103 | Hindsight is Not 20/20

I don’t think hindsight is 20/20.

Yes, if you have a good memory, the technical facts of the story are easier to retrace once you have seen them play out.

But remembering the precise emotions, priorities, consequences, trade offs, relational dynamics, or rationale of a decision or event does not get clearer as time passes.

I think it gets infinitely fuzzier, because you can't ever fully recreate the moment right before something happened.

Whether it’s replaying the result of a game.

Or a hard conversation.

Or a job change.

Or reflecting on a big purchase.

Or reviewing past investment decisions.

Or criticizing the decisions of leaders and individuals in March 2020 or October 2008.

Considering hindsight 20/20 discredits the past self and torments the current self.

After the fact, we know what went according to plan and what created other challenges.

After the fact, we can’t recreate the moment in a way that respects the adrenaline-, emotion-, anxiety-filled decision that was made when the outcome was actually up in the air.

After the fact, we can’t objectively re-simulate the decision or event because this time we’re able to ignore the hypothetical worst-case scenarios that didn’t happen after the first take.

Hindsight makes it too easy to woulda-shoulda-coulda our way through life wondering why we, or someone else, didn’t get it more right the first time.

Once we can acknowledge that hindsight isn’t 20/20 then it becomes a little easier to extend ourselves some grace and put the what-ifs to sleep.