Flipped Character (Part 1)

Flipped Character (Part 1)

When Jesus begins the Sermon on the Mount in Matthew 5, He doesn’t start by telling people what to do. He starts by telling them who they must become. He starts with character — Kingdom character.

And that’s why this message is Flipped — Character, Part 1. Because Jesus is about to flip our understanding of what a blessed, godly, Kingdom‑shaped life actually looks like.

He flips the values.

He flips the priorities.

He flips the character traits we think matter.

Before we even get into the Beatitudes, let me show you what I mean.

Opening Story — The “Perfect Life” That Wasn’t

I once knew a man who looked blessed by every worldly standard. He had the job, the money, the toys, the weekends at the lake, the big truck, the full calendar. People looked at him and said, “Man, he’s got it made.”

But if you got close enough, you’d see the truth: he was exhausted, empty, and constantly trying to outrun his own pain. He had everything the world calls “blessed” — and none of what Jesus calls blessed.

And maybe you can relate to that — the perfect life that wasn’t. Maybe on the outside everything looks fine, but inside you’re tired, hurting, or carrying things no one else sees.

And that’s exactly what Jesus is doing in the Beatitudes. He flips the whole idea of blessing upside down. He says the blessed ones aren’t the ones who look strong, but the ones who admit they’re poor in spirit. Not the ones who avoid pain, but the ones who mourn. Not the ones who dominate, but the meek. Not the ones who chase pleasure, but the ones who hunger for righteousness.

Jesus is showing us what Kingdom character really looks like — the life we were created for, the life the fall flipped upside down, and the life we are called to walk in as followers of Christ.

A Working Definition of “Blessed”

To be blessed, according to Jesus, is to live in the favor, nearness, and rule of God — regardless of circumstances — because your life is aligned with His Kingdom and shaped by His character.

And Scripture backs this up again and again. Blessing in the Bible is never about comfort or circumstances — it’s about God’s presence and God’s favor.

In Psalm 1:1–3 “Blessed is the man who walks not in the counsel of the wicked, nor stands in the way of sinners, nor sits in the seat of scoffers; but his delight is in the law of the Lord, and on his law he meditates day and night. He is like a tree planted by streams of water that yields its fruit in its season, and its leaf does not wither. In all that he does, he prospers.”

The blessed person is the one who delights in God’s Word and walks in His ways — not the one with the easiest life.

In Psalm 32:1–2 “Blessed is the one whose transgression is forgiven, whose sin is covered. Blessed is the man against whom the Lord counts no iniquity, and in whose spirit there is no deceit.”

David says the blessed person is the one whose sins are forgiven and whose heart is clean before God. In Psalm 84:4–5 “Blessed are those who dwell in your house, ever singing your praise! Selah Blessed are those whose strength is in you, in whose heart are the highways to Zion.”

Here we see blessing is tied to being near God and finding strength in Him.

Jesus says in Luke 11:28 that the blessed ones are those who hear God’s Word and keep it. And Paul repeats David’s words in Romans 4:7–8: blessed are those whose sins the Lord will never count against them.

All of that reinforces what we will see Jesus is saying in Matthew 5: Blessing isn’t about what you have — it’s about who you belong to. Blessing isn’t about your situation — it’s about your standing with God. Blessing isn’t about outward success — it’s about inward transformation.

So when Jesus says “Blessed are…,” He’s describing the life lived under God’s rule, shaped by God’s character, and filled with God’s presence — even in hardship.

1. “Blessed are the poor in spirit…” (Matthew 5:3)

Matthew 5:3 ““Blessed are the poor in spirit, for theirs is the kingdom of heaven.”

When Jesus talks about being “poor in spirit,” He’s talking about people who know they don’t have it all together — people who come to God with empty hands.

David understood this deeply. In Psalm 51:17, he says God is drawn to “a broken and contrite heart.” And remember — this is David talking. A man who committed adultery. A man who arranged a murder to cover it up. A man who knew what it was like to hit the bottom spiritually. He’s not speaking as someone who got everything right — he’s speaking as someone who finally stopped pretending and threw himself on the mercy of God.

