In many ways my role as an executive pastor is to expect the unexpected. It’s the responsibility of any executive, really. Plans change. People surprise us. Hurricanes rearrange weekend services. To expect the unexpected is to be ready. It’s a lifestyle of not only anticipation, but preparation. 
Centuries ago the Israelites prepared for the greatest event in Jewish history, the coming of the Messiah. In fact, the English word advent (derived from the Latin adventus) simply means “coming” and speaks to the expectation and longing the Jewish nation experienced as they waited for their Messiah. Ironically, despite centuries of preparation, the Jews made one devastating mistake. They didn’t expect the unexpected. They assumed the Messiah would be a political King. They assumed He would be a man of wealth and prominence. They assumed He would rise to power wielding a sword for the sake of national dominance. They expected…what was expected. 
As a result, they missed Him.
Today, thousands of Jews continue to wait for a Messiah who has already come. They aren’t the only ones harboring preconceived notions about who Jesus ought to be. We do it too. We expect Jesus to insulate us from tragedy. We expect a good God to grant our deepest desires. We expect Him to provide peace without persecution and satisfaction without suffering. 
As a result, we miss Him.
Like John the Baptist, we find ourselves sitting in our own version of prison, asking, “Are You really the Messiah, or should we wait for another?” (Luke 7:18-19). 
To expect the unexpected is to orient our hearts and minds around the reality of who Jesus is, not who we think He should be. To expect the unexpected is to judge our circumstances in light of Christ, rather than judging Christ in light of our circumstances. Admittedly, it’s easier said than done. Rejecting preconceived notions about Jesus and aligning our hearts with the truth is a daily discipline. It requires a rhythm of turning our attention and affection toward Christ. 
The observance of Advent creates opportunity to reshape and reorient our way of thinking as we approach Christmas. In fact, this is how the season came to be celebrated in the first place. Christians in the first centuries began to recreate the feeling of anticipation for Christ with purposeful prayer, fasting, and repentance as they focused attention not on the birth of Jesus, but on His second coming. They used the season to prepare them for Epiphany, a Christian celebration in early January, commemorating the manifestation of Christ to the Gentiles/Magi.
Just as generations of Jews waited with delayed hope, these Christians wanted to remind themselves that life is short, this world is temporal and the Savior, the Messiah would one day return. By the Middle Ages, Christians had begun using Advent to prepare to celebrate Christ’s birth, and yet it retained the longing for the second coming as well. Thus, worshippers mingled the penitential preparation for the Christ’s return with the joyous anticipation of Jesus’ birthday.
And so we continue in this tradition today. Excitement. Joy. Celebration. The Savior has come and with Him, our salvation. Anticipation. Longing. Hope. The Savior will come again, and with Him, the restoration of all things. As the popular Christmas carol, Joy to the World, reminds us:

No more let sins and sorrows grow,

Nor thorns infest the ground;

He comes to make His blessings flow,

Far as the curse is found.

When we expect what’s expected, we’re often disappointed. But when we expect the unexpected, we open the door to a world of wonder. A world where a King could be born in a manger. A world where shepherds worship with angels. A world where death leads to life and agony ends in glory.
This Advent season, as you give gifts and hang wreaths, it is our prayer at Grace Church that you would be touched with unexpected joy. That you would be filled with unexpected hope. And that you would encounter Jesus in fresh and unexpected ways.