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🧠 Where You DON'T Want to Be Antifragile

September 9, 2026
🧠 Where You DON'T Want to Be Antifragile
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Welcome to Long-Term Mindset, the Wednesday newsletter that helps you invest better.

Today's Issue Read Time: <2 minutes

  • Lesson: The limits to an antifragile life
  • Timeless Content: Why the stock market has to crash.
  • Stock Dive: A full breakdown
  • Resource: AI's Bar Mitzvah Moment?

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Friends,

Brad Stulberg is the author of The Way of Excellence and Peak Performance, and writes on performance and well-being for the New York Times. But his recent post Nonchalance is a cop out. Caring is cool, might be his best [short] work yet.

The key nugget:

"Caring deeply is the cost of admission to a big and textured life."

Stulberg believes that too often, we think that caring is a sign of weakness, that it leaves us open to be disappointed, and that we endure more pain than necessary because of it.

His retort to this tendency: "the things you care about are the things that break your heart [and] the things that fill your life with meaning and joy."

You don't get one without the other -- and you never will.

Antifragility

If there's one word that appears in this newsletter a lot -- a word that you probably don't hear very much in your everyday life -- it's "Antifragility." The term was coined by Nassim Nicholas Taleb and explored in his best-seller: Antifragile: Things that Gain from Disorder.

The concept is simple. Everything in life breaks down into one of three categories:

  • The fragile: Things that get weaker or break down under pressure. Think: a delicate vase.
  • The robust: Things that are unaffected by most forms of pressure. Think: an iron bar.
  • The antifragile: Things that get stronger under (certain types of) pressure.

In general, this is a great mental model for thinking about the world. Instead of avoiding stressful situations, you should seek out scenarios where you're exposed to non-fatal acute stress and then get lots of rest to grow back stronger.

This is the mental model I (Stoffel, here) have used when selecting companies for my own portfolio. While it isn't perfect, it has given me the confidence to select stocks and stick with them for the long haul -- far outperforming the S&P 500.

There are limits to everything

So what do these two things -- Stulberg's praise for caring and Taleb's idea of antifragility -- intersect?

It has become commonplace for those who want to be "Antifragile" to signal to the world that they detest any form of being fragile.

But let's be honest: is there anything more fragile than deeply caring about something? Ask any parent what it's like to send their kid out into the world, and they'll tell you it can be heart-wrenching. They also wouldn't trade it for anything. Why? Because the very act of caring offers purpose and meaning.

That's where we need to distinguish between fragility and strength. Personally, I think the most sensible way to approach life is to have one or two things you are willing to be totally fragile for. For me, one of those things is my family. If I lost them tomorrow, I would be a total wreck -- and my life is better for caring so much.

But for everything that might fall outside of this designation, it's fine to eschew fragility. Because my family is at the center of what matters to me, the things I build around it -- my career, my network, my portfolio -- should be antifragile.

I'm pretty sure that was always understood inside of Taleb's writing. And I'm pretty sure that once you decide what you're willing to be fragile for, the best long-term investment is that thing, and building antifragility around it.

Wishing you investing success,

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Brian Feroldi, Brian Stoffel, & Brian Withers

Long-Term Mindset

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One piece of timeless content

Recessions and stock market pullbacks aren't fun, but they are a natural part of the economic cycle. Ben Carlson puts all of this in perspective in his piece: Why the Stock Market Has to Crash.

One resource

We are huge fans of NYU professor Aswath Damodaran's writings. So when he publishes a piece about the business of AI, we take note. Check out AI’s Bar Mitzvah Moment? From Hope & Hype to Hard Business Questions!​

One Stock Dive

A Stock Simplifier user asked if we could create a "one-page" overview of a company after a stock was rated.

We thought that was a great idea. So we built it.

Here is Feroldi's one-page overview of Shopify (NASDAQ: SHOP).

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To make a one-page overview of any stock, simply rate each category, and the download button will appear.

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Brian Feroldi

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Brian Stoffel

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Brian Withers

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