Advent Waiting: Trusting God's Unexpected Ways

Devotional

Day 1: When Jesus Doesn’t Meet Our Expectations

Advent teaches honest waiting in a world where prayers sometimes seem to land with a thud. John the Baptist knew that tension—confined in a dungeon, he sent a question straight to Jesus: “Are you the One, or should we look for another?” You may know the ache—an illness unhealed, a job that didn’t open, a prodigal not yet home. Jesus’ reply did not scold; it redirected hope and invited trust even when the script changes. He gently says, “Happy is the one who doesn’t trip over me,” because disappointment can harden into offense if we let it. Bring your confusion to Christ and keep your heart open to the surprising ways he is at work [33:01]

Matthew 11:2–6: John, from prison, sent messengers to ask Jesus if he truly was the One to come. Jesus answered, “Go tell John what you’re seeing and hearing: the blind are seeing, the lame are walking, those with leprosy are being cleansed, the deaf are hearing, the dead are being raised, and the poor are receiving good news. And blessed is the one who doesn’t stumble over me.”

Reflection: Where do you feel most disappointed with God right now, and how could you bring that specific disappointment to Jesus this week—perhaps by praying Psalm 13 aloud and naming your hope before him?

Day 2: Let Scripture Reset Our Expectations

Many of us carry assumptions about how God must act—picked up from culture, family sayings, or flashy promises. Jesus asked the crowds, “What did you go out to see?” exposing how mismatched expectations can blind us to God’s real work. He pointed to Isaiah to clarify what Messiah would actually do, not what people imagined he should do. When our expectations don’t align with Scripture, we risk missing grace standing right in front of us. Let God’s word recalibrate your hopes so you can recognize his kingdom as it actually arrives [35:19]

Isaiah 35:4–6: Tell the anxious heart, “Be strong; do not fear—your God will come to save.” When he comes, blind eyes will open and deaf ears will hear; the lame will leap like deer, and those once mute will sing. The dry places will bloom with the life of God’s presence.

Reflection: What is one concrete expectation you have of God this month, and which Scripture passage will you sit with to test and reshape that expectation into a promise God has actually made?

Day 3: Patient Like a Farmer, Steady at Heart

Patience is not passivity; it is active trust. James points to a farmer who waits through early and late rains, doing the quiet, necessary work that a harvest requires. You cannot grow wise, love well, or build deep relationships in a hurry; the heart must be established, not rushed. Advent invites you to slow down and strengthen your inner life, even as you keep your hands faithful in daily tasks. The Lord’s coming is near, and patience is how we make room for his timing [38:28]

James 5:7–11: Be patient, like a farmer who waits for the valuable harvest and the needed rains. Strengthen your hearts, because the Lord’s coming is close. Don’t grumble against each other. Remember the prophets and Job—how they endured—and see how the Lord’s purpose proved good, full of compassion and mercy.

Reflection: In one pressured area of your week, what is a small, specific way you will slow down (for example, a five-minute pause to pray before a meeting) so your heart can be established in the Lord’s timing?

Day 4: Waiting Practices: Prayer, Confession, Healing, Truth

We do not wait idly; we wait with practices that shape us. James urges simple, trustworthy speech; prayer in trouble; songs in joy; and calling the elders to pray for healing. He commends confessing sins to one another, because honesty and intercession open real pathways for restoration. These habits train our hearts to notice grace and become channels of God’s mercy to others. In seasons of delay, these are the tools that keep hope alive and community strong [40:25]

James 5:13–16, 19–20: If you’re suffering, pray; if you’re joyful, sing. If you’re sick, call the elders to pray and anoint you in the Lord’s name. Confess your sins to each other and pray for one another so that you may be healed—the earnest prayer of the faithful is powerful. And if someone wanders, seek them; turning one back from straying helps save a life and cover a multitude of sins.

Reflection: Who is one trusted believer you could ask this week to pray with you (for healing, confession, or encouragement), and what exactly will you share with them?

