New Wine and Old Wineskins: Trusting God With What He Is Beginning
“They pour new wine into new wineskins, and both are preserved.” Matthew 9:17
When something ends, and God prepares us for what is new.
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Something ends. A term on the field comes to its last week. A role is handed to someone else. A door we expected to stay open quietly closes. Our first instinct is often to move on quickly and answer the question everyone is asking: so what now?
But sometimes something has to end before God can begin something new, and the season in between is where He prepares us.
New Wine and Old Wineskins
When John the Baptist's disciples asked Jesus why His followers did not fast, He answered with a wedding. Guests don't mourn while the bridegroom is with them, He said, but "the time will come when the bridegroom will be taken from them; then they will fast" (Matthew 9:15). Then He gave a picture from ordinary life. No one pours new wine into old wineskins, because the old skins will burst. "No, they pour new wine into new wineskins, and both are preserved" (Matthew 9:17).
Jesus was speaking about Himself and the newness He had come to bring. And notice that the new wine would come through loss. The bridegroom would be taken. There would be mourning before there was joy.
Why the Old Feels Better
Luke adds a line Matthew does not include: "And no one after drinking old wine wants the new, for they say, 'The old is better'" (Luke 5:39).
In its setting, Jesus seems to be describing why many held back from what He was bringing. It is an honest observation about people, not a rule that old is bad and new is good.
Jesus does not mock the old wine. Old wine is often very good, and that is exactly why it is hard to hold loosely. The old is familiar. We understand it and know how to explain it. We may have given years of our lives to it, and others may have given alongside us. And sometimes God really did use it.
So the question is not whether yesterday was good. Often it was. The question is quieter: Have I confused faithfulness to God with faithfulness to the way God worked before?
Faithfulness does not always mean continuing in the same place or doing things the same way. Sometimes it means persevering through difficulty and remaining where God has called us. Other times, it may mean recognizing that a season has come to an end. Discerning the difference requires humility, prayer, wise counsel, and a willingness to examine our own hearts. We must be careful not to assume that every difficult circumstance is a sign that God is leading us elsewhere, but neither should we assume that staying is always the more faithful choice.
We can honor what God did yesterday without requiring Him to do it the same way tomorrow.
Unless a kernel of wheat falls to the ground and dies, it remains only a single seed." John 12:24
Unless a Seed Falls: John 12:24
Just days before the cross, Jesus said, "Unless a kernel of wheat falls to the ground and dies, it remains only a single seed. But if it dies, it produces many seeds" (John 12:24). Jesus was speaking first about His own coming death and the life that would come through His sacrifice. But He also invited His followers into a life of surrender, where following Him may require releasing what we would naturally want to preserve (John 12:26).
This doesn't mean every ending is something God has ordained or that every loss will lead to something greater. But it reminds us that following Jesus sometimes requires letting go of what we have known and trusting Him with what comes next. The fruit belongs to God, and we don't always get to see what He is doing.
Between the cross and the resurrection there was a Saturday. The women who had followed Jesus had watched Him die, and then they "rested on the Sabbath in obedience to the commandment" (Luke 23:56). Jesus had spoken of His resurrection, but His followers did not yet understand what was coming. They were living in the space between what they had lost and what God was about to do. Redemption did not skip the burial.
Many missionaries know that day. Something has ended and nothing new has appeared. Debriefing is often where we first name what has ended and let ourselves grieve it, instead of carrying it quietly behind a mask.
Room to Rest When Something Ends
Jesus told a simple story about a seed. A farmer scatters it on the ground. "Night and day, whether he sleeps or gets up, the seed sprouts and grows, though he does not know how" (Mark 4:27).
The farmer sleeps. The seed grows anyway. We do not make new life happen by staying busy or by worrying over it. Some seasons look empty from the outside while something is being restored underneath. Part of what a debriefing retreat offers is simply room to stop and rest before the next thing begins.
hold fast what is good
Many of us carry a season we loved that did not end the way we hoped. A ministry, a team, a place we called home. For me, it was a ministry I gave many years to and deeply loved. I never imagined my story would take the turn it did, and to be honest, there are still things I grieve.
When a season ends painfully, it can make us question everything that came before it. Was it all good? Did it matter? How do we make sense of the good when there were also things that were deeply painful?
I have had to wrestle with those questions. Perhaps you have too.
But I keep coming back to something Paul wrote: "Test all things; hold fast what is good" (1 Thessalonians 5:21).
We don't have to pretend that everything was good to acknowledge that God was at work. We can recognize what was difficult, even what was wrong, without dismissing the fruit that came from those years. I think about the lives that were changed, the relationships that were built, and the ministry that continues today. Those things matter. And I am reminded that God has not forgotten the years of love and service poured into others Hebrews 6:10
That season was very hard. Some of my hardest days were spent trying to understand why things happened the way they did. I asked question after question, hoping that somehow I could make sense of it all. But slowly, I had to come to terms with the reality that there were things I could not change and answers I might never receive.
