My Cup Runneth Over: Living in God's Overflow

Psalm 23 moves from God’s guidance to God’s abundance, and David’s words do not sound like barely getting by. “My cup runneth over” is not a half-glass way of thinking. God is not a half-glass God. The shepherd does not just keep the sheep alive. He makes them lie down in green pastures, leads them beside still waters, restores their souls, anoints their heads with oil, and causes their cups to overflow.

David declares overflow from a life that knew caves, battles, betrayal, and heartache. His cup runs over right in the middle of trouble, not just after everything gets easy. The believer can be going through hell and still say, “my cup runs over,” because God’s abundance is not measured by circumstances or possessions. El Shaddai, the all-sufficient one, gives more than enough grace, more than enough mercy, more than enough power, and more than enough strength.

Psalm 23 also puts the oil before the overflow. The anointing comes first because the Holy Spirit breaks off what keeps a life full of the wrong stuff. Bitterness, unforgiveness, worldly thinking, and “bugs in the brain” leave no room for the fullness of God. The shepherd’s oil heals the bites, quiets the torment, and suffocates what has been crawling around in the mind. Overflow begins where surrender begins.

Jesus shows the same truth at Cana. Empty vessels became the place where the best wine appeared. Emptiness is not always bad, especially when a person has run out of lesser things and is ready for Christ to fill the life with what only He can give. John 7 takes it even further: Jesus does not offer a thimble full or a spoonful. He gives living water that becomes a river flowing from within.

Ephesians 5:18 calls God’s people to “be filled with the Spirit,” meaning keep being filled. Life leaks. Ministry drains. Trials exhaust. Battles wear people down. Yesterday’s filling was wonderful, but today’s battle requires today’s filling. God’s word, consistent worship, continual prayer, connection to the body of Christ, and daily yielding to the Holy Spirit keep the cup from running dry. The question becomes simple: how does the cup look today? Empty, half full, running low, or overflowing? The shepherd is still El Shaddai, still more than enough, still pouring in the oil and the wine, and still filling lives until they run over.

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Key Takeaways

• 1. God is not half-glass God Psalm 23 does not present a shepherd who barely keeps sheep alive. The text shows green pastures, still waters, restored souls, fresh oil, and an overflowing cup. Scarcity thinks in terms of just enough, but David’s confession pushes the soul toward God’s extravagant goodness. [31:27]
• 2. Overflow can stand in trouble David’s cup ran over even though David knew caves, battles, betrayal, and heartache. Trouble does not prove that God’s supply has stopped. A life can be under pressure and still be filled, because the source is not the ease of the moment but the nearness of the shepherd. [32:50]
• 3. Oil comes before overflow Psalm 23 places anointing before the cup runs over. The Holy Spirit does not merely decorate a life, He breaks yokes and clears out what has been occupying the soul. Bitterness, unforgiveness, and stinking thinking have to lose their grip before fullness can become overflow. [36:41]
• 4. Empty vessels receive the best At Cana, the lack became the opening for Jesus to fill what had run dry. Emptiness can feel like failure, but it can also mark the end of self-supply and the beginning of Christ’s best provision. The empty place becomes holy when it turns toward Him instead of toward the world. [42:49]
• 5. Today requires fresh filling Ephesians 5:18 calls for continual filling because life leaks. Battles, trials, ministry, and ordinary weariness drain even faithful people. Yesterday’s strength cannot carry today’s obedience unless the believer keeps coming back to the Spirit’s river.
  
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Youtube Chapters

• [00:00] - Welcome
• [27:59] - Psalm 23 and the Overflowing Cup
• [28:32] - Living on Empty
• [31:08] - God Has No Half-Glass Mentality
• [32:50] - David Declares Overflow in Trouble
• [34:22] - More Than Survival
• [35:39] - El Shaddai, More Than Enough
• [36:41] - The Oil Comes Before Overflow
• [38:50] - Bugs in the Brain
• [42:26] - Cana and Empty Vessels
• [45:16] - Rivers of Living Water
• [48:23] - Keep Being Filled
• [52:05] - How to Stay Filled
• [56:55] - Stay Connected and Yield Daily
• [60:25] - How Does the Cup Look Today?

