This small group discussion guide draws directly from the sermon “Showcase - Sunday Morning Worship Service 10:45am” so you can keep engaging with the message all week. Read, reflect, and share it with your small group or friends.
Small Group Discussion Guide
"Wisdom's Folly: Life Is More Than What You Think You Know"
Based on Ecclesiastes 1:12–18
A Note to Facilitators: Welcome, and thank you for leading your group this week! This guide is designed to work for any facilitator — whether you've led groups for years or this is your first time. You don't need to have all the answers. Your job is simply to create a safe space for honest conversation and let the questions do the work. Read through the guide before your meeting, pick the questions that feel right for your group, and trust the Holy Spirit to do the rest. You've got this!
OVERVIEW
In this sermon from Ecclesiastes 1:12–18, we explored one of life's most important and humbling truths: life is about more than what you think you know. Drawing on Solomon's honest autobiography as the wisest and wealthiest man of his era, the message showed us that even the most impressive human wisdom, achievement, and knowledge ultimately leave us empty — like trying to shepherd the wind. The good news is that Solomon's dead ends point us toward something — and Someone — greater: Jesus Christ, in whom all true wisdom, meaning, and satisfaction are found.
GETTING STARTED: A WORD ABOUT YOUR TIME TOGETHER
This guide is designed for a 60–90 minute meeting. You likely won't get through every question — and that's perfectly okay! Follow the energy of your group. If a question sparks a rich conversation, stay there. The goal isn't to finish the guide; it's to help each other grow.
Suggested Time Breakdown:
| Section | Time |
|---|---|
| Welcome & Icebreaker | 5–10 min |
| Scripture Reading | 5 min |
| Discussion Questions | 30–45 min |
| Personal Application | 10–15 min |
| Prayer Focus | 5–10 min |
| Optional Deep Dive | If time allows |
SECTION 1: ICEBREAKER
(5–10 minutes)
Start here to warm up the group and ease into the topic naturally. This question is intentionally light — no right or wrong answers!
Opening Question: "Think of a time you were absolutely convinced you knew what you were doing — only to discover you were completely wrong. Maybe it was directions, a recipe, a home repair, a relationship decision, or a career move. What happened, and what did you learn?"
[Leader Tip] Keep this fun and lighthearted. Share your own story first to model vulnerability and set the tone. If the group is quiet, try: "Has anyone ever been totally confident about something that turned out to be completely off base?" Laughter here is a gift — let it happen.
SECTION 2: SCRIPTURE READING
(5 minutes)
Have someone in the group read the passage aloud. Consider asking two different people to read it — hearing it twice helps it land.
PRIMARY TEXT: Ecclesiastes 1:12–18 (English Standard Version)
"I the Preacher have been king over Israel in Jerusalem. And I applied my heart to seek and to search out by wisdom all that is done under heaven. It is an unhappy business that God has given to the children of man to be busy with. I have seen everything that is done under the sun, and behold, all is vanity and a striving after wind.
What is crooked cannot be made straight, and what is lacking cannot be counted.
I said in my heart, 'I have acquired great wisdom, surpassing all who were over Jerusalem before me, and my heart has had great experience of wisdom and knowledge.' And I applied my heart to know wisdom and to know madness and folly. I perceived that this also is but a striving after wind.
For in much wisdom is much vexation, and he who increases knowledge increases sorrow."
SUPPORTING TEXT: Ecclesiastes 12:13–14 (ESV) (The conclusion of the whole book — the destination Solomon is heading toward)
"The end of the matter; all has been heard. Fear God and keep his commandments, for this is the whole duty of man. For God will bring every deed into judgment, with every secret thing, whether good or evil."
SUPPORTING TEXT: Matthew 12:42 (ESV) (Jesus' own words about Solomon — and about Himself)
"The queen of the South will rise up at the judgment with this generation and condemn it, for she came from the ends of the earth to hear the wisdom of Solomon, and behold, something greater than Solomon is here."
SUPPORTING TEXT: Proverbs 3:5–6 (ESV) (Referenced in the sermon as a companion to Ecclesiastes)
"Trust in the Lord with all your heart, and do not lean on your own understanding. In all your ways acknowledge him, and he will make straight your paths."
A Quick Word About Ecclesiastes: Ecclesiastes can feel strange or even discouraging at first read. Solomon seems almost too pessimistic. But here's the key the sermon gave us: read the book backwards. Every passage makes sense in light of the ending — fear God and keep his commandments. Solomon isn't promoting despair; he's dismantling every false hope so we'll run to the only true one.
