In Matthew 20:17–28, Jesus turns our ideas of power and success completely upside down. As He predicts His suffering and death, the disciples are still chasing status and position—prompting Jesus to redefine what true greatness really looks like. In this episode, we explore the tension between ambition and humility, the meaning of “drinking the cup,” and Jesus’ radical call to servant leadership.

In this episode, we walk through Matthew 19:22–20:16 and take a closer look at how Jesus challenges the way we think about success, reward, and fairness. From the rich young man who can’t quite let go, to the disciples wondering what following Jesus will really cost them, and finally to the surprising parable of the workers in the vineyard, we see just how different God’s kingdom is from the systems we’re used to.

Jesus invites us to wrestle with some honest questions: What are we holding onto? What do we expect in return for our faithfulness? And how do we respond when God’s grace feels… unfair?

This passage reminds us that following Jesus isn’t about earning our place—it’s about trusting a God who is generous beyond measure, whether we arrive early or late.

In Matthew 19:1–22, Jesus addresses some of the toughest questions people still wrestle with today—commitment, obedience, and what it truly means to follow Him. From conversations about marriage and faithfulness to a powerful encounter with the rich young ruler, this passage challenges surface-level religion and points toward wholehearted discipleship.