Living With Regret

 

Living with Regret: How to Stop Drowning in the Past and Start Moving Forward

What Is Regret?

Regret is the quiet voice in the night that whispers “if only…”

It is a form of emotional pain that focuses on past actions (or inactions) that we believe led to negative consequences, whether real or imagined. Regret often involves:

• Missed opportunities

• Harm done to others or ourselves

• Words left unsaid—or words said too quickly

• Relationships lost

• Roads not taken

• Choices that now seem irreversible

Living with regret is like walking through life with a backward-facing mirror strapped to your face. Everything is filtered through what went wrong, never what could go right.

But regret, though painful, is not inherently destructive. It is part of being human. It is a sign of conscience, of capacity for empathy, and of moral growth. The key is how we respond to regret. How we carry it, learn from it, and eventually transform it.

Why Regret Hurts So Much

Regret blends memory with emotion, combining:

• Guilt (about what we did)

• Shame (about who we were)

• Grief (for what was lost)

• Helplessness (about the fact that we can’t change it)

It can become cyclical: replaying the same memory, magnifying its significance, or imagining different outcomes. This mental loop, known as rumination, keeps us trapped in the past and can contribute to anxiety, depression, and low self-esteem.

Common Types of Regret

1. Action Regret

• “I shouldn’t have said that.”

• “I cheated/lied/lost control.”

• “I ruined the relationship.”

2. Inaction Regret

• “I should’ve taken that opportunity.”

• “I never told them how I felt.”

• “I waited too long.”

3. Existential Regret

• “I wasted my youth.”

• “My whole life could have been different.”

• “I chose the wrong path.”

What Can Be Done About Regret?

Regret cannot be deleted, but it can be integrated. It can become a teacher rather than a tormentor. Here’s how:

1. Acknowledge the Regret Without Judgment

Let yourself say:

“Yes. I wish I had done that differently.”

“That moment hurt me, and it hurt others.”

“I can’t change the past, but I can change how I relate to it.”

You are not alone. Regret is universal. Suppressing it doesn’t remove its power—it strengthens it. Begin by allowing the feeling to exist.

2. Distinguish Between Guilt and Shame

• Guilt says: “I did something wrong.”

• Shame says: “There’s something wrong with me.”

Regret becomes destructive when it becomes fused with shame. Guilt can motivate change. Shame paralyzes it. Learn to separate what you did from who you are.

3. Make Meaning of the Regret

Ask yourself:

• What did I learn from that moment?

• Who have I become because of it?

• How has it made me more aware, more empathetic, more responsible?

• How can I use that insight now?

Transformation doesn’t erase regret. It reframes it; as a scar, not a wound. As something that hurt, but shaped.

4. Make Amends Where Possible

If your regret involves harm to others, explore the possibility of making amends.

• Apologize sincerely, without expecting forgiveness.

• Take responsibility for your part.

• Don’t explain away the pain you caused—honor it.

• Commit to different behavior going forward.

Not every relationship can be repaired—but every mistake can inform how we treat people from now on.

5. Stop Rewriting the Past

We fantasize that if we’d chosen differently, everything would have been perfect. But that’s a myth. There is no parallel universe where you avoided all pain.

That version of the past doesn’t exist.

Instead, ask:

“What do I want to do now, with the time and life I still have?”

The past can guide you. It cannot imprison you—unless you let it.

6. Practice Self-Forgiveness

Self-forgiveness is not about excusing what happened. It’s about acknowledging your limitations and humanity.

Try saying:

• “I was doing the best I could with the awareness I had.”

• “I didn’t know then what I know now.”

• “I am allowed to grow from this—not just suffer for it.”

Forgiving yourself doesn’t erase responsibility. It reclaims your capacity to live.

7. Turn Regret Into Responsibility

Use your regret to fuel action:

• Be the person now that you wish you had been then.

• Speak up for someone else.

• Support someone facing the same choice you once did.

