This is the derasha I delivered on Shabbat.
Nearly 900 years ago, in the summer of 1140, Yehuda HaLevi, the great poet and thinker, waited aboard a ship at port—waiting to embark on the next leg of his pilgrimage to Eretz Yisrael. He waited for the winds to shift, the sails to billow forth and push the craft into the indigo blue waters of the Mediterranean. The wait might have been hours or even days until a wind from the west would move with force to the east, bringing him closer to his destination. The poet he was, Yehuda Halevi could not resist putting ink to paper and he penned a letter (in the form of a poem) to his family who he had left behind in Spain:
Greetings of peace to sisters, brothers, family and friends
from a prisoner of hope who has been sold
to the sea, his spirit hostage to the winds
seized by the west, forced to the east
this one leads on, this one repels. 
I believe this poem works well as a metaphor for the protracted trials of the exile. אסירי תקוה, Prisoners of hope, we are subject to the unpredictable conditions of our captivity—sometimes catching a favorable wind and brought closer to our destination; sometimes stymied or cast back for interminable periods without a glimmer of respite.
I often feel this way during the three weeks. Stuck, waiting for a journey to begin. I feel frustrated. I want the winds to shift and set things in motion. I wonder, we have been in exile waiting for our redemption for almost 2000 years…is there anything good—anything redeeming—about waiting? Or is it just a purgatory, filled with suffering? How well the following stanza from the same poem describes our fears and frustrations at so many stages of our exile:
Seasick, fearful of Gentiles,
from pirates and tempests.
The captain and crew, these riffraff
are lords and masters of this place.
The fame of a sage means nothing here, and nothing
you have learned has any use
unless you’ve learned to swim.
Are we doomed to a life of mourning and yearning, in which, as Yehuda HaLevi describes in perhaps his most famous poem, “My heart is in the East and I, at the far reaches of the West/ How can I enjoy my food? What pleasure can it have for me?”
As a depressed person finds no joy in eating, can we find no joy in this broken world?
Shortly after the destruction of the Second Temple, there were a group of pious Jews who took this approach and refrained entirely from eating meat or drinking wine. Rabbi Yehoshua asked them, “Why are you not eating meat or drinking wine?” They responded, “How can we eat meat from which sacrifices were offered upon the altar? How can we drink wine from which libations were offered upon the altar? Our Temple is in ruins!”
Rabbi Yehoshua responded, “If that’s the case, then you shouldn’t eat bread on account of the grain offerings; and you should abstain from fruit on account of the first fruit offering; and you shouldn’t drink water on account of the water libation!”
They were silent. He said, “My children, I cannot tell you to not mourn at all…the decree has already been pronounced. But, you equally cannot mourn to such an extreme.” (Bava Batra 60b; read in Mekor Hayim, vo. 4, 203:19, p. 185)
We cannot live a life of constant sorrow. But does that somehow dishonor the memory of what once was? Does experiencing joy mean we are not truly waiting? That our hope is not real?
For the three weeks leading up to Tisha B’Av our vision darkens—we are cast down and feel the weight of exile. On each of the three Shabbatot of this time period we read haftarot of puranut, punishment, in which we are castigated by the prophets and are called to take account of our sins and repent. Today marks the final of those three Shabbatot—Shabbat Hazon. In today’s haftorah, we read the opening chapter of Sefer Yeshayahu in which the people are called sinners and murderers—comparable only to the likes of the people of Sedom and Amora! The only nechama, consolation, is the assurance that if we pursue justice and righteousness we shall be redeemed. "Tzion through justice shall be redeemed and her repentant ones through righteousness."
After Tisha B’Av the tone shifts dramatically. For the next seven Shabbatot we read haftarot that are entirely consolation. We are told to take comfort, rise up and ultimately to rejoice! The bright vision of our future is placed ever more luminously in front of us until we can experience the joy of our festivals in the month of Tishrei.
But how can we make this transition? How do we go from the depths of sorrow to experience the joy of our festivals once more?
I would argue that the sasson, the joy, of the holidays can only be experienced in the wake of mourning—after fully confronting what was and what we lost. How so?
It boils down to a simple truth that I believe the Rambam stated best at the end of Hilkhot Purim: the true joy of our festivals is, in fact, לשמח לב עניים—to cause the heart of the impoverished to rejoice. "לְהַחֲיוֹת רוּחַ שְׁפָלִים, וּלְהַחֲיוֹת לֵב נִדְכָּאִים"—“To revive the spirit of the lowly, to revive the heart of the downtrodden.” We rejoice not just because we have received good. We rejoice in our ability to emulate the Divine Presence—to be a conduit of the ultimate good! This joy is only tainted by our inability to fulfill this ideal to the highest degree! Without this realization—which is only brought about by mourning the catastrophic results of not living up to this ideal—we cannot experience any joy at all!
Isn’t it perfect? The ultimate source of joy—the commitment to justice and righteousness, to answer the call of the widow and the orphan, the homeless and impoverished—is also that which brings about our ultimate redemption!
But how can we stand to wait? What gives us the patience to wait for this ultimate state of being? This time of greatest joy?
After relating the difficulties of his wait, Yehuda Halevi concludes his letter:
These thoughts throw shadows on my face,
but only briefly, for my core,
my inner self, is joyous. Soon
I will be pouring out my heart
to G-d, where once the ark and altar stood.
There I will repay Him, giving thanks
as due to Him from me, imperfect man,
and offering Him my best: my song and praise.
There is a sweetness to waiting for something good—it gives meaning to all the steps along the way. Being an אסיר תקוה, a prisoner of hope, is a strange state of being…on one hand you are a prisoner, on the other, you are a prisoner to the most wonderful of wardens: hope. Hope keeps one bound as long as the end has not come, but the boundaries of that prison give life meaning.
So, the next time you are waiting, bored, frustrated, and angry at time…think deeply about your destination. Where are you headed? What are you doing along the way? Let that bring a smile to your face.
May we all merit the fulfillment of our prayers:
וְתֶחֱזֶינָה עֵינֵינוּ בְּשׁוּבְךָ לְנָוְךָ, לְצִיּוֹן בְּרַחֲמִים, כְּמֵאָז.
May our eyes see your return to your abode, to Tzion with mercy, as it once was.
 All translations of Halevi’s poetry are adapted from Scheindlin, R. The Song of the Distant Dove: Judah Halevi’s Pilgrimage. NY:Oxford University Press, 2008; and Halkin, H. The Selected Poems of Yehuda Halevi. Nextbook, 2011.