against satanic attacks, and encounters with demonized people who “couldn’t touch us”; what do these stories teach about the authority of Jesus, and what parts of modern Christianity (including evangelical “safety” culture or skepticism about the demonic) do they challenge in your own instincts and habits? JumpstartAnother way to ask: Clayton tells stories about spiritual warfare—singing when strangers approached, praying for protection from satanic attacks, and meeting people he thought were demonized. What do these stories say about Jesus’ authority, and what beliefs in modern Christianity (like feeling “safe” all the time or doubting the demonic) do they challenge in you?