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Hindsight and Regret: Break the Cycle.

Hello pilgrims Welcome back.

How crazy is this year? Anyone remember when the world thought Kim Jong –un died? NASA basically confirmed UFOs, Beyoncé sent boxes to her clique, people lost their minds over Popeye’s chicken sandwiches. That was all this year.

I'm sure, I’m not the only one who wished they knew at the top of the year, what they know now. But as they say... Hindsight is 20/20 (or 2020 in our case). That’s the topic of this week’s segment.


Looking back is fine when you are gauging your journey to see how far you’ve come. It’s also okay when you remember some things that you’ve overcome or to better understand your journey. Where you’ve been has shaped your perspective and your perception, but we should not get so stuck on the things that are behind us and we can appreciate how they made us the people that we are. We have got to continue on our growth and not get stuck on that hindsight is 20/20, because that might be the only thing that is clear is hindsight. So as we go forward. I want us to continue on with our reflection, scope, self-examination, and all the other techniques we have gone over in this challenge.

Types of Hindsight Biases

  • Cognitive: People tend to distort or even misremember their earlier predictions about an event. It may be easier to recall information that is consistent with their current knowledge.

  • Metacognitive: When we can easily understand how or why an event happened, that event can seem like it was easily foreseeable.

  • Motivational: People like to think of the world as a predictable place. Believing an outcome was "inevitable" can be comforting for some people. 1


When you look back on your journey, it may be easy for you to pinpoint particular moments that ‘changed everything’. Do you lay awake at night thinking about what could have been if you hadn’t done that one thing? Do you wish you could go back and try that thing you were too afraid to do? Are you ashamed of what you said, and you wish you could take it back?

I know that people often say that you should have no regrets, but I don’t think that is a fair edict. If you have regret, then you are feeling sad or disappointed about something that has passed. Which are normal emotions to feel. Too often, we are asked to suppress or downplay our ‘negative’ emotions. While we shouldn’t dwell in negative emotions, we should allow ourselves the proper time to grieve and process our traumas.

There’s some stuff I wish I could go back and change, and I know I can’t. I’ve made my peace with it with accepting that it is, what it is. At the same time, If I had the opportunity to change it, I would do so in an instant.

While guilt can eat you up, I would like to offer a new perspective.:

"Regret is an indication of growth."

The regret you feel says that if that same situation were to arise again, you would do things differently.

You can have regrets and acceptance.


We’ve all had that moment. That gut-clenching moment, when something irrevocable has happened. The instant regret. The mind-racing thought of how you can go back 10 seconds. If you could only go back this otherwise insignificant amount of time.

Looking back now that you know what outcomes are is natural everybody feels it thinking that if this would have happened if that would not have happened things would be perfect things would be okay, things would be different. Ultimately, we have to realize that we can’t go back. And though we can see the past so clearly from our perspective right now.


The alternate timelines that we imagine are just more illusions. Our focus should be on not allowing them to prevent us from being happy or achieving our goals. A part of hindsight is forgiveness.

To forgive is to relieve of any obligation or debt. (See my self-care Sunday blog about forgiveness for more details.)

We should forgive those who have wronged us, we should forgive the circumstances we found ourselves in, and we should forgive ourselves.

In each of the types of hindsight bias, we must forgive ourselves for not knowing then what we know now. You made the best decision that you could, based on the information that you had at the time. You are no longer the same person. You have a new perspective and understanding.

If you constantly look backward at things that you can’t change you will miss the opportunities around and ahead of you. And the moment, and the opportunities that exist in this exact moment right now, because we’re so focused on what could have been instead of what is and what could be.

I’m sure that all of us at some point wished we could go back to a particular point and changed something. If we could go back to January 1st, we would have bought stock in Purell and 3m, traveled more, stocked up on TP, warned that person not to go. We all think about that one butterfly that would flutter its wings and fix everything. Alas, in this timeline we all don’t have access to the time machine that would fix everything.

I do rejoice in knowing that somewhere in some parallel universe, I am having the best year ever. I can't change what has already happened, but I can, at this moment, make decisions so that I have less regret tomorrow.

Until Next Time,


Did you enjoy this read? Be sure to join us November 22nd to discuss with fellow pilgrims your favorite segments of the 2020 journey.

References Featured in this article:

1 How Hindsight Bias Affects How We View the Past by  Kendra Cherry


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