Is a Life Free of Regrets Really What We Should Be Striving For?

The idea that the ideal life lived is one free of regrets is a philosophical position that most of us have been exposed to consistently and regularly from a very early age. It was preached as gospel in books, movies, television, and every other form of mass media by friends, peers, colleagues, presidents, kings, queens, prime ministers, and everyday Joes and Janes. The deathbed speech in which the dying person says “I have no regrets” with a smile on their face, as they take their last breath is a classic and highly cliched example. Basically the idea goes that when we die if we can honestly say that we have no regrets that means we had a good life. That does not imply that we had a perfect life or never made mistakes or only made good decisions. It only means that we recognize that even if some of our choices were less than ideal, we still accept them as a part of life and understand that sometimes what seem like bad choices may lead to good outcomes in unexpected ways. Essentially, that life is unpredictable and that we are fallible beings who don’t always do the right things. We do not regret the bad decisions we made, we accept them as a normal part of life and of being human. Importantly and most critically, if we could go back in time we would not change anything with respect to the decisions we made because ultimately it was the sum total of all those decisions and choices, both good and bad, that led us to where we are today, dying in our deathbeds thankful that we can honestly say we have no regrets.

Until very recently I never really thought all that much about it. I simply shrugged my shoulders, said to myself, that sounds about right, and went on about my business. It seems patently obvious that this ages old wisdom must be true. Ages old wisdom can be some of the most dangerous and misguided and anything which seemingly cannot be questioned is a thing which I can guarantee you I will be questioning the shit out of. This is a very annoying feature of my personality to many people and the world in general, but I have always been this way and I don’t foresee that changing any time soon if ever. This morning I was eating a bowl of cereal and just standing there in the kitchen when it occurred to me that maybe striving for a life free of regrets is actually a bad idea. Maybe it is counter productive and harmful and should not be thought of as some sort of optimal towards which we all should aim. How could that possibly be the case?

Upon much reflection the conclusion I ultimately arrived at is that the idea of a life without regrets is a good one. It is a very positive thing to aim for, and it would seem to be a very excellent thing to be able to achieve. The problem is not with the idea itself, but rather the difficulty of actually accomplishing it. It sets an almost impossible bar for most regular people to achieve. And, because most regular people know this, and most do have some regrets, they continually beat themselves up over and over again over it, and eventually begin to believe that they are somehow less valuable as as people because of it. Essentially we are told that if we have regrets, we have failed life in some manner. The regret is bad enough, but on top of that is now layered an extra layer of guilt about the having of the regret(s) at all.

Because of this I think many people lie to themselves and others about the situation and say they don’t have any regrets when they actually do. Others just don’t talk about it. They bury their regrets deep inside and try to forget about them. There are very, very few people who are honest about their regrets and willing to talk openly about them. The big problem is that none of the strategies besides talking about them have any chance of helping one to come to terms with their regrets. Sometimes, people find that by talking through their regrets with others they realize that maybe they should not regret the things they do. Other people can help us see how what we regret may have led to highly positive outcomes for ourselves or for others, often times in very unexpected ways. However, even if that is not the case, and the things we regret are entirely negative for ourselves and the universe in general (very unlikely but not impossible I guess) not talking about them or lying about them will not make them go away. It is only by bringing these things out into the open that we can find a way to forgive ourselves for the things we regret. That needs to start by being honest with ourselves and others and stop feeling ashamed about what is a natural human tendency to question the wisdom of our past decisions which could include regretting some which were not the smartest.

This is yet another problem with the idea of a life without regrets, the fear of having regrets this idea instills in us can cause us to avoid questioning our past decisions. After all, if we think too deeply about our past choices we might decide we do regret them. Better to simply forget about them and move on. We can’t change them in any case, right? It is true we cannot change our past decisions, but it is definitely not the case, that avoiding analysis of them is a smart approach to mental health or life in general. It is a truism that those who forget the past (aka those who avoid thinking about the past) are doomed to repeat it. They will make the same mistakes over and over again. Past regrets serve a positive function in that they (hopefully) give us a mechanism (usually guilt) for avoiding making the same or similar mistakes again in the present or in the future. If we never had regrets about poor decisions made, we would continue to make poor decisions.