R. Lucas Stamps, on how the Advent season ought to be marked more by mourning than feasting or rejoicing:

The joyful mystery of the Nativity is set against the backdrop of pain. The coming of the Lord only makes sense to a people who know what it means to wait—to a “people prepared,” as Zechariah prays in his Benedictus (Luke 1:17). Advent invites us, like righteous Simeon and faithful Anna, to wait for the consolation of Israel and the redemption of Jerusalem (Luke 2:25, 38). Advent is not about sappy sentimentalism, gauzy nostalgia, and cheap grace. It is about a “weary world” in desperate need of rejoicing. The land of Advent is spotted with deep valleys, impassable mountains, and crooked paths (Isaiah 40:4). As the Lord himself would remind us, “Those who are well have no need of a physician, but those who are sick. I came not to call the righteous, but sinners” (Mark 2:17).

And so, Advent welcomes our mourning. It has a place for our pain. It allows us the freedom to be honest about our losses, either through our own sins or the sins of others. It tunes our heart to sing, not only of God’s grace, but also of our sin and guilt and suffering. To be sure, we already live in the luminous reality of the first advent. No season of the year is entirely devoid of that joy. We need not pretend otherwise for some kind of pious effect. But we also live in the time between the times, in the overlap of the ages. The kingdom of Christ has been definitively inaugurated through the incarnation, birth, life, death, and resurrection of Jesus, but it is not here in its full glory and felicity. We, too, wait for consolation and redemption. And in this liminal space between the two advents, we can welcome a third, “middle advent,” as many spiritual writers have articulated: the coming of Christ in our hearts through the ministry of the church and personal devotion.

The season of Advent invites us to a kind of delayed gratification. We mourn before we rejoice. We sing of our weariness and captivity before we herald “Joy to the World!” In some traditions, Advent, like Lent before Easter, is a penitential season of fasting and self-examination. Only after the long night of sorrow can we rejoice that “the dayspring from on high” has visited us (Luke 1:78). Advent reminds us that Jesus didn’t come to a people who had their stuff together. He came to a broken world longing for healing.

The whole piece is worth your time. I do worry that the cultural pressures of the season (i.e., to consume, to celebrate, to gratify one’s desires) will overwhelm the ascetic impulse required to observe Advent in the way Stamps describes. And I very much include myself in that worry.