Old Paths and Old Wineskins

There was a dirt path that cut through a field near where I used to live. I walked my dog there often.

In the spring, after the rains, it was a pleasure to walk. The earth was dark and soft. If a large puddle blocked the way, it was no trouble to step off into the tall grass, your feet sinking just slightly into the damp ground, and find your way around it. The path was a suggestion, a guide, not a demand. The whole landscape felt open and accessible.

But by late summer, after months without rain, the path was transformed. The same soil was baked by the sun into something hard as pavement. Deep cracks appeared. The path was no longer a gentle depression in the earth but a hard rut. To step off it was to risk turning an ankle on the unyielding, lumpy ground. You kept to the path not because it was pleasant, but because it was the only safe way forward. It had lost all its give. It had no capacity for anything new, no room for deviation.

This image of a path, once soft and forgiving, becoming a hard and rigid rut, often comes to my mind when I sit with one of Jesus’ most searching parables. It speaks to a danger we all face in our spiritual lives: the slow, almost imperceptible hardening of the very things that once gave us life.

The story is found in Luke’s Gospel. Jesus is in the early days of his ministry, and he’s already causing problems. He calls a tax collector, a man seen as a traitor, to be one of his closest followers. Then he sits down and eats a meal with him and his friends, a whole crowd of people considered unclean by the religious authorities. When confronted about why he and his disciples don't follow the proper rules of fasting, Jesus doesn't debate the regulations. He tells a story about containers.

“He also told them a parable: ‘No one tears a piece from a new garment and sews it on an old one; otherwise, the new will be torn, and the piece from the new will not match the old. And no one puts new wine into old wineskins; otherwise, a new wine will burst the skins and will be spilled, and the skins will be destroyed. But new wine must be put into fresh wineskins. And no one, after drinking old wine, desires new; for he says, ‘The old is good.’” (Luke 5:36-39)

As a spiritual director, I have come to see this not as a threat, but as a tender and honest diagnosis from a God who knows us completely. It is an invitation to look at the containers of our own lives and ask a difficult question: Have my paths become ruts?

A Living Process Needs a Living Container

To feel the force of Jesus’ words, we have to understand what he’s talking about. In the first century world, new wine was not a finished product. It was living, active grape juice. As the natural yeasts went to work, the wine would bubble and ferment, releasing gases and creating pressure. It was a process of transformation.

A new wineskin, made from an animal hide, was prepared for this. It was treated with oil, making it supple and elastic. It had room to stretch. It could expand as the wine expanded, safely containing the powerful process of fermentation until the wine was ready.

An old wineskin was the opposite. It had already held wine, already been stretched to its limit. Over time, it had become dry, stiff, and brittle. It had no more give left in it. To pour new, active wine into such a container was to guarantee a disaster. The unyielding leather could not absorb the pressure. It would burst. And in that moment, everything would be lost: the container would be ruined, and the precious new wine would spill out onto the ground.

What Jesus was saying to the religious leaders was clear. He was the new wine. The forgiveness, radical welcome, and new life he was bringing into the world could not be contained by their old, rigid structures. Their rules and traditions had become brittle. Trying to force his new work into their old containers would only lead to ruin.

Identifying Our Own Wineskins

This is where the parable stops being about ancient agriculture and becomes deeply personal. As a spiritual director, I see this dynamic play out constantly. It’s a recurring theme, especially for people entering the middle passage of their lives. A quiet realization dawns: the tools that brought me to this point in my faith are not the tools I need for the journey ahead.

Our early spiritual tools, our first wineskins, are often designed for building. We build careers, families, a solid framework of belief. They are about certainty and structure. They serve us well. But midlife is often a season not of building, but of questioning what we have built. The new wine of complexity, of limitations, of grief and of unanswered questions begins to ferment inside us.

I once sat with a man whose marriage was ending. His spiritual wineskin was woven from the threads of a good Christian marriage and a successful family life. That container gave his world shape and meaning for decades. But the new, devastating wine of divorce was now fermenting in his life, and the pressure was immense. “Everything I thought I knew is breaking apart,” he told me.

The tools of his earlier faith, tools of certainty and simple formulas, were useless now. His old container simply could not hold the new wine of a life that had proven to be unpredictable and complex. He needed a new wineskin, one that could make room for lament and hold the reality of his brokenness.

The Powerful Appeal of the Old

With his deep insight into our hearts, Jesus adds one last, crucial line: “And no one, after drinking old wine, desires new; for he says, ‘The old is good.’”

This is not a criticism. It is a statement of fact about human nature. Old wine is smooth, familiar, and predictable. New wine can be sharp and cloudy. It is still in process. And we almost always prefer the finished product over the messy process.

Of course we prefer the old. The old ways, our old reliable tools, are comfortable. It is the hard, dry path we know. We know every crack and every turn. It requires no thought, no risk. We say, “The old is good,” because it feels safe. It doesn't challenge us or ask us to grow. It allows us to keep walking in the same familiar rut, using the tools we have already mastered. But the God of Jesus is a God of newness, of life, of springtime ground that is soft and full of possibility.

Praying for Rain

So what is the invitation? It is not to smash our old containers or throw out every tool. The invitation is to cultivate flexibility. The focus is on the container itself. We are the wineskins. The call is for us to remain soft, pliable, and ready for what God is doing right now.

This is the slow, patient work of an honest spiritual life. We are softened when we pray honestly, admitting to God where we have become rigid and fearful. We become more pliable when we listen, truly listen, to people whose lives and beliefs are different from our own. We regain our stretch when we practice silence, letting go of our need to be in control.

God is always doing a new thing. He is always pouring out new wine. The question the parable leaves us with is not about him, but about us. Will we have the courage to set down the tools that no longer serve us, and ask God for the new wineskins we need for the road ahead? Will we ask for the rains of his Spirit to soften the hard ground of our hearts, to turn our ruts back into paths? A path can lead us to new places. A rut only takes us where we have already been.