with twenty-twenty hindsight

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with twenty-twenty hindsight

With the benefit of one's current knowledge or experience, thus allowing them to see why something in the past was wrong or how some mistake could have been avoided. Said when examining some negative past event retrospectively. Sometimes stylized as "with 20/20 hindsight." I spent my whole life working, almost every minute of every day. Now, with twenty-twenty hindsight at the end of my life, I see that I squandered the time I could have been spending with my family. Of course, with twenty-twenty hindsight, it's easy to laugh at the quack doctors of the early 19th century, but back then, even legitimate medicine was still largely rooted in superstition and pseudoscience.
See also: hindsight
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.

twenty-twenty hindsight, with

With complete after-the-fact knowledge. This expression, usually preceding a statement like “I would have done or said such-and-such,” uses the optometrist’s term for perfectly normal vision. The idea that hindsight, with its superior knowledge, is better than foresight has been stated since at least the nineteenth century. “If a man had half as much foresight as he had hindsight, he’d be a lot better off,” wrote Robert J. Burdette (Hawk-eyes, 1879). The Hollywood screenwriter Billy Wilder is quoted as having said, “Hindsight is always twenty-twenty.”
The Dictionary of Clichés by Christine Ammer Copyright © 2013 by Christine Ammer