(Delivered September 27, 2025)
Shabbat shalom!
In these weeks of intense preparation leading to and through the High Holidays, I frequently find myself riding on a roller coaster of overconfidence and anxiety. On the one hand, I say to myself, “Self, you’ve never missed a deadline, you’re not going to miss one now.” And then on the other hand, I say to myself, “This is really a lot of writing. What if I run out of ideas?”
Amidst this recurring loop, one phrase that’s been turning in my mind is a saying that was made famous in a 1995 movie about the American space program. The movie was called Apollo 13, and it chronicled a flight to the moon that almost went terribly wrong. In the film, the three astronauts aboard the Apollo 13 mission encounter technical problems that make it unclear whether they will be able to return to earth safely. After a feature film’s worth of tension, argumentation, suspense, and good old American ingenuity; the astronauts and their ground control crew miraculously overcome what could’ve been disastrous, and bring the rocket and its crew safely home. The movie had a tagline that became a catch phrase which entered the cultural lexicon: failure is not an option. When I’m reminding myself that I’ve never missed a deadline, the phrase, “Failure is not an option,” seems basically plausible.
But this week’s Torah portion teaches something quite different. Indeed, as we make our way through Deuteronomy chapter 31, which constitutes the entirety of Parshat Vayelech, we get the undeniable, unbearable impression that failure is inevitable—that failure is not optional. Indeed it’s God who says so. In preparing Moses for his looming death, God does not offer comfort, but rather says:
הִנְּךָ שֹׁכֵב עִם־אֲבֹתֶיךָ וְקָם הָעָם הַזֶּה וְזָנָה אַחֲרֵי אֱלֹהֵי נֵכַר־הָאָרֶץ
אֲשֶׁר הוּא בָא־שָׁמָּה בְּקִרְבּוֹ וַעֲזָבַנִי וְהֵפֵר אֶת־בְּרִיתִי אֲשֶׁר כָּרַתִּי אִתּוֹ
Look, you are going to die soon, and afterward this people will go astray with the alien gods in their midst, in the land they are about to enter.
They will forsake Me and break the covenant I made with them.
Such a vote of confidence!
Despite—or perhaps because of—the 40+ years of wandering, of rupture and repair, of relationship-building, God has grown quite pragmatic about the Israelites’ flaws. God seems convinced, and not without reason, that as soon as the Israelites are granted the land flowing with milk and honey, a land that they have been longing after for all this time, they will shortly find a way to mess it up.
When Moses retells this part of the narrative towards the end of the parsha, he essentially says the same thing. Verse 27 reads:
כִּי אָנֹכִי יָדַעְתִּי אֶת־מֶרְיְךָ וְאֶת־עָרְפְּךָ הַקָּשֶׁה
הֵן בְּעוֹדֶנִּי חַי עִמָּכֶם הַיּוֹם מַמְרִים הֱיִתֶם עִם־יי וְאַף כִּי־אַחֲרֵי מוֹתִי
I know all too well your rebelliousness and your stubbornness
while I’m still alive and with you! You rebel against God now!
How much worse will it be after my death!
In a classic expression of irony, God and Moses know what we also know but the Israelites don’t: that humans are fallible, that we constantly make mistakes, that failure is indeed inevitable.
The beauty of Torah, and of Judaism as a whole, is that it doesn’t leave us in this place of degradation. The Torah knows, as we do, that being human will always involve moral and behavioral crises, that we will always be tempted to turn away from what’s eternal, and follow after trivial, ephemeral matters. We are made in the image of God, but we are not God. Our human makeup is ultimately weak in some truly fundamental ways. They say you can’t fight Mother Nature. Perhaps, you also can’t fight human nature.
Even so, the Torah gives us tools to try. For managing the inescapable lapses that we are bound to have, the parsha offers two notable and seemingly contradictory strategies.
The first of these is courage. No less than three times in this short portion, courage is called for. In verse six Moses tells the Israelites חִזְקוּ וְאִמְצוּ—be strong and courageous. In the following verse, he says the same to Joshua, his successor, חֲזַק וֶאֱמָץ. Finally, in verse 23, God also tells Joshua חֲזַק וֶאֱמָץ. Ibn Ezra suggests that the Israelites can be courageous because they know that God accompanies them in battle, that this is earned courage, a faith rooted in experience.
Likewise, off the battlefield, knowing that we have overcome past challenges can strengthen us for future ones. If we find ourselves, as the parsha predicts, falling into patterns of focusing on the wrong things, we can derive courage from the knowledge that we have surmounted similar transgressions and made our way forward. In this season when we bring our attention to the work of teshuvah, of repentance or return, this is useful to remember. Failure, while not optional, does not have to be irrevocable.
The parsha’s other strategy for confronting failure takes an entirely different approach, a softer approach. God, knowing that the Israelites will succumb to their humanity in one way or another, offers a decidedly human way of coping: poetry and song. In anticipation of the times when the people will stray and God will turn away, God instructs Moses to redirect and re-inspire them through הַשִּׁירָה הַזֹּאת—this poem or this song.
This phrase should ring a bell, since it’s also in the daily prayers, in a different context. When we reenact standing at the shore of the Sea, reliving a moment of crisis and recovery; the words of Shirat Hayam, the song of the sea, accompany us and steady us. They remind us we have faced the impossible before.
I think it’s actually kind of magical and forward-thinking that the Torah offers creative expression as an antidote to moral failure. Thousands of years ago, our tradition already knew that sometimes when we make consequential mistakes, it’s a sign of a soul out of balance. Easing into timeless words of beauty and meaning can show us not only where to go next, but why. It can remind us that the teachings that guide us are already בְּפִנוּ—in our mouths.
In this season of teshuvah, as we grapple with our own failures, may we hold to the creativity and poetry of our ancient texts, and may they give us strength and courage to move forward and bring ourselves safely home.
Shabbat shalom & gmar chatimah tovah!