Dying Every Day

Dying Every Day

šŸ“® The Tyranny of Self-Improvement

Letters from a Seeker (Vol. 58)

J.W. Bertolotti's avatar
J.W. Bertolotti
Apr 25, 2026
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The Rise by Winslow Homer (1900)

Never stop learning how to live!

šŸ“® Letters from a Seeker

ā€œLetters from a Seekerā€ is a weekly series of short contemplations that explore the mystery, meaning, and art of living. The word ā€˜Seeker’ in the title is inspired by the Delphic maxim: ā€œBe a seeker of wisdom.ā€ *** This series is exclusive to members.



Dear Fellow Traveler,

Have you observed a change in the language?

Not about actions themselves, but how people now describe them.

Nobody simply reads anymore; they ā€œinvest in their development.ā€ Instead of just cooking, they ā€œoptimize their nutrition.ā€ Rather than going for a walk, they ā€œget their steps in.ā€

At some point, without fully realizing it, we transformed everyday experiences into a set of performance metrics. The most surprising aspect isn’t the language used but how seamlessly it has integrated into daily life. The original activities—the meal, the walk, and the book—now feel almost awkward to discuss without linking them to some form of productivity.

As though living well and improving constantly had become the same project.

They haven’t. And the confusion between them, I’ve come to think, is one of the more elegant traps of modern life—elegant because it is so difficult to object to.

Who argues against growth?

Who defends stagnation?

The trap works precisely because its premise is unimpeachable. Of course, you should be better tomorrow than you are today. Of course, the gap between who you are and who you could be deserves your attention.

What the premise quietly assumes is that the gap is the most important thing about you.

Michel de Montaigne (1533–1592), a French magistrate of modest ambition and immodest curiosity, thought otherwise. At thirty-eight, he retired to his tower, lined it with a thousand books, and spent the rest of his life writing about himself. Not to improve himself. Not to construct a philosophy.

Simply to see what was actually there—in his thinking, appetites, fears, and contradictions—when he looked honestly and without an agenda.

What he found was not a coherent self waiting to be refined. He found a creature of moods and inconsistencies, surprising appetites, opinions that shifted between morning and afternoon. A man afraid of horses. Preoccupied with his kidney stones. Capable of holding two incompatible ideas with equal conviction depending on the day.

He was, in his own cheerful assessment, undulating and diverse. He was not troubled by this. He was fascinated.

That reaction—showing fascination instead of alarm—distinguishes Montaigne from almost all self-help traditions before and after him. The modern self-improvement approach tends to start with the belief that the self is a problem to fix, viewing contradictions as mistakes and inconsistencies as flaws needing correction. In contrast, Montaigne’s approach was completely different. He saw his contradictions not as problems to solve, but as raw data—integral parts of human life that are often more bizarre and fascinating than any polished, optimized version we might aspire to.

He called his essays ā€œattempts.ā€ Not conclusions. Not programs. Attempts.

The essay, as he invented it, was a form of thinking that didn’t know where it was going. It followed curiosity rather than argument. It changed its mind between chapters and didn’t apologize. It was a literary form that embodied his philosophy: that honest attention to who you actually are is more valuable—and considerably more difficult—than constructing who you think you should be.

This is where he becomes most useful, because much of what the culture calls self-improvement is not really curiosity about the self at all.

It involves managing anxiety about the self. The morning routine, reading list, and regular review of personal flaws are valuable, but there's a version of these that, for anyone familiar with the project, is less about genuine growth and more about staying busy to avoid facing one's true self. The idea of perfecting or ā€œcompletionā€ never truly materializes; instead, the focus shifts elsewhere.

The project can never truly reach a state of being finished, because that would mean it ceases to exist as a project.


A Game of Croquet by Winslow Homer (1866)

Montaigne described the desire to completely overcome discomfort—to transform into something beyond a flawed, conflicted human through enough self-improvement—as a pursuit of angelic mastery. However, he viewed this not as admirable but rather somewhat humorous. Our nature is rooted in appetite, limitations, and flesh.

Rather than being barriers to a good life, these are its very foundation.

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