Regrets: Toss them Away?

Marlena Fiol
3 min readJul 23, 2021


Source: Priscilla du Preez on Unsplash

You’ve heard the advice: Let go of regrets; strive to live regret-free lives.

My guest on this week’s YouTube show, Jennifer O’Brien, author of The Hospice Doctor’s Widow: A Journal has a lot to say about this. Jennifer’s husband Bob was diagnosed with stage IV metastatic cancer. She traces their journey together during the 22 months following his diagnosis until he died, as well as her early years of widowhood. She’s all about being fully present during even the toughest moments, honoring grief, and going forward after devastating loss.

Jennifer writes, “Precious time is when you say what you need to say and don’t say what you’ll later regret” (emphasis added). “We only have one chance to get this right…There are no do-overs in end of life.”

Regrets Are Toxic

Lingering regrets, the kind we hang onto for years, re-enacting the scenes over and over in our minds, can lead to all-consuming guilt and pain, and ultimately to depression and hopelessness. They can result in chronic stress, negatively affecting hormonal and immune system functioning.

Regrets often take the form of “should-haves” or “could-haves.” I know. I’ve experienced my share.

- I could have kept my mouth shut.

- I should have told her how much she meant to me.

- I could have just left.

On and on. Around and around. Like a bad ear worm.

And yet…

Despite the known negative consequences of regrets in our lives, they seem to be universal cognitive or emotional states we don’t easily let go of. To learn more about why this is so, I did a bit of research. Here’s what I found.

Why Do We Hold onto Regrets?

It turns out there are understandable reasons we may hold onto regrets despite their many known negative effects.

Regrets May Foster Comfortable Avoidance

Catriona Wrottesley, a couple’s psychotherapist at Tavistock Relationships suggests that sometimes regrets can feel like a safe haven. We keep them around and wallow in them to prevent some part of us from moving on into what may look like dangerous territory. Hiding behind our regrets can protect us from the perceived pain and risks of fully throwing ourselves into life.

Regrets May Protect Us from Even Deeper Pain

David Morgan, of the Institute of Psychoanalysis explains that, even though regrets are painful, they may protect us from the deeper pain of remorse. While regrets are an admission of our mistakes, leading us to feel a measure of sorrow for ourselves, we don’t feel deep sadness or remorse for those who were hurt by our behaviors. Staying stuck in our regrets prevents the compassionate ache of remorse from pulling us outside of ourselves and toward authentic mutual healing.

My Take?

Rather than tossing away regrets, might it be wiser to open ourselves to the pain of our regrets, to understand them, and to learn from them? Learn to accept ourselves with all the warts of regretful decisions and behaviors, to recognize that we made those decisions based on the values and the wisdom (or lack thereof) we had at the time, and open up to remorse and greater self-knowledge?

Instead of “tossing away” regrets, my deep wish for each of us is that we might embrace the freedom and courage to say, “I got that one wrong,” express remorse, learn from our failures, and only then move on.

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