One of the most tragic figures in the Torah is Reuven. His haunting story is replete with squandered potential and the road not traveled. When he wanted to bring his mother flowers, he might have waited until Leah was alone. After Rachel’s death, he might have spoken directly to his father instead of moving the beds.
One of his defining missed opportunities is when the brothers resolved to dispose of Joseph, and Reuven convinced them to change their scheme:
וַיִּשְׁמַע רְאוּבֵן, וַיַּצִּלֵהוּ מִיָּדָם; וַיֹּאמֶר, לֹא נַכֶּנּוּ נָפֶשׁ. וַיֹּאמֶר אֲלֵהֶם רְאוּבֵן, אַל-תִּשְׁפְּכוּ-דָם–הַשְׁלִיכוּ אֹתוֹ אֶל-הַבּוֹר הַזֶּה אֲשֶׁר בַּמִּדְבָּר, וְיָד אַל-תִּשְׁלְחוּ-בוֹ: לְמַעַן, הַצִּיל אֹתוֹ מִיָּדָם, לַהֲשִׁיבוֹ, אֶל-אָבִיו – But when Reuven heard, he tried to save him from their clutches. He said, “Let us not take his life.” And Reuven went on, “Shed no blood! Cast him into that pit out in the wilderness, but do not touch him yourselves”—intending to save him from them and restore him to his father. (37:21, 22)
Yet his good intentions never materialize:
וַיָּשָׁב רְאוּבֵן אֶל-הַבּוֹר, וְהִנֵּה אֵין-יוֹסֵף בַּבּוֹר; וַיִּקְרַע, אֶת-בְּגָדָיו. וַיָּשָׁב אֶל-אֶחָיו, וַיֹּאמַר: הַיֶּלֶד אֵינֶנּוּ, וַאֲנִי אָנָה אֲנִי-בָא – When Reuven returned to the pit and saw that Joseph was not in the pit, he rent his clothes. Returning to his brothers, he said, “The boy is gone! Where do I go now?” (37:29, 30)
R’ Shamshon Raphael Hirsch wonders whether his previous failures might have crippled him, or that he felt threatened by Joseph; what is certain is that by deferring action to avoid the tension of confrontation, the moment fizzled out and disappeared.
The Midrash laments the missed opportunity, saying that if Reuven had known that the Torah would record for posterity that “when Reuven heard, he tried to save him from their clutches”, he would have carried Joseph back to his father on his shoulders; and the Midrash concludes with the lesson that we should do everything wholeheartedly.
But if you think about it, that’s the wrong message. If Reuven would act because of his audience, he wouldn’t be saving Joseph because he cared at all! Isn’t the Midrash honing in on the wrong point?
R’ Elya Meir Bloch observes that since the Torah spans centuries and generations, it has time skips. The stories and sagas that make the cut resonate not just in the protagonist’s lives, but in the lives of their readers for all time.
R’ Shlomo Farhi teaches that we can never know which moments in our lives are the inflection points. The Midrash is not about insincerity; it’s about indecisiveness. If we knew which moments would be the ones that mattered, we’d be fully present and engaged to give our all.
If Reuven had only known, says the Midrash. If he’d known that the future was watching that moment, he might have found the conviction to follow through. But Reuven could not know. He had not read the story. None of us can read the story of our life – we can only live it.
As R’ Jonathan Sacks notes, it is impossible not to recognize in Reuven a person of the highest ethical sensibilities. His heart is in the right place and he only means the best. But though he had a conscience, he lacked courage and conviction. He knew what was right, but dwelling on his mistakes had robbed him of the resolve to act boldly and decisively; and in this particular moment, more was lost than Joseph. So too was Reuven’s chance to become the hero he could and should have been.
The feeling of regret is the pain of what could have been. To minimize regret, engage in every moment wholeheartedly and fully present.
The future is watching.