My part was to surrender, to trust the Lord, and to release the control I thought I needed.
And God was faithful.
He met me in the wilderness. He cared for me when I didn't know what was next. Looking back, I can see His faithfulness in ways I couldn't recognize at the time.
I have come to believe that God can use even the hardest seasons of our lives. That doesn't mean everything that happens is good or that He intended every painful circumstance. But He is able to redeem what has been broken, to shape us through what we have walked through, and to bring beauty from ashes (Isaiah 61:3).
And that is where the new wineskin becomes personal.
Something new is not simply the old season in a new place. A new ministry, a new role, or a new home does not replace what came before, and it does not need to. It has its own calling and its own shape. But God can take both the good and the difficult parts of our past and use them to prepare us for what He is doing now.
I have seen that in my own life. The things I walked through have shaped the way I listen, the way I care, and the way I sit with others who are carrying difficult stories. Paul wrote that God “comforts us in all our troubles, so that we can comfort those in any trouble with the comfort we ourselves receive from God” (2 Corinthians 1:4). I see that Scripture differently now. Not because I have all the answers or have worked through everything perfectly, but because I know what it is to need the Lord to meet me in a place I never expected to be.
If you are stepping into something new while still carrying the last season, you are not behind. Bring all of it to Him. He can use what you carry.
Tears and Shouts of Joy: Ezra 3
There is a passage in Ezra that has become particularly meaningful to me when I think about seasons of transition.
When the foundation of the new temple was laid in Jerusalem, many of the older priests and leaders who had seen the first temple "wept aloud," while others "shouted for joy." Ezra tells us that "no one could distinguish the sound of the shouts of joy from the sound of weeping" (Ezra 3:12–13).
What a picture of the complexity of new beginnings. Some were celebrating what God was doing, while others were grieving what had been lost. And perhaps some were experiencing both.
I think that is often what a new beginning sounds like. The tears do not mean we are ungrateful for the new, and the joy does not mean we have forgotten the old.
We can grieve what is gone and still praise God for His faithfulness. We can be thankful for what He did in a previous season while acknowledging that there were things we wish had been different.
Ecclesiastes 3:4 reminds us that there is "a time to mourn and a time to dance." Sometimes those seasons overlap. And part of surrender, I am learning, is holding both the grief and the gratitude before the Lord without feeling that we have to resolve every question.
When Israel stood at the edge of the Jordan, they were instructed to follow the ark of the covenant, "since you have never been this way before" (Joshua 3:4).
I love that reminder. There are seasons when we simply don't know the way forward. We cannot see what God is preparing, and we may still be grieving what we have left behind. But we can stay close to Him, remembering His faithfulness in the past while trusting Him with the road ahead.
Perhaps embracing something new doesn't mean we have to forget what came before. Maybe it means learning to carry forward what was good, surrender what we cannot change, and remain open to what God is doing now.
"You have never been this way before." Joshua 3:4
Discerning Together: How Debriefing Helps
When the early church faced difficult questions about how God was working among the Gentiles, the apostles and elders gathered to listen, consider what God had done, and examine the Scriptures together (Acts 15). Their letter included the words, "It seemed good to the Holy Spirit and to us" (Acts 15:28).
Although the circumstances were different, I think there is something we can learn from their willingness to listen and seek understanding together. We were never meant to navigate every difficult season alone.
Proverbs 20:5 reminds us, "The purposes of a person's heart are deep waters, but one who has insight draws them out."
I love that picture. Sometimes we carry things in our hearts that we haven't fully understood or even found words for. Having someone who will listen carefully, ask thoughtful questions, and help us reflect can bring things to the surface that we might otherwise overlook.
This is part of what we seek to provide through debriefing at Compass Asia. It is a confidential, unhurried space for global workers to look back over a season of life and ministry, process both the joys and the difficulties, and prayerfully consider what God may be doing in their lives.
And for churches and mission agencies, one of the most meaningful ways we can care for those serving on the field is to give them the space and support to process their experiences honestly, without feeling pressured to have everything figured out.
"A planting of the LORD for the display of his splendor." Isaiah 61:3
A Planting of the Lord: The Garment of Praise
The same verse that promises beauty instead of ashes also promises those who mourn "a garment of praise instead of a spirit of despair." Then Isaiah adds, "They will be called oaks of righteousness, a planting of the LORD for the display of his splendor" (Isaiah 61:3).
I love that picture. A planting of the Lord. Something He tends, nurtures, and establishes in His time.
