Choose Well, Trust Well

Ecclesiastes 7:1-29 July 19, 2026 Pastor Chris Oswald
Thesis When you have a choice to make, wisdom helps you choose well; when you have no choice, wisdom helps you trust well—but wisdom without humility spoils into folly.
Series
Ecclesiastes
Type
Expository
Tone
pastoraldidacticprophetic
Method
grammatical-historicalcanonicalapplicatory
What's in this sermon

The shape of the argument

45 units across exposition, application, illustration, theological claim, and conclusion. The pastor's argument is built from these moving parts.

Pastoral correction · unit #43
"Final charge to the congregation: pursue wisdom aggressively, but simultaneously pray for humility. Acknowledges that fallen discernment cannot be trusted without humility."
Doctrinal loci· 7 surfaced
Sanctification · 11 Providence / Sovereignty · 10 Hamartiology · 8 Ethics / Moral Theology · 3 Pastoral Theology · 2 Theology Proper · 2 Doxology / Worship · 1
Bible citations· 23
Ecclesiastes 7:1-29 | Genesis 3 | Colossians 2 | Ecclesiastes 7:1-7 | Ecclesiastes 7:1-5 | Proverbs 14:12 | Ecclesiastes 7:7-8 | Ecclesiastes 7:7 | Ecclesiastes 7:11-12 | Ecclesiastes 7:13-14 | Ecclesiastes 7:14 | Ecclesiastes 7:13 | Ecclesiastes 7:14-15 | Ecclesiastes 7:16-19 | Ecclesiastes 7:20-24 | Ecclesiastes 7:25-29 | 1 Kings 11:1-8 | 2 Corinthians 12
Illustrations· 6
  1. personal story · unit #5 — Uses counterfeit Rolex watches to illustrate that anything of high value will attract imitations—setting up the argument that wisdom has counterfeits.
  2. personal story · unit #18 — Pastor applies the warning about pride spoiling wisdom to himself, confessing that his own pursuit of wisdom is at risk if pride enters.
  3. cultural reference · unit #20 — Uses the reality show 'Storage Wars' to illustrate the skill of rapid value assessment—scanning an environment to identify what is valuable and what is not.
  4. historical example · unit #28 — Establishes Thomas Boston's credibility to write on contentment in hardship by detailing his suffering: wrecked health, six children dead, wife bedridden for a decade. He wrote from experience, not theory.
  5. personal story · unit #34 — Personal story of recognizing pride immediately after a prayer of humility. Illustrates the self-defeating circularity of wisdom: even humility can become an occasion for pride. Ecclesiastes 7 warns that wisdom's trap is self-congratulation.
  6. historical example · unit #42 — Uses Paul's thorn in the flesh (2 Corinthians 12) as parallel to Boston's crook in the lot: God gives hardship proactively to prevent pride after granting insight. The thorn preserves Paul's wisdom.
Theological claims· 17
  1. Wisdom helps you choose well when you have choices; wisdom helps you trust well when you have no choices. unit #2
  2. Wisdom is an attribute of God, and its presence in our lives is a direct indicator of how godly we are. unit #3
  3. Because wisdom is presented in Scripture with superlative language as the supreme prize, it inevitably produces counterfeits. unit #4
  4. Counterfeit wisdom has been present since the fall, when the serpent tempted Eve with fruit that promised to make her wise. unit #6
  5. The pursuit of wisdom contains a frustrating circularity: distinguishing true wisdom from counterfeit wisdom requires wisdom itself. unit #7
  6. Counterfeit wisdom is true wisdom fused with pride and self-centeredness. unit #9
  7. The essence of wisdom is 'You are God and I am not,' which makes worship the most wise activity and covenant marriage the second most wise—both feel like death but lead to life. unit #13
  8. Unlike salvation, there is no 'once wise, always wise'—wisdom can be lost after acquisition and does not automatically persist with age. unit #14
  9. Humility is the preservative for wisdom—it prevents wisdom from spoiling into foolishness through contamination by pride. unit #16
  10. Wisdom includes the discernment to know when action is futile and when stillness, contentment, and trust are the wise response to circumstances beyond your control. unit #24
  11. Anxiety, worry, and obsessive control are counterfeit wisdoms—foolish responses to uncertainty. True wisdom trusts in God's goodness and sovereignty. unit #26
  12. God made the unchangeable hardship in your life—he did not merely permit it at arm's length. Biblical wisdom requires affirming God's absolute sovereignty, not diminishing it to make theology more comfortable. unit #29
  13. The pastoral comfort of divine sovereignty is that hardship is carefully measured and sent by God, not random chaos outside his control. unit #30
  14. The unchangeable hardship God sends is the great engine of providence for revealing what is actually inside us—it shows us who we really are. unit #31
  15. Humility is the supreme human virtue because it is the destination for both halves of wisdom: when you have choices, choose humility; when you have no choices, be humble and accept God's work. unit #33
  16. Wisdom grants status, status breeds pride, and pride destroys wisdom—Solomon's life is the archetypal warning that wisdom without humility ends in ruin. unit #40
  17. God brings humbling circumstances (mourning, rebuke, hardship) into the lives of the wise as mercy—these things preserve wisdom by preventing the pride that would destroy it. unit #41
Quotations· 2
"Good, better, best. Never let it rest until your good is better and your better is best." — Youth group saying from speaker's childhood (unit #3)
"I would tremble to think if the hardship that has come to my life was not carefully measured out and sent to me by my father's hand." — Charles Spurgeon (unit #30)
Read it

