There’s a lot going on when Jesus enters Jerusalem on Palm Sunday. One of the things that amazes me is how he heads right into the belly of the beast.

He knows what he’s getting into. From the episode in the Garden of Gethsemane we also know that he’s not exactly thrilled about it. There’s a deep pain there.

But, his face is set like flint towards Jerusalem. There is no waver, there is no detour.

And, Jesus isn’t just heading towards those who are plotting his death. I suppose one could easily imagine him valiantly and bravely staring down the forces of darkness.

But, he’s not just coming to reckon with Pilate and the Sanhedrin. Jesus is also going to Jerusalem to disappoint his followers.

Jerusalem is an occupied city, bent over backwards by the Romans. There is constant threat to life, liberty, and the religious and spiritual ideals which had been kindled in God’s people since the days of Abraham.

The people of Jerusalem weren’t just hungry for freedom and victory. They ached for it. Yearned for it.

And, when the Messiah walked into Jerusalem that day riding on a donkey they knew this was big.

They just didn’t know what “big thing” Jesus had in mind.

The palm branch and the cry of “hosanna” had been associated with the Feast of Tabernacles for centuries, but ever since the Macabbean revolt in the 160’s BCE they were also the penultimate symbols of nationalistic pride. They were reminders that God could do miraculous and amazing things, and could conjure a victory from the deep recesses of oppression.

When Jesus rode into Jerusalem the crowds didn’t sing their hosannas and wave their palm branches because they were so incredibly captivated by Jesus’ message of love and grace. For them, the Messiah was coming to raise up an army, and with the help of God, Rome would be sent running with their pagan tales between their legs.

You see, Jesus wasn’t just staring down his professed enemies. He was also coming to Jerusalem to disappoint his devotees in colossal fashion.

They were ready for an uprising and a military/ political victory.

Jesus, on the other hand, was ready to take up his cross. And die.

And into Jerusalem, and to the cross he went.

As I said before, there’s a lot going on when Jesus enters the Holy City. Things of great theological, soteriological, and christological significance.

But, what we also have is an icon of Christ moving towards conflict, pain, and the reality that he would end up being a great disappointment to others who had laid so many expectations upon him.

He went anyway.

Brené Brown, in her quite wonderful book Daring Greatly, talks about how creativity and living fully requires vulnerability. If we’re going to do great things, then we need to be willing to dare to do great things. This demands us to bear risk: risk of failure, risk of disappointing others, the risk of disappointing ourselves. Again and again.

It’s the risk to believe that the little tape inside which whispers over and over again “you aren’t ______ enough” us is wrong.

We are enough. Our worth doesn’t spring out of our accomplishments and successes—and so it’s OK to risk and fail. It’s OK to say “no,” and do something else.

Jesus is the icon of many great things, but he is the perfect image of a life lived without shame. Jesus does not begin with the sick assumption that he is not enough. That he needs more friends, more “likes” on Facebook, more people to tell him that he’s right.

In fact Jesus’ popularity peaks very early in his ministry. Not long after he’s baptized he’s got thousands of people following him around, listening to him, asking to be healed, asking to be fed. But, not long after that people begin to walk away from him, until the circle around Jesus is pretty small.

If Jesus approached life like most of us, he’d be crushed—internally pulverized from all the rejection and persecution.

In this sense, Palm Sunday is just a microcosm of his ministry: the brief attention of a multitude, which quickly leads to the rejection of the same multitude.

To brave that takes a huge heart. To brave that and still be in love with those who reject him—and be willing to die for them?…Well, that’s just amazing.

Five days after Jesus risked it all and entered Jerusalem he was nailed to a cross in brutal and humiliating fashion. If the story of Jesus ended there, we’d say that he was an absolute failure.

Worthless.

Oh…he had so much potential…he could have done so many things and changed the world…but he had to go and be…a great disappointment.

But, Jesus shows us that disappointment doesn’t have to have the last word. In fact, disappointment can walk out of a tomb and shatter the present powers of this world.

Jesus is enough. We are enough.