Learning to Lose Well: Take Up Your Cross

Jesus meets His disciples at Caesarea Philippi, surrounded by false gods, the so-called Gate of Hades, and all the darkness that place represented. Peter has just confessed, “You are the Christ, the Son of the living God,” and Jesus has told him that he is a rock who will be part of the church Christ builds to carry light into dark places. Then Jesus shifts gears and says that He must go to Jerusalem, suffer, be killed, and rise on the third day.

Peter cannot handle it. Peter hears suffering and death, and apparently misses the resurrection. Peter wants a Messiah who conquers Rome, restores Israel, and makes everything go up and to the right. Jesus calls Peter a stumbling block because Peter has his mind set on the things of man, not the things of God. Peter has bought into a theology of glory, the idea that if somebody does faith right, then life will turn out great.

The theology of glory still sounds good to broken people. The if-then god promises that if somebody worships enough, gives enough, or behaves well enough, God will make life easy, prosperous, and safe. Jesus does not make that promise. Jesus tells His disciples that He came to suffer and die because this world is broken, and His people will keep dealing with that brokenness until He returns or calls them home.

Christ calls His people to lose their minds, meaning they must lose the false way of thinking that says God owes them an easy life. Christ calls His people to deny themselves, take up their cross, and follow Him, not because following Him keeps pain away, but because He walks through pain with them. Loss still comes. Water can pour through a house. A phone call can bring news that a father is dying. A brother or sister can confront sin. Death can take somebody loved deeply.

The cross gives loss a different ending. Jesus lost His life to save His people’s lives. Jesus suffered and died so that sin, sickness, shame, and death would not have the final word. His resurrection means that every hard road is headed toward His victory. His grace meets His people on their knees at the foot of the cross, redeems them again, and makes them whole again.

Romans 12 flows out of that gift. Genuine love, hatred of evil, service, celebration, and weeping with those who weep do not earn God’s love. Christ has already given everything. A young man’s death from cancer brings real tears and real loss, yet Christ’s victory means death does not get the last word. Jesus never lets His people go. Therefore, those who are saved can take up their cross and follow Him, learning to lose well because Jesus has overcome.

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Key Takeaways

• 1. Lose the theology of glory The theology of glory treats God like an if-then transaction: faithful behavior in exchange for a comfortable life. Jesus confronts that thinking in Peter because the Messiah’s path runs through suffering before resurrection. Faith does not control God or insulate anybody from a broken world. Faith clings to Christ when the world does not go the way it ought to go. [44:19]
• 2. Christ suffers before He conquers Jesus does not stumble into suffering as though the cross were an accident or defeat. Jesus must go to Jerusalem because His death is the way He saves sinners from eternal suffering and death. His resurrection is not a footnote after pain but the victory that gives suffering its limit. Christ’s people follow a crucified and risen King. [39:50]
• 3. Loss does not mean abandonment Broken homes, dying parents, painful confrontation, sickness, and grief can make it feel as though everything is crashing down. Christ does not promise that His people will avoid those losses. Christ promises His presence in the middle of them and His grip that will never let them go. The cross proves that God has entered suffering rather than standing far away from it. [47:18]
• 4. The cross teaches believers to lose well Losing well does not mean pretending loss is small or refusing to weep. Losing well means coming to the foot of the cross and receiving the grace of the One who has already overcome death. Christ gives His righteousness, calls His people children of God, and anchors their hope beyond every present defeat. His victory makes endurance possible without making sorrow unreal. [49:12]
• 5. Genuine love flows from grace Romans 12 does not become a ladder for earning more of God’s love. Christ’s finished work frees His people to love sincerely, hate evil, serve one another, celebrate, and weep with those who weep. Christian love becomes especially visible when it stays near suffering people instead of offering easy answers. Grace creates the kind of love that carries another person’s grief.
  
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Youtube Chapters

• [00:00] - Welcome
• [32:22] - Football Season and Learning to Lose
• [34:55] - Coaching Kids Through Wins and Losses
• [37:34] - Losers Finders in Matthew 16
• [38:11] - Caesarea Philippi and the Gate of Hades
• [39:50] - Jesus Foretells His Suffering and Death
• [41:12] - Peter Rebukes Jesus
• [42:20] - Get Behind Me, Satan
• [43:23] - Losing the Theology of Glory
• [46:38] - Taking Up the Cross in a Broken World
• [48:23] - Jesus Invites His People to Lose Well
• [49:12] - Grace at the Foot of the Cross
• [51:45] - A Young Man Who Lost Well
• [55:10] - Living in Christ’s Victory

