The Problem with Success Stories

Now that fewer people read books, reading itself has become treated as a virtue. An objective good. Something that can only help you.

But this is a dangerous assumption.

While reading undeniably strengthens attention and expands vocabulary.

Its primary function is far more important, it installs mental models. Text is a technology that builds implicit maps of how the world works. One book can reorient your entire worldview, but it can also mis-calibrate you.

That’s the entire plot of one of the best selling novels of all time, Don Quixote. A man reads so many chivalric romances that they overwrite his perception. Windmills become giants. Inns become castles. He rides out expecting one world and encounters another, yet he cannot stop interpreting what he sees through the old map.

The greatest danger in life is absorbing the wrong map and having the conviction to act on it.

The Fiction of the Success Story

Success stories are the most common source of "bad mapping." When you read a biography, or ask someone how they “made it”, you are absorbing a their retroactive causal model of their own life.

And when people look backward, they naturally simplify. We all do it. We all remove dead ends, smooth over uncertainty, don’t recognize the luck in our lives. Many succesful people feel like they are agents of destiny. When in reality that isn’t the case.

Nassim Taleb called this the narrative fallacy. We are pattern‑seeking animals, and a story with a clean cause and a satisfying effect feels truer than the messy truth. Business biographies are especially prone to this distortion. You’d assume they’d be treasure troves of good advice. In reality, most are useless.

Some books resist that temptation. Shoe Dog is one of them. About the rise of Nike. Phil Knight writes about near-bankruptcies, supplier disasters, and decisions driven by necessity rather than grand strategy. He leaves the disorder visible. That’s why the book works.

@connorbcurran

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The antidote isn't to stop reading. It's to read biographies differently.

Strip away the story. Look at the terrain. Ask what game they were actually playing, not what narrative they constructed afterward.

Separate direction from timing.

The goal isn’t to copy someone’s sequence of events. That never works. The goal to extract the underlying variables that travel across contexts.

Shoe Dog and the Rise of Nike

Look at the story of Nike through this filter. Separate Direction from Timing.

Phil Knight stayed in Oregon when serious brands operated out of New York or Los Angeles. Those cities had capital, media, distribution networks. Oregon had low rent and no spotlight. He couldn’t compete in Manhattan. But he didn’t need to. Low burn rate meant survival. He could make mistakes quietly and keep going.

But Oregon had something else. Knight's old track coach at the University of Oregon. Bill Bowerman was obsessed with making better running shoes, tinkering in his garage, pouring rubber into waffle irons. In New York, Knight would have hired designers and consultants. In Oregon, he had direct access to someone actually building things.

The town of Eugene, Oregon had a weird concentration of runners before the rest of America discovered jogging. University of Oregon was called Track Town USA. Knight was sitting inside the subculture before it spread across the country

Japan was similar. American shoe companies sourced from Germany and Italy, established suppliers with premium pricing. Knight looked at post-war Japan, high manufacturing quality, lower wages, hungry exporters. The manufacturing company Onitsuka Tiger hadn't heard of him. They didn't care. They were hungry for an American distributor, any American distributor. He could get in.

That is Direction.

Then the timing hit. He started selling running shoes in the early '60s when Americans didn't run. They bowled. They golfed. Running was something you did if you were late for the bus. But jogging became a thing. Health and fitness became something regular people did. Knight was already standing there selling running shoes when demand increased.

He incorporated Nike in 1971, right before the running boom turned into running mania. Onitsuka tried to cut him out and he needed his own brand or he'd die. It was out of necessity not some vision. He went public in 1980 when capital markets were hungry for growth stories and IPO windows were wide open. If he'd tried that in '74 or '82, different story. Markets were closed. But in 1980, timing worked.

Direction kept him alive. Timing made him rich.

Directional Awareness

It’s better to be wrong on timing than wrong on direction.

Wrong direction leads to stagnation or collapse but wrong timing just usually caps your upside. It’s better to be in the right city at the wrong time than the wrong city at the perfect time. Better to be in a growing industry with imperfect execution than a dying industry with flawless timing. Better to want the same relationship structure (marriage, kids, location) with bad conflict resolution than to want fundamentally incompatible futures with perfect conflict resolution.

In order to get out of the day-to-day headspace, allocate 20% of your time to direction and you’ll improve vision..

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If the terrain is declining, no amount of "hustle" will save you. This requires Directional Awareness, the ability to evaluate the terrain before you commit to the climb. This skill looks like asking different questions:

Not “How do I get promoted?” but “Is this profession expanding or shrinking?”

Not “How do I get more clients?” but “Is this industry structurally advantaged over the next decade?”

Not “How do I make this relationship work?” but “Are we aligned on the shape of the life we want?”

These are harder questions because they challenge the terrain itself. And terrain evaluation is destabilizing. It threatens identity. It suggests that effort may not be enough.

Alcohol and Marijuana

Direction often appears as a subtle shift in the cultural "vibe" before it shows up in the data. Consider the shift from alcohol to marijuana.

Alcohol consumption among young people is falling. Gen Z drinks significantly less than previous generations. The perception that drinking is bad for your health is up very significantly. The majority of people say drinking one to two drinks a day is bad for your health.

Meanwhile, marijuana use continues to surge. We are slowly transitioning to a marijuana society from an alcohol society.

Most people treat this as a cultural quirk. But I think It’s structural.

What I noticed with drinking alcohol is it forces downward integration, it drags consciousness back into the body. Thought back into the gut.

Screen life doesn't need that. Screen life needs you fast, light, and abstract. All cognition, no weight. This is why marijuana is so popular. It doesn't pull you down into the body the way alcohol does, it intensifies whatever's already happening in your head without the physical drag.

A screen based life rewards sustained cognitive engagement and rapid attention shifts. Alcohol impairs that mode. It slows reaction time, reduces focus, and increases physical heaviness. Substances that maintain or intensify mental immersion fit more naturally into a screen dominated culture. Like Marijuana.

Direction sometimes appears this way, not fully quantified, not fully proven, but sometimes perceptible before it becomes obvious.

In This Newsletter

1) Choosing Direction is Hard Now: In a world where terrain shifts faster than ever, picking the right game matters more than optimizing how you play it.

2) Deep Timing and the Rise of Chronotherapy: Once the direction is correct, timing becomes the decisive variable. But timing isn't something you "will" into existence, it is a structural alignment with biological or economic rhythms.

Choosing Direction Is Harder Than Ever

Modern life has made choosing direction harder than at any point in recent history.

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