The garment of praise does not always come with a new ministry, a restored relationship, or the answers we have been waiting for. Sometimes it comes right in the middle of grief, as we begin to recognize His comfort and faithfulness even when our circumstances have not changed.
Perhaps you are in a season where something has ended, and you don't yet know what comes next. Maybe you are still grieving what was lost or struggling to understand why things unfolded as they did.
You don't have to rush to make sense of it all.
There is a time to grieve, a time to rest, and a time to begin again.
The Lord who was faithful in the past is still faithful today, and we can trust Him with what we cannot yet see.
And perhaps, in time, we will recognize that even in the waiting, He was at work in ways we couldn't yet understand.
A few honest questions may help:
What has ended that I have not yet allowed myself to grieve?
Am I rushing toward the next thing because God is leading, or because the quiet feels too difficult?
What from that season do I want to hold fast, and what do I need to surrender?
Who could walk alongside me as I process this season?
Lord, You know what has ended and what is beginning. Help me not to rush past this season. Meet me in the waiting. Prepare my heart for what You are doing next, and in Your time, clothe me again with praise.
At Compass Asia, we recognize that transitions in ministry are not always easy. Sometimes they come with unexpected grief, unanswered questions, or the challenge of discerning what comes next.
Through debriefing, we provide global workers, couples, and families with a confidential, unhurried space to reflect on their experiences, process both the joys and the difficulties, and prayerfully consider what God may be doing in their lives.
Whether you are preparing for a new assignment, returning from the field, or navigating an unexpected ending, you don't have to walk through that season alone.
Frequently Asked Questions
Q: What did Jesus mean by new wine and old wineskins?
A: In Matthew 9:14–17, Jesus used the illustration of new wine and old wineskins while answering a question about fasting. New wine needed flexible wineskins that could expand during fermentation, while old, brittle skins could burst. Jesus was illustrating the newness of what He had come to bring and why it could not simply be contained within existing religious practices and expectations. Luke adds that those accustomed to old wine often prefer it, saying, "The old is better" (Luke 5:39). This reminds us how difficult it can be to release what is familiar, even when God may be leading us into something new.
Q: What does John 12:24 mean?
A: In John 12:24, Jesus used the illustration of a seed falling to the ground and dying to describe His coming death and the life that would come through His sacrifice. He then called His followers to a life of surrender and faithful obedience (John 12:25–26). While this passage does not promise that every painful ending will lead to something greater, it reminds us that following Jesus sometimes requires letting go of what we would naturally want to preserve. We may not always understand what God is doing, but we can trust Him with what comes next.
Q: What happened on the Saturday between Good Friday and Easter?
A: After Jesus' crucifixion and burial, His followers entered a time of grief and uncertainty. Luke 23:56 tells us that the women who had followed Jesus "rested on the Sabbath in obedience to the commandment." Although Jesus had foretold His resurrection, His disciples did not yet fully understand what was coming (Luke 18:31–34). That quiet Saturday reminds us that there are seasons when we cannot see what God is doing. We may be grieving what has ended, uncertain about what comes next, and struggling to make sense of our circumstances. Yet even in the waiting, we can trust that God has not abandoned us.
Q: What does Ezra 3:12–13 teach about grief and new beginnings?
A: When the foundation of the second temple was laid in Jerusalem, those who remembered the first temple wept aloud, while others shouted for joy (Ezra 3:12–13). The sounds of weeping and rejoicing were so great that they could not be distinguished from one another. This beautiful picture reminds us that grief and gratitude can exist together. We can mourn what has been lost while also rejoicing in what God is doing. Embracing a new beginning does not mean we have to forget the past or dismiss the good that God accomplished in a previous season.
Q: How can we prepare our hearts for something new from God?
A: When the Israelites prepared to cross the Jordan River, they were instructed to follow the ark of the covenant because they had never traveled that way before (Joshua 3:3–4). The ark represented God's presence among His people, reminding them of their need to follow His leading into unfamiliar territory. In seasons of transition, we can prepare our hearts by remaining close to the Lord through prayer and His Word, remembering His faithfulness in the past, and seeking wise counsel as we discern what comes next. We can acknowledge the grief that sometimes accompanies change while trusting God with a future we cannot yet see.
Q: How can missionaries process the end of a ministry season?
A: The end of a ministry season can bring a mixture of emotions, including grief, gratitude, disappointment, and uncertainty. Processing these transitions begins with making space to acknowledge what has ended, recognize the good that God accomplished, and honestly grieve what was lost. Rather than rushing into the next assignment, it can be helpful to take time for rest, prayer, and reflection. Debriefing provides global workers, couples, and families with a confidential, supportive environment where they can share their experiences, process difficult emotions, and prayerfully discern what God may be doing in their lives.