Bible Reading

Psalm 23:5
“You prepare a table before me in the presence of my enemies; you anoint my head with oil; my cup overflows.” [20:35]

Ephesians 5:18
“And do not get drunk with wine, for that is debauchery, but be filled with the Spirit,” [48:27]

John 7:37-38
“On the last day of the feast, the great day, Jesus stood up and cried out, ‘If anyone thirsts, let him come to me and drink. Whoever believes in me, as the Scripture has said, “Out of his heart will flow rivers of living water.”’”

John 2:1-10
“On the third day there was a wedding at Cana in Galilee, and the mother of Jesus was there. Jesus also was invited to the wedding with his disciples. When the wine ran out, the mother of Jesus said to him, ‘They have no wine.’ And Jesus said to her, ‘Woman, what does this have to do with me? My hour has not yet come.’ His mother said to the servants, ‘Do whatever he tells you.’ Now there were six stone water jars there for the Jewish rites of purification, each holding twenty or thirty gallons. Jesus said to the servants, ‘Fill the jars with water.’ And they filled them up to the brim. And he said to them, ‘Now draw some out and take it to the master of the feast.’ So they took it. When the master of the feast tasted the water now become wine, and did not know where it came from (though the servants who had drawn the water knew), the master of the feast called the bridegroom and said to him, ‘Everyone serves the good wine first, and when people have drunk freely, then the poor wine. But you have kept the good wine until now.’”

Observation questions

1. In Psalm 23:5, what three things are happening around the believer in that one verse, and what do those details show about the Shepherd’s care? [31:48]
2. What are some of the hard places David had known, even while still saying, “my cup overflows”? [32:50]
3. In Psalm 23:5, what comes first—anointing with oil or the overflowing cup—and why does that order matter in the passage? [37:04]
4. In the Cana story, what was empty, what were the servants told to do, and what kind of provision did Jesus give in the end? [42:49]

Interpretation questions

1. David speaks about an overflowing cup while enemies are still present. What does that suggest about the kind of abundance God gives, and how is it different from the way people usually measure blessing? [33:22]
2. The oil comes before the overflow. How should that shape the way a believer thinks about surrender, healing, and the work of the Holy Spirit in a life that wants fullness? [39:08]
3. Jesus turned empty vessels at Cana into a place of abundance. How can seasons of emptiness become an opening for Christ’s best work instead of only a sign of failure? [43:31]
4. Ephesians 5:18 calls believers to keep being filled with the Spirit. What does that reveal about everyday Christian life, especially in seasons where people feel drained, distracted, or worn down? [48:40]

Application questions

1. How does the cup look today—empty, half full, running low, or overflowing? What has been the clearest sign of that in this season of life? [01:00:25]
2. Bitterness, unforgiveness, worldly thinking, and “bugs in the brain” leave little room for the fullness of God. Is there any area like that taking up space right now that needs to be brought to the Shepherd? [37:45]
3. Overflow is not about possessions but about God’s presence. When life gets hard, is there a tendency to judge God’s nearness by circumstances? What would it look like to say, even in trouble, “my cup runs over”? [41:04]
4. When the soul feels empty, there is usually a choice between turning to the Shepherd or turning somewhere else for relief. Where is the first instinct usually to go when tired, frustrated, or worn out? [44:28]
5. Life leaks. What has been draining the most lately—ministry, stress, family pressure, disappointment, spiritual weariness, or something else? What kind of fresh filling is needed now, not just what was needed yesterday? [51:59]
6. Fresh filling is often tied to simple habits like Scripture, worship, prayer, staying connected to the body of Christ, and daily yielding to the Holy Spirit. Which one of those has been strongest lately, and which one has been neglected? [52:05]
7. Sometimes the next step of yielding is very simple—apologize, be quiet, give something, obey a prompting, or go where God leads. Is there a specific nudge from the Holy Spirit that needs to be obeyed this week? [57:57]