Discussion Questions

Clayton said moving into York was partly a “demonstration that you can be faithful living in the city”; what does that reveal about what God expects of His people when circumstances feel spiritually risky, and how does that challenge the way you make housing and career decisions? JumpstartAnother way to ask: Clayton said moving to York showed you can stay faithful in a city. What does that say about what God expects when a place feels spiritually risky, and how should it affect your housing and job choices?

Clayton connected early formation (“Train up a child…”) with appreciating city mission work; what specific “little comments” or home assumptions do you think most shape a child’s view of outsiders, and how might that line up—or conflict—with God’s desire to form humility and love? JumpstartAnother way to ask: What small comments or “normal” ideas at home shape how kids think about people who are different from them? Do those messages match what God wants to grow in us—humility and love—or fight against it?

Clayton joked that he’d “pray for” people who never want to live in a city because Revelation pictures God’s people entering a holy city; how does the Bible’s positive use of “city” (including New Jerusalem) confront the reflex to equate “city” with “danger” or “worldliness”? JumpstartAnother way to ask: If the Bible ends with God’s people in a holy city, how should that change the way we think of cities as only dangerous or worldly?

Clayton argued that living in the city was historically the safer norm for most of human history and that the “safe country” idea is a recent American reversal; how should Christians decide what “wisdom” looks like when cultural instincts contradict long-standing human patterns and biblical imagery? JumpstartAnother way to ask: If our culture says the country is safest but history and the Bible often picture cities positively, how should Christians decide what “wisdom” really is?

Clayton challenged common assumptions with statistics (who lives in cities, who receives welfare, farm subsidies as welfare); what does it suggest about the human heart that we so easily label “those people,” and how might God want to expose and heal that in the church? JumpstartAnother way to ask: What does it show about our hearts that we quickly label others as “those people” when we hear certain statistics? How might God want the church to face and heal that?

Clayton reframed “crime” by comparing murders with OSHA-related deaths and street theft with embezzlement that goes unreported; how does this discussion complicate the way you define “sin that’s out there,” and what kinds of wrongdoing do you personally find easiest to excuse because they look respectable? JumpstartAnother way to ask: How does comparing street crime with hidden “respectable” crimes change what you think of as “sin out there”? What wrong actions do you find easiest to excuse because they look normal or successful?

Clayton confessed that his “cheerleading for city missions” sometimes made others feel “not quite as spiritual”; what does that confession teach about zeal, pride, and motives in ministry—and how can a church advocate for costly obedience without creating a new status hierarchy? JumpstartAnother way to ask: What can we learn from Clayton saying his passion for city missions made others feel less spiritual? How can a church call people to hard obedience without creating a prideful ranking system?

Clayton told the story of getting an 800 number so youth could call without cost, and later concluded, “be intentional wherever you are… but be strategic, go where the needs are”; what would “intentional” and “strategic” obedience look like in your actual weekly rhythms rather than in ideals? JumpstartAnother way to ask: What would it look like for you to obey God on purpose in your normal week, not just in big plans? And what would it mean to be strategic—going where needs are greatest—in your real schedule?

Clayton described city people saying of Mennonites, “I didn’t think they let you out,” and also said many assume you must be “born Mennonite”; what early-Christian assumptions about conversion and belonging (welcoming strangers, forming a new people) challenge an ethnic or cultural understanding of church? JumpstartAnother way to ask: How do early Christian ideas about welcoming outsiders and becoming a new people challenge the idea that church is mainly for one culture or for people “born into it”?

Clayton claimed “most Mennonite churches are not friendly churches,” gave the “Mennonites have eye problems” staring example, contrasted it with how Mormons “swarmed” visitors, and tied it to winsomeness, asking questions, and his mom’s warning: “People that you make fun of, you will never win for Jesus”; what concrete changes would have to happen in your congregation (after-service patterns, cliques, humor, listening) for strangers to feel honored as image-bearers rather than inspected as outsiders? JumpstartAnother way to ask: What specific things would need to change in your church (how people greet, cliques, jokes, listening after service) so visitors feel respected and welcomed, not stared at or treated like outsiders?