This question makes me think of the Robert Frost poem "The Road Not Taken.." The hard but simple answer is that we cannot fill in the dots. We cannot know what would've been had we take taken a different route. As it is easy to be too optimistic about the future, it is even easier to be way too optimistic about what would have occurred had we taken a different path. We unavoidably can only speculate. That is why we need not dissipate energy over regrets, but instead spend our efforts redeeming the present.
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