I've heard this scripture all my life. And I always thought of it as Jesus' version of "you can't teach an old dog new tricks." Which it sort of is. But I took both of those things to mean that the old wineskins and old dogs just have to move aside and make way for the new wineskins and young dogs.
But, let's face it, if you grew up in the church, you've probably developed an old wineskin. Some manage to stay fresh, but most get hardened over time and either settle into old habits or complain about how you can't change things anyway.
Which just shows how little we actually believe in resurrection. We claim to follow a man who not only rose from the dead, but assured us that His resurrection meant that our resurrection was possible. That a new world could be made of the old one.
You can't teach an old dog new tricks. But Christ can make him a new dog.
You can't pour new wine into old wineskins. So if Jesus plans to pour new wine into you, He may have to rip you a new wineskin.
That was what the first year or so of church planting was for me. It felt like the old skin was being flayed off of me. It was beyond painful.
But when the new wine starts to flow, it's all worth it.
Suffering sucks. But it passes. Often it even serves a purpose. Often we are being made into new wineskins in order that we might hold new wine.
If we are a people who believe in resurrection, we can afford to die. We can afford to shed our old lives and habits and ways and to walk in a new way, the Way of Jesus.
So if you're asking for God to make you new, don't be surprised if it hurts. A lot.
And if it feels like God's ripping you a new wineskin, hold on. New wine is coming.