Jesus: The Great Reversal of Blessings and Woes

Devotional

Day 1: The Great Reversal—Blessings and Woes in Luke 6

Jesus’ Sermon on the Plain in Luke 6 presents a striking contrast between those who are blessed and those who receive woes, revealing that God’s values often stand in opposition to the world’s priorities. Jesus comes down to stand among the people, humbling Himself to be with them, and teaches that true blessedness is not found in earthly wealth, satisfaction, or popularity, but in belonging to God’s kingdom. The blessings He pronounces are for those who are poor, hungry, weeping, and persecuted for His sake, while the woes warn those who trust in riches, comfort, and human approval. This reversal is not about desiring suffering, but about recognizing where our trust and hope truly lie—whether in the temporary things of this world or in the eternal promises of God. [02:47]

Luke 6:20-26 (ESV)
And he lifted up his eyes on his disciples, and said: “Blessed are you who are poor, for yours is the kingdom of God. Blessed are you who are hungry now, for you shall be satisfied. Blessed are you who weep now, for you shall laugh. Blessed are you when people hate you and when they exclude you and revile you and spurn your name as evil, on account of the Son of Man! Rejoice in that day, and leap for joy, for behold, your reward is great in heaven; for so their fathers did to the prophets. But woe to you who are rich, for you have received your consolation. Woe to you who are full now, for you shall be hungry. Woe to you who laugh now, for you shall mourn and weep. Woe to you, when all people speak well of you, for so their fathers did to the false prophets.”

Reflection: In what area of your life are you tempted to trust in temporary things—wealth, comfort, or approval—instead of the promises of God? How might you shift your focus today to what is truly lasting?

Day 2: Christ’s Humility and Our Blessing

Jesus’ willingness to humble Himself and come down among us is the foundation of our hope and blessing. He does not remain distant or above us, but enters into our world, sharing in our struggles and temptations, yet without sin. His obedience, even to death on a cross, secures for us the ultimate blessing—salvation and eternal life. Because He has walked among us and understands our weaknesses, we can trust that His promises are sure and His blessings are given by grace, not by our own merit. This humility of Christ is both our comfort and our example, calling us to receive His gifts with gratitude and to walk in humility ourselves. [03:30]

Philippians 2:7-8 (ESV)
…but emptied himself, by taking the form of a servant, being born in the likeness of men. And being found in human form, he humbled himself by becoming obedient to the point of death, even death on a cross.

Reflection: How does knowing that Jesus humbled Himself for you change the way you view your own struggles and the way you treat others today?

Day 3: The Deceptiveness of Earthly Appearances

The world often measures success by wealth, satisfaction, and popularity, but Jesus warns that these outward signs can be deceptive and do not reflect a person’s true spiritual reality. Those who appear to have it all from a worldly perspective may actually be spiritually impoverished if their trust is in themselves or their possessions. Conversely, those who seem to lack much in this life may be rich in faith and heirs of God’s kingdom. Jesus calls us to examine our priorities and to recognize that what matters most is not how we are seen by others, but our relationship with Him and our trust in His promises. [08:49]

Hebrews 4:15 (ESV)
For we do not have a high priest who is unable to sympathize with our weaknesses, but one who in every respect has been tempted as we are, yet without sin.

Reflection: Where are you tempted to judge yourself or others by outward success? What would it look like to see yourself and others through the lens of God’s grace instead?

Day 4: Trusting in the Lord—Roots That Bear Fruit

Those who trust in the Lord are like trees planted by streams of water, drawing strength and nourishment from God’s Word and His gifts. Even in times of drought or difficulty, their roots go deep, and they do not cease to bear fruit. This steadfastness is not the result of human effort, but of God’s grace at work within us, enabling us to share His blessings with others and to remain firm in faith regardless of our circumstances. The promise of God’s presence and provision is sure, and it is this trust that allows us to flourish and bless those around us. [15:35]

Jeremiah 17:7-8 (ESV)
“Blessed is the man who trusts in the Lord, whose trust is the Lord. He is like a tree planted by water, that sends out its roots by the stream, and does not fear when heat comes, for its leaves remain green, and is not anxious in the year of drought, for it does not cease to bear fruit.”

Reflection: What is one way you can deepen your roots in God’s Word this week, so that you can bear fruit even in challenging times?

Day 5: The Certainty of God’s Promises in Christ

God’s promises of forgiveness, life, and salvation are not dependent on our achievements, possessions, or status, but are made sure by the blood of Jesus. Because of Christ’s finished work, we are blessed—present tense—members of His kingdom, and nothing in this world can take that away. This assurance gives us hope and confidence to face whatever comes, knowing that as long as Jesus lives, we live, and His gifts are ours for eternity. In Christ, our lives are turned right side up, and we are called to live each day in the joy and security of His unchanging promise. [16:38]

Romans 8:38-39 (ESV)
For I am sure that neither death nor life, nor angels nor rulers, nor things present nor things to come, nor powers, nor height nor depth, nor anything else in all creation, will be able to separate us from the love of God in Christ Jesus our Lord.

