What Does It Really Mean To "Win" At Life | Cornerstone Church | Pastor Linn Winters · Rewind

What Does It Really Mean To "Win" At Life | Cornerstone Church | Pastor Linn Winters · Rewind

Linn Winters · Jul 27, 2026

Big Idea

If you live your life as an owner you will always lose, but if you live your life as a manager who knows everything is on loan from God, you are guaranteed to win.

Everything in your hands — your life, your time, your talents, your money — is not yours; it was entrusted to you by God and ownership never passed to you. The hopeful truth is that when we live as faithful managers instead of owners, God blesses us beyond whatever we give back, and one day we get to hear Him say, well done.

Key points

1
1The rich fool in Luke 12 lived as an owner, and Jesus called him a fool for it.
Pastor Linn walks through the parable of the rich fool, whose land yielded such a harvest that he tore down his barns to build bigger ones and told himself to take life easy. He never once asked why God had given him the abundance or what God hoped he'd do with it, because he was certain it was all his. God calls him a fool because that very night his life was demanded of him, and none of the pile did him any good.
2
2Playing life like an owner is playing the game the wrong way, because everything goes back in the box.
Using the board game The Game of Life, Pastor Linn points out that whoever ends the game with the biggest pile of wealth only has an illusion of winning, because it all gets sold off and returned to the box at the end. Living to accumulate the biggest house, car, or pile leaves a person no better off when they die than when they were born.
3
3In the parable of the faithful servant, ownership of the bags of gold never passes to the servants — it's on loan.
Working through Matthew 25:14-19, Pastor Linn identifies the master as God, the servants as us, and the bags of gold as everything God places in our hands: life, time, talents, and finances. Two servants invested what they were given and doubled it, while one buried his, but the passage still calls it his master's money — proof that ownership never transferred.
4
4One day every one of us will settle accounts with God over what we did with what He loaned us.
Pastor Linn describes the master returning to settle accounts with the two faithful servants, who are told well done, good and faithful servant, and entrusted with even more. He frames this as a coming appointment where God will ask what we did with the life, time, talents, and finances He let us borrow.
5
5The servant who buried his one bag of gold reveals three things we all struggle with: forgetting God's collaboration, comparison, and distrust of God's heart.
Pastor Linn unpacks the third servant's excuse — that the master is a hard man who reaps where he didn't sow — and imagines God answering that He provided the soil, the rain, the strength, and even whispered in the interviewer's ear. He suggests the servant given the least struggled most because of comparison to the other servants, and ultimately because he didn't trust that God's heart toward him was good.
6
6Faithfulness with what God has given leads to being entrusted with more.
Pastor Linn notes that both faithful servants who doubled their bags of gold were given charge of more, showing that had the third servant been faithful with even his one bag, God would have given him more too. He ties this to the promise that God blesses whoever is faithful with what they already have, whether or not it's money.

Application

Pastor Linn's challenge is to swap the owner's mindset for a manager's, asking God directly what He wants done with what He's loaned you.

Pray the seven-day manager prayer
For the next seven days, ask God what He wants you to do with your life, your time, your talents, and your finances, even if the answer scares you a little.
Stop treating what's in your hand as yours
Recognize that your life, time, talents, and money are on loan from God rather than possessions you've earned and own outright.
Leverage a portion of what you have for the kingdom
Whatever God has entrusted to you, take part of it and use it for His glory rather than keeping all of it for yourself.
Trust the heart of God enough to give back
Let go of comparison and fear that God is a hard master, trusting instead that He will bless you beyond whatever you sacrifice to Him.

Take it into your week

Sign in to ask Rewind about this sermon

7-day devotional

A personal reading plan from this message — scripture, reflection, and prayer for each day.

Sign in to track your progress through this devotional.

Day 1

Pastor Linn opened with a picture that lingers: a man with a bumper crop, tearing down barns to build bigger ones, telling himself to relax, eat, drink, and be merry. He had it all figured out — except that God called him a fool, because his life would be demanded that very night. What struck Pastor Linn most was the question the man never asked. He never wondered why God gave him such a harvest or what God might want him to do with it. He simply assumed it was all his. That assumption is easy to slip into. When the paycheck clears or the plan comes together, something in us quietly whispers, "I earned this. It's mine." Pastor Linn compared it to The Game of Life — you can win the whole board, and at the end all your carefully stacked wealth just goes back in the box. You're no better off for having won. The invitation this week isn't guilt over what you have. It's a gentler, more honest question: what if none of it was ever meant to be hoarded? What if it was all a gift, waiting for you to ask the Giver what He had in mind?

For reflection

Where have I quietly assumed something in my life is simply 'mine' without ever asking God about it?

Pray

Pray for honesty about where you've been living like an owner instead of asking the Giver.

Small-group discussion guide

For leading a group conversation about this message.

Open

Think of a board game like The Game of Life that Pastor Linn mentioned — at the end, all the money and pieces go right back in the box. What's a game you've "won" only to realize the winnings didn't come with you afterward?

Discussion questions

1
Read Luke 12:15-21 aloud together. What do you notice about the way the rich man talks and plans in these verses?
2
Pastor Linn pointed out that the rich man never asked why God gave him the harvest or what God wanted done with it. Why might someone skip those questions when good things come their way?
3
In the parable of the bags of gold, the master hands his wealth to the servants before leaving on a journey. What does it change about how we see our lives, time, talents, and money when ownership stays with the master the whole time?
4
When the third servant explains why he buried his one bag, he says he was afraid and saw the master as harsh. How do fear, comparison, and distrust of God's heart tend to keep people from investing what they've been given?
5
The two faithful servants hear 'well done' and are entrusted with more. What does this picture suggest about the kind of accounting the sermon says every person will one day have with God?
6
Pastor Linn's challenge was to spend seven days asking God specifically what He wants done with our lives, time, talents, and finances — and he said a slightly scary answer is often a sign it's genuinely from God. How might we encourage one another to take that kind of question to God this week?

Pray together

Trusting that God's heart is good, and asking Him for open hands to manage well what He has entrusted to us.

Sign in to save this message.

Topics

Generosity Obedience Stewardship Trust in God

Powered by Rewind · make your church's Rewind →