HEALTHY REGRET VS. UNHEALTHY REGRET

Dr. Debi Gilmore LMFT

What exactly is regret? Regret is an emotional experience that arises when you believe something in the past could have been better if you had acted differently. Regret involves painful emotions such as sorrow or disappointment and is usually the result of thinking about a past choice, action, or missed opportunity. When we reflect on what could have been, (basically “Monday Morning Quarterback Syndrome) we might be overcome with shame or misapplied guilt because we believe our life might be better if we had done something differently, better, or more perfectly.  

Key Aspects of Regret

Regret can be categorized into three key areas.

1.     Counterfeit Thinking: This type of regret involves imagining, “If only I had done ______, things would be different.” This thought fuels comparison, evokes painful feelings, and is a major assumption without fact. Basically, we have written the story we believe might have been fulfilled and reinforce the feelings of failure.

2.     Values and Morals There is a moral dimension to the experience of regret. Regret may be disappointment about loss of money, loss of a job, or a painful relationship rupture. However, regret may also be based on something we did or said that hurt someone we care about.

3.     Double Trouble The third category is the double nature of regret in that sometimes regret can be helpful and healthy—a motivator for change. However, regret can be deeply harmful if we ruminate, punish ourselves, or feel paralyzed believing we are a doomed failure as a human with no ability to repair or request a redo.

Basically, regret is our mind’s way of looking backward, comparing reality with what might have been — and the heart’s way of reminding us of what truly matters. Regret can be both healthy and unhealthy, depending on how it’s experienced and processed.

Healthy Regret

When the experience of regret is utilized as a motivator for change, and in a positive attitude of growth, we allow the thoughts and emotions to serve as a learning signal. Healthy regret inspires swift action and is an opportunity to do damage control before hurt expands into broken trust or reduced credibility. We might ask, “What can I do differently next time?” In fact, we might first want to ask, “How can I offer my deep personal regret to the person I have hurt or offended?” Then we can proceed to ponder on growth, change, and responsibility to do better.

One example might be if during a very difficult and taxing day, we snapped at our partner in a moment of anger. Approaching them with “I can see I hurt you. I regret speaking that way to you, and I want to do better next time.” Healthy regret motivates us to acknowledge the mistake, to accept responsibility, and to allow the experience to influence our efforts toward self-improvement.

Unhealthy Regret

Unhealthy regret happens when we fixate on the past without resolution or determination to correct our mistake. We might tell ourselves, “I will never forgive myself. If only I had done things differently. I am a fool and a failure.” This thought process fuels shame, reinforces rumination, and results in utter paralysis. Our story becomes, “I have ruined my life by choosing that career, and there is nothing I can do to make up for it.” Unhealthy regret often involves absolutes and rigid assumptions of failure. It generates lower self-worth, and an inability to challenge ourselves to do hard things. Unhealthy regret keeps a person stuck, drains emotional energy, and often feeds self-criticism rather than growth.

The Difference Between Healthy and Unhealthy Regret

Healthy regret looks forward resulting in personal growth and learning, with the ultimate blessing of change and resilience. Unhealthy regret looks backward including rumination, shame, and self-punishment.

Ways To Turn Unhealthy Regret into Healthy Regret

When we refuse to buy into the idea that we have failed and are doomed, the following are some practical steps to fuel growth and replace shame with hope and new direction.

Identify the Roots

It is helpful to pause long enough to ask: “Am I regretting because I want to learn, or am I punishing myself?” Awareness helps shift your mindset from self-condemnation to self-compassion.

What Have I Learned?

Instead of replaying “I wish I hadn’t done that,” ask: “What does this regret teach me about what I value?” or, “What can I do differently if this situation arises again?” Once you have asked yourself those questions, write down one or two concrete lessons to carry forward.

Practice Self-Compassion

Talk to yourself as you would to a close friend. You might say something like, “I made a mistake, but mistakes don’t define me. I can learn and do better.” This gentle offering of self-compassion shifts the emotional tone from shame into growth and self-acceptance.

Take Reparative Action

It is essential that if the regret involves having hurt a loved one or close friend, apologize, make amends, or correct the course where you can. Apologies that backfire are, “I’m sorry!” Instead, acknowledge the pain you have caused, validate their disappointment, and let them know you are committed to being more aware of respect and kindness. Even small steps such as a note, a change in behavior can help transform regret into healing.

Limit Rumination

We are all prone to fixate or ruminate on the mistake we made. However, awareness is the first step toward interrupting the process of rumination. Set a personal boundary by giving yourself 10–15 minutes to reflect, then shift to action or self-care. Each time regret resurfaces, remind yourself: “I’ve already learned from this, now I’m moving forward.”

Reframe the Story

Instead of telling yourself, “I have ruined everything,” try telling yourself, “That decision didn’t turn out how I hoped, but it gave me clarity for the future.” As you ponder on what you wish you had done differently, commit to yourself to improve, act more swiftly, or do the hard thing you wish you had done.  Reframing clarifies healthy meaning and purpose rather than reinforcing paralysis and an inability to find ways to become better.

Bottom Line

Unhealthy regret is an evaluation of your worth. Basically, we are telling ourselves, “This is just who I am. I am incapable of change.”

Healthy regret focuses on behavior, and conveys the message, “This is what I did, and here’s how I’ll grow from it.”