Closing Thoughts: Regret

A couple of years ago, I helped organize a reunion of my former staff. Quite a few people came, and it was wonderful to see them. My friend Jay Mehaffey flew in for the reunion. When I mentioned that there were a few things I might have done differently, he remarked, “Don’t have any regrets. No regrets.”

This is the time of the year when we ask God to not be a tough judge on us, but to recognize that we all have flaws, that we are human and we fail, and that He should have mercy on us. Well, if God is willing to be merciful, then so can I. I promise to show mercy on everyone. I don’t stand in your shoes, I don’t know what you are thinking, and I trust all of you to do the right thing, so I will try not to judge you but to be merciful, even if I don’t totally agree with you.

Rosh Hashanah and Yom Kippur is the time when we ask God for forgiveness. It would be nice if we had no regrets, and we certainly should act so that regret is unnecessary, but we are imperfect and do make mistakes.

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There are two kinds of regret. The first is for the things that we did and wish we hadn’t. The second is for the things we wish we had done and didn’t do. Regret for the things we did is best handled at Yom Kippur. Regret for the things we didn’t do can be part of our commitment for the New Year, to do them if it is possible to do them, as some things are available for only a short period of time. For example, I regret that I did not buy a house. We didn’t want to pay the asking price. That chance is now gone.

Regret for things you did but wish you hadn’t can lead to action. If you don’t feel regret for a past deed, then you are not likely to go the next step and actually make the changes necessary for real teshuvah, for forgiveness. Regretting one’s actions is a healthy part of the forgiveness process. I will leave that for Yom Kippur.

I want to focus on the “why didn’t I,” and the “what was I thinking when I didn’t?” We eat away at ourselves for not taking that “other” job, not making that phone call, not saying how you feel, not finishing that degree, not sending your child to that school, not supporting that charity, and not buying Apple stock in the 1990s. We beat ourselves up for a personal history we can’t change instead of moving on to change the present. We carry the burden of regret over roads not taken, ideas not developed, books not written, achievements we might have had, people we might have known. We lug around the nagging feeling that we could have done it better or done it differently; the ache of realizing we won’t be able to change those could-haves and would-haves into did-dos. Those regrets weigh on us. They change the way we live now. Although some regrets are about things we didn’t do because we couldn’t do them at the time, or things we didn’t do because they weren’t right for us at the time, we don’t cut ourselves any slack. What we should have done always seems so clear in retrospect!

What plagues us is not the sins that we committed, but the things we didn’t do. What causes us greatest angst are the things we might have done, which we let pass by, and even the things we want to do in the future but fear we may not.

I recently read, for the second time, a wonderful book called “Taken at The Flood.” It’s about the life of Albert Lasker, the father of modern advertising, and a very successful businessman, as well as an advisor to U.S. presidents. After going to a psychiatrist for his depression, he summarized what psychoanalysis is all about. He said it is about learning to forgive yourself. Learning to forgive yourself is about dealing with regret and getting over it. It’s about the things you did and wish you hadn’t, and the things you didn’t do and wish you had. So when you ask for forgiveness, remember to begin with yourself.

The bottom line: For the New Year, 5782, we have an opportunity to commit to fixing some of our regrets. I will share with you one that I’ll be working on: I will publish my book now in draft form. I don’t want to regret not finishing and publishing it.