The Deeper Thinking Podcast by The Deeper Thinking Podcast

March 17, 2025 🎙️ The Psychology of Regret: Why We Dwell on Past Mistakes

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.