Reflection: What fear or uncertainty are you facing today? How does the certainty of God’s promise in Christ give you courage and peace right now?

Sermon Summary

In Luke’s account of Jesus’ “Sermon on the Plain,” we see the Lord physically coming down to stand among His people, humbling Himself to be with them as one of their own. This posture is not just a detail—it’s a powerful sign of how Jesus meets us where we are, sharing in our struggles and showing us the heart of God’s kingdom. Jesus presents a striking contrast between blessings and woes, teaching that what the world values—wealth, satisfaction, popularity—are fleeting, while the true blessings of God are given by grace to those who trust in Him. These blessings are not earned, but are gifts, present and future, secured by Christ’s saving work.

The world’s perspective is often deceptive, tempting us to envy those who seem to have it all. Yet Jesus warns that those who build their lives on temporary things will find them empty in the end. Instead, He calls us to see reality as God sees it: those who appear poor, hungry, or rejected for His sake are, in fact, already blessed with the riches of His kingdom. Our worth and security are not determined by outward circumstances, but by our belonging to Christ.

This “great reversal” is not simply turning the world upside down, but setting it right side up. In Christ, the values of the kingdom are revealed: trust in God, not in earthly things; joy in suffering for His name; and a life rooted in His promises. Like the tree planted by water in Jeremiah’s image, those who trust in the Lord are nourished and fruitful, regardless of outward trials. Our calling is to live as stewards of these blessings, sharing them with others, confident that God’s promises are sure and eternal.

No matter what we face—poverty, grief, rejection—our present and future are secure in Jesus. His promise of forgiveness, life, and salvation is unchanging, grounded not in our achievements but in His sacrifice. As long as Jesus lives, so do we, and in Him, our lives are truly turned right side up.

Key Takeaways

1. Jesus’ act of coming down to stand on a level place with the people is a profound demonstration of His humility and solidarity with us. He does not remain distant or above, but enters into our reality, embodying the nearness of God and inviting us to see ourselves as He sees us—beloved and valued, regardless of our status in the world. [01:42]
2. The contrast between blessings and woes is not a condemnation of material things, but a warning about where we place our trust and find our identity. When our hearts are set on temporary satisfactions—wealth, comfort, popularity—we risk missing the eternal blessings that only Christ can give. The true measure of our lives is not what we possess, but whom we trust. [08:49]
3. The blessings Jesus pronounces are both present and future realities. Even when we feel poor, hungry, or rejected, we are already recipients of God’s kingdom, satisfaction, and joy. These promises are not dependent on our circumstances or achievements, but are secured by Christ’s grace and faithfulness. [12:02]
4. Our spiritual health is like the tree planted by water in Jeremiah’s vision: rooted in God’s Word and nourished by His gifts, we are able to withstand drought and bear fruit. This fruitfulness is not our own doing, but the result of God’s grace flowing through us, enabling us to bless others and glorify Him in all seasons. [15:35]
5. The certainty of God’s promise is anchored in the unchanging work of Jesus. Our forgiveness, life, and salvation are not subject to the ups and downs of this world, but are guaranteed by Christ’s blood. As long as He lives, we live; as long as we have Him, we have all we need for today and eternity. [16:38]
** [16:38]

Youtube Chapters

[00:00] - Welcome
[00:52] - Context: Sermon on the Plain vs. Sermon on the Mount
[01:42] - Jesus Comes Down Among Us
[02:47] - The Great Reversal: Blessings and Woes
[05:41] - Struggling with Worldly Inequity
[07:00] - Earthly Perspective vs. Spiritual Reality
[08:49] - Warnings About Trusting in Temporary Things
[11:22] - The Certainty of Jesus’ Blessings
[12:02] - Present and Future Promises
[12:54] - Our True Identity in Christ
[15:35] - Jeremiah’s Contrast: Shrub vs. Tree
[16:38] - God’s Unfailing Promise
[17:55] - In Jesus, All Is Turned Right Side Up

Bible Study Guide

Bible Reading

Luke 6:17-26 (ESV) — > And he came down with them and stood on a level place, with a great crowd of his disciples and a great multitude of people from all Judea and Jerusalem and the seacoast of Tyre and Sidon, who came to hear him and to be healed of their diseases. And those who were troubled with unclean spirits were cured. And all the crowd sought to touch him, for power came out from him and healed them all.
>
> And he lifted up his eyes on his disciples, and said:
> “Blessed are you who are poor, for yours is the kingdom of God.
> Blessed are you who are hungry now, for you shall be satisfied.
> Blessed are you who weep now, for you shall laugh.
> Blessed are you when people hate you and when they exclude you and revile you and spurn your name as evil, on account of the Son of Man! Rejoice in that day, and leap for joy, for behold, your reward is great in heaven; for so their fathers did to the prophets.
>
> “But woe to you who are rich, for you have received your consolation.
> Woe to you who are full now, for you shall be hungry.
> Woe to you who laugh now, for you shall mourn and weep.
> Woe to you, when all people speak well of you, for so their fathers did to the false prophets.”