Bible Reading

Matthew 16:21–26

21 From that time Jesus began to show his disciples that he must go to Jerusalem and suffer many things from the elders and chief priests and scribes, and be killed, and on the third day be raised. [39:50]

22 And Peter took him aside and began to rebuke him, saying, “Far be it from you, Lord! This shall never happen to you.” [41:12]

23 But he turned and said to Peter, “Get behind me, Satan! You are a hindrance to me. For you are not setting your mind on the things of God, but on the things of man.” [43:23]

24 Then Jesus told his disciples, “If anyone would come after me, let him deny himself and take up his cross and follow me.” [46:38]

25 “For whoever would save his life will lose it, but whoever loses his life for my sake will find it.” [47:18]

26 “For what will it profit a man if he gains the whole world and forfeits his soul?” [48:23]

Romans 12:9–15

9 Let love be genuine. Abhor what is evil; hold fast to what is good. [49:51]

10 Love one another with brotherly affection. Outdo one another in showing honor.

11 Do not be slothful in zeal, be fervent in spirit, serve the Lord.

12 Rejoice in hope, be patient in tribulation, be constant in prayer.

13 Contribute to the needs of the saints and seek to show hospitality.

14 Bless those who persecute you; bless and do not curse them.

15 Rejoice with those who rejoice, weep with those who weep. [21:04]

Matthew 16:13–20

13 Now when Jesus came into the district of Caesarea Philippi, he asked his disciples, “Who do people say that the Son of Man is?”

14 And they said, “Some say John the Baptist, others say Elijah, and others Jeremiah or one of the prophets.”

15 He said to them, “But who do you say that I am?”

16 Simon Peter replied, “You are the Christ, the Son of the living God.” [39:14]

17 And Jesus answered him, “Blessed are you, Simon Bar-Jonah! For flesh and blood has not revealed this to you, but my Father who is in heaven.”

18 “And I tell you, you are Peter, and on this rock I will build my church, and the gates of hell shall not prevail against it.” [39:35]

19 “I will give you the keys of the kingdom of heaven, and whatever you bind on earth shall be bound in heaven, and whatever you loose on earth shall be loosed in heaven.”

20 Then he strictly charged the disciples to tell no one that he was the Christ.

Observation questions

1. What had Peter just confessed about Jesus before he strongly objected to Jesus’ suffering and death?
2. What parts of Jesus’ future does He name in Matthew 16:21, and which part seems hardest for Peter to hear? [40:19]
3. What reason does Jesus give for calling Peter a hindrance or stumbling block in verse 23?
4. In Romans 12:9–15, what actions describe genuine love, especially toward believers who are suffering? [55:10]

Interpretation questions

1. Why would Peter expect the Messiah to conquer and restore Israel rather than suffer and die? How does Jesus’ resurrection change the meaning of His suffering? [41:48]
2. Jesus says Peter’s mind is set on “the things of man” rather than “the things of God.” What kinds of expectations about God can make suffering feel like proof that God has failed or left someone?
3. What does it mean to take up a cross and follow Jesus if it does not mean earning salvation or looking for pain? [56:03]
4. Romans 12 calls Christians both to rejoice in hope and to weep with those who weep. How can both responses be true when a Christian family is grieving a real and painful loss? [53:43]

Application questions

1. Where does the “if-then” view of God show up most easily: “If I pray enough, obey enough, give enough, or do faith well enough, then life will go the way I want”? How might that belief affect the way someone responds when life falls apart? [44:52]
2. Think of a recent loss, disappointment, illness, conflict, or fear. What would it look like to bring that loss honestly to the foot of the cross rather than pretending it does not hurt? [49:21]
3. Jesus does not promise a pain-free life, but He promises to walk with His people through hardship. What specific hard place needs to be met this week with the reminder, “He will never let me go”? [54:45]
4. Is there a situation in which someone has been tempted to rebuke Jesus in the heart—asking, “Why would You allow this?” What would honest prayer in that moment sound like while still holding on to Christ?
5. Romans 12 says to “weep with those who weep.” Who is carrying grief, sickness, loneliness, or another heavy burden right now? What would genuine love look like in a practical action this week—being present, listening, providing a meal, sending a message, or praying with them? [55:32]
6. Is there a brother or sister in Christ who may need loving confrontation about a harmful pattern of sin? How can truth be spoken with humility, affection, and a desire for restoration rather than condemnation? [48:05]
7. Christ’s victory means loss and death do not have the final word. How can that hope help someone grieve deeply without being crushed by despair? [55:10]