Woulda, Coulda, Shoulda

When I was younger, I always said I never wanted to live with shoulda, woulda, coulda… however, life has a strange way of somehow deciding things for us.  Regrets, what do you regret?  Do you regret not getting to say goodbye to someone? Staying longer than necessary in a relationship that you knew was bad?  Not taking a chance on a person that you know could be great?   Financial or poor work choices?

Or the worst; agonizing or spending too much time over friends and being liked, your body, your weight, your looks?

Regrets that linger, the ones that you reminisce about for years are great company, they keep returning to keep you living of an alternative version of you life and career.  They can even be useful if they drive you forward, to ensure you do not make the same mistakes again.

Instinctively, however, we understand that regrets that are left can control our mood and make us miserable.

Regret is widely advertised as one of the most prevalent negative emotions- I have observed this in my counselling practice.  Most people wish to turn back time, and wish certain parts of their life went differently, or contemplate what may have been.

Shai Daidai, a psychology professor and an author of “A recent Study of Regret,” articulates that the solution is not to repress the thoughts or take on some kind of delusional no regrets bravado. It is better to look into our oldest despairs and become familiar with their nature and how we respond to them.

Research on the types of regrets that have incredible staying power, are the ones about what we could have done, not the ones that we did do wrong.  Although we experience both types, studies indicate that it is the regrets about inactions that haunt us more for longer periods. 

You are more likely to feel anguish about never auditioning for that performing arts school when you were younger, or never teaching English in Japan, than you are to regret a bad real estate move or a nightmare job that you accepted.

According to psychologists who theorized why this asymmetry exists, action related regrets allow reparation work, this means we can deal with them and let them go. 

If you missed your son’s graduation, you can apologize and arrange and alternative celebration.  If you moved to another city for work and regret leaving your extended family, you can promise to fly home for every holiday.

However, there is nothing to be done about the goals you didn’t act on to begin with. – The one who “got away”, may now be married to another person; some talents can only be developed if you start young; a once in a lifetime job opportunity comes around only once.

These two types of regrets are also processed differently.  If you sell your house at the wrong time, we translate that as a lesson learned or exposes a silver lining. 

If you miss someone’s birthday, you may spend some time questioning your motives and your relationship with that person, because you feel guilty about having messed up. 

It’s difficult to leave that type of issue unresolved.  We don’t feel the same pressure when we process regrets for paths we don’t take, mostly due to the absence of action, it does not elicit a large emotional response such as anger or guilt the way making a mistake does.

Another layer to this taxonomy of regret is inspired by self-discrepancy theory, which states that we have a trinity of selves: the actual, the ideal (your most majestic self) and the ought (the one that meets all expectations of one’s social role)  According to this theory, there are regrets of inaction related to your ideal self, and inaction related to your ideal self and regrets of action related to your ought self.  A six-part study revealed to psychologists that the regrets of inaction related to our ideal selves cause the most long-time distress.

If most of us are still haunted by images of an ideal self that never fully materialized in our dying days, it would appear that we should pursue our dream job, our dream life, right NOW!

In a survey carried out by individuals aged 35-60 where there were no rules, just one question- “what’s your biggest regret?” here are the top eight regrets of middle age.

  1. Not doing the “right thing when someone died

Regrets regarding death cut the deepest.  Included in this is not being there for someone close to them when they died’ not being able to prevent a friend’s suicide, having a fight just before someone died in a car crash.

Several individuals wished they tried harder to fix a relationship while they still had the opportunity. Spent more time with a loved one.  The surface regrets were still upsetting and made them more conscious of their close relationships of nurturing those that mattered.

  • Spending too much time worrying and being afraid

People regretted hiding or burying their feelings and not speaking up for their own needs and desires, trying too hard to please others- or backing away from opportunities they could have taken. Fear had led to regret around things they had not done, like taking risks, trying different things, dating more people, pursing less popular career paths and travelling.

  • Not having enough adventure- staying in the comfort zone

Playing it safe and clinging to security.  Taking few risks with their lives and now feeling the weight of responsibility, children, partners, mortgages, aging parents, debt, work pressure- that it was too late.

  • Staying too long in a bad situation – work/relationships.

Staying too long in a job they hated or were completely bored with.  Clinging to an unsatisfactory, or even toxic relationship was a common theme, including loving the wrong person- and having their heart broken by them.

  • Not being smarter with money

Almost everyone in some way or another had this in common.  Purchases they should have made, like property.  Beyond personal grief, money worries us the most.

Not getting more education- or choosing the wrong path.

Wishing they had the determination and courage to study more and do what was in their heart. In all the cases, this was because they didn’t like the path they were on now but didn’t know how to change it or felt it was too risky.

  • Lost Opportunities

These regrets were often attached to things beyond their control.  Like not finding a loving life partner or being unable to have a child.  Being rejected by the person they loved. Or throwing away a great relationship.  Several people expressed their regret in marrying and having a family too young and not fulfilling their work/career aspirations.

  • Doing stupid or mean things

Hurting others (lovers, friends and parents), alcohol abuse, drugs, too much sex with the wrong people.  One person admitted being a bully.  Others referred to being too self-absorbed. Being naïve, dumb, inexperienced, avoidant, inability to apologize. Things that can make us cringe. Things that we should all be better at in middle age but are not always.

Now that you know what most people regret, we can look at ourselves ad say “what type of person am I?”

Are you the type of person that has big dreams or who thinks that the most important thing is responsibility for other people? 

This research reveals to us to stop passively pining for the what ifs, and do what we can to remove their sting.

If you are in a job that perhaps you don’t necessarily enjoy and may regret have chosen in 10 years ago, feeling stuck is fine, but you should treat that as an emotion. 

If you can’t change your job, or the circumstance of your job, you can do the psychological work through therapy or trying to reframe it.

You can try to shift the scales a little bit toward that neglected ideal self and begin to let go of the regret in its grasp.

In these large and small ways, Gilovich says, you “can shift the scales just a little bit” toward that neglected ideal self and begin to let go of the regret in its grasp.

Regret can be valuable, it makes us aware of the mistakes we have made, the not so great we have treated other or ourselves and if we allow it, it can guide our future decisions.

However, it can also keep our focus on thing we have failed to do rather than all that we have done and still can do.

The past informs us of who we are, it is not possible to fully live while we look over our shoulders.  What do you regret?  If it can be changed, maybe it is the time to loosen your grip on it, and if it can- why not start now?


Nimmo, K, 2020; Top Regrets of Middle Age, Medium.com https://medium.com/on-the-couch/the-top-8-regrets-of-middle-age-9b68abfdc2aa

Davidai, S., & Gilovich, T. (2018). The ideal road not taken: The self-discrepancies involved in people’s most enduring regrets. Emotion, 18(3), 439–452. https://doi.org/10.1037/emo0000326


I believe you can learn something new everyday.


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