The Thing About Hindsight

Life can only be understood backwards, but it is meant to be lived forwards ~ Soren Kierkegaard

“They” say that hindsight is 20/20 and that’s the bitch of it, isn’t it? Looking back, it’s so easy to see what I missed when I was standing in the thick of it. The clues, the cues, the flags that should of, would of, could of indicated a different path or a different decision, but I just didn’t see it. Or I chose to ignore it. Or I simply, just made a different decision. It becomes so easy to say, “I wish I didn’t do that,” or “yep, definitely should have done that.” I just don’t have the luxury of hindsight in the moment, instead, often flying by the seat of my pants, and putting one foot in front of the other, making decisions because I have to.

I try not to regret anything. The key word in that sentence is try. Regret is a wasted emotion. I can’t go back in time and change the decisions that I have made, yet, I still do have regrets.




feel sad, repentant, or disappointed over (something that has happened or been done, especially a loss or missed opportunity).


a feeling of sadness, repentance, or disappointment over something that has happened or been done.

I would add that regret is also a feeling of disappointment over something that was not done or did not happen. In fact, I used to say that I would much rather regret something I did, rather then something I didn’t do.

As I was reading about regret, I started with definitions in the dictionary and then a description from Wikipedia and felt that lightbulb moment; that sensation when you suddenly realize why you are feeling a certain way. According the Wikipedia description:

Regret is related to perceived opportunity. Its intensity varies over time after the decision, in regard to action versus non-action.

The problem with hindsight is that we have it.

This super power, designed for growth, learning and self-development, can create the powerful gut-punching ache of regret and disappointment. Which is where I currently sit. Wrestling with the ache of regret and struggling with questioning my intentions, my decisions and my choices.

The other thing about hindsight is that we can look back on our decisions, our actions and non-actions, with the knowledge of the results, and clearly see where we went wrong. I now have the power of a result. I know how the decisions I made have played out in my life. I can clearly see that I made a decision, I chose a course of action that led me down a path that was not right for me and is now forcing me to course correct. Knowing that, having that nugget, and the power of hindsight has created my aching regret.

As a rational person, making decisions that lead to mistakes, sucks; but, through my rationalizing process I can view the positives that result. I can chalk up those mistakes to personal growth and attempt to figure out why I made the decisions I did; what beliefs, behaviours and ingrained patterns do I have that led me to make these mistakes? This process of self development, reflection, self awareness and introspection, is uniquely human; and if taken on bravely, can lead to great self satisfaction and resulting happiness. According to research, humans are rationalizing machines. After the sting of the mistake fades, our brains go into overdrive to find the “silver linings”, the positives, the learning opportunities. This is where we often fall back on the “everything happens for a reason” mode of thought. Or as I’m currently figuring out, perhaps shit happens and then we make up the reasons so we don’t feel like such an asshole for the decisions we have made.

Research has also shown, repeatedly, that we have greater regret over the opportunities, decisions, choices, that we did not make. That regret over non-action is far worse. Is that because we don’t have the luxury of knowing the result? It remains a giant question mark, that we can then morph in our minds, to equate to having missed the most life-changing, career advancing, love of our lives, opportunity that is no longer available to us. The crushing ache of longing and desire to have that decision back in front of us and to make a different one can be crippling.

Being the hopeless romantic that I am, I look back to decisions I made over the last year. I think of those I walked away from and those I walked towards and I find myself wondering how and why I made those choices. In my heart, I know that I walked away from some amazing people and the only reason I can come up with is because they didn’t look good on paper. They didn’t fit the predetermined, cardboard cut out of love and relationship that I have long held in my mind. I made assumptions, I reduced someone to a checklist and ignored the kindness, the interests and the undeniable spark and connection because I made an assumption on fit, desirability, intention and ‘shoulds’. I feel the ache every time I think about them.

Recognizing the reasons and motivations using my hindsight is a powerful tool. Learning and growing can, potentially, equate into different decisions and different outcomes in the future, but forgiving myself is the only true path forward.

Regret and hindsight prevent me from being truly present and appreciating who is in my life. Swallowing my pride and reaching out to those I miss, those I have question marks about, and those I wonder about is brave. But most of all, I am showing true kindness, in forgiving myself.

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