SECTION 3: DISCUSSION QUESTIONS
(30–45 minutes)
Work through as many of these questions as time allows. They move from lighter and observational to deeper and more personal. Feel free to skip questions that don't fit your group, or linger on ones that spark rich conversation.
THEME A: What Stood Out to You?
Start here to get everyone talking before diving deeper.
Question 1: What was one thing from Sunday's message that stuck with you — something that surprised you, challenged you, or that you're still thinking about? Why did that particular thing stand out?
[Leader Tip] This is a great first question because there are no wrong answers and it invites everyone to participate. If someone says "nothing really stood out," gently ask: "Was there anything that made you a little uncomfortable or that you disagreed with? That counts too!"
Question 2: The sermon described Solomon as "the wisest fool who ever lived." What do you think that phrase means? How can someone be both very wise and a fool at the same time?
THEME B: The Pursuit — What Are We Really Chasing?
Question 3: Solomon says he applied his whole heart — sincerely, diligently, thoroughly — to the pursuit of wisdom and meaning. He had unlimited resources, unmatched intellect, and access to the greatest minds of his day. And still, he came up empty.
What are the things people in our culture most commonly pursue as sources of meaning, purpose, or satisfaction? What makes those things so appealing — and what do you think eventually happens when people reach them?
[Leader Tip] This question works well because it starts with culture before getting personal. Common answers might include: wealth, career success, relationships, education, fame, pleasure, health. Affirm all responses — the goal is honest observation, not judgment.
Question 4: The sermon used a vivid image: "striving after the wind." The preacher suggested it's like trying to be a shepherd of the wind — you can never catch it, and even if you could, you'd be holding a handful of nothing.
Can you think of a time in your own life when you chased something you were convinced would bring satisfaction — and when you got there, it felt hollow or incomplete? What was that experience like?
(You don't have to share details you're not comfortable with — even a general description is helpful.)
[Leader Tip] This is one of the most important questions in the guide — give it time. Model vulnerability by sharing your own experience first if the group is hesitant. Remind the group that this is a safe space and that honesty here is a gift to everyone.
THEME C: The Problem — A World That Can't Be Fixed
Question 5: Solomon says in verse 15: "What is crooked cannot be made straight, and what is lacking cannot be counted." The sermon explained that this isn't a call to give up or stop trying to make a difference — but it is a warning against looking for ultimate meaning and satisfaction in fixing a broken world.
How do you personally hold the tension between working to make things better in the world around you, while also accepting that some things are broken in ways only God can fix? Where does that tension show up in your life?
Question 6: The sermon made a bold and maybe surprising claim: that God intentionally designed life to feel like "an unhappy business" — not to be cruel, but so that we would never settle for finding our deepest satisfaction apart from Him.
How does that idea land with you? Does it feel comforting, frustrating, confusing, or something else? Why?
[Leader Tip] This question may generate some pushback — and that's healthy! Some group members may struggle with the idea that God would design difficulty. Let the tension breathe. You might follow up with: "How does knowing God is sovereign over even the hard things change — or not change — how you feel about them?"
THEME D: The Pain — The More You Know, the More It Hurts
Question 7: Verse 18 says: "For in much wisdom is much vexation, and he who increases knowledge increases sorrow." The sermon illustrated this with the image of a parent watching an adult child make destructive choices — you can see where the road leads, and it breaks your heart precisely because you know.
Where in your life has greater knowledge or awareness actually increased your burden rather than lightened it? How do you carry that weight?
Question 8: The sermon pointed out that Solomon didn't just study wisdom — he also studied "madness and folly," trying to understand life from every perspective before drawing conclusions. The preacher compared this to watching Fox News and CNN, reading liberal and conservative thinkers, listening to all sides.
Why is it important to genuinely understand perspectives different from our own before forming our convictions? How does this kind of intellectual humility connect to spiritual humility?
THEME E: The Answer — Someone Greater Than Solomon
Question 9: The sermon's climax was this declaration: "Something greater than Solomon has come." Jesus doesn't just have more wisdom than Solomon — He is the wisdom of God (1 Corinthians 1:24). He doesn't just point the way — He is the Way, the Truth, and the Life (John 14:6).