Day 5: Singing “Come, Lord Jesus” with Steadfast Hope

God’s character steadies us: he keeps faith forever, and the resurrection of Jesus proves he is making all things new. Advent songs teach us to pray, “Come, Lord Jesus,” while also asking, “How long, O Lord?”—honest lament married to durable hope. Like a father with a surprising last gift, God’s goodness often arrives after we thought the story was over. Keep singing, keep asking, keep trusting; there is more of the Father’s heart yet to see. You can wait a little longer because you are waiting with him [47:04]

Revelation 22:20: The One who bears witness says, “I am coming soon.” Our response is simple and strong: “Amen; come, Lord Jesus.”

Reflection: What short Advent prayer or song line will you carry each day this week (for example, “Come, Lord Jesus”), and when exactly will you pause to pray it—morning drive, lunch break, or before bed?

Sermon Summary

In Advent we learn to wait. I told a simple story about Ralphie from A Christmas Story and the ache of wanting one gift, only to open a box and find something else. That ache is not just about Christmas; it’s the ache of life and prayer when our hopes don’t show up on our timetable or in the shape we imagined. John the Baptist knew that ache too. From Herod’s dungeon he sent messengers to Jesus, asking, “Are you the One?” He had proclaimed Jesus boldly, but in a dark and lonely season he faced his own questions about God’s timing and methods.

Jesus didn’t scold him. He sent John back to Scripture: the blind see, the lame walk, lepers are cleansed, the deaf hear, the dead are raised, and the poor hear good news (Isaiah 35). In other words, God was doing exactly what He promised—just not in the way people expected. That’s why Jesus says, “Blessed is the one who is not offended by me.” Disappointment can turn into a stumbling block when our unspoken expectations harden into demands. Advent invites us to check our expectations against God’s Word and God’s character.

James 5 calls us to patient endurance like a farmer who waits for early and late rains. Waiting isn’t idleness; it’s training. Establish your heart, James says, and practice the habits of a waiting people: forbearance instead of grumbling, simple truthfulness, prayer over hurts, songs over joys, confession and mutual intercession, seeking the wandering, all rooted in the mercy of God. These practices don’t shorten the road; they make us strong enough to walk it well.

I said it’s good for kids to get bored on long road trips because it builds capacity. The same with us: as we wait with prayer, confession, forgiveness, fasting, and song, we actually grow more able to wait. We glimpse God’s goodness in small ways and our hearts steady. Advent’s music gives us a voice for this: “O come, O come,” and the psalmist’s “How long, O Lord?” Honest songs train hopeful hearts. And like the father in the film who had “one more gift,” our Father’s heart, revealed in Jesus and confirmed in the resurrection, assures us there is more to come. We can wait a little longer—because we are waiting with Him.

Key Takeaways

1. Don’t stumble over unmet expectations Our disappointments often come from assuming God must act on our timeline and in our preferred way. Jesus warns that offense at His ways can trip us up more than the adversity itself. Bringing our assumptions into the light of His words protects our trust from the quiet erosion of entitlement. Faith matures when we learn to receive the real Jesus, not the one we scripted. [33:01]
2. Let Scripture reset your hopes When John doubted, Jesus pointed to Isaiah’s promises fulfilled in real time: sight, cleansing, resurrection, and good news to the poor. Scripture trains our imaginations so we can recognize God’s work when it arrives in unfamiliar clothing. Hopes rooted in the text can flex yet endure, because they lean on what God has actually pledged. [36:02]
3. Waiting forms us into readiness James pictures a farmer who works while he waits—preparing for fruit he cannot manufacture. Spiritual waiting is not passivity; it is disciplined attentiveness that makes us capable of receiving what God gives. We become people who can carry blessing without breaking, because patience has strengthened the frame of our souls. [38:28]
4. Build capacity for steadfast patience Capacity grows by practice. Like children learning long roads without constant entertainment, we learn longer obedience through repeated, ordinary faithfulness. As we pray, confess, forgive, and sing in the in‑between, God enlarges our hearts to hold both longing and joy at once. Over time we discover we’re less frantic, more steady, and more free. [43:27]
5. Pray your delay with honest songs Advent’s “O come” and the psalmist’s “How long?” are not complaints but covenants of trust voiced aloud. Honest prayer names reality without surrendering hope, and in doing so keeps cynicism from hardening our hearts. These songs don’t just express waiting; they shape it into worship. [46:02]

