"I should've known” is one of the worst mindsets in life and business.
Believing past events were more predictable than they really were — that’s a big fat flaw we all share.
Psychologists call this Hindsight Bias.
It’s when we judge our past choices with today's clarity and ignore the uncertainty we faced back then.
Hindsight bias makes things seem obvious after the fact and leads to unfair self-blame.
And it feeds a huge misunderstanding about choice-making that impacts our ability to lead and live well: that bad outcomes mean bad decisions.
Life's messier than that.
Of course, bad decisions do exist. If we don’t bother to understand the context, if we don’t clearly think about the facts we have, or if we ignore them entirely — and then make a decision — that’s bad.
But a decision isn't bad just because it didn't work out. Read that again.
The job you took that wasn’t for you.
The party you skipped that turned out to be amazing.
The marketing decision that led to a loss.
The person you hired that turned out to be an absolute fucking nutjob.
“I could’ve known.”
But could you, really?
Maybe. But chances are, you couldn’t have.
We overestimate our ability to predict outcomes, especially when looking back. It's easy to mix up what we know now with what we knew then.
So, how do we tackle this bias that's so deeply ingrained? While we can likely never get rid of it entirely, here’s what helps me:
- Remember: decisions always come with uncertainty.
It's easy to be a genius after it's over. But uncertainty means, by definition, that there’s some unknown that can simply turn out to be shit. And there’s nothing you can do about it.
- Write down your thoughts when making big choices.
Capture your reasoning in the moment. It'll help you see your decisions in the right light, free from hindsight's distortions. Focus on how you came to a decision, not what the decision led to as an outcome.
- Give yourself (and others) a break.
If you spend 10% of the energy you waste beating yourself up over past choices on taking action to correct course, you’d come out ahead every single time.
Understanding hindsight bias leads to a kinder, more realistic view of your life.
It frees you from the trap of "I should've known better," and helps you appreciate the complexity — and unpredictability — of every decision.
And it makes you a better leader by assessing the quality of someone’s decision by the process they applied to arrive at it rather than the result it generated.
Recognize hindsight bias and empower yourself and others to make peace with the past and confidently navigate the future.
Embrace the unpredictability. And keep moving forward.
