That's a common sentiment. It's good for people to reflect on the wrong turns they've made in life. Sometimes that's due to impetuous, foolhardy choices. This can be a source of contrition. Learning wisdom through sorry experience. But sometimes things turn out badly through no fault of their own. If only we had the benefit of hindsight at the time we were at that fork in the road, we'd opt for the road not taken.
However, we can flip that around. Sometimes we might make the same choice, despite painful or frustrating consequences, even though, or even because we had the benefit of hindsight.
For instance, suppose a man is a conscientious husband, yet in spite of that, his wife deserts him. Suppose the angel Gabriel appears to him and offers him a chance to go back in time and make a different choice. This time around, forearmed with the knowledge of how that marriage would turn out, he now has a second chance to finally have the life he planned and wanted. Wouldn't you jump at the offer?
But let's complicate the offer. Suppose he fathered two sons by that ill-fated marriage. When his wife walked out on the marriage, she left him with his two sons.
Would he still take God up on the offer? Would he exchange his two sons for an alternate timeline with a happy marriage, and, perhaps, sons by a different wife? Let's say he won't even recall the troubled marriage. God will erase his memory. He will start from scratch, as if that never happened.
Yet I suspect most men would refuse. Although that alternative might be hypothetically preferable, you've formed an unbreakable bond with your actual sons, and you wouldn't trade that experience for anything. The ill-fated marriage was worth it on their account.
By the same token, consider mothers who've had abortions. But suppose, instead, that at the last minute, they changed their mind and raised the child. Suppose they decided to keep the child for a perfectly frivolous reason. But having raised the child, suppose Mephistopheles appears to them and offers them a chance to step into the time machine and have the abortion they originally contemplated. I suspect most mothers would refuse. Because they didn't go through with an abortion, they formed a unique maternal bond with their child.
Abortion is like shooting someone with a sack over his head. That makes it easier to shoot the victim. An anonymous victim. Can't even see his face. Can't see his pleading eyes.
But suppose, after pulling the trigger, you remove the sack over their head and see that you just shot your father or mother or brother.
When we say, "If I knew then what I know now," we usually mean that given a chance, we'd make a different choice. Yet there are situations in which we wouldn't make a different choice. For retrospection cuts both ways. Paradoxically, we may come to appreciate the outcome, even though it's not the choice we would have made if, at the time, we were better informed about the consequences of the choice. For the consequences may be both good and bad. The good consequences may outweigh the bad consequences. Depends on whether we're privy to the good consequences as well as the bad consequences. And it depends on actual experience.
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