What does Judaism say about regret? I'm not talking about regretting sins that I've committed, I'm talking about choices that I made and things I didn't do that I should have done that would have changed my life for the better. Thanks.

There is an interesting story about a Reb Susya who was a major scholar and very pious man.    At his death bed his students saw that he was crying and assumed it was out of fear.   They asked Reb Susyah what he had to fear from G-d since he had led such a pious and exemplary life.    He answered that if G-d asked him why he had not become another Moshe Rabeinu (Moses our teacher) he would answer that he wasn’t given the leadership qualities of a Moshe.   If G-d asked why he had not become another Dovid Hamelech (King David), he would answer that he had not been given the poetic gifts of Dovid.   If G-d asked him why he had not become another Rebbie Akiva, he would answer that he wasn’t given the intellect of Rebbie Akiva.   However, if G-d asked, “Reb Susya, why didn’t you become a Reb Susya”, he would have nothing to answer G-d, and it was that question which he feared.

From this story we can deduce that one should always try to fulfill one’s potential.   I, however, deduce something else.   If even a Reb Susya can question his accomplishments and in essence regret missed opportunities, then the rest of us are quite human to do the same.   I believe we all have regrets about missed opportunities, but Judaism does give us a direction as to how to deal with them.   Interestingly enough the direction is found in the contradiction between our belief in G-d’s omniscience and our free will.

Our Rabbis tell us, “Everything is in G-d’s hands except the fear of G-d”.   Even though G-d is the grand conductor of our lives, we still have free will to choose, or not to choose a life direction.   There is no satisfying answer to this contradiction, but the contradiction gives us a way to live.   Here is a suggestion.

Draw a circle around where you are sitting right now.   The religious perspective would say that you are exactly where you should be at this moment, dealing with exactly what you should be dealing with, and connecting with exactly those people with whom G-d wants you to connect.   Your whole life has been preparing you for this very moment (perhaps reading this comment).   Everything that you have gone through and have learned can now be put to use in the next few seconds.   All the regrets you may feel are part of what you were suppose to learn up until right now.   The exciting reality, however, is that at this very moment you have the opportunity to make a free will choice as to what you are going to do in the next few seconds and for the rest of your life.   Using the Torah as your moral guide and moving in the direction that you believe is toward your greatest growth (all the better if it is to eventually help other people) will direct you all the more toward your constantly emerging life purpose.   May you have a wonderful New Year filled with learning, growth and few regrets.