The Problem with Deathbed Wisdom

Sources of wisdom, like fashion, diet and so many other things these days chase trends.

I noticed that today’s social media obsession is with deathbed regrets. We’ve all heard the famous phrase repeated: "Nobody on their deathbed wishes they'd spent more time at the office." Platforms like TikTok and Twitter treat the dying as prophets.

After all, who knows life better than those losing it?

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When did this start? I’d say it was about ten years ago the deathbed wisdom genre transformed from occasional poignant anecdotes into a full-blown philosophy. The origin was with Australian hospice nurse Bronnie Ware who published her observations after a decade of recording her patients' final regrets. Her list quickly went viral, according to her, the five most common regrets shared by people nearing death were:

1. I wish I’d had the courage to live a life true to myself, not the life others expected of me.

2. I wish I didn’t work so hard.

3. I wish I’d had the courage to express my feelings.

4. I wish I had stayed in touch with my friends.

5. I wish that I had let myself be happier.

These sentiments appear profound on first reading, who would argue against authenticity or happiness?

However, this list suddenly became the blueprint for "authentic living," amplified across social media and self-help industries as the definitive guide to a well-lived life. The message is straightforward: just reverse-engineer your life from the regrets of the dying, and you'll avoid their fate and live the “good life.”

The Lindy Effect and the Deathbed Wisdom

This modern fixation on deathbed regrets does not seem to have a historical precedent. Aristotle never urged students to “ask the dying for answers.” Plato’s dialogues don’t climax with Socrates gasping, “Actually, forget everything I said, here’s my real philosophy!”

Classical thinkers didn’t ignore deathbed moments; they just refused to crown them as wisdom. Although deathbed scenes exist throughout classical literature, they usually reinforce life's philosophy or confront mortality itself, rather than extracting lessons specifically from regret.

Consider Seneca's quote in Letter 78:"They cry out repeatedly that they have been fools because they have not really lived, and, if only they escape from their illnesses, how differently they will live. But if the same people happen to be set free from danger, they relapse into their former way of life."

Seneca is emphasizing that people who believe they have deep insights on the brink of death frequently discard those insights as soon as the crisis passes. For Seneca, these aren't lasting revelations but merely fleeting emotional reactions driven by fear or regret. He argues that the path to genuine wisdom and meaningful living lies in constant reflection throughout life, not in emotional declarations made at the end.

The philosopher Epictetus put it more bluntly: “When you see a man trembling at death… it is not death he fears, but the realization he has never lived. His final gasps are not wisdom, they are indictments.”

Here, Epictetus is dismissing the notion that dying individuals possess special insight. Instead, he frames their regrets as an admission of failure.

Classical thinkers remind us wisdom isn’t something you hastily grasp at the end, but something cultivated steadily over the span of an entire life. Perhaps wisdom shouldn't be chased at deathbeds, but nurtured well before.

Four Reasons DeathBed Wisdom Fails

Despite its recent popularity, deathbed wisdom contains these fundamental flaws.

1) The Deathbed Perspective is an Extremely Unusual State 

Facing imminent death creates a psychological state unlike any other in human experience. It's not merely unusual, it's existentially singular. It’s incredibly extreme. They are hyper-focused on the past, unmoored from the future, and often detached from the present. While most of our lives require balancing present satisfaction against future consequences, the dying have no such calculus. This isn’t how we navigate most of our lives, especially in youth and middle age, where future planning is essential.

This explains why lifelong atheists suddenly embrace religion, or feuds spanning decades dissolve into abrupt forgiveness. Such acts aren’t wisdom, they’re the bargaining of a mind severed from life’s rhythms.

The legal system recognizes this psychological discontinuity, which is why deathbed decisions face heightened scrutiny in courts worldwide. There are countless examples of this happening. Remember J. Howard Marshall II, the oil tycoon who married Anna Nicole Smith at 89. His deathbed decision to include her in his will sparked a Supreme Court battle. The courts sees through this, why don’t we?

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Or how Doris Duke the tobacco heiress, dramatically altered her will shortly before her death in 1993, leaving control of her $1.2 billion estate to her butler, Bernard Lafferty.

Even religious traditions, while accepting deathbed conversions as spiritually valid, implicitly acknowledge the exceptional nature of the dying mind. These conversions aren't treated as reasoned theological conclusions but as special cases, moments of grace or fear that bypass normal processes of spiritual development. They represent a break from, not a culmination of, the person's lifelong beliefs.

When we elevate deathbed wisdom, we're privileging insights from a psychological state that bears almost no resemblance to the conditions under which we must actually live our lives.

2) Life is About Tradeoffs

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