Dear Me: Riddle Me This

Devotional

Day 1: When Righteousness Meets Ruin

Solomon stares at life’s uneven scales: a good man dies young while a wicked man thrives. His pen scratches raw honesty – “In my futile life I’ve seen it all” – as he names the tension we feel when blessings and suffering defy our moral math. [40:46]

This ancient king refuses to sanitize life’s chaos. He watches God’s people wrestle with the same questions we whisper during hospital visits or layoffs. The Teacher’s courage to voice our secret “why?” dismantles the lie that faith requires tidy answers.

When have you choked back questions about life’s unfairness? Name one situation where God’s timing confused you. How might His perspective differ from your balance sheet of “good” and “bad”?

“In my vain life I have seen everything. There is a righteous man who perishes in his righteousness, and there is a wicked man who prolongs his life in his evildoing. Be not overly righteous, and do not make yourself too wise. Why should you destroy yourself? Be not overly wicked, and do not be a fool. Why should you die before your time? It is good that you should take hold of this, and from that withhold not your hand, for the one who fears God shall come out from both of them.”
(Ecclesiastes 7:15-18, ESV)

Prayer: Ask God for courage to bring Him your unanswered questions without sugarcoating.

Challenge: Write down one “why” you’ve been afraid to voice, then read it aloud to God.

Day 2: The Pharisee in Your Mirror

Solomon warns against “excessive righteousness” – the toxic brew of rule-keeping and scorecards. Jesus later exposed this in Pharisees who tithed mint but neglected mercy. Both teachers target the same danger: when our spiritual resume makes us forget we’re still beggars needing bread. [56:00]

Self-righteousness doesn’t wear robes today. It appears when we tally church attendance but ignore our critical spirit, or when we withhold forgiveness because “they don’t deserve it.” This fake righteousness builds walls, not bridges.

Where does comparison creep into your spiritual life? Identify one relationship where you’ve felt morally superior this week. How can you trade judgment for grace today?

“He also told this parable to some who trusted in themselves that they were righteous, and treated others with contempt: ‘Two men went up into the temple to pray, one a Pharisee and the other a tax collector...’”
(Luke 18:9-10, ESV)

Prayer: Confess one area where you’ve trusted your performance more than Christ’s sacrifice.

Challenge: Text someone you’ve judged negatively with a specific encouragement.

Day 3: Wickedness on a Leash

“Don’t be excessively wicked,” Solomon shrugs, sounding more like a survival guide than a prophet. His jarring advice acknowledges our bent toward rebellion. Like parents warning teens about curfews, he knows some lessons come only through skinned knees. [01:03:37]

This isn’t permission to dabble in sin but a reminder: our hearts naturally drift toward destruction. The Teacher echoes Jeremiah’s diagnosis – “The heart is deceitful above all things” – preparing us to welcome the Surgeon who heals from within.

What “small” compromise have you excused lately? How might that foothold become a stronghold if left unchecked?

“The heart is deceitful above all things, and desperately sick; who can understand it? ‘I the LORD search the heart and test the mind...’”
(Jeremiah 17:9-10, ESV)

Prayer: Name one recurring temptation aloud, asking the Spirit to expose its roots.

Challenge: Delete one app/account that feeds unhealthy desires, then call an accountability partner.

Day 4: Scars That Answer

Solomon’s riddle finds its solution on a hill outside Jerusalem. The only truly righteous man hung naked between thieves, His goodness rewarded with nails. Yet through this ultimate injustice, God wrought eternal justice. [52:40]

The cross reframes our questions. When we ask “Why do good people suffer?”, Jesus answers with scarred hands. His resurrection promises that no righteous tear falls unnoticed, no wicked deed escapes the Judge.

Where are you demanding immediate justice instead of trusting eternal purposes? How might Christ’s scars speak to your current frustration?

“He himself bore our sins in his body on the tree, that we might die to sin and live to righteousness. By his wounds you have been healed.”
(1 Peter 2:24, ESV)

Prayer: Thank Jesus for absorbing history’s greatest injustice to secure your justice.

Challenge: Write “2 Corinthians 4:17-18” on your mirror to view trials through eternity’s lens.

