“I’d not really read much Kafka before and had grown up led to believe that it was a paranoid and hyperbolic work, dystopian fiction in the style of George Orwell,” Aaron Swartz wrote of The Trial at the end of 2011. “Yet I read it and found it was precisely accurate—every single detail perfectly mirrored my own experience.” Earlier that year, in January, Swartz had been arrested by police in Cambridge, Massachusetts, for downloading several million articles from JSTOR, a database of academic journals. Six months later, he was indicted on multiple felony counts by a federal grand jury.

At the time of his arrest, Swartz was a brilliant computer programmer, well-known activist, and prolific writer. He had helped to develop, among other projects, RSS, which syndicates news from across the Internet onto one reader; Reddit, a message board that allows users to curate the front page; and SecureDrop, a platform for protecting anonymous leaks used by The New Yorker, The Guardian, and The Intercept, among others.

The government, his family later said, wanted to make an example out of him: The charges were extreme, the federal prosecutors overzealous. For downloading a small fraction of JSTOR’s data—which remained unaltered on JSTOR’s own servers—Swartz was charged with 11 violations of the Computer Fraud and Abuse Act and two counts of wire fraud, for which the maximum penalty includes up to 50 years in prison, $1 million in fines, restitution, and asset forfeiture. Whether Swartz intended to use the downloaded articles for his own research or to distribute them to other people remains unclear.

In retrospect, the aggressive prosecution was, as Swartz wrote of Kafka’s novel, “a vivid illustration that bureaucracies, once they get started, continue doing whatever mindless thing they’ve been set up to do, regardless of whether the people in them particularly want to do it or whether it’s even a good idea.” Swartz committed suicide in his Brooklyn apartment two years after his arrest and weeks before his trial. He was 26 years old.

His thoughts on Kafka appeared in his annual “Review of Books,” an annotated list of the books he had read. Swartz averaged about 100 books each year, but in 2011, he noted, he had read less than usual because it had been “a stressful year, in many ways.” Titles bolded on that year’s list of 70 volumes—­among them The Lean Startup and Harry Potter and the Methods of Rationality—were “those that were so great my heart leaps at the chance to tell you about them even now.” This enthusiasm—­intimate, casual, urgent—animated each of the posts on his blog, which he kept regularly from the age of 15 until his death.

A suicide invites those in its wake to read the life lost as a trail of clues, whose mystery, if only deciphered sooner, might have led to a different resolution. It is tempting, and not difficult, to comb the 1,478 posts that Swartz published on his personal blog for signs and warnings. The Boy Who Could Change the World, an edited collection of these writings from Swartz’s blog and elsewhere, largely avoids this temptation.

Introduced by Swartz’s friends, mentors, and collaborators, the selections seem to suggest that the capacious vivacity of his life—of any life, really—might collapse if read too closely in the service of its overdetermined ending. The collection sidesteps Swartz’s personal posts about depression, romantic crushes, and existential frustrations in favor of his arguments about copyright law, political corruption, transparency, and the soul-crushing structure of the educational system.

Each entry in The Boy Who Could Change the World notes not just the date and URL of the post, but also Swartz’s age at the time of its composition—a marker that, like the book’s title, broadcasts his precocity and our loss. But revisiting Swartz’s writing is important not just for its unrealized promise, accurate premonitions, or boyish genius, but also for its earnest, restless, and contradictory reflections. There was nothing impersonal about the way that Swartz challenged himself and his readers to reconsider their beliefs—which is why, despite its selective focus, the book’s curated tour of Swartz’s legacy reads less like a posthumous time capsule and more like the record of one mind thinking, beautifully, against itself.

* * *

Part of the strangeness of reading a blog is the immediacy of the author’s voice. Swartz’s was often charming but firm, confident but kind, a voice particularly well suited to blogging. His curiosity led him to produce a staggering amount of opinions on a range of topics, from why he hated classical music to the politics of drug-policy reform. His programming projects emerged from his thinking on how to make accessing and sharing information not just easier or faster but more equitable. In blogging, these impulses could be channeled as medium and message.

By its nature, a blog is provisional, in progress, protean. Swartz’s own ideas were likewise always in formation, but he thought they were best achieved through conversation, experimentation, and self-education. “I don’t consider this writing, I consider this thinking,” he wrote about blogging in a 2006 post. “I like sharing my thoughts and I like hearing yours and I like practicing expressing ideas, but fundamentally this blog is not for you, it’s for me. I hope that you enjoy it anyway.”

Swartz was committed to democratizing information. On his blog, he proposed alternate systems for the compulsory licensing of music—ones that rerouted earnings to the artists themselves. In his free time, he wrote scripts to make the deep web, which is not indexed by conventional search engines, visible to non-programmers. “One of the most striking things about blogs to me is how they almost never talk down to their readership,” he reflected in a post praising the advent of new media. “Indeed most seem to think higher of their readership than they do [of] themselves.”