Full transcript

33,211 characters 45 units ~37 min reading time Listen instead →

0 · Sets the scope of the sermon (Ecclesiastes 7, entire chapter) and identifies the controlling theme (wisdom) that will dominate multiple chapters going forward

You'll open your Bibles to Ecclesiastes chapter 7. We'll be in the whole chapter today. A little bit more of the chapter next week. Well, we need to begin to talk about wisdom because, as I mentioned in the call to worship for the next several chapters, wisdom will be a primary theme.

1 · Establishes working definition of wisdom with two components: (1) capacity to judge rightly in life and conduct, and (2) coping/acceptance/contentment when judgment is not possible

Let's start with the definition. Well, what is wisdom? When you go to the Hebrew lexicons and consult sort of the academics, they will give you, they can't just give you one definition. There's too much of a semantic range in the words, and they all mean a little bit different things. But I think if you were trying to simplify it as much as possible while remaining true to the concept, it would be something like, wisdom is the capacity to judge rightly in matters relating to life and conduct. But it's important that I add a side B definition here, and I also say that there's a lot in the Bible that would describe at least some expressions of wisdom as simply coping or accepting or just contentment. And so those are the kind of broadest descriptions of wisdom that work for us as we think about it.

2 · Establishes the sermon's controlling thesis: wisdom serves two functions depending on circumstances—choosing well when agency exists, trusting well when it does not

This is how I would describe this sermon is about this following thesis. When you have a choice to make, wisdom helps you choose well. When you have no choice, wisdom helps you trust well. There are parts of our lives where we have no options. Those choices have been made for us. Often these are not happy times. These are not happy pieces of our life. But we certainly can understand that there are certainly moments in our life where we're out of choices. There are no more choices to make. And of course, this chapter focuses on death a fair bit. And that's the classic example of that moment when what does a wise dying person do? Do they make good choices? Well, I mean, fundamentally, your wisdom on your deathbed will manifest itself in how you trust God. Right? How you acknowledge that you don't have choice right now. That you are on a one-way train and the rails are fixed and you're headed to the final stop. And in that moment, wisdom is just a trusting action. It's a contenting action. But most of the time in the wisdom literature, wisdom is presented as something that helps you make choices. And to make better choices. And so on and so forth.

3 · Elevates wisdom from pragmatic skill to divine attribute, making it a measure of godliness

And in many respects, you know, let's not lose sight of the fact that wisdom is an attribute of God. It's just like love. It's just like mercy. It's just like anger. These are attributes of God. And so the presence or absence of this attribute in our life is a direct indicator of how godly we are. And we would certainly never say that wisdom has come from us, although there's a tension there. We're going to talk about that today. There's just a lot of layers. And if you were to read Ecclesiastes 7 straight through, you'd see, man, there's not a lot of, like, really tight, linear structure. Like, not a three-part argument or something like that. He's sort of visiting the subject from multiple angles. But I think we can pull a lot of benefit out of this.

4 · Establishes that wisdom's dual utility (contentment plus good judgment) makes it supremely valuable in Scripture, and that supreme value inevitably produces counterfeit versions

Because wisdom is so useful in that it gives you both contentment, but also the capacity to make good choices, wisdom is used in the Bible. Wisdom is described in the Bible with the most superlative language. It's gold. It's treasure. It's riches. It's the thing you should pursue. It's the best woman ever. Lady wisdom. It's always presented as this kind of ideal prize to attain. And, you know, because it is an ideal prize, it has counterfeits. Everything that is worth something will wind up with a counterfeit.

