It’s impossible to live a life without regrets. Every day, you make choices. Most have little impact on the direction your life has taken. Yet some choices linger and keep you up in the middle of the night. There were days when you said something you wish you hadn’t, or stayed silent when you knew you needed to speak up. Days when you chose a path that now feels wrong for you.

Those 3 am thoughts that keep you awake: If only I had… I wish I could turn the clock back… Why did I do that? Sometimes these feelings pass quickly—fleeting remorse that fades within days. But other times, the regret cuts deeper. Heart-aching sadness, anger or guilt that stays with you for months, years, or even decades. And it seems impossible to get past this.

It’s these deep regrets I want to invite you to explore. Together, we can choose a new perspective and heal any open wounds from past decisions so you can finally sleep peacefully.

The greatest regrets arise when there was an opportunity, but you feel you missed the boat. At the time, you had your reasons. Some were valid. Others stemmed from fear, pride, or limiting beliefs about what you deserved.

Missed opportunities: mole hills or mighty mountains to overcome?

Regrets are deeply personal, yet they loosely fall into these broad, sometimes overlapping categories.

Mole-hill-sized regrets

Small decisions or actions that led to unsatisfactory outcomes:

• Not studying hard enough, failing exams, finally succeeding, but regretting the wasted time of having to restudy and re-sit the exams.
• Pushing life-admin to one side, only to discover lapsed insurance or unpaid bills. The consequences cost you more money or time to sort out.
• Not joining in with a family, social, or work event, then feeling you missed out.

Regrets connected to those you love

When thoughtlessness or a lack of time leaves you feeling sad or guilty about your inattentiveness:

• Losing contact with a special friend because you allowed other decisions to take you in a different direction.
• Not telling your partner, mum, dad, sister, brother, and dear friends how much you love them, then realising how much you hurt them with your silence. Especially if you missed the chance to tell them before their sudden death.
• Prioritising work and your career over your family, then realising how much you missed out on everyday precious moments.

Regrets about behaving badly

When your choices, consciously or subconsciously taken, were mean, spiteful, or humiliating to others:

• Believing you were better than others and, in your superiority, demeaning another’s work, values, faith, or life choices.
• Times when spite led you to be mean to another, only to later feel guilty about how childish your words or actions were.
• When you crossed your own boundaries to take advantage of another, unwilling in the moment to see or acknowledge your wrongdoing. Only when you calmed down did regret surface at your words or deeds.

Mighty mountain-sized regrets

These may take any form, and it can feel like you’ll never overcome these feelings. Yet holding on to them is rarely helpful:

• At university, you fell madly in love with a special person, someone you thought was ‘the one’. But you broke up because you felt too young to settle down, or they didn’t fit your perfect picture of what your partner should be like.
• You had a dream of running your own business, building your own home, and taking on big adventures. Yet it all felt too risky, so you played it safe. Now you feel you’re too old, it’s impossible, or that time has passed you by.
• You wanted to break the mould of poor parenting you received as a child, but despite your best intentions, you lost your temper too often. Now your children are grown up, and they keep a distance from you.

Whether your regrets feel like molehills or mighty mountains, the path forward begins with understanding what really happened—and why.

The ‘What if?’ exercise

We cannot change our past. But we can see it through more compassionate eyes and begin to see and understand the bigger picture.

For this exercise, jot down a few lines in a journal, or on your phone/laptop. Write about a big regret you still think about regularly. Start with the facts, then add, I could have… or I should have… and write what it is that you regret. Now choose the emotion wrapped around it. Is it sadness, anger, shame, or guilt?

Now you’ve got this far, consider the why of it all. This is the missing part of letting go. Regrets focus on what was done or said, but not the driving factors that led you there.

On all such occasions, there was a circumstance, situation, or a trigger. What was it for you? Shyness, an unmet need, loneliness, embarrassment, or uncertainty? Please don’t judge yourself harshly. Rather, have compassion for your younger self who made a mistake.

Forgiving yourself for when you got it wrong

You, I, no one is perfect. We all make mistakes.

In over 20 years of helping people on their healing journeys, I’ve yet to meet someone who hasn’t screwed up big time at least once in their lives. Forgiving yourself isn’t always easy, especially when dealing with huge regrets. But you can heal these wounds.

Sometimes, the ‘What if…’ exercise can help you let go. Sometimes, you need to reach out to say sorry or to make amends. And sometimes you may need professional help. Then I, or another therapist, can help you. There’s no shame in asking for help and letting go will help you feel so much better. If you wish to explore this with me, you can book a complimentary 30-minute Zoom call to have a chat about how I may help you.

You are a magnificent work in progress

I believe we are all magnificent works in progress. Every day and every moment of our lives, we make choices based on our life experiences, what’s going on at the time, our tools, and our level of personal development. Through the eyes of being a magnificent work in progress, you can keep growing and getting better, while also recognizing that in your past, you did not have the abilities you have now.

How do you know whether things would have turned out better?

Another way to turn past regrets around is to consider whether the missed opportunity has become idealized or have even become a fantasy that is far removed from the probable reality.

Take the relationship that didn’t last—perhaps deep down there were incompatabilities. Or the career choice you turned down—it may or may not have turned out better in the long run than what you’re doing now.

There’s no way of knowing for sure. But rather than look back and wish for something else, honour your journey through all of the good and the not-so-good parts of it. Appreciating everything that has come your way helps put the not-so-good into perspective. See my earlier article, How does your perspective change things?.

Letting past regrets become your guiding light

Look back at your deepest regrets and recall the changes you made afterward so as not to repeat these decisions. These changes have made you a better person.

We all strive to do well in our lives and hope we won’t make big mistakes or blunders. Yet we all occasionally fail at this intention. If we are kind to ourselves, we can see our mistakes are our greatest teachers.

Our mistakes show us where we got it wrong. We can consider what to do next time and how to make things right. In this way, it becomes easier to let go of past regrets and use the learning as a guiding light.