In what specific area of your life right now do you most need to stop "leaning on your own understanding" (Proverbs 3:5) and trust Jesus instead? What would that actually look like in practice?
[Leader Tip] This is the heart of the application. Give people time to think quietly before sharing. You might say: "Take just 30 seconds to think about this before we share." Some people may not be ready to answer aloud — that's okay. The reflection itself is valuable.
Question 10: The sermon closed with the image of a little girl lost in London who couldn't remember her address or phone number — but she knew one thing: "If you can just get me to the cross, I can find my own way home."
What does "getting to the cross" look like in everyday, practical terms — not just as a theological idea, but as an actual way of living? What habits, practices, or postures help you return to the cross when you've drifted?
SECTION 4: PERSONAL APPLICATION
(10–15 minutes)
These questions are more personal and reflective. You may want to give people a minute of quiet before sharing, or invite people to journal their answers first. Remind the group that no one is required to share anything they're not comfortable with.
Reflection Question 1 — Honest Inventory: The sermon invited us to do what Solomon did in verse 16: "I said in my heart..." — to examine our own lives honestly.
If you were to sit quietly and take an honest look at your life right now, where are you most tempted to look for meaning, purpose, or satisfaction in something other than God? Be as specific as you can — even if you only share it with yourself.
Reflection Question 2 — Where Do You Need Him? The closing prayer invitation was simple: "Tell the Lord where you need Him. Tell Him how you need Him."
Finish this sentence — either silently, in writing, or aloud if you're comfortable: "Lord, I most need You right now in the area of _________________, because ________________."
Reflection Question 3 — The Crooked and the Lacking: Solomon identified two realities: the world is crooked (broken in ways we can't fix) and lacking (missing things we can't supply).
Is there a situation in your life right now — a relationship, a circumstance, a struggle — that feels "crooked" or "lacking"? What would it look like to hand that specifically over to God this week, rather than trying to fix or rig it yourself?
Reflection Question 4 — Community Challenge: The sermon opened with a beautiful story about three women at Shiloh who simply "adopted" a young visitor in their pew — praying for him, encouraging him, making him feel seen. The preacher said: "We don't just come to get a blessing. We come to be a blessing."
Who in your life right now — at church, at work, in your neighborhood, in your family — might need someone to simply show up for them the way those women did? What's one small, specific thing you could do for that person this week?
✅ THIS WEEK'S CHALLENGE
Choose one (or more) of the following to practice before your group meets again:
The Proverbs 3:5 Practice: Each morning this week, before you check your phone or plan your day, pause and pray: "Lord, I choose to trust You today — not my own understanding. Show me where I'm leaning on myself instead of You." Notice what comes up.
The Examination: Set aside 15 minutes this week to do what Solomon did — examine your life honestly. Ask yourself: Where am I chasing the wind? What am I hoping will finally satisfy me that hasn't delivered yet? Write down what you discover.
The Blessing: Identify one person in your circle who might need a handshake, a smile, a prayer, or an encouraging word. Do it. Don't overthink it. Just show up for them.
The Reading: Read Ecclesiastes chapters 1–3 on your own this week. As you read, ask: What false hope is Solomon dismantling here? What is he pointing me toward?
SECTION 5: PRAYER FOCUS
(5–10 minutes)
Close your time together in prayer. Here are some suggested focuses — you can pray through all of them, assign them to different people, or simply use them as a guide.
Suggested Prayer Topics:
Confession — Lord, we confess the ways we've looked for meaning, satisfaction, and security in things other than You. Forgive us for chasing the wind.
Surrender — Help us to trust You with the things in our lives that feel crooked and broken — the things we've been trying to fix on our own.
Gratitude — Thank You that Someone greater than Solomon has come. Thank You that Jesus is the Way, the Truth, and the Life — and that the cross is always within reach.
Others — Bring to mind someone in our lives who is lost in the pursuit of meaning and hasn't found it yet. Give us courage and compassion to point them toward the cross.
Our Group — Knit us together in authentic community. Help us to be a blessing to one another — and to the people God brings across our path.
[Leader Tip] If your group is comfortable with open prayer, invite people to pray briefly for one of these areas. If your group is newer or quieter, you can pray through all of these yourself, or ask one or two people to close. Either way, prayer is the most important thing you do together — don't rush or skip it.