5 · Uses counterfeit Rolex watches to illustrate that anything of high value will attract imitations—setting up the argument that wisdom has counterfeits

I really like watches, and I will never be able to afford or would probably never want to pay, you know, $30,000 for a Rolex Submariner. But I could just go to Manila in a couple weeks. 20 bucks. I'm solid for at least three days of Rolex-ing until it gets wet or sees the sun or something like that. Anything that's super valuable will have counterfeits.

Where this fits

Recent preaching context

The three sermons immediately preceding this one in the preaching schedule.

Jun 28, 2026
Ecclesiastes serves as God's wake-up call to displace our worldly intoxications with sober reality, but only Jesus Christ — the greater Solomon — provides both the full revelation of eternal life and the power to live rightly in light of it.
Ecclesiastes 2:13-3:22
Jul 5, 2026
Friendship is a great glory and potent means of grace, but like other means of grace, it rarely feels profound in the moment — it mostly just feels like doing life together, and we should treat it pragmatically rather than with romanticized expectations that rob us of contentment.
Ecclesiastes 4:7-12
Jul 12, 2026
Contentment is not a circumstantial achievement but a complex gift from God that we are responsible to pursue through the gospel, and without it we will inevitably alienate those we love and forfeit the ability to enjoy what God has given.
Ecclesiastes 5:18-19, 6:1-3
July 19 · This sermon
Choose Well, Trust Well
When you have a choice to make, wisdom helps you choose well; when you have no choice, wisdom helps you trust well—but wisdom without humility spoils into folly.
Ecclesiastes 7:1-29
Take it further

Discuss · apply · pray

Small-group discussion

6 questions for your group this week

  1. In the opening of Ecclesiastes 7, Solomon presents a series of counterintuitive valuations: a good name is better than fine perfume, the day of death better than the day of birth, a house of mourning better than a house of feasting. What do you make of these claims? Which one strikes you as most difficult to accept, and why?
    Ecclesiastes 7:1-7
    → Can you think of a time in your own life when something that initially seemed bad—a loss, a failure, a hard word spoken to you—actually produced something good in you?
  2. The sermon teaches that wisdom serves two functions: it helps you choose well when you have choices, and it helps you trust well when you have no choices. Where in your life right now do you have genuine agency—real choices to make? And where are you facing circumstances you cannot change?
  3. Solomon says, 'Consider what God has done: Who can straighten what he has made crooked?' (Ecclesiastes 7:13). The sermon calls this 'the crook in the lot'—the unchangeable hardship God has woven into your life. What does it mean to you that God *made* your hardship, rather than merely allowing it to happen?
    Ecclesiastes 7:13-14
    → How does affirming God's sovereignty over your hardship change the way you respond to it—compared to seeing it as random or as something God merely tolerated?
  4. The sermon identifies counterfeit wisdom as 'true wisdom fused with pride and self-centeredness.' Can you name a time when you pursued something you believed was wise—a choice, a strategy, a way of handling a relationship—only to discover later that pride had corrupted your discernment?
    → What made you realize the wisdom had become folly?
  5. Solomon's life stands as a warning: a man granted unparalleled wisdom who ended in idolatry because wisdom without humility became folly (1 Kings 11:1-8). The sermon teaches that unlike salvation, 'there is no once wise, always wise'—wisdom can be lost after acquisition. What does this suggest about how we should approach our own spiritual growth and discernment?
    1 Kings 11:1-8
  6. The sermon closes by calling us to pursue wisdom aggressively while simultaneously pursuing humility even more aggressively. What would it look like this week to actively choose humility in a situation where you naturally want to assert your own wisdom or judgment?
    → Who in your life is a model of wisdom held by humility—someone whose good counsel carries weight precisely because they don't trust their own discernment alone?
Daily readings · Monday–Friday

5-day reading plan

This week traces wisdom's arc: from its supreme value as God's attribute, through the peril of pride that spoils it, to the humility that preserves it—and the hard mercies God sends to keep us humble.