• Start the project. Reach out. Try again.

Redemption doesn’t lie in erasing the past—it lies in building something new because of it.

Final Thoughts: The Gift Hidden Inside Regret

Regret shows that you care. That you are capable of reflection. That you have a moral compass. It can be agonising but it can also be a path to maturity, wisdom, and integrity.

Regret is not your enemy. It is the ghost of an unlived lesson, asking to be seen, understood, and transformed.

You are not your past. You are the person who survived it, who regrets it, and who now gets to decide what to do next.

Here is an index of associated and relevant source books on the theme of living with regret, including psychological insights, philosophical perspectives, practical tools for self-forgiveness, and memoirs exploring reflection, choice, and emotional growth.

Psychology, Regret, and Emotional Healing

The Power of Regret: How Looking Backward Moves Us Forward – Daniel H. Pink

A groundbreaking exploration of the science of regret, reframing it as a tool for growth and insight.

Emotional Agility: Get Unstuck, Embrace Change, and Thrive – Susan David

Practical psychology for navigating difficult emotions like regret with flexibility and self-compassion.

Radical Acceptance: Embracing Your Life With the Heart of a Buddha – Tara Brach

Combines mindfulness and self-compassion practices to release shame, regret, and self-judgment.

The Gifts of Imperfection – Brené Brown

Guides readers to embrace vulnerability and let go of shame and regret as barriers to wholehearted living.

Self-Compassion: The Proven Power of Being Kind to Yourself – Kristin Neff

A key resource for turning regret into healing through self-kindness rather than self-criticism.

Letting Go: The Pathway of Surrender – David R. Hawkins

Describes how to release the emotional hold of past events and regrets to find peace in the present.

Philosophical and Spiritual Reflections on Regret

The Art of Happiness – His Holiness the Dalai Lama & Howard C. Cutler

A spiritual and psychological conversation on how to let go of emotional pain and cultivate inner peace.

Falling Upward: A Spirituality for the Two Halves of Life – Richard Rohr

Explores how failures and regrets can be spiritual teachers, leading to a deeper, richer second life stage.

The Untethered Soul: The Journey Beyond Yourself – Michael A. Singer

A guide to releasing internal blocks, including past regrets, to live more freely and consciously.

The Wisdom of Insecurity – Alan Watts

A philosophical perspective on regret and the impossibility of control over the past or future.

Memoir and Personal Experience of Regret and Redemption

When Breath Becomes Air – Paul Kalanithi

A neurosurgeon’s moving reflection on mortality, purpose, and what truly matters before time runs out.

Man’s Search for Meaning – Viktor E. Frankl

Classic memoir exploring meaning-making in the face of suffering, loss, and moral dilemmas.

This Is Water – David Foster Wallace

A short but profound reflection on consciousness, compassion, and the hidden weight of daily regrets.

Tiny Beautiful Things – Cheryl Strayed

Advice columns turned essays that address regret, forgiveness, and human resilience with tenderness.

Tuesdays with Morrie – Mitch Albom

A series of life lessons from a dying professor on regret, love, and what truly matters.

Practical Guides for Forgiveness and Rebuilding

Forgive for Good: A Proven Prescription for Health and Happiness – Dr. Fred Luskin

Applies forgiveness science to unresolved regret, hurt, and disappointment.

How to Be an Adult in Relationships – David Richo

Focuses on healing past emotional wounds that fuel regret in present relationships.

The Grief Recovery Handbook – John W. James & Russell Friedman

While aimed at grief, this guide also addresses unresolved regrets and emotional unfinished business.

What Happened to You? – Dr. Bruce Perry & Oprah Winfrey

Explores how early trauma and choices shape our responses—including regret—and how to shift them.

The Five Invitations: Discovering What Death Can Teach Us About Living Fully – Frank Ostaseski

Invites readers to reflect on life’s impermanence and let go of the regrets that keep them from living fully.