Always Feeling Regretful? When It’s More Than Bad Choices

by Andrea Blundell

Left feeling regretful with every decision you make? With a sense of sorrow for all the things that might have been?

Is regret always a bad thing?

Sometimes we really do make a bad decision, and our regret guides us to change for the better. If we, say, lie to someone we love and feel terrible after, we know not do it again.

Why do I feel regretful with every decision I make? 

But why do some of us experience a constant state of regret, where we feel we are always messing up? Psychologists have several theories about regret. 

1. You are an idealist.

Research around regrets show that we tend to forgive ourselves for mistakes we actually make. It’s idealism that drives us to be mired in regrets. 

A study looking at how regret relates to self-concept found that, “people’s most enduring regrets stem more often from discrepancies between their actual and ideal selves. People are quicker to take steps to cope with failures to live up to their duties and responsibilities than their failures to live up to their goals and aspirations.”

So we are likely to forgive ourselves for buying a car that turns out to be a bit of a lemon, but be endlessly regretful for, say, not trying to make a career out of singing.

  • Are you beating yourself up over something that is simply idealistic over realistic?
  • How are you using regret to not accept your life as it is, and see what IS going well? 
  • Where did you learn to always compare yourself to an unrealistic ideal? Or from whom? Is this really a thought pattern you want to continue?

2. You are overwhelmed by too many choices. 

It turns out that after decades of creating a society where we thought choice was freedom, our brains falter in the face of too many options.

A famous (if now dated) study by American psychologists Iyengar and Lepper looked at how likely people were to buy jam if they were faced with many options. It turns out people were more likely to buy from a small display of six choices than a bigger one of 24. A more recent 2018 study used brain scans to show that although we enjoy knowing we have choice, our brains goes into ‘choice overload’ beyond 12 choices. 

  • Are you always seeking more and more choice? Is it possible this is a form of self-sabotage
  • What would if feel like to stop seeking options and work with the choices you already have? 

3. You are falling into perfectionism. 

American psychologist Barry Schwartz, In his paper The Tyranny of Freedom, points out that the more our choices, the more complicated things are.

But we don’t recognise that it’s an unrealistic situation and instead blame ourselves, and are left feeling regretful.

“With all the choice available, people should never have to settle for things that are just good enough. In short, life is supposed to be perfect,” Schwartz point out. “Not only do people expect perfection in all things, but they expect to produce this perfection themselves… this kind of causal attribution [to self over situation] is just the kind to promote depression when people are faced with failure.

When you really are making bad decisions

feeling regretfulBut what if you really ARE making bad decisions? If others are always despairing at your choices? There can be several psychological reasons for this.

1. You put others before yourself.

If we are people pleasers, we reject our own needs to meet those of others. So even if we don’t feel great about a decision, we soldier on as it is what other around us want. We end up feeling regretful, or, worse, bitter.

2. Your belief system is getting in the way.

Despite telling yourself in your mind you deserve better, we aren’t driven by our conscious thoughts. Instead it is our set of unconscious beliefs that secretly direct our choices in life. The things we decided were ‘true’ based on our childhood experiences.  These ‘limiting beliefs’ can sound like: 

3. You are a drama addict.

Who would you be without all your mess ups? If your first instinct is to say someone boring, it’s worth looking at whether your identity is tied up with seeming exciting, even if that means endless bad decisions that leave you with a story to tell.

4. You are mired in the victim mentality.

If you gain your sense of agency from secretly manipulating others to feel sorry for you, then the victim mentality will keep you making bad decisions that ensure that sympathy is in constant supply.  

5. Misery is your comfort zone. 

If we grew up in a miserable, unstable environment, then mess and unhappiness can feel like ‘home’. Good things can be uncomfortable or even feel dangerous, so we unconsciously make bad decisions and sabotage opportunity that might improve our lot. 

Can therapy help me stop feeling regretful?

A therapist can help you look at any childhood roots of bad decision making. He or she can also act as a sounding board when you have choices to make, and can teach you new ways of seeing that help you make positive steps forward.

Time to stop feeling regretful and start making positive choices? We connect you to top London-based psychotherapists and counselling psychologists who can help. Or use our booking platform to find affordable UK-based registered therapists and online counsellors


Still have a question about always feeling regretful, or want to share your own advice with other readers? Use the comment box below. 

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