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Regrets & how to overcome them

So here’s the story: After a lifetime of handcopying ancient texts, an elderly monk became abbot of his monastery. Realizing that for centuries his order had been making copies of copies, he decided to examine some of the monastery’s original documents. Days later, the other monks found him in the cellar, weeping over a crumbling manuscript and moaning, “It says ‘celebrate,’ not ‘celibate!'”

Ah, regret. The forehead-slap of hindsight, the teary fuel of country ballads, the self-recrimination I feel for playing a game on my phone in a crafty but unsuccessful attempt to avoid writing this column. If you’ve ever made a bad decision or suffered an accident, regret has been your roommate, if not your conjoined twin. It’s a difficult companion, prone to accusatory comments and dark moods, and it changes you, leaving you both tougher and more sensitive to guilt or shame.

You get to decide, however, whether your toughness will look like unreachable bitterness or unstoppable resilience; your tenderness the raw vulnerability of a never-healing wound, or a kindness so deep it heals every wound it touches. Regret can be your worst enemy or your best friend. You get to decide which.

There are at least two time zones where you can choose to make regret’s powerful energy healing rather than destructive: the past and the future. Both can be transformed by what you decide to do right now, in this moment.

Let’s start by changing the past. If you think that can’t be done, think again. Literally. The past doesn’t exist except as a memory, a mental story, and though past events aren’t changeable, your stories about them are. You can act now to transform the way you tell the story of your past, ultimately making it a stalwart protector of your future. Try these steps, more or less in order.

1. Get Beyond Denial

As long as you’re thinking, “That shouldn’t have happened or I shouldn’t have done that,” you’re locked in a struggle against reality. Many people pour years of energy into useless “shouldn’t haves.” “If only’s.” If only they’d married Sebastian, or gotten that promotion, or heeded the label’s advice not to operate heavy machinery, they would be happy campers instead of les misérables.

This is unproductive regret and it can be the story we continue to repeat to avoid the responsibility of creating change or taking responsibility.

  • List your “should have/could have/if only’s

  • Write down an alternative learning lesson and positive action for each one

2. Separate Regret’s Basic Ingredients

Of the four basic emotions—sad, mad, glad, and scared—regret is a mixture of the first two. Your particular situation may involve enormous sadness and a little anger (“My father died before I ever met him. Damn cruel fate!”) or enormous anger with a side of sadness. Whatever the proportions, some regretters feel sadness but resist feeling anger; others acknowledge outrage but not sorrow. Denying either component will get you stuck in bitter, unproductive regret.

Considering anger and sadness separately makes both more useful.

  • Right now, think of something you regret.

  • With that something in mind, finish this sentence: “I’m sad that ……… until you run out of the sad reasons

  • Now do this but with the words “Im angry that…..’

3. Grieve What is Irrevocably Lost

Sorrow is a natural reaction to losing anything significant: a dream, a possession, an opportunity. Productive grief passes through you in waves, which feel horrific, but which steadily erode your sadness. The crushing mountain of sorrow eventually becomes a boulder on your back, then a rock in your pocket, then a pebble in your shoe, then something you gain strength from—not because circumstances change but because you become strong enough to accept the world as it is.. You’re finished grieving when you see someone gaining what you regret losing and feel peace or even joy—maybe even secret gratitude that circumstances forced you to enlarge your own capacity for joy Regret is telling you to seek out a part of whatever you’ve lost.

Write down the things you feel grief towards/or you are still holding onto with grief

4. Reclaim the Essence of Your Dreams

You can’t change the fact that you dropped out of xyz too soon, never stood up for yourself at work, or spent decades in a bitter relationship. But you can reclaim the essential experiences you missed: following your dreams backing yourself or demanding more from relationships and yourself.

  • In this moment, resolve that you’ll find ways to reclaim the essence of anything you can’t stop grieving.

Explore your dreams, passions and values

5. Learn to Move Past Fear So the ultimate lesson of regret, the one that will help guide you into a rich and satisfying future, is this: Every time life brings you to a crossroads, from the tiniest to the most immense, go toward love, not away from fear. Think of every choice in terms of “What would thrill and delight me?” rather than “What will keep my fear—or the events, people, and things I fear—at bay?”

Caroline Williams is a registered counsellor and nationally registered homicide / major crimes counsellor in New Zealand working with individuals and couples to help them make the life they love happen. With over 15 years training and experience in anxiety, depression, addictions and trauma she is a prolific writer and workshop facilitator.

Contact her at for in person or zoom counselling and make this year the one that counts!

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