Monday Proverbs 14:12

Solomon warns that 'there is a way that appears to be right, but in the end it leads to death.' This is why wisdom matters at the moment of choice—our instincts deceive us, our desires mislead us, and the culture around us packages death as righteousness. Wisdom is the God-given faculty that stops us at the fork and says: not that way.

Tuesday Genesis 3

The serpent's first lie was 'Did God really say...?'—casting doubt on God's word—and the second was 'you will be like God, knowing good and evil.' Eve was tempted not by foolishness but by the *appearance* of wisdom: the fruit promised knowledge, discernment, and equality with the divine. The counterfeits we face today wear the same mask—they always promise us godlike power over our circumstances, our bodies, our outcomes.

Wednesday 1 Kings 11:1-8

Solomon was granted unparalleled wisdom—more than any man before or after him—yet he ended his reign enslaved to his own appetites, his heart divided among a thousand women and a thousand false gods. His wisdom did not protect him from pride; instead, his wisdom *enabled* his pride by giving him the power to justify whatever he desired. Status and success are the soil where pride grows, and pride is wisdom's poison.

Thursday Ecclesiastes 7:13-14

Solomon tells us to 'consider what God has done: who can straighten what he has made crooked?' The 'crook in the lot'—the hardship you cannot fix, cannot escape, cannot negotiate away—is *God's making*. And in the prosperity he also made, you forget to be humble; in the hardship he also made, you are forced to see who you actually are. This is mercy, not punishment. Wisdom sees it as such.

Friday 2 Corinthians 12

Paul was granted extraordinary visions—a form of wisdom and knowledge—but God sent him a 'thorn in the flesh' to keep him humble, 'so that I will not become conceited.' This is the pattern: God gives wisdom and blessing, then sends the hardship that will keep us from pride. We spend our prayers asking God to remove the thorn; wisdom teaches us to pray instead that the thorn keeps us humble, because humility is what allows us to use wisdom at all.

Sunday-evening family table

The Crook in Your Lot

For the parent

This prompt invites your family to think about a hard situation—something unchangeable in their lives—and to see it the way Solomon teaches: as God's handiwork, not as accident or punishment. Listen for whether your kids see God's hand in difficulty, or whether they experience hardship as random and unfair.

Solomon says that God makes some things crooked—hard things we can't straighten out ourselves. Can you think of something in your life right now that feels crooked? It might be something about your body, your family, your school, or your circumstances. What is it? And what do you think God might be doing by letting that crooked thing stay in your life?
works for ages 8+
Couples · three questions over coffee

Wisdom and Humility in Our Marriage

  1. What choice have you faced this week where you sensed God calling you toward wisdom—and what did that look like? Where do you see the other person choosing wisely that you want to affirm?
  2. Where in our marriage do you see pride (in either of us) starting to spoil wisdom into foolishness? What unchangeable hardship has God used lately to humble us or show us who we really are?
  3. How can we pray for each other this week—that we would pursue wisdom aggressively while pursuing humility even more aggressively?
Memory verse this week

Ecclesiastes 7:13-14

Consider the work of God: who can straighten what he has made crooked? In the day of prosperity be joyful, and in the day of adversity consider: God has made the one as well as the other, so that man may not find out anything that will come after him.

Why this verse: This verse captures the sermon's central claim that wisdom requires both choosing well when we have agency and trusting well when we do not—and that true wisdom affirms God's absolute sovereignty over both the good and the crooked in our lives. Without this verse, the pursuit of wisdom devolves into pride; with it, wisdom becomes the gateway to humility.

Where this was preached

About the church

Providence Community Church
Lenexa, KS
Sundays · 10:00 AM
About us · What we believe
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# Providence Community Church

A church preaching expository sermons through the books of the Bible.

## Sermons
- [Narcan for the Soul (Ecclesiastes 2:13-3:22, 2026-06-28)](/ProvidenceLenexa/sermons/narcan-for-the-soul-2026-06-28)
- [Friendship (Ecclesiastes 4:7-12, 2026-07-05)](/ProvidenceLenexa/sermons/friendship-2026-07-05)
- [The Mechanics of Happiness (Ecclesiastes 5:18-19, 6:1-3, 2026-07-12)](/ProvidenceLenexa/sermons/the-mechanics-of-happiness-2026-07-12)
- [Choose Well, Trust Well (Ecclesiastes 7:1-29, 2026-07-19)](/ProvidenceLenexa/sermons/choose-well-trust-well-2026-07-19)

## About
- [About the church](/about)
- [Plan a visit](/visit)

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