Regrets of the Dying

Would it be helpful to create a forum or community site specifically for them? Then they can vent and bond anonymously, or with people far away who don't have conflict of interests with them.

Probably a combination of things, but I suspect one reason is, from a relatively young age they make themselves a standard bearer for a belief system and from then on are never allowed the freedom to question it.

They spend their lives attempting to persuade others of the truth of a belief system that many people naturally question as they mature, but priests/ministers have to suppress that tendancy.

It's not until they're on their deathbed do they realize how trapped they were their entire lives, how invested in being trapped they were, and resent it.

Reminds me of the scene at the end of No Coutry For Old Men:

Sheriff Bell: "I always figured when I got older, God would sorta come inta my life somehow.

And he didn't."

Yes, you're right, assuming that fulfilling your dream is not compatible with pursuing your career.

After working two post-college years at a top software company, I quit the cushy life and lived life by trial and error and my plans only went as far as 3 months ahead. 11 years later I still don't know which country I'll be living or working out of within the next 3 months.

Yes I did start to regret losing out on some of the structure, discipline, and optimal professional self-improvement path of living the life that society hands you. I feel I have the experience of a guy 6 years my junior. On the other hand, I know more about myself than my peers because I tried so many things and tested myself under so many different environments.

Looking back, I don't think I would have made a different choice but I would spent my leaves (from the typical path) a lot more directed and focused. I think I could have learned about life and myself in a quicker way just by doing things instead of just being.

But of course, learning to be -- and breaking automatic habits of action -- is the key to being happy as well.

As you guessed, there is no right or best answer.

But again, if your career and your dreams are one and the same, then this one dimension could be resolved.

I guess it remains to be seen conclusively when I fall terminally ill or get close to death of old age, but in my mind, it is not possible to have a life without some kind of theoretical regrets. Every choice you make to spend every moment a certain way is necessarily mutually exclusive with spending it any other way, and there are only so many moments and so many things one can realistically do.

I'm quite positively certain that if asked to reflect on all the things I regret near death, and truly chose to entertain the question from that angle, then I would find something to regret no matter how I lived my life until that point. There will always be could-have-beens, should-have-beens, what-ifs and maybe-if-I-did/didn'ts.

Furthermore, in a practical sense, life is an economically bounded experience; life in a world with finite resources, finite time, and within a society of other people always entails strong elements of concession, compromise and accommodation. You cannot lead a purely hedonistic life unconstrained by material or political limitations. What you do will always be subsumed to some extent by exigencies you would rather not have, by the needs and wants of others, by nature, and various forces you can't control. So, I don't think it's intelligible to implore people to "lead a life without regrets."

I'm not saying there isn't wisdom in being aware that life is short, and you only get one, and that there are some things you will wish you had done if your life ends up being a lot shorter than you expected. However, it seems to me that an important part of finding peace is acknowledging and coming to terms with the objective facts of the human condition and the inescapable psychological truths that accompany them. Seeing your existence as it is and not as it could hypothetically be is an important pillar of peace and comfort for the soul. The reality is, you will always have "regrets": there are always infinite alternate possibilities for any conditional branch, there are practically infinite variables.

"Live a life you won't regret" is the wrong way to look out at the world and your relationship to it. A more constructive approach may be to say, "Lead a good life," whatever that means to you. It is not logically equivalent to "lead a life about which you will never wish something could have been different."

Edit: Also, it is important to emphasise the critical distinction between a) regretting that you had not done something differently, in that all it would take for you to not regret it is to have made a different - and equally accessible - choice, versus b) regretting that you could not have done something differently, in the sense that you wish circumstances or conditions had been such as to make possible or make more likely that you could have made - and actually carried out - a different choice.

It's better to optimize your life around what you value now, not a prediction of what your old, dying self might value differently. Because your prediction is unlikely to be right, and you're probably making better decisions now than while facing death.