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How to Handle Regret and Disappointment

Developing more adaptive strategies to deal with difficult situations

When we make decisions to change or stay put we are acting in a world of uncertainty. No matter how much information we collect or how rational our decision-making might be, there is always a chance that the outcome will be less than what we expected. How can you handle the inevitable disappointments that come with living in the real world?

@Taychilla Unsplash License Used with Permission
Source: @Taychilla Unsplash License Used with Permission

I have been interested in decision-making for many years since many of my clients and I have had to deal with regrets. Some people have regrets for a short time while others can go on for months or even decades with regret. We all need a mental strategy for dealing with regret.

Take the example of Joanna who has decided to take a new job, hoping it will improve her life substantially. After four months in the new job, she has found that the work and her boss are not exactly what she had in mind. She is now feeling depressed and annoyed, and it seems to Joanna that there is nothing in her current job that is worth doing. She complains to others and she blames herself for making such a stupid decision. She feels miserable.

There are five ways of thinking that add to her regret. Each of them is worth examining and worth asking if there are more adaptive ways of viewing the current situation. Think about your own regrets and see if you can use these ideas in your own life.

1. Essentialism vs. Relative Preferences

Joanna believes that there are certain things in a job that are essential. She thinks her job has to be interesting, meaningful, never boring, and always self-fulfilling. She has been told by others to follow her dream. This is not her dream. She believes that all of these very positive qualities are absolutely essential. This is what I have called Existential Perfectionism. She dreams of a perfect life, perfect job, and perfect emotions.

This kind of fantasized world is not only an illusion, it’s a trap. It leads to disappointment and disillusionment. But what if she were to look at her job in terms of relative preferences? According to this view, we might prefer 100 percent but we can see the value in 80 percent. The qualities that she views as essential are a figment of her demanding imagination. If they were essential then everyone would need those qualities in their work. They are preferences, not essential needs.

2. Hindsight Bias

We often look back at our decisions and think that we should have known better. It’s as if Joanna thinks she is stupid because the outcome wasn’t what she wanted. But she made the decision with the information available at the time. All of us are good at predicting what happened yesterday. But we aren’t always accurate about predicting tomorrow. Just watch the weather forecasts. A rational way for Joanna to look at this is that she made a decision under uncertainty and now the results are in. Uncertainty means a range of possibilities. This is one of them.

3. Flexibility of expectations

We all have expectations about the way things should be. Joanna had expectations about the ideal job and now she finds it’s not perfect. She complains, “This is not what I expected.” That is true. But our expectations are simply arbitrary thoughts that we have. They are not fixed in concrete. I can expect that the train will arrive at 10:05 because that is what the schedule says. But if it arrives anywhere between “on time” and 20 minutes late, I might be wise to change my expectations to match reality. If we are flexible about our expectations we can change disappointment into manageable reality.

4. Acceptance of tradeoffs

You have heard the old adage, “There is no free lunch.” There isn’t. Everything has a tradeoff. What are the positives of the new job for Joanna? She is able to acknowledge that she is learning new skills, the company has more opportunities for advancement than her old job, and the pay is better. The downside is that the work is boring at times and the boss can seem overly demanding. Is there anything in life without tradeoffs? When we are overly demanding and we regret that we aren’t getting everything we want, we might not realize that any option will have tradeoffs. The free lunch has a hidden cost.

5. Self-critical vs. self-correction

We often end up criticizing ourselves when the outcomes don’t work out. Joanna is thinking that she is stupid because she doesn’t have the ideal job. We looked at her abilities and accomplishments and many other decisions that she has made and she knows that she is generally very capable. We examined that people she knows and respect have often made decisions that didn’t work out. I suggested that she might examine “self-correction” rather than “self-criticism” as an option. When she looked at how she was thinking she realized that she might correct the idea that she needed the perfect job. She could focus more on making the best of the situation rather than putting herself down because things didn’t work out as expected.

How do you handle your regrets and disappointments? There is always another way of looking at things. We will be discussing this in future posts.


Leahy, R. L. (2022) If Only. Finding Freedom from Regret. New York: Guilford Publications

Perspectives in Psychological Science. Hindsight Bias.

Clinical Psychology Review. Psychological Flexibility as a Fundamental Aspect of Health.

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