Learning From Mistakes: The Torah’s Approach to Leadership

Parshas Vayeishev 5782

If you run for office today, prepare to have every one of your skeletons dragged from the closet. It is the role of a campaign manager to not only make his own candidate look his very best, but for the opponent to look his very worst. Every error and blunder of the past will be drudged up and displayed for public consumption, making the statement, “Is this really who you want to serve as your leader?” 

In today’s environment, Yehudah could never be king. That the Torah believes otherwise demands our attention.

After the brothers sold Yosef, the Torah states, “וירד יהודה מאת אחיו—And Yehudah descended from amongst his brothers.” Rashi comments that the Torah is hinting to something larger than just a geographical relocation: 

שֶׁהוֹרִידוּהוּ אֶחָיו מִגְּדֻלָּתוֹ כְּשֶׁרָאוּ בְצָרַת אֲבִיהֶם, אָמְרוּ: אַתָּה אָמַרְתָּ לְמָכְרוֹ, אִלּוּ אָמַרְתָּ לַהֲשִׁיבוֹ הָיִינוּ שׁוֹמְעִים לְךָ:

^{רש׳׳י לח:ו} 

His brothers brought him down from his position of authority when they saw the distress of their father. They said, “You told us to sell [Yosef]. Had you told us to return him, we would have listened to you.

^{Rashi 38:6}

Yehudah’s career begins with a major failure. It was on his advice that Yosef was sold and the blame of Yaakov’s subsequent mourning is laid squarely at his feet by his brothers. Yehudah moves away from his family and begins a new life, apparently unable to reside in his brothers’ company following this early debacle. 

The next episode that the Torah records is the story of Tamar, who marries two of Yehudah’s sons in succession, both of whom die. Frightened by the prospect of a third son dying, Yehudah turns Tamar aside with the pretext that his next son is not yet old enough to marry her. Yehudah meets Tamar next while she is disguised as a harlot in an attempt to find her way back into Yehudah’s family. Not recognizing her, Yehudah and Tamar are intimate and she becomes pregnant, a scandal which initially results in her being sentenced to death.

Yehudah has committed another error in not doing more to protect his daughter-in-law and ensure her place in the family. But something incredible happens. Upon realizing that he was indeed the father, Yehudah recognizes his guilt and comes to her aid. Yehudah admits his mistake and sets about trying to change it.

Yehudah’s road to renewed leadership is not done. In next week’s parsha, we find Yaakov reluctant to allow Binyamin to descend down to Egypt, a demand made by the viceroy (actually Yosef) as a precondition for reentering the land to purchase more provisions during the famine. The family is growing hungry, but Yaakov remains unwilling to send his precious Binyamin, the last remaining son of his beloved wife, Rachel. Yehudah steps up again. 

Yehudah has been marinating for years in his failure to protect Yosef and the resulting heartbreak of his father. Now Yehudah sets about correcting that failure. Refusing to let his family starve, but insisting that his father not lose yet another son, Yehudah now promises his father that he will take personal responsibility for Binyamin and ensure that he be returned to his father unharmed. Later, when Yosef threatens to imprison Binyamin in Egypt, it is Yehudah once more who takes the lead, approaches Yosef, and demands Binyamin’s release.

It is unhealthy to become debilitated by errors of the past. Ultimately, we must move on and recognize all that can still be achieved. But simply putting the past behind us is also not the way forward. In Yehudah, the Torah presents a different approach. Yehudah is not perfect, but he strives for perfection and insists on correction. Yehudah admits his mistakes and takes ownership over them, doing his best to right the wrongs of the past.

Many generations later, one of the brightest stars to ever emerge from Yehudah’s descendants would ascend the throne of the Jewish People. David Hamelech was not perfect, and his missteps are recorded in Tanach. What makes David Hamelech such an extraordinary personality, though, is that he owns those errors, begs forgiveness, and tries to correct them. Every morning we begin the Viduy confession with the words “ויאמר דוד אל גד נפלה נא ביד ה׳ כי רבים רחמיו—And David sad to Gad, may we fall into the hand of G-d, for His mercy is great.” One of the many instances of David’s owning up to his own mistakes becomes the paradigm for each of us to properly process our sins. Teshuva is not a sweeping under the rug of past mistakes; it is tackling them head on, understanding where they came from, and developing into people who can be better.

A person can become completely hamstrung by mistakes of the past. An error or sin can become so overwhelming in one’s mind, that they are sent into a tailspin of self-doubt and feelings of inadequacy from which they never recover. This is not the Jewish way. But neither is the attitude of simply moving on without ever really addressing what went wrong. It is in analyzing our own mistakes that our most profound strides are made in improving our character. It is this approach that the Torah highlights as a necessary criterion for Jewish leadership.

It is unlikely that Yehudah would win an election today. And that’s a shame. Because the errors of the past that would be gleefully portrayed by his adversaries are errors that the Torah itself insists we should take note of, along with how Yehudah admitted to them, learned from them, and did his best to correct them. In the eyes of the Torah, past mistakes need not be hidden from others so long as we do not hide from them ourselves.