Swartz knew that the choices of programmers were “political choices, not technical ones”; that software functioned to make “certain kinds of features possible” and obscured others. He questioned whether the complicated features of even a relatively benevolent platform like Wikipedia might privilege the actions of some users over others. To a certain extent, he anticipated the criticism of social media’s invisible, seemingly neutral design features, which often serve to curtail user privacy.

Swartz was fascinated by why certain platforms succeeded and others didn’t. When he was 12, he developed an award-winning website with a premise similar to that of Wikipedia, but he did not develop Wikipedia. He was frustrated by the inefficiency of both NGOs and political pollsters, neither of whom spent enough time, in his opinion, measuring the outcomes of their expensive efforts. As a result, his favorite charity was GiveWell, a nonprofit that evaluates and recommends charities according to their cost-effectiveness. “To learn what works and what doesn’t,” he urged, “we need to share our experiences and be willing to test new things—new goals, new social structures, new software.”

What would a left-leaning technology policy look like? If code were law, what kind of laws should be written? Swartz was trying to figure this out—not through blogging or analytic philosophy, but by helping to craft open standards for the web. As a tween, he collaborated with leading lawyers and programmers on the architecture of the Creative Commons (CC) licensing code, which permits the free circulation of works with attribution. His ultimate goal in developing successful projects was not to boost an IPO, but rather to maximize—for lack of a better word—human freedom.

There was nothing idle or naive about Swartz’s belief that technologies that transformed our capacity to think, manipulate, and collectively act on the world could be both liberating and coercive. Freedom, for Swartz, didn’t inevitably follow from the existence of the Internet; it needed to be considered, designed, and maintained. And yet his own definition of “freedom” was foggy, perhaps best articulated by Isaiah Berlin’s description of it as a word “so porous that there is little interpretation that it seems able to resist.” This might explain why Swartz’s commitment to the “freedom of information” was at once unwavering and fraught.

In the ambiguous terrain of digital reproduction, it was (and remains) unclear whether rights to a creation should lie with the consumer or the creator, with the user or the developer, with both, or with neither. On the one hand, Swartz advocated for free culture, a view that at times aligned him with libertarians. On the other, he was never anti-statist: Swartz was not, pace the Justice Department, an anarchic pirate calling for a revolution to overthrow all forms of authorship. Rather, he seems to have been searching for a middle ground. “You can’t just punish people because they took away a potential sale,” he explained in an interview in 2004. “Earthquakes take away potential sales, as do libraries and rental stores and negative reviews. Competitors also take away potential sales. So the question then becomes what’s a reasonable form of taking away sales, and what’s an unreasonable one.” In an attempt to be reasonable, Swartz was, in some respects, an avatar for the seeming discrepancy at the crux of intellectual-property debates: Information wants to be free, but people also need to be paid.

Consider the contradictions of Creative Commons. Designed for the intensive climate of online content circulation, CC’s licenses allow creators to keep their works open for use by others while ensuring that they receive attribution. At the same time, CC also contains licensing options that let authors ban derivative works, which replicates the commercial monopoly enshrined by traditional copyright. These restrictive provisions, critics contend, lead to a fragmented commons at the expense of an ethics of sharing that, as the Free Culture Foundation puts it, “takes away freedom from all cultural participants.”

Reformist critiques notwithstanding, Swartz knew that “copyleft” solutions like Creative Commons could only go so far in their challenge to traditional IP so long as copyrights continued to be accumulated and policed by those who played no part in the works’ creation. “The world’s entire scien­tific and cultural heritage, published over centuries in books and journals, is increasingly being digitized and locked up by a handful of private corporations,” states the “Guerilla Open Access Manifesto,” an anonymously written work that Swartz contributed to in 2008. “We can fight back. Those with access to these resources—students, librarians, scientists—you have been given a privilege. You get to feed at this banquet of knowledge while the rest of the world is locked out. But you need not—indeed, morally, you cannot—keep this privilege for yourselves. You have a duty to share it with the world.”

* * *

Running throughout Swartz’s writing is an alternating current of self-aggrandizement and self-effacement. He was an optimist who believed that he could, in fact, save the world, but his pessimism ensured that no solution would be good enough. He was interested in so many things that many of them failed to hold his interest for very long.

Swartz wasn’t afraid to change his mind, and did so whenever he found it necessary. “My beliefs are much more shaken by converts—­people who were strong believers in X but converted to believing in Y,” he wrote. His own fluency in conversion was rare and, to some, frustrating.

He often doubted whether he was working effectively, or even on the right problems. This was because he wanted to maximize his impact on promoting “the most overall good.” As he admitted in 2005:

The other night, when [redacted] asked me why I switched from computer science to sociology, I said it was because Computer Science was hard and I wasn’t really good at it, which really isn’t true at all. The real reason is because I want to save the world. Maybe I didn’t say that because it sounds sort of crazy.

While he continued to code, Swartz eventually veered away from programming, moving toward politics, public intellectualism, and teaching. In his essay “A Non-Programmer’s Apology,” he justified this decision in instrumentalist terms. “Any specific task I could do with the knowledge,” he wrote of his programming skills, “would be far outweighed by the tasks done by those I’d explained the knowledge to.” He wrote the essay, he explained, under the influence of David Foster Wallace’s discursive style.

