Inductive Way-back Thinking
There's a popular plot device amongst lit-rpgs and light novels that I think exposes a fascinating part of our psychology: the ability to go back in time with our memories intact, fixing what mistakes we made and otherwise overcoming an impossible situation with only our foreknowledge. Mother of Learning is a great example of this, I enjoyed reading it.
I think this is a desire we all have, once we reached the cognitive maturity to engage in counterfactuals. It is the desire to have control over our destinies, and of course, to go back to a better time perhaps, when we were younger, more energetic, had more time and stamina to do what we wanted to do. (Or perhaps to get revenge on all the people that screwed us over, the revenge time loop fantasy is also quite common.)
So let us indulge in that fantasy for a while. Let's go back and imagine with as vivid of details as possible what we would do at the time of our choosing, should we go back...
Here's something banal: not selling shares of AMD at $15 to make 2 dollar difference, haha.
After indulging in that day dream, let's do a step of induction. What would our future selves do in our situation should they have gone back in our present? I'd imagine there are some similarities which our present-to-past exercise revealed. For by the same principle that I project myself back in time, acting with confidence in knowledge and maturity, that future self will project onto me. As I had become irreverent of the concerns that so worried my past, so will that future self become totally immune to whatever that bothers me. As I am chasing after goals not imaginable to my past, so will that future self be troubled by desires and goals unbeknownst to me.
What can we learn from this exercise? If the Stoics had read light-novels from our times they would be horrified, but they would probably remark on the transience of all that concerns us, and all that delights us.
There's no difference between the one and the other - you didn't exist and you won't exist - you've no concern with either period. (Seneca, 127)
What remains unchanged however, is the source of regrets. The future is truly unknowable, not uncertain in the sense of a random die toss, but unknowable in the sense that we don't know the generating distribution, or the rules of the game. How can we expect our past self to predict where we are now? We acknowledge that the particulars of decisions don't matter, yet we still regret the outcomes of decisions made in ignorance. This is a contradiction in terms of principles, therefore the source of regret is not so much as making the wrong decision as making the unprincipled decision.
The unprincipled decision is not acknowledging the extent of my ignorance, and accommodating for inherent unknowns. Not making the best use of time, energy, information that is self-consistent, at the level I will make peace with now and in the future.
The unprincipled decision is one made without an understanding of risk, and made with the lack of confidence that overly credits the certain, the here, the material, the observable. By forgetting how much have changed since I started, and "memento mori" - remember that I must die.
We should not accept the tyranny of the future either. Make peace with yourself. Accept that your past did the best they could with the knowledge they had. But now that we have this way of thinking, the responsibility is on us.
Campbell, Robin, and Seneca. Letters from a Stoic : Epistulae Morales Ad Lucilium. London, Penguin, 2004.