How to Deal With Regretful Decisions

An introspective brain dump on how to deal with the regret from decisions you’ve made and not dwell on what could’ve been.

Surreal Thoughts Think Tank
6 min readMay 21, 2021
Photograph by Janko Ferlič: https://unsplash.com/@itfeelslikefilm

One of the greatest traits of being a human is the ability to reflect on our decisions. It’s also one of the biggest things keeping us up at night. This last week, I faced some big decisions myself…

1.) Deciding whether or not to accept a job in a new industry

2.) Deciding if I should take the plunge and publish my writing online.

I’ve taken the job and you’re reading this article, as you can see, the decisions have been made. The question is — why do I keep wanting to look back?

The Anatomical Breakdown of a Decision

We can break down decisions into the three following components.

  1. Observation
  2. Selection
  3. Reflection

For this brain dump, I want to focus on what I call the ‘Sunday Scaries’ of decision making. For me, the ‘Sunday Scaries’ occur during the Reflection Phase of decision making, but to tee up that discussion we’ll go through an overview of how we get to that point.

The Observation Phase

The first step in making a decision is the Observation Phase. This is where information on the situation is gathered and organized for assessment. It’s usually in this phase we realize a decision must be made or a problem must be solved.

Events that trigger the Observation Phase can range from trivial matters like finding out a horrible smell is coming from your cat’s litter box to more complex issues like receiving a job offer or deciding whether to take crypto profits. In all these scenarios we realize a decision must be made and we begin to make observations and gather data to lay out our options.

The Selection Phase

When we’ve understood the problem we’re up against and have identified the options available, we enter the Selection Phase. The whole goal of this phase is to assess the different options to make a decision.

Depending on the problem, we may even take the results of a previous decision into account. In my earlier example of horrible smelling cat litter, previous experience tells me to clean the litter ASAP rather than wait (unless I want my apartment smelling like a Taco Bell bathroom).

At the conclusion of the Selection Phase, a decision is reached and we will have selected an option in regards to the decision at hand. Nice, that was easy. Right?

Unfortunately, there are problems in life a lot more difficult to act upon than cleaning cat litter. Depending on the complexity of the problem, some people may be overwhelmed and fall into a state of mental paralysis. Should paralysis occur, the window of opportunity to select an option may pass, leaving the person regretting their inaction.

Inaction itself is a decision and as Dale Carnegie once said:

“Inaction breeds doubt and fear. Action breeds confidence and courage. If you want to conquer fear, do not sit home and think about it.”

If we follow the same train of thought, choosing inaction would result in choosing doubt and fear. The ideas formed and choices made during the Selection Phase are what get carried over into the Reflection Phase of our decision. Ultimately, it’s these ideas that become the seeds of our reflection and the ‘Sunday Scaries’ of decision making.

Why Reflection Is One of Our Greatest Gifts and One of Our Worst Nightmares

Photograph by Clem Onojeghuo: https://unsplash.com/@clemono

The Reflection Phase is the last component of making a decision. It’s during this phase that we reflect on the outcome(s) of our decision.

Reflection and introspective thought are huge assets to us as humans. It helps us better understand the impacts of our decision, providing us with learning opportunities that may give us insight during the next decision we face.

Thoughtful reflections on decisions compounded throughout our lifetimes are what allow us to grow smarter and wiser as we live life. In most important decisions, there’s some aspect of the ‘Sunday Scaries’ that forces us to reflect on and assess the choice we’ve made.

But there’s a catch.

Sometimes the Reflection phase never ends or it takes place over years. The results are ‘Sunday Scaries’ that consume a person’s life. Sounds like a nightmare.

For some people facing exceptionally difficult decisions, it’s not uncommon for them to dwell in the Reflection Phase long after the decision has been made. The person may be filled with doubt over their choice and may long to go back in time for a re-do.

Wishing for a real-life mulligan is common, especially when new information comes to light after the decision is made. In the worst cases, a person may live in constant regret over a past decision, removing themselves from the present.

If the purpose of making a decision is to free yourself from a problem, trapping yourself in the shadow of doubt may feel like you’ve not gained any freedom at all. So how do we move out from under the shadow of doubt?

Acceptance of a Decision Is a Lot Easier Said Than Done

I’m going to preface this section by acknowledging that the following ideas are a lot easier said than done…

First thing’s first, let’s state a fact. Once a decision has been made, you can’t change the past to alter the present. There’s no use in regretting past actions or dwelling on what could’ve been.

Having your mind live in the past or alternate present won’t improve your current situation. Allow yourself to reflect on a decision to learn how you can adjust your approach for the next problem but even then, don’t overthink or linger in the reflection.

As I stated before, let’s assume the purpose of making a decision is to free yourself from a problem. If that’s the case, release yourself from the burden of that past problem and focus on your current situation. Now, it may very well be that the decision you selected resulted in many other new problems but there’s no use in throwing yourself a pity party.

Think back and identify what you can do better next time around. Once you’ve done that, take a breath and look forward. If you can’t figure out what you did wrong or could’ve done better, then accept that fact and again… look forward. Look forward and observe the new challenges before you.

Whether these challenges are a result of previous choices you’ve made or circumstances outside of your control, they must be met either way. Sitting in regretful reflection and risking the path of inaction won’t help you overcome the problems that are now in front of you.

Lastly, a quick plug from the book Man’s Search For Meaning by Viktor Frankl. If you haven’t read it, I highly recommend it. There’s an idea from the book that lends itself very well to the topic of How to Deal with Regretful Decisions. In the book, Frankl says:

“Everything can be taken from a man but one thing: the last of the human freedoms — to choose one’s attitude in any given set of circumstances, to choose one’s own way.”

Bottom line is that not every decision we make will be the right decision. One bad decision can take everything away from us. We can’t change the current situation or the past but we always have the ability to choose how we approach upcoming challenges.

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