Observation Questions

In Luke 6:17, what is significant about Jesus coming down and standing on a level place with the people? How does this detail set the tone for the rest of His teaching? ([01:42])
What are the specific blessings Jesus pronounces in verses 20-23, and who are they for?
What are the specific woes Jesus gives in verses 24-26, and what kinds of people do they describe?
According to the sermon, how does Jesus’ list of blessings and woes challenge the way people usually measure success or happiness? ([08:49])

Interpretation Questions

Why does Jesus contrast blessings and woes in this passage? What is He trying to teach His disciples about what really matters in life? ([02:47])
The sermon says Jesus’ act of coming down among the people is a sign of His humility and solidarity. How does this shape our understanding of God’s character and how He relates to us? ([01:42])
The sermon mentions that the blessings Jesus gives are both present and future realities. What does it mean for someone to be “already blessed” even if their circumstances are hard? ([12:02])
How does the image of the tree planted by water (from Jeremiah, referenced in the sermon) help us understand what it means to trust in God rather than in temporary things? ([15:35])

Application Questions

The world often tells us that wealth, comfort, and popularity are signs of success. Can you think of a time when you felt pressure to measure your worth by these things? How did it affect your relationship with God or others? ([08:49])
Jesus says, “Blessed are you who are poor…hungry…weep…when people hate you because of the Son of Man.” Have you ever felt left out, overlooked, or rejected because of your faith? How did you respond, and what would it look like to see yourself as “blessed” in those moments? ([12:54])
The sermon talks about the danger of trusting in temporary things. Is there something in your life right now that you tend to rely on for security or identity instead of Christ? What would it look like to shift your trust to Jesus in that area? ([08:49])
The “great reversal” is not just about turning things upside down, but setting them right side up. Where in your life do you need God to help you see things from His perspective instead of the world’s? ([05:41])
The image of the tree planted by water is about being rooted in God’s Word and nourished by His gifts. What are some practical ways you can stay rooted in God’s promises this week, especially when life feels dry or difficult? ([15:35])
The sermon says our worth and security are not determined by outward circumstances, but by our belonging to Christ. How can you remind yourself of this truth when you’re tempted to compare yourself to others? ([12:54])
Jesus came down to be with us and share in our struggles. How can you follow His example this week by coming alongside someone who is hurting or feeling left out? ([01:42])

Sermon Clips

what theologians have often called Jesus's great reversal that is the crucial distinction between the blessedness that God bestows upon the things that endure namely the things of the Lord and his curse or woe upon those things that are only temporary in nature namely the things of man or this earth we see this contrast laid out for us in two sections in this text in verses 20 through 23 we're told that Jesus quote lifted up his eyes on his disciples and said blessed are you and then he follows that with the list of blessings but in verses 24 through 26 Jesus says but woe to you and he follows that with the list of woes that is warn us now why does Jesus give us this contrasting list of blessings and woes well as with all things it's ultimately because he loves us [00:02:51]

But at the same time, they see what appears to be an obvious inequity.I know that is a catchword in today's world. It still was or was even back then, and it has been throughout the ages. But it is a supposed inequity between the poor, hungry, and oppressed people and the rich, satisfied, and happy people around them.And they are struggling with it, struggling to figure out what's really important. [00:05:07]

So to get them and us to understand and see the answer, He comes down among us today in His Sermon on the Plain. And He shows us the difference between those who are brought into God's kingdom by His grace and those who reject Him and His kingdom in unbelief.To do that, Jesus reverses that which we know from the world completely around. Now, it's not as if we often think of it as Jesus turning the way of the world upside down, but more accurately, it is Jesus taking the way of the world and reversing things so that now we perceive and know them to be right side up. [00:05:50]

That means when you get down...to it. This blessings and woe teaching of Jesus fits very well, not only as a lesson of law and gospel, but also as a foundational lesson about the proper understanding of Christian stewardship.How Christ has saved us and gifted us with His abundant gifts, so that we can now bear fruit as His people with a purpose. [00:06:42]

The way that we and our world see things from the human perspective can be very deceptive.And Jesus understands that struggle.He lived it while He was here on earth among us. Hebrews 4 .15 tells us that Jesus was in fact tempted in every respect as we are.But while you and I far too often fall into sin when we are tempted, that same text says that Jesus did not. He remained without sin. [00:07:13]

