Discussion Questions
The speaker opens by publicly confessing his post-basketball bragging to Justin Wadle and says it stayed on his conscience for years—what does that kind of confession assume about God’s seriousness regarding “small” pride, and how does it challenge the way Christians often treat boasting as harmless? JumpstartAnother way to ask: What does the speaker’s public confession of “small” bragging say about how seriously God takes pride? How does that challenge the idea that boasting is harmless?
The speaker calls humility “the absence of self,” then quotes C.S. Lewis: “He will not be thinking about himself at all”—how does that definition confront modern Christian habits of constant self-focus (self-image, self-care, personal branding), even when packaged as “testimony” or “ministry”? JumpstartAnother way to ask: If humility means not thinking about yourself much, what does that say about Christian habits like self-image, self-care, or personal branding? How can those show up even in “testimony” or “ministry”?
William Law says humility is “a true and just sense of our weakness, misery, and sin,” not pretending we’re worse than we are—how do you distinguish truthful self-knowledge from false self-hatred, and what would each one look like in a church setting? JumpstartAnother way to ask: How can you tell the difference between honest self-understanding and unhealthy self-hate? What would each one look like at church?
St. Francis’s line—“For what a man is in the sight of God, so much he is and no more”—puts God’s evaluation over human reputation; what practices in your life most tempt you to live as though man’s esteem is the real scoreboard (and how would humility re-order that)? JumpstartAnother way to ask: What parts of your life tempt you to care more about people’s approval than God’s view of you? How would humility change what you chase after?
The speaker says, “Without humility, can one truly follow Christ?” and then anchors it in Matthew 18 (“unless you…become as little children”); what do you think Jesus is making non-negotiable about entering the kingdom, and why is that hard for competent, accomplished adults? JumpstartAnother way to ask: What is Jesus saying you must have to enter the kingdom in Matthew 18 (becoming like a child)? Why is that so hard for successful adults?
In the Naaman story, Naaman expects a dramatic personal encounter (“he will surely come out to me…wave his hand”) but gets a messenger and a simple command—where do you see your own “Naaman expectations” about how God should deal with you, and how might those expectations be rooted in pride? JumpstartAnother way to ask: Where do you expect God to treat you in a “special” or dramatic way, like Naaman did? How might that expectation be connected to pride?
The speaker highlights the servants’ compassion and willingness to contradict Naaman (“My father, if the prophet had told you to do something great…”); what does that moment suggest about the kind of community humility creates, and how would an early Christian church have practiced this kind of truth-telling across rank and status? JumpstartAnother way to ask: What do Naaman’s servants teach us about how humble people speak the truth to each other? How might the early church have done this across different ranks or social status?
William Law warns that pride can “grow as well upon our virtues as our vices,” especially for people making “advances in a pious life”—what are realistic examples of pride feeding on obedience, sound doctrine, separation from the world, or “being more biblical,” and how do those show up in conversations about other churches? JumpstartAnother way to ask: What are some real ways pride can grow from doing “good” Christian things like obedience, right beliefs, or being “more biblical”? How does this show up when people talk about other churches?
The speaker argues we learn pride through childhood praise, honor rolls, patriotism (Superman’s “American way,” the Pledge of Allegiance), and even church identity claims (“one true church,” “forefront of God’s kingdom”); which of those forms of pride feels most “normal” to you, and what would repentance look like in concrete terms rather than just a new opinion? JumpstartAnother way to ask: Which kind of pride feels most normal to you—school success, patriotism, or church identity? What would real repentance look like in actions, not just changing your opinion?
The speaker says overcoming pride involves daily repentance and praying specifically for humility, because you can’t “constantly pray” for a virtue while living contrary to it; what would a daily, specific humility-prayer sound like for you, and what changes would it force in the way you talk about your family, your achievements, your nation, or your spiritual life? JumpstartAnother way to ask: What would a short, daily prayer for humility sound like in your own words? What would it change about how you talk about your family, your wins, your country, or your spiritual life?