SECTION 6: OPTIONAL DEEP DIVE
(For groups wanting to go further — use if time allows or assign for personal study)
Deep Dive Question 1 — Ecclesiastes in Context: The sermon made an important interpretive point: to understand Ecclesiastes, you need to read it in light of progressive revelation — meaning the full story of Scripture, culminating in Jesus. Solomon was writing before the incarnation, before the cross, before the resurrection.
How does knowing that Jesus is the fulfillment of everything Solomon was searching for change the way you read Ecclesiastes? Read Colossians 2:2–3 together:
"...that their hearts may be encouraged, being knit together in love, to reach all the riches of full assurance of understanding and the knowledge of God's mystery, which is Christ, in whom are hidden all the treasures of wisdom and knowledge."
What does it mean that all the wisdom Solomon was searching for is now "hidden in Christ" and available to us?
Deep Dive Question 2 — Wisdom in Scripture: The sermon distinguished between worldly wisdom (intellectual, human, "under the sun") and godly wisdom (rooted in the fear of God). Read these two passages together and compare them:
Proverbs 1:7 — "The fear of the Lord is the beginning of wisdom; fools despise wisdom and instruction."
1 Corinthians 1:18–21 — "For the word of the cross is folly to those who are perishing, but to us who are being saved it is the power of God. For it is written, 'I will destroy the wisdom of the wise, and the discernment of the discerning I will thwart.' Where is the one who is wise? Where is the scribe? Where is the debater of this age? Has not God made foolish the wisdom of the world? For since, in the wisdom of God, the world did not know God through wisdom, it pleased God through the folly of what we preach to save those who believe."
What is the difference between the wisdom the world values and the wisdom God offers? Why does the cross seem like "foolishness" to the world — and what does it take to see it differently?
Deep Dive Question 3 — The Examined Life: The sermon highlighted Solomon's habit of self-examination: "I said in my heart..." — he didn't just observe the world; he observed himself observing.
What does a regular practice of honest self-examination look like for a follower of Jesus? Read Psalm 139:23–24:
"Search me, O God, and know my heart! Try me and know my thoughts! And see if there be any grievous way in me, and lead me in the way everlasting."
How is inviting God to search us different from — and better than — examining ourselves on our own? What makes this kind of honest self-examination difficult? What makes it necessary?
SUPPLEMENTARY RESOURCES
For facilitators or group members who want to explore further:
Related Scripture passages to read this week:
- Ecclesiastes 3:1–14 (God's sovereignty over all of life's seasons)
- Ecclesiastes 12:1–14 (The conclusion of the whole book)
- Proverbs 3:1–8 (Trust in the Lord, not your own understanding)
- 1 Corinthians 1:18–31 (The wisdom of God versus the wisdom of the world)
- Colossians 2:1–10 (All wisdom hidden in Christ)
- John 14:1–6 (Jesus as the Way, the Truth, and the Life)
A note on Ecclesiastes as a book: Ecclesiastes is part of the Bible's "Wisdom Literature," alongside Proverbs, Job, and Psalms. It's written from the perspective of someone searching for meaning — which is why it sometimes sounds more like honest wrestling than confident proclamation. That's intentional. Solomon wants us to feel the emptiness of life without God before pointing us to the only true answer. Think of it as a long, honest journey toward the destination of Ecclesiastes 12:13: "Fear God and keep his commandments — this is the whole duty of man."
FACILITATOR'S QUICK-REFERENCE CARD
Tear out or screenshot this section for easy use during your meeting.
| Time | Section | Key Goal |
|---|---|---|
| 0–10 min | Welcome + Icebreaker | Build comfort, get everyone talking |
| 10–15 min | Scripture Reading | Ground the group in the text |
| 15–50 min | Discussion Questions | Explore, wrestle, connect |
| 50–60 min | Personal Application | Make it real and actionable |
| 60–70 min | Prayer | Close with dependence on God |
| If time | Deep Dive | For groups wanting more |
If your group gets stuck, try:
- "Does anyone want to push back on that or see it differently?"
- "What would this look like in real life — not in theory, but on a Tuesday morning?"
- "Has anyone experienced something like this personally?"
- "What do you think Solomon would say to someone in our group who's going through that right now?"
Remember: Your job is not to teach — it's to facilitate. The best thing you can do is ask a good question, then listen well and create space for others to respond. Silence is okay. It usually means people are thinking.
This guide was prepared for small group use at Shiloh Church based on the Sunday morning message from Ecclesiastes 1:12–18. Permission granted for local church use.