🎙️ The Psychology of Regret: Why We Dwell on Past Mistakes

The Deeper Thinking Podcast

🎙️ The Psychology of Regret

Why We Dwell on Past Mistakes and How It Shapes Us

Regret is one of the most powerful and enduring human emotions. It lingers in memory, reshapes identity, and influences future decisions. But what exactly is regret? Is it a psychological affliction to be overcome, or can it serve a deeper purpose?

This episode challenges conventional wisdom about regret, exploring it not as a simple emotion but as a cognitive, moral, and existential force. From counterfactual thinking and the illusion of the perfect choice to philosophical debates on whether regret is necessary for wisdom, we examine why regret holds such a grip over human consciousness.

The Science and Philosophy of Regret

This episode traces regret across three interwoven dimensions:

1. The Cognitive Science of Regret – Why We Fixate on "What If"

Cognitive psychologists like Daniel Kahneman and Neal Roese reveal that regret is not random—it follows specific mental patterns. The brain prioritizes near-misses over distant failures, making regret sharper when an alternative outcome seemed just within reach. But what if our memory of lost opportunities is systematically distorted?

2. The Ethics of Regret – Is It a Moral Reckoning or a Futile Obsession?

Philosophers from Jean-Paul Sartre to Bernard Williams have explored the moral implications of regret. Is regret simply an acknowledgment of personal responsibility, or does it burden individuals with unnecessary guilt? Does it push people toward moral growth, or does it paralyze action?

3. Regret and Time – The Psychological Trap of the Past

Why do some regrets fade while others feel permanently present? Henri Bergson’s concept of duration suggests that regret collapses time, making past mistakes feel immediate rather than distant. Neuroscientists have found that emotionally charged regrets are stored with more vividness, reinforcing the illusion that they are still relevant.

The Unavoidable Question: Can We Let Go of Regret?

Different traditions offer competing answers. Stoicism and Buddhism argue that regret is an irrational fixation on the unchangeable past, while Nietzsche’s idea of eternal recurrence suggests that regret should be transformed into self-affirmation. Modern psychology, through concepts like self-compassion and cognitive reframing, provides strategies to lessen its impact.

But is letting go of regret the right goal? What if regret is not just about what was lost, but about what was learned?

Why Listen?

🔹 What does neuroscience reveal about why we hold onto regret?
🔹 Do we overestimate how much better things could have been?
🔹 Is regret a necessary part of moral growth, or can we live without it?
🔹 How do literature and film—from Hamlet to Eternal Sunshine of the Spotless Mind—mythologize regret?

Further Reading

📖 Thinking, Fast and Slow – Daniel Kahneman
🔹 Explores decision-making biases, including how regret distorts our perception of past choices.
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📖 Moral Luck – Bernard Williams
🔹 Explores how chance influences morality and the ethical significance of regret.
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📖 The Remains of the Day – Kazuo Ishiguro
🔹 A literary exploration of lifelong regret and missed opportunities.
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📖 The Gay Science – Friedrich Nietzsche
🔹 How to affirm life despite regret.
🔗 Amazon affiliate link

📖 Atonement – Ian McEwan
🔹 Examines the desire to undo past mistakes and the impossibility of erasing regret.
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What if regret is not a flaw, but a hidden form of wisdom? What if letting go of regret means losing part of who we are?

1. Philosophy of Regret: Existentialism, Ethics, and Moral Responsibility

📖 Moral Luck: Philosophical Papers 1973–1980 – Bernard Williams
🔹 Explores how chance influences morality and the ethical significance of regret.
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📖 Being and Nothingness – Jean-Paul Sartre
🔹 A cornerstone of existentialist thought, discussing freedom, responsibility, and regret.
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📖 Existentialism Is a Humanism – Jean-Paul Sartre
🔹 A concise introduction to Sartre’s belief in personal responsibility and how regret reflects bad faith.
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📖 Twilight of the Idols – Friedrich Nietzsche
🔹 A critique of moral values, arguing against regret and in favor of embracing life as it is.
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📖 Letters from a Stoic – Seneca
🔹 A Stoic perspective on why regret is irrational and how to cultivate inner peace.
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📖 Eichmann in Jerusalem: A Report on the Banality of Evil – Hannah Arendt
🔹 Analyzes moral judgment and collective regret, exploring responsibility in history.
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2. The Science of Regret: Cognitive Psychology, Neuroscience, and Decision-Making

📖 Thinking, Fast and Slow – Daniel Kahneman
🔹 Explores decision-making biases, including how regret distorts our perception of past choices.
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📖 The Paradox of Choice: Why More Is Less – Barry Schwartz
🔹 Examines how too many choices increase regret and decision paralysis.
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📖 The Seven Sins of Memory: How the Mind Forgets and Remembers – Daniel L. Schacter
🔹 Explores memory biases, including why regretful events are recalled with greater intensity.
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📖 Counterfactual Thinking – Neal Roese
🔹 A comprehensive study on why the mind constructs "what if" scenarios and how they fuel regret.
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📖 Learned Optimism: How to Change Your Mind and Your Life – Martin Seligman
🔹 Explores how regret can be reframed through cognitive restructuring.
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3. Regret, Time, and Memory: Temporal Distortion and Emotional Recall

📖 Creative Evolution – Henri Bergson
🔹 Explains how human perception of time affects the experience of regret.
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📖 The Feeling of What Happens – Antonio Damasio
🔹 A neuroscientific exploration of how emotions like regret shape consciousness.
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📖 In Search of Lost Time – Marcel Proust
🔹 A literary meditation on how regret and memory intertwine.
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4. The Cultural and Literary Representation of Regret

📖 Crime and Punishment – Fyodor Dostoevsky
🔹 A psychological study of guilt, remorse, and redemption.
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📖 The Remains of the Day – Kazuo Ishiguro
🔹 A literary exploration of lifelong regret and missed opportunities.
🔗 Amazon affiliate link

📖 Atonement – Ian McEwan
🔹 Examines the desire to undo past mistakes and the impossibility of erasing regret.
🔗 Amazon affiliate link

📖 Hamlet – William Shakespeare
🔹 A tragedy centered on hesitation, action, and the fear of future regret.
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📖 Eternal Sunshine of the Spotless Mind – Charlie Kaufman (Screenplay)
🔹 A film exploring whether erasing regret is truly desirable.
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📖 In the Mood for Love – Wong Kar-wai (Film)
🔹 A cinematic study of unspoken regret and lost love.
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5. Overcoming Regret: Psychological and Philosophical Approaches to Letting Go

📖 Man’s Search for Meaning – Viktor Frankl
🔹 Explores how suffering, including regret, can be transformed into meaning.
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📖 Self-Compassion: The Proven Power of Being Kind to Yourself – Kristin Neff
🔹 A psychological approach to overcoming regret through self-forgiveness.
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📖 Wherever You Go, There You Are – Jon Kabat-Zinn
🔹 A mindfulness-based approach to regret and emotional resilience.
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📖 Shame and Guilt – June Tangney & Ronda Dearing
🔹 Distinguishes regret from guilt and explains their psychological impact.
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