Reuven was overcome by guilt because he detected the true reason why he failed to rescue Yosef.  He shared his brothers’ resentment toward Yosef, and these feelings prevented him from committing himself wholeheartedly to rescuing him. 

  The Torah in Parashat Vayeshev tells the famous and tragic story of mekhirat Yosef, how Yosef’s brothers plotted to kill him and then decided to sell him as a slave.  We read that Reuven intervened to save Yosef after the brothers initially decided to kill him, recommending that instead of killing Yosef directly, the brothers should instead throw him into a pit and allow him to die there.  Reuven’s intent was to later return and lift Yosef out of the pit to safety.  But in the interim, Yosef was lifted from the pit and sold as a slave, and when Reuven went to the pit, he found it was empty.  He said to his brothers, “Ani ana ani va” (37:30), which Rashi explains to mean, “Where can I escape?”  Reuven knew that he – and his brothers – would now have to watch their father wallow in agony over his lost son, and expressed his anguish on now being compelled to witness his father’s pain.

            Rav Shimshon Raphael Hirsch disagrees with this interpretation, noting that this pain of witnessing Yaakov’s grief would be experienced by all the brothers, and not just Reuven.  Moreover, the word “ba” means “come,” as opposed to “go,” and thus Reuven here cannot be saying, “Where can I escape” but rather, “Where can I come to myself,” or, in Rav Hirsch’s words, “I can find no place where I can rest quietly.”  In short, Reuven experienced severe pangs of conscience.  He felt he would never again be able to live at ease, knowing that he failed in his attempt to rescue Yosef.  Reuven began the process, but he did not complete it, and this failure, he figured, would never allow him any peace of mind.

            Rav Hirsch proceeds to explain the particular reason for Reuven’s pangs of guilt:

Why should just he [Reuven] have felt like that?  Possibly quite simply because he felt himself to blame for not having more energetically acted to oppose and prevent what had happened.  He had started the mitzva and had then left it.  But what was behind this lack of energy, he was, after all, the eldest brother?  Perhaps because he was not really completely free from fault himself, and his conscience now smote and depressed him.  The consciousness that in his innermost heart he had really had slight leanings in agreement with his brothers, he felt had prevented his standing up more strongly and energetically against their plans.

Reuven was overcome by guilt because he detected the true reason why he failed to rescue Yosef.  He shared his brothers’ resentment toward Yosef, and these feelings prevented him from committing himself wholeheartedly to rescuing him.  He mustered enough moral courage to suggest that Yosef be thrown into the pit, but if he was truly and wholly devoted to rescuing Yosef, he would have done it right.  He would not have allowed the circumstances to unfold as they did.

            While we must all recognize our limits and ensure not to have unreasonable expectations of ourselves, at the same time, we must also avoid the tendency to ease our consciences with shallow excuses.  Sometimes we do not succeed because the task was beyond our reach, but other times we do not succeed because we were not sufficiently invested in the effort.  When something is important to us and atop our priority list, we give it a great deal of attention and invest a great deal of energy to ensure our success.  We, like Reuven, must carefully assess whether we are truly investing all we can in the truly important areas of our lives, or if we use the excuse of “I can’t” to absolve ourselves of responsibility.