Youtube Chapters

[00:00] - Welcome
[09:49] - Advent joy; Collect and intercession
[14:38] - Blessing the children
[26:28] - A Christmas Story and longing
[28:54] - When prayer meets disappointment
[30:07] - John the Baptist’s question to Jesus
[33:01] - Expectations and the unoffended heart
[35:19] - Isaiah’s signs of the Kingdom
[36:40] - James 5: learning to wait
[39:56] - Practices for a waiting people
[42:22] - Learning patience on the road
[46:30] - Advent songs and the Father’s heart
[55:39] - Communion: Invitation and Prayer
[77:05] - Benediction and sending

Bible Study Guide

Bible reading
- Matthew 11:2–6

Observation questions

In Matthew 11:2–6, John’s disciples go to Jesus with a direct question about whether he is the Messiah. What differences do you notice between John’s earlier public witness (e.g., “Behold the Lamb of God”) and his question now in prison? [30:07]
Jesus answers by pointing to signs from Isaiah (the blind see, the lame walk, lepers cleansed, the deaf hear, the dead raised, the poor hear good news). Which of those concrete signs stands out most to you when you hear Jesus describe his work? Why? [35:19]
Jesus says, “Blessed is the one who is not offended by me.” In the passage and the sermon illustrations, how is offense connected to unmet expectations? What exactly does Jesus warn against here? [33:01]
James uses the farmer waiting for early and late rains as an image of patient endurance. What actions or images in that section show waiting as active work rather than passive idleness? [38:28]

Interpretation questions (third person)

How does Jesus’ appeal to Isaiah’s promises (sight for the blind, liberty for the oppressed, good news to the poor) reframe the disciples’ and John’s expectations about what the Messiah would do? [35:19]
What does the statement “Blessed is the one who is not offended by me” imply about the relationship between expectation and faithfulness? How might hardened expectations become a spiritual stumbling block? [33:01]
In what ways does James’ farmer image change the group’s understanding of what “waiting for the Lord” looks like in ordinary life? What kinds of preparation or cultivation does waiting require? [38:28]
What role do community practices named in James (confession, mutual prayer, anointing and singing) play in sustaining steadfastness during long seasons of waiting? [39:56]

Application questions (personal, specific)

Unmet expectations can harden into demands that cause offense at God. Which particular expectation in your life feels most like a demand right now (a healing, a relationship, a job, a timing)? What would it look like this week to bring that expectation before Scripture and ask whether it matches God’s promises? [33:01]
Scripture trains the imagination to recognize God’s work even when it comes in unexpected forms. What recent small, concrete signs of God’s mercy or presence have you noticed (healed relationships, unexpected provision, changed desires)? Take two minutes now to name them aloud to the group. [35:19]
Waiting is formative, not passive. Which one habit from James — prayer over hurts, singing over joys, regular confession, asking elders to pray — is missing or weak in your life? What single, realistic step will you take this week to begin practicing that habit? Set a time and accountability. [38:28]
Capacity for patience grows from repeated, ordinary practices (learning to be bored on a road trip builds endurance). What “small training” could you adopt that would help you grow steadiness (a short daily fast, a five‑minute morning silence, a regular confession partner)? How will you start and how long will you try it before reassessing? [43:27]
Honest songs and psalms give language to faithful waiting (“How long, O Lord?”; “O come, O come, Emmanuel”). Which Advent carol or psalm will you use as your daily prayer this week? When each day will you sing or pray it, and how will you let it shape your longing for Christ? [46:02]
James urges the community to seek the wandering and restore those who have drifted. Who in your life needs a gentle outreach or a restoration conversation right now? What is one practical next step (a text, a visit, a prayer phone call) you will take in the next seven days? [39:56]