Isaiah echoes this in Isaiah 57:15, where God says He dwells with the lowly and revives their hearts. That’s the picture: God meets us in humility, not self‑sufficiency.

Jesus reinforces this in Luke 18:9–14 with the tax collector

Lets take a look and see.

Luke 18:9–14 “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. The Pharisee, standing by himself, prayed thus: ‘God, I thank you that I am not like other men, extortioners, unjust, adulterers, or even like this tax collector. I fast twice a week; I give tithes of all that I get.’ But the tax collector, standing far off, would not even lift up his eyes to heaven, but beat his breast, saying, ‘God, be merciful to me, a sinner!’ I tell you, this man went down to his house justified, rather than the other. For everyone who exalts himself will be humbled, but the one who humbles himself will be exalted.””

What does the tax collector do? He simply cried out for mercy — and Jesus says that man went home right with God, justified like he had never sinned.

All of Scripture points in the same direction: God moves toward the humble.

2. “Blessed are those who mourn…” (Matthew 5:4)

Matthew 5:4 ““Blessed are those who mourn, for they shall be comforted.”

Mourning in Matthew 5:4 is the honest grief that comes when we see our sin, our pain, and our brokenness the way God sees it — and we bring it to Him for healing.

When Jesus says mourners are blessed, He’s not talking about people who enjoy pain — He’s talking about people who stop running from it and bring it honestly before God.

Paul calls God “the Father of mercies and the God of all comfort who comforts us in all our afflictions” in 2 Corinthians 1:3–4, reminding us that comfort isn’t something we manufacture — it’s something God gives and it happens when we are are under distress.

One of the most tender promises in Scripture, Psalm 34:18, says the Lord is near to the brokenhearted and saves those crushed in spirit.

David understood this kind of mourning too. After his sin with Bathsheba and the death of her husband Uriah, he didn’t just feel bad — he was shattered. Psalm 51 is the prayer of a man who knows he has nothing left to offer God but repentance. And God met him there.

So when Jesus says mourners are blessed, He’s saying, “You don’t have to hide your hurt — I meet you there.”

And I’ll be honest with you — I lived this way for years. Before Christ saved me at 36, I carried the weight and consequences of a fallen lifestyle. I tried to numb pain, hide my shame, and fix myself. And even now, I still feel the ripple effects of choices I made outside of Christ. There are days I have to remind myself that Jesus is more than I could ever be, that He is enough, and that His blood has covered my past sins that I am forgiven.

What I could never do on my own, He accomplished at the cross. And what He did for me, He wants to do for anyone who will repent and believe Mark 1:15.

3. “Blessed are the meek…” (Matthew 5:5)

Matthew 5:5 ““Blessed are the meek, for they shall inherit the earth.”

Meekness isn’t weakness — it’s strength under God’s control. Meekness is not the absence of strength — it’s the refusal to use strength in a way that harms.

David describes this beautifully in Psalm 37:11

“But the meek shall inherit the land and delight themselves in abundant peace.”

David says the meek are the ones who trust God instead of reacting in anger or trying to force outcomes. They’re steady. They’re surrendered. And they’re the ones who inherit the land.

And we actually see this kind of meekness all the time in everyday life. Think about a godly parent in a grocery store with a toddler melting down — screaming, kicking, everyone staring. That parent has the power to dominate the moment, to snap, to react out of embarrassment. But instead, they kneel down, speak softly, hold the child close, and choose compassion over control. That’s not weakness. That’s strength — restrained, patient, and guided by love.

Jesus Himself models this in Matthew 11:29, where He describes His own heart as “gentle and lowly.” If the Son of God — with all authority — chooses gentleness, then meekness isn’t optional. It’s Christlikeness.

So when Jesus says the meek will inherit the earth, He’s saying, “Those who trust My Father instead of themselves — they’re the ones who truly win.”