Day 5: Grace in the Messy Middle

Solomon’s spectrum – from self-righteousness to rebellion – leaves us stranded. But the gospel plants a flag in the middle ground: “While we were still sinners, Christ died for us.” Our place isn’t earned through moral extremes but received through a cross. [01:11:44]

God’s grace transforms both the rule-keeping Pharisee and the unapologetic rebel. It meets us in failed resolutions and secret shames, not to leave us there but to remake us daily.

Where are you trying to earn what Christ already bought? What would it look like to rest in “God’s person” status today?

“But he said to me, ‘My grace is sufficient for you, for my power is made perfect in weakness.’ Therefore I will boast all the more gladly of my weaknesses, so that the power of Christ may rest upon me.”
(2 Corinthians 12:9, ESV)

Prayer: Ask God to reveal one area where you’re striving, then verbally release it to Him.

Challenge: Perform one act of kindness today with no possibility of human recognition.

Sermon Summary

Solomon names the riddle most people carry: the righteous perish and the wicked prosper, so what does that do to the way life is lived under the sun. Ecclesiastes 7:15-18 says it straight, then drops the shocker lines that sound upside down: do not be excessively righteous or overly wise, and do not be excessively wicked or foolish. The text pushes against a tidy formula where right inputs guarantee right outcomes on demand, exposing the frustration of trying to make life a scorecard. Solomon’s realism refuses a neat bow and instead points toward fearing God as the path that holds both warnings in hand.

The passage lays out four extremes. Excess righteousness and over-wisdom name a self-manufactured spirituality that slides into self-righteousness. That spirit treats God like a vending machine and turns obedience into Skee-Ball tickets, then grows cold to grace, quick to compare, slow to forgive. Excess wickedness and folly name the other ditch, the refusal to reckon with accountability before a holy God and the danger of dying before one’s time. Ecclesiastes does not bless a little sin as harmless; it calls a person to sober realism about the deceitful heart and the pull of folly.

God’s justice and timing refuse manipulation. The cross and resurrection snap the “God owes me” mindset, because perfect righteousness led Jesus to the cross, not to an easy life. That unjust death became the place where real justice landed, where the penalty was paid and grace opened. In that light, the text’s grid drives to one conclusion: the fear of God keeps a person from the pride of spiritual performance and the presumption of moral anarchy. Grace meets a person in the messy middle, not to excuse sin or applaud self-trust, but to transform. The Spirit changes taste buds over time, and the journey looks more like a roller coaster than a clean upward chart.

Ecclesiastes finally reframes the question behind the riddle. “Am I a good person” is not the question a holy God will ask. “Am I God’s person” is the only answer that holds. The one who fears God takes both warnings to heart, abandons scorekeeping, and lives out of received mercy.

Key Takeaways

1. Fear of God holds tensions Fearing God keeps a person from both ditches, because reverence humbles the self-righteous and sobers the reckless. Wisdom here is not a formula but a posture that refuses to demand outcomes on a schedule. The text promises that the one who fears God “will end up with both of them,” holding the warnings together without cynicism or despair. [43:14]
2. Self-righteousness inoculates against grace Excess righteousness breeds entitlement, turns prayer into performance, and treats God like Skee-Ball for spiritual prizes. The tell is comparison and withheld forgiveness, because merit always needs someone worse to feel secure. Grace collapses that ladder and restores relationship over scorekeeping. [59:45]
3. Be a realist about sin’s pull Excess wickedness and folly are not edgy; they are suicidal. The heart’s deceit is deeper than self-knowledge, and the slide into destruction rarely looks dramatic at first. Realism about indwelling sin is not self-loathing but clear-eyed dependence on God’s help. [63:37]
4. The cross reframes fairness forever Perfect obedience led Jesus to a cross before it led to a crown, so “I did right, now I deserve ease” is not a Christian script. At Calvary, innocent suffering accomplished true justice and opened the door of mercy for the guilty. God’s timing proved better than immediate payback. [51:44]
5. Identity shifts from good to God’s “Good person” is a moving target; “God’s person” is a settled name. Adoption, not moral math, will mark a person before the throne. Grace secures belonging first, then the Spirit reshapes character over time. [68:44]

