1

It is hard for me to understand the underlying meaning of

"with hindsight, I should never have gone"

Does it mean that I regret that I had gone? Or that in case I knew the outcome before that I should never have gone?

The excerpt comes from a dictionary definition.

Hindsight

2

You're exactly right!

Think of "hind" as behind, like past. Sight means vision, so hindsight is like "to view the past."

If the person in the sentence was able to see what was going to happen if he went, he would never have chosen to go. However, since it's not possible to look into the future, he made his best guess and went.

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