Sermon Clips

I mean, what's going on? You maybe see some TV preacher who's all fancy telling you if you just believe, you're going to get everything you ask for. And what's going on? As Jesus was doing his ministry in Matthew chapter 11, we read that John the Baptist sent two of his disciples to Jesus to ask him point blank, look, are you the Messiah, the Christ, or should we be waiting for someone else? That's what they say in verse 3. And this is kind of odd. It's kind of embarrassing. [00:29:36] (32 seconds) #IsHeTheMessiah

Sometimes we open the scripture and we are feeling like we need a word of comfort from Jesus and what we actually hear is a word of challenge or maybe even rebuke or chastisement. Sometimes we look at ourselves and we come expecting a word of judgment and instead we receive an unexpected invitation of grace. One of the things about Jesus, about our Lord, is he surprises us. He doesn't always do what we expected. [00:32:40] (30 seconds) #JesusSurprises

And I think waiting is so difficult for us hectic 21st century people. I mean, we like stuff to be fast, right? We like fast food and fast coffee and fast Amazon deliveries. And, you know, we want stuff to be like that. But learning to wait is critical for our spiritual maturity as disciples of Jesus. And we all know fast isn't always good for you, right? Think about it. You cannot grow wise in a hurry. You cannot savor the blessings that God has poured on your life in a hurry. You cannot build deep and meaningful relationships in a hurry. You cannot love in a hurry. You cannot grow virtuous in a hurry. [00:37:23] (53 seconds) #WisdomTakesTime

As James is encouraging the Christian believers to wait in this kind of way, with these kinds of habits and practices, he reminds them of the steadfastness of Job and of the other prophets in the Old Testament who waited patiently, even through times of suffering and adversity. And ultimately, he says, that kind of steadfastness is rooted in the character of God. That's what he says in verse 11. You've seen the steadfastness of Job and you have seen the purpose of the Lord, how the Lord is compassionate and merciful. It's because he's compassionate and merciful and good that I can rely on him. I can wait for him to fulfill his good purposes in me. [00:40:49] (48 seconds) #SteadfastInGod

Sometimes I look around and I know, like many of you, I wonder why God isn't doing more or doing what I expect or doing it now with my expectations in view. But I'm learning to trust him whose ways are higher than my ways, whose thoughts are higher than my thoughts. He probably knows what he's doing. He's God. I'm not. And I trust he is growing good fruit in me and in his waiting people. [00:41:36] (34 seconds) #TrustHisWays

As we wait for the Lord, not with constant grumbling. Are we there yet? But with prayer. With confession. With both receiving and offering forgiveness with other people. With fasting. With singing over our blessings. Praying over our hurts. As we wait like that, what I have found in many saints is that we develop more capacity and trust to wait upon the Lord. Because we see him moving. We see his goodness. We behold his glory glimpsed in little ways in our lives. We get better at waiting. More patient. More steadfast. [00:43:34] (44 seconds) #WaitWithPrayer

We maybe get more like Job. Maybe more like John. Who's not a breed blown around by every wind. He's steadfast. Who's not soft and pampered like the people in the palace. He's disciplined. We become more like that. As we wait. Ultimately, we look at the character of Jesus. And we see God that we can wait for. A God that we can trust. He, as the Psalm says, he's always faithful. He always keeps faith forever. We look at the resurrection of Jesus and we see actually God does have a plan to deal with the bitter injustices and the brokenness of this fallen world. He knows what he's doing and we can trust him. [00:44:18] (45 seconds) #FaithfulInWaiting

The funny thing about that is his father, up to this point in the movie, has not struck me as a particularly, like, generous or, you know, he doesn't have this softer side to his character. But more of his character gets shown to us in the gift that Ralphie had to wait for. And there is still more and more to come from the heart of our Heavenly Father, for he is good. We look at Jesus and we see his heart. And we say, I can wait a little longer. Because I'm waiting with you. I see your good purposes. [00:46:49] (33 seconds) #GodsGenerousHeart

Ask a question about this sermon

Chatbot

What expectations of Messiah did Jesus overturn?

Which practices train patience during Advent waiting?

Why did John doubt from Herod's prison?