The Center and The Periphery

I wrote a piece about jailbreaking iPhones as a teenager, LLM distillation, Huaqiangbei, Charles Dickens, Henry Ford, and the spirit that lives between copying and creating

When I encountered the word “jailbreaking” again in 2023, it took me a moment to realize it no longer meant what I remembered. For teenagers coming of age today, it has nothing to do with Apple’s iOS—it refers to circumventing the safety architecture of large language models. Though even that definition is already aging. The prompt injection methods that circulated on Reddit a year or two ago, once so clever, have been overtaken by the very systems they sought to outwit. The most hacker-minded people I know (perhaps just millennials, I realized Gen-Z aren’t interested in jailbreaking at all)?—have gone quiet. Fast-moving AI keeps lapping them, and jailbreaking AI no longer carries the same thrill.

And yet I found I couldn’t quite let the word go. Something in it still felt warm to me. I thought of my high school years in northern China, which were long in the way Chinese high schools tend to be long, and pressured in the ways they tend to be pressured. There were breaks between classes. During those breaks, we teenagers broke into our precious, expensive, novel iPhone 4s.

So I wrote a piece about it, partly for nostalgic reasons, partly to probe the nature of innovation itself.¹ This essay has just been published in The Ideas Letter. The piece situates itself within larger questions that many great minds behind books have explored: whether actions like jailbreaking, copying, imitation—even something that shades into plagiarism—might be a less disreputable part of how technological innovation emerges than we generally like to admit. W Brian Arthur’s 2009 classic The Nature of Technology tells us:

Invention is a matter of problem solving—meeting needs—by putting together or combining existing pieces, and solving and re-solving the issues that arise along the way.

Writing this piece meant returning to early 2010s China, to the long winters of Taiyuan and my formative years juggling Gaokao, SAT, Twilight, and iPhones. The nascent era when companies like Xiaomi were just starting. When my high school had moved into a vast new suburban campus where the front road hadn’t been paved yet. When the country was mid-transformation in ways that were technological and physical at once, not always distinguishable from each other.

This piece is also, I’ll admit, somewhat self-serving. I find myself feeling an unwanted shame when reading headlines like “Chinese AI labs distilling our models”—then immediately remembering my high school self, excited and urgent, jailbreaking every iOS system I could reach. That hungry leapfrogging state is hard to suppress with warnings that “you’ve crossed a line.” I felt that hunger. I wanted to make the connection clear.

I also touch upon Charles Dickens—a recent preoccupation of mine, and a documented casualty of what I’ve started calling Yankee innovation. The connection will make sense when you read it.

The first few paragraphs follow. The rest is at The Ideas Letter:

The Center and The Periphery

The summer I started high school in Shanxi, I learned that the world had a new texture. It was the early 2010s and I held in my hand for the first time an iPod Touch. I still remember dragging the unlock bar across the screen. The gesture was new—the whole paradigm of touch was new—and the device responded with a light, precise click, a sound as clean as some cosmic voice. I was holding a piece of the future in my hand, and the future had been designed somewhere else.

Apple had reached a particular kind of peak in China that inspired almost religious devotion. A notorious story that still lingers in people’s minds is that of a teenager who exchanged a kidney for an iPhone. (Even in 2026, “one kidney” remains an ironic term for an iPhone.) While the students in my high school weren’t trading their organs for iPods, those little devices conferred something much more important than a kidney: status. Roughly half the students carried iPods; the other half had feature-rich Nokias. I had both: Nokia N79 and iPod Touch, a hedge and a devotion.

The highest-status students were invariably from privileged families. Crucially, they were also tech-savvy, owning the latest Apple products and possessing the ability to jailbreak devices for themselves and their peers. In a province that didn’t have an official Apple Store yet, owning an Apple device was a symbol of worldliness, extending one’s status beyond the locality. This was also the era when America was still, unambiguously, China’s technological North Star.

Looking back, 2011 feels like a hinge moment. The mobile internet age had just begun. Xiaomi’s founder Lei Jun delivered a prophetic speech that has since passed into tech folklore. Xiaomi—an enormous consumer electronics corporation—had just celebrated its first anniversary, and Lei Jun stood before a small audience in Shenzhen and said: Apple is five years ahead of the market. The only question worth asking was how Xiaomi could claim a place in the future Apple had created, rather than disappearing into it the way Nokia and Motorola already were.

Back then, students exchanged Apple jailbreak tutorials the way they swapped exam prep notes. Once jailbroken, the whole world opened: pirated games, paid software, colorful customized icons, everything the App Store contained but priced out of reach. Between classes we played paid Doodle Jump or Fruit Ninja and competed obsessively for high scores, the leaderboard a minor social order running parallel to academic rank. Under the immense pressure of the Gaokao (China’s exacting national examination for all undergraduates), our little 30-min hacker-house subculture became a liberating escape.

The word itself deserves attention. In Chinese, jailbreaking was translated with unusual fidelity: 越狱 (yueyu)—to cross out of prison. The concept arrived in the language already carrying its moral charge. A jail implies a jailer. A break implies the confinement was unjust. In that era, jailbreaking was a no-brainer. Apple’s closed ecosystem, combined with the near-impossible cost of paid apps relative to a middle-income family’s budget, had created a moral situation with an obvious answer.

It helped that we had a ready mythography. Prison Break, a TV show of five seasons, was enormously popular in China—and loved in my high school. The protagonist Michael Scofield engineers an elaborate escape to rescue his innocent brother from prison, framed and condemned by corrupt politicians reaching all the way to the Vice President’s office. The wicked elite had built the system. The system had imprisoned the innocent. The only recourse was technical ingenuity in the service of justice. I was fifteen. My Apple device was innocent. The closed ecosystem was the apparatus. Who could resist this?

……click HERE to keep reading.

Picture of Ford Model-T's that just came off the assembly line. Ford’s expectations of making "a motor car for the great multitude" had been exceeded. Source.

1. This essay is prompted in part by a friend, Tianyu, who wrote about his own jailbreaking stories on Reboot

Out of the Sandbox