Time and time again, I hear people claim they have no regrets about how they’ve lived their life up to this point.
Taken literally, that means to me that they’d live their entire life the same way if they had a chance to live it over. Really?
There’s three problems here, as I see it. One is viewing “good/bad” (in a growthfulness, not a moral sense) as two polarities, not a continuum. The second is “no regrets” is imprecise, and probably doesn’t mean what it literally says in such cases. The third relates to the first second and impinges upon issues of free will.
The first issue? I believe life, and life issues, can be more, or less growthful. Even ones I regret going through because of bad decisions on my part. (Although I may guilt-trip myself, I can’t honestly be regretful about issues where my range of choice was constrained, or I was reacting to a bad decision/choice by another person; that’s the free will angle.) So, “regret” isn’t totally a bad thing. If I can look back, and see something to learn from the situation, to see how I didn’t handle it as well as I could have, or as well as I could have with more knowledge, then regret’s not bad.
At the same time, that “more knowledge” is another key. If there’s no way I could have known more at the time, whether conscious or unconscious knowledge, that is that. I’ll get to that more in a minute, too.
The imprecision of language? This is one of the few areas where I have fairly substantial agreement with Plato, with the caveat that I don’t limit myself to writing as a way of allegedly obscuring, or even bending or destroying meaning. Oral communication, contra him and the pre-Upanishad Brahmin priests of India, can be manipulated just as well, even when in a mnemonically-driven sacral structure.
I think what people really mean is, “I don’t have any regrets about past actions to which I am too attached.” That’s much healthier – if true. But … maybe it isn’t always true?
Maybe it isn’t so bad to retain a modicum of regret as a learning tool NOT as a “kick myself” tool but as a learning tool.
Finally, there's all sorts of free will aspects.
To the degree free will even exists, it may not exist on a conscious level. To the degree it exists within semiconscious subselves, it's constrained by past elements in our lives and how they've shaped the psyches of those subselves, as well as the fictitious unitary self that claims to be in the driver's seat. The idea of regret may be the right idea in one sense, but not at all in another sense. How can we regret an action that was not undertaken or done with full freedom? There may be a partialness of regret, but, can there be anything more?