Youtube Chapters

[00:00] - Welcome
[37:43] - Next Gen Vision Sunday preview
[38:33] - Ecclesiastes series continues
[40:28] - The riddle of justice
[41:53] - Reading Ecclesiastes 7:15-18
[43:56] - Can Scripture say that?
[51:44] - The cross and real justice
[53:38] - Four qualities and a grid
[55:25] - Excess righteousness and pride
[58:05] - Skee-Ball and scorekeeping
[62:15] - Don’t be excessively wicked
[67:02] - Grace in the messy middle
[68:44] - From good person to God’s person
[74:17] - Prayer and gospel call

Bible Study Guide

Bible Reading
Ecclesiastes 7:15-18 (ESV)
In my vain life I have seen everything. There is a righteous man who perishes in his righteousness, and there is a wicked man who prolongs his life in his evildoing. Be not overly righteous, and do not make yourself too wise. Why should you destroy yourself? Be not overly wicked, neither be a fool. Why should you die before your time? It is good that you should take hold of this, and from that withhold not your hand, for the one who fears God shall come out from both of them.

Observation questions

What two extremes does Solomon warn against in Ecclesiastes 7:15-18, and what reasons does he give for avoiding them?
The sermon compared self-righteousness to treating God like a “Skee-Ball machine” for spiritual prizes. What does this analogy reveal about the danger of transactional faith? [58:05]
According to the passage, what is the outcome for those who “fear God” (v. 18)? How does this contrast with the extremes mentioned?

Interpretation questions

Why might Solomon caution against being “excessively righteous” (v. 16) if righteousness is generally a good thing? How does self-righteousness distort our relationship with God?
The cross is described as the place where “real justice landed” despite Jesus’ perfect obedience leading to suffering. How does this reframe our expectations of fairness or immediate outcomes? [51:44]
What does it mean to shift from asking “Am I a good person?” to “Am I God’s person?” How does this change our identity and security? [01:08:44]

Application questions

When have you felt tempted to keep a “spiritual scorecard” (e.g., comparing yourself to others, withholding forgiveness, or expecting God to “owe” you blessings)? What practical step could help you recenter on grace instead? [59:45]
The sermon warns that sin’s pull is “deeper than self-knowledge.” What habits or relationships could help you stay “soberly realistic” about your weaknesses while relying on God’s strength? [01:03:37]
How might trusting God’s timing—instead of demanding immediate “justice” or outcomes—change how you respond to a current frustration or unanswered prayer?
The phrase “God’s person” emphasizes belonging over performance. What would it look like to live today as someone secure in that identity rather than trying to prove your worth?
Reflect on a time when suffering or injustice confused you. How does Jesus’ unjust death and resurrection offer hope when life feels unfair? [51:44]

Sermon Clips

45s

“I can't answer that question. Am I a good person? Here's the question that I can answer. I'm God's person. I'm God's person. So when I stand before a perfect and a holy God, he's not gonna ask me the question, am I a good person? How do you where do you even begin to decipher that? He's gonna identify me as his child. And that's it at the end of the day. That is grace.”

41s

“So today, if you don't have a relationship with Christ and you're, you feel like you're either don't need him because you're a good person or you feel like you can't have him because you're a messed up person, nothing disqualifies us from a relationship with the living God. You don't have to clean yourself up. You don't have to prepare yourself to to a new life like none of that. Jesus meets us where we are. He changes us where we are and he loves us enough to not leave us as we are. He continues to conform us into his image.”

36s

“Or here's a real biggie, when you withhold forgiveness in your heart, I'm not gonna forgive that person. They look what they did. They know they were doing that. They don't deserve my forgiveness. I'm better than that. When we slip down that mentality, that's a deadly path to go down. Because look, we have to remember, I've said it before, this is when we gather together as a community of faith, this is a grace party.”

40s

“When I was dead, when I was messy, when I was gross in my sin, he sent his son to die for me so that I could have eternal life with him. Excessive righteousness is a dangerous path to go down. When we feel like we're a a spiritual all star because of the things that we've done or the things that we do, You know, we might not come right out and say it but you know you know you're slipping into that mindset when you start comparing yourself to other people.”

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Dear Me: Riddle Me This

Devotional

Day 1: When Righteousness Meets Ruin

Day 2: The Pharisee in Your Mirror

Day 3: Wickedness on a Leash

Day 4: Scars That Answer

Day 5: Grace in the Messy Middle

Sermon Summary

Key Takeaways

Youtube Chapters

Bible Study Guide

Sermon Clips

Dear Me: Riddle Me This

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