Heaven Keeps Receipts: Who Stayed & Who Strayed

This study is based on the sermon titled Heaven Keeps Receipts: Who Stayed & Who Strayed by Matthew Maher below.

Sermon Study

In Heaven Keeps Receipts: Who Stayed & Who Strayed, Pastor Matthew Maher of Landmark Church walks us through the closing thoughts of the Apostle Paul in 2 Timothy 4, showing how our faithfulness—and failures—leave a lasting record in heaven. As Paul nears the end of his life, he reflects on who remained loyal and who walked away. Relationships matter deeply in ministry and life, and Scripture reminds us that even the strongest need strong companions. Like David with Jonathan or Jesus with His disciples, enduring presence through trials is a divine gift. Paul longed for Timothy to come quickly, knowing his time was short—his urgency echoes the need for faithful friends who don't flee when life gets hard.

The sermon draws a sharp contrast between those who strayed and those who stayed. Demas, once a fellow laborer, fell in love with the world and abandoned the mission. In contrast, Luke stayed near, Mark found redemption after failure, and Titus proved to be a trustworthy and vital partner in the gospel. Even lesser-known names like Crescens and Tychicus had essential roles. Pastor Matthew reminds us that heaven takes note—not just of who starts with us, but who finishes faithfully. We can't serve both comfort and conviction. Like Demas, divided loyalties will eventually lead us away from Christ. But those who remain rooted in the Word will remain useful to the Lord, no matter how their story began.

Paul also mentions betrayal by Alexander the coppersmith, offering a sober reminder: faithfulness will face resistance. Yet Paul entrusts justice to God, showing how to fight spiritual battles with trust rather than vengeance. Even at the end of his life, Paul values his cloak, books, and parchments—showing that physical needs, intellectual pursuits, and spiritual devotion endure in importance. Heaven Keeps Receipts is a call to examine where we stand—are we finishing well? When trials come, will we stray for the comfort of the world or stay faithful to Christ? In every season, God is watching, rewarding not just the visible labor but the unseen loyalty.

Discussion Questions

  • What does Paul’s longing for Timothy’s presence near the end of his life teach us about Christian companionship and vulnerability in leadership? Follow-up: Who has strengthened your hand in the Lord like Jonathan did for David?

  • Demas forsook Paul because he “loved this present world.” How can we guard our hearts from drifting toward the world’s comforts instead of remaining faithful to Christ? Cross-reference: 1 John 2:15, James 4:4, Matthew 6:24

  • Paul found Mark to be “useful” again despite past failure. What does this tell us about God’s redemptive work in broken relationships? Follow-up: Can you think of someone in your life whom God is calling you to reconcile with or restore?

  • Tychicus, though lesser known, faithfully served behind the scenes. Why is it important to value and encourage those with unseen or “relief pitcher” roles in ministry? Sticky thought: One ploughs, one plants, one pours, one picks—but the Lord gets all the praise.

  • Alexander opposed Paul and “did much harm.” How should we respond when we are hurt or opposed by others within or outside the church? Cross-reference: Romans 12:19, Psalm 62:12 — How do we entrust justice to God without falling into bitterness?

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