December 12, 2019

Regret – Is it your tormentor or teacher?

I’ve been thinking a lot about regret lately.

Some of you, I know, are struggling with regret related to your career.

I’m trying to learn from past regret to avoid some “deja-vu regret” in my own life.

Today I’m on a mission to help you with a process for dealing with regret that shifts it from being a tormentor to a teacher.

Because unfortunately there’s no expiration date on regret. It will live on forever inside of us unless we do something about it. It’s very sticky and tenacious. It could likely outlast Superglue in a competition.

Regret is something we all experience. It can even be a healthy emotion.

There’s the regret we feel when we eat a whole bag of potato chips. Or stay up too late binging on Netflix.

No biggie. This kind of regret we can sleep off and it barely moves the needle on the regret-o-meter.

Then there’s the regret that feels like it burns a hole in our soul. Maybe we lost a chance with the love of our life, or we spent 20 years in a profession we never chose. Ouch.

Depending on how we let regret affect us, it will either torment or teach us.

When regret is our tormentor, it plays a tape in our head that goes something like this:

Why did you do that? What’s the matter with you? Why didn’t you do x, y, z? You’re a loser. I’m so mad at you. Why did you do that?…”

(Regret can also be about not doing something, not taking action, letting too much time go by.)

The blame and judgment blind our vision. When we look back to the past, it is through a tiny peephole that shows us only a narrow, biased perspective. We might even see ourselves in prison stripes. Guilty.

The tape keeps playing and there’s no way to rewrite the script or feel anything else besides bad.  Unlike those old cassette tapes, this tape never wears out. It’s Gorilla tape.

Torment is feeling bad about something we can’t change.

If we let regret be our teacher, the pain of regret can be turned into pearls of wisdom that will help us move forward with the self-knowledge that has the power to change our future for the better.

I’ve never had a pearl necklace, but it sounds a lot better to me than the choke collar of regret.

For regret to be our teacher, we need to put on the detective’s cap and look back at whatever we’re regretting with curiosity and compassion rather than judgment and blame.

What follows is a process you can use to address regret and let it actually help you.

Here we go!

Put yourself in your old shoes

When you look back, whether it’s a month, a year, or a decade ago, realize you aren’t the same person now. You are not in that specific setting, you are not feeling the same feelings, and you have the wisdom of hindsight. You are a biased judge as you are privy to information and knowledge that you didn’t have then.

We can never go back in time AND recreate an experience and how it affected us internally.

The truth is, if you could have acted differently, you would have. Try to first accept that you had your reasons for doing what you did at that time. Put yourself back in those shoes and try to remember, with compassion, what it was like for you. 

Make a case for yourself – come to your defense

In any trial, there are always two sides presented. When you revisit your own experience, instead of blaming yourself, pretend you are your own defense and make a case for yourself. You had your reasons for doing what you did. Consider what factors influenced you and people who might have directly or indirectly impacted your decision –  not to blame anyone, but to understand the bigger picture.

Even if you did something that was a big mistake, or wrong, or not what you would ever do again, you deserve to take your side and advocate for yourself. Suspend the judgment and get curious about what was going on.

Find a way to make your peace with regret

As long as we’re still holding onto regret, we are anchored in the past. There is a part of us that cannot move forward because we have not resolved this issue. We cannot change what happened but we can release regret’s negative grip by forgiving ourselves.

A sense of peace can come from acknowledging that you are on a journey. As a human being trying to figure life out, the journey is going to have bumps and detours as well as joys and successes. Life is messy and imperfect. But it is still yours. You get to decide if you allow mistakes and missteps, or if perfection is the only option.

Ask yourself if this is “deja-vu regret?

Sometimes we do something we regret and it’s a one and done. Other times, there’s this unsettling feeling of “haven’t I been here before?” This is deja-vu regret. You start to notice a pattern of having regrets over something familiar. For example, it could be a pattern of saying yes when you want to say no, not being clear on what you want or ignoring longer-term consequences. Or it might be playing it safe and missing out on opportunities or ending up in dead-end relationships, or the wrong job.

Try to identify what is underneath a pattern and cycle of regret.

Evaluate what you wished you’d done instead

What do you wish you’d done differently? How would your life be different now? Is there anything you want or need to do now to address how this regret is affecting your current situation? You can get a lot of clues about what to focus on going forward by getting clear on what is missing.

What is regret trying to teach you?

If you give regret the freedom to 100% be your teacher and not your tormentor, what is it here to teach you?  If you listen to what regret is telling you about what matters to you and take corrective action, you will not only avoid deja-vu regret, but you will be going forward with a stronger sense of who you are and how you want to live your life.

I created a worksheet entitled, “Regret. What is it here to teach you?”

If’ you’d like to address any regret you are feeling, you can click here to download the worksheet.

I’d love to hear from you about how you’ve dealt with regret and what you’ve learned from your own experiences. It is likely others may be going through something similar.

Til next time,



  1. Great article as always Heather!!

    I think this is something that everyone (in every walk of life) goes through at some point if not in many. Learning to cope and deal with it is a necessary step in one’s own unique evolution.

    • You are so right Ramin! And if we are not having any regrets, we may not be asking enough of ourselves or our life. Maybe we are, but I have to agree with you that regrets are part and parcel of life. And they can be great fuel to propel us forward in an empowered and conscious way. Thank you very much for reading and your kind support!

  2. WENDY CRAVEN says:

    This is a very valid emotion that I have experienced in my life with my career choices. Thank you for writing about this. I’ve learned to come to peace with my career choices, but it took me much anguish and tears to finally let go.

    • Hi Wendy, you are most welcome. I like how you referred to regret as a valid emotion. It definitely is! I’m so glad that you have found your peace with your career choice- even if it has been a tough path. More power to you for doing the hard inner work to find peace and acceptance. Thank you for taking the time to read and comment.

Post Your Comment