That's why he came down among people that day to help them to help us see that the earthly view of things in life does not accurately display the reality of a person's internal spiritual life or reality there are those as Jesus says in his list of woes who are rich who are full who laugh now these are the ones about whom verse 26 says all people speak well of you in other words they are the ones whom the world defines as having made it in life they're successful hey let's just be honest these are the ones that we envy at least from an earthly point of view [00:07:49]

well I know those of you more pious among us i know you're still saying ah no pastor not me i don't want to be rich or have a full stomach or be well liked to that i say give me a break you really want us to believe that you wake up in the morning and you say oh goody i want to starve today i want to be so poor that i can't pay my bills i can't wait to have everyone treat me like they hate my guts of course and you see jesus isn't saying any of us should desire that kind of life but he is giving us a set of very important woes that is warnings in your own personal scale of what's important to you when you set your priorities in life and you figure out what or who it is that you are really trusting in for this life now and for your life to come in eternity what is it what is it that comes out on top who is it that you cannot do without [00:08:46]

those who focus their purpose upon saving and building earthly wealth who fall day after day to the temptation of gluttony and and center their lives upon self -gratification as well as basing the determination of whether or not their life's purpose is about how popular they are or whether they are always happy from an earthly point of view these are the people to whom jesus issues a strong word of warning a woe here today Because all that they have here and now in this temporary world is still all that they are ever going to have.In fact, in the end, it will be taken away from them.In eternity, when Jesus returns, He says that they will actually be hungry and will mourn and weep, because their earthly gods will be shown to be nothing at all.Everything that they believe was important will be revealed as having no importance at all.That's the warning, the woes. [00:10:07]

Jesus has come down, friends, to shower us with His blessings, here and now and eternally.You see, each one of the blessings that Jesus pronounces upon us in verses 20 through 23 have both a...a temporal and a spiritual reality, both a present and a future promise attached to them.And all of them already have been given to each and every member of God's kingdom of believers.We didn't, and we couldn't, earn any of them.They are ours exclusively by the gracious saving work of Jesus, even before He went to the cross and paid for the sins of the world.That's how certain and sure His promise is. [00:11:25]

Notice, for example, in verse 20 that He says, Blessed are you who are poor, for yours is the kingdom of God. That's present tense. A present tense promise to those people there among Him, even before He suffered on the cross for their salvation. [00:12:17]

He wants them to see and know that however the world might have viewed and judged them, it did not determine their reality in God's eyes.On the outside, just like with many of us, they might have looked like poor, hungry, weeping people.They may even face, as Jesus says in verse 22, people hating them, excluding them, reviling and spurring them as being evil, because they follow and believe in Jesus above all that the world thinks should be important.But those things are not what really matter in God's eyes. [00:12:54]

In the grand scheme of His purpose and plan for us, in this life, in His life, in His life.to eternity no jesus says their reality our reality as his people redeemed by the blood of his sacrifice in our place is that we belong to the kingdom of god that we will be satisfied by the bread of eternal life and we will laugh for joy because of our release from the bondage of sin and death with which the devil holds those who reject jesus in hell forever [00:13:37]

even when things are difficult in this life right now even when we are filled with hunger and weeping and grief and persecution jesus says we already have our reward in fact this is how he calls us to use his gifts even now as his stewards so that others may see and believe and be blessed as well rejoice and leap for joy he says for behold your reward is present tense great in heaven [00:14:13]

the person who trusts in the things of man is the one whose heart turns away from the lord and ends up parched he says in bear in a barren wilderness in the end but the person who trusts in the lord even more it says whose trust is the lord is like a tree planted by one he or she She is established and firm in this life because of the spiritual roots that go deep, that are constantly being fed by the Word of God and His gifts of spiritual strength. [00:15:09]

We are blessed by Jesus because of Jesus' work and power to share the blessings that we have received from Jesus far and wide, for the good of those around us, and always to the glory of God.So no matter what you're going through, YouTonight, in this life, at this moment, or the next, you are blessed. Present tense. You are a part of His kingdom today and forever. [00:16:19]

The God who created the heavens and the earth has promised never to leave you, never to forsake you, in a promise that is not dependent upon money, food, business, what kind of piece of paper you've got that says you've gone to all these classes at CU, or whatever it might be, or your fame, because of that paper, maybe. No.It is a promise made sure only by the blood of His Son, Jesus. [00:16:53]

That means it is a promise of forgiveness, life, and salvation that can never fail, never change, never decay with time. His promise, His blessing upon you is sure today and forever.So as long as Jesus lives, you will live.And as long as you have Jesus, you have His gifts for eternity. [00:17:25]

Only in Jesus are our lives, today and forever. reversed. That is, in Jesus, everything is turned right side up. Amen. [00:17:55]

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