4. “Blessed are those who hunger and thirst for righteousness…” (Matthew 5:6)

Matthew 5:6 ““Blessed are those who hunger and thirst for righteousness, for they shall be satisfied.”

Hunger and thirst are powerful images. They maybe things we don’t think about much, but fast for a day or two and the body will let you know what it needs. To hunger and thirst describes people who want God more than anything else.

David captures this in Psalm 63:1, saying he longs for God like someone in a dry and weary land — not casually, but desperately.

Psalm 63:1 “O God, you are my God; earnestly I seek you; my soul thirsts for you; my flesh faints for you, as in a dry and weary land where there is no water.”

Jesus connects righteousness with love in John 14:15, where He says, “If you love Me, you will keep My commandments.” In other words, righteousness isn’t about rule‑keeping — it’s about relationship.

And the promise is this: in Psalm 107:9, God satisfies the longing soul. Jesus echoes that in John 6:35 when He says He is the bread of life — the One who truly satisfies.

Psalm 107:9 “For he satisfies the longing soul, and the hungry soul he fills with good things.”

John 6:35 “Jesus said to them, “I am the bread of life; whoever comes to me shall not hunger, and whoever believes in me shall never thirst.”

And what’s beautiful is that David — the same man who failed so deeply — became a man who hungered for righteousness. Not because he was perfect, but because he had tasted the bitterness of sin and the sweetness of God’s mercy. Maybe that is you today. You have failed deeply and tasted the bitterness of sin and want to taste the sweetness of God’s mercy. Like David God is there for you. Sometimes the people who hunger for righteousness the most are the ones who know what unrighteousness has cost them.

So when Jesus says those who hunger and thirst for righteousness will be satisfied, He’s saying, “If you want Me — really want Me — I will fill you.”

Closing Gospel Invitation

As we look at these Beatitudes, it becomes clear that Jesus isn’t describing different kinds of Christians. He’s describing the work God does in every heart that comes to Him — whether for the first time or the thousandth.

Maybe today you feel spiritually empty — and Jesus is saying, “Blessed are the poor in spirit… the Kingdom is open to you.”

Maybe you’re carrying grief, guilt, or regret — and Jesus is saying, “Blessed are those who mourn… I will comfort you.”

Maybe you’re exhausted from trying to control everything — and Jesus is saying, “Blessed are the meek… I will carry what you can’t.”

Maybe you’re hungry for something real — and Jesus is saying, “Blessed are those who hunger and thirst for righteousness… I will fill you.”

For some of you, this is an invitation to begin a relationship with Jesus — to repent, believe, and trust Him with your life for the very first time. He lived the life you couldn’t live. He died the death you deserved. He rose to give you new life. And He is ready to forgive, cleanse, and make you new if you will come to Him in faith.

For others — for believers in the room — this is an invitation to return, to realign your heart with the character of the Kingdom. Maybe you’ve drifted. Maybe you’ve been carrying things alone. Maybe you’ve been trying to look strong instead of being poor in spirit. Maybe you’ve been numbing pain instead of mourning before God. Maybe you’ve been reacting instead of walking in meekness. Maybe your hunger has shifted from righteousness to something else.

And hear this clearly: the way back is the same as the way in — repent and believe. Repent where you’ve wandered. Repent where you’ve tried to do life in your own strength. Repent where your heart has grown cold or distracted. And believe again that Jesus is enough, that His grace is sufficient, that His Spirit is at work in you even now.

Jesus is calling you back — not with shame, but with blessing. He is inviting you to step again into the life you were created for, the life the world has flipped upside down, the life He is restoring in you by His Spirit.

Whether you need to come to Christ or come back to Christ, the invitation is the same: Bring Him your emptiness. Bring Him your pain. Bring Him your striving. Bring Him your hunger. He will meet you. He will comfort you. He will strengthen you. He will satisfy you.

This is the blessed life. This is the Kingdom life. This is the abundant life Jesus is offering you right now.