Do you find yourself ruminating on past decisions, actions, or conversations?

How much time do you spend regretting these past experiences? If the answer is more time than I would like, then this episode is for you. I am covering why we hold onto regrets, the high cost of regret, and why we should let regrets go. Most importantly, you will learn how to let go of your regrets with a five-step reflection exercise.

Prefer the audio? Listen here.

Why Regret Is Friggin’ Pointless

While it is normal to feel guilty, wish we had done something different, or want to make amends for something in the past, I have had clients who spend their entire life in regret.

This is as productive as bashing your skull against a stone wall. Regret does nothing except keep you anchored in the past. 

What happens when we anchor ourselves in the past? 

We miss our one-and-only amazing life in this present moment, which will never come again. 

You also miss opportunities to make choices and decisions you won’t regret right now. 

Regrets weigh us down. They are exhausting. They stunt our growth and keep us small. They take bandwidth. I don’t know about you, but I need all the bandwidth I can get! 

None of us wants to waste our precious life force energy making ourselves feel like crap about things we’ve done in the past…So let’s not.

Why Do We Hold Onto Regrets?

One reason we might hold onto regret is fear. As humans, we are fear-based. We often have good reasons for wanting to avoid mistakes – for example, to avoid rejection or embarrassment.

But ruminating on regrets is not a productive way to avoid future regrets. Keeping our “badness” close to our hearts only keeps our self-assessment low.

Sometimes, we hold onto regrets because we become defined by them. Maybe you are defined by the relationship you blew up because you weren’t ready for it, and now that person’s status as “the one who got away,” is written in stone (Potentially, defining you as a person who self-sabotages).

Additionally, nurturing specific regrets for an extended time is likely to draw similar experiences into your life. Where our attention goes, our energy flows. 

Think about how long we live. It is one thing if you are in your twenties and have some regrets. But collecting regrets from your twenties, thirties, forties, and fifties can lead to a whole life of regret. 

Occasionally having regrets is part of the human experience. Ruminating on regrets is different because it takes a ton of valuable bandwidth and is counterproductive. It will not change how you feel or what you experienced.

We might also hold onto regrets if we have an overly developed superego. Maybe you are a perfectionist or were not allowed to make mistakes as a child. Or maybe you are an empath and feel the way you’ve made others feel more deeply than those who aren’t empaths.

Instead of Regret, Focus on Self-Compassion

We all make mistakes. We are human, and we are all flawed. 

When you make a mistake, instead of letting your inner mean committee take charge, I encourage you to treat yourself the same way you would treat a close friend if they made a mistake. Self-compassion is a critical part of this process. 

Give yourself some grace. Have faith that you did the best you could with the level of consciousness, the skills, and the self-awareness you had at the time. 

I could spend the rest of my life regretting the mistakes I made and continue to make, but I do not. I have forgiven myself for my appalling behavior in my twenties before I got sober. I understand I did things when I was drunk I would not do when sober. 

There has to be self-acceptance and self-awareness. There are reasons why you did the things you did, even if they were misguided. 

None of us were trained on how to handle the difficulties in life, nor was it modeled for most of us. In my 25 years as a psychotherapist, not one of my clients has said, “My parents modeled problem-solving and expert communication skills perfectly.” 

Extend compassion to yourself. Be gentle with yourself when you make a mistake because you are human. 💕

How Can We Learn From Our Mistakes?

As I love to say, if you are willing to roll up your sleeves and get your hands dirty, every crap stew of a situation holds a gem of wisdom. These gems might help us avoid similar situations in the future or help us make amends, but you have to actively seek them out. 

I have learned many things about myself, my family, and my friends by revisiting even the most painful situations. 

I encourage you to view your regrets through the lens of learning. Think about what you might discover about yourself. Can you actively and compassionately forgive yourself? 

I’ve created a five-step reflection exercise you can practice to let go of your regrets. You can download it here. 

How I Journal Through Regrets

Even though I have worked through the regrets I’ve had in my life, occasionally, I still get flashes of regret about something I said or did.

When I do, I write about it. 

Flashes of regret tell me an experience is still charged in some way and that part of me has more to say about it. 

When this happens, I go to my journal and ask these questions: 

  • Why are you having this flash of regret now?
  • What happened? Did a precipitating event inspire the thoughts?
  • Is there anything you can do?
  • Did something happen recently to remind you of this regret?

Write freely about whatever comes to mind. Flashes of regret are like cuts that start hurting again because they become infected – something needs to come out before the cut can heal. As you journal, imagine yourself expressing what needs to come out so you can heal. 


We all have regrets. Whether you ruminate on them or not is personal, but virtually no healthy human has lived a life with zero regrets. We all make missteps. 

The human experience is the light and the dark, not just the light. Acknowledging the bad, the sad, and our mistakes is how we fully integrate as human beings. 

I invite you to do the reflection exercise found in the guide because I want you to have all the bandwidth in the world to create the life, relationship, career, and experiences you want. 

Let me know your thoughts in the comments below or over on Instagram (@terricole). I hope you have a wonderful week reflecting and letting go of regrets, and as always, take care of you. 

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  1. Hi,
    This is a great help for me. I think a lot about my past unhealthy relationships. I do try to forgive myself and I tell myself I want to be free from my past. I am not the same person. I know not to repeat it.

    I am clearing out the clutter and fear slowly.

  2. Hello, I've worked through Boundary Boss with a small group of wonderful women and it has shifted my thinking. I can feel my life opening. Thank you Terri for your straight talk and making sacred space for us to unfold, unfurl and shake off the old chains.

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