Swartz read widely. He liked George Saunders, Matt Taibbi, and Chuck Klosterman. He railed against the neoliberal “immorality of Freakonomics.” He devoured best-selling self-help books—works that made him “rethink the entire way [he] approached life”—as well as those pitched to businessmen and politicians, like What It Takes: The Way to the White House, The Fifth Discipline: The Art & Practice of the Learning Organization, and How to Win Friends and Influence People. He was fascinated by the ruthless urban planner Robert Moses and his unyielding control of New York City, as depicted by Robert Caro in his celebrated biography The Power Broker.

When he was 17, Swartz read Noam Chomsky’s Understanding Power, a thick collection of lectures from the 1990s on globalization, the military-industrial complex, intellectualism, social movements, and the media’s “propaganda model.” “Reading the book, I felt as if my mind was rocked by explosions,” Swartz reported. “At times the ideas were too much, and I literally had to lie down…. I remember vividly clutching at the door to my room, trying to hold on to something while the world spun around.” After reading Chomsky, Swartz felt alone in his despair. He wrote that he didn’t know whether he could share his new worldview with friends; he didn’t want to sound obvious or paranoid. It took him two years, he said, to finally put to paper the “shocking brokenness I’d discovered.”

Reading often pushed him toward new revelations. On Poor Economics, a cautionary tale about how the good intentions of philanthropists and economists play out terribly in practice, he wrote: “It’s a stunning feeling to have the basic building blocks of your world crumbled and questioned before you—and a powerful lesson in the value of self-skepticism for everyone who’s trying to do something.”

One of Swartz’s clearest conversions can be found in his thinking on transparency. He initially believed that freeing information “could change the world,” that all that was needed for people to act was for them to know. When he was 17, he proposed the idea of a WikiCourt: a kind of high-school debating society, but online and editable. The idea was to ask a team of experts to weigh the evidence for and against a given statement—for example, “[Al] Gore claims to have invented the Internet”—and then decide its ultimate truth. At 21, Swartz launched Watchdog.net, which would provide searchable data sets on political contributions, demographics, lobbying, and voting records in order to “pull people into politics.” A kind of prototype for Change.org, the project’s first step was to post data about every elected representative and give people a way to write to them. At the time, Swartz hoped that the project would be “not so much a finished solution as a direction, where I hope to figure more of it out along the way.” A year later, he had taken a more cynical turn.

“It’s hard to think of any good examples of transparency work accomplishing anything, except perhaps for more transparency,” he wrote in 2009. “Putting databases online isn’t a silver bullet, as nice as the word transparency may sound.” In the essay “When Is Transparency Useful?,” he argued that calls for greater transparency in politics only led to reforms that addressed the appearance of corruption rather than the thing itself. Dumping or leaking information was pointless, since bribes and dark money could always move out of transparency’s spotlight.

Swartz was disillusioned with the limits of existing structural reform, and he worried that the links in that process were not tightly connected to each other. Technologists and journalists both insisted that their work was neutral, with the former declaring that it was up to others to contextualize their data, and the latter never following up on the aftermath of their investigations. Meanwhile, the politicians ultimately tasked with cleaning up the corruption exposed were often too invested in the status quo to do so. The key to making information useful, Swartz thought, would be to purposefully dismantle the “arbitrary divisions between ‘technology’ and ‘journalism’ and ‘politics.’”

Because he criticized himself as intensely as he did others, Swartz came to the conclusion that his work as a programmer and a writer would not protect the political values he treasured without the force of legislation. He advised himself and other technologists to “stop passing the buck by saying our job is just to get the data out there and it’s other people’s job to figure out how to use it.” This is what led him to study the architecture of American power and to consider entering the formal domain of politics himself.

* * *

Savvier than most programmers turned do-gooders twice his age, Swartz understood the “naïveté” of the technocratic approach to politics. “Whenever geeks turn their eyes to politics,” he pointed out, “they always have the same reaction: There’s so much inefficiency!”

His goal in analyzing the pressure points of politics was not to make the existing system more frictionless but to allow groups of outside activists to change it efficiently. He co-founded the Progressive Change Campaign Committee and Demand Progress. He wrote papers and gave presentations on campaign finance and strategy, congressional casework, legislative gridlock, staff ethics, lobbying, the rise of the think tank, and the attraction of centrism. His political analyses aren’t particularly groundbreaking, but they do display a mind keen to understand politics as a system built on the all-too-human phenomena of power, corruption, and lies.

But Swartz had his own technocratic tendencies as well. He wanted to launch small campaigns with tight feedback loops to test out electoral strategies. At the same time, he was keen on parpolity, or “participatory polity”— a nesting structure that would make it possible for each citizen to have a face-to-face discussion with a direct representative. His participatory vision at times stood in contrast to his desire to redesign the system from scratch as he saw best: He wanted to change not just a district but also, as he put it, “the world.”

In politics, as in programming, he was tempted to wonder about “elegant mathematical effectiveness.” In an e-mail to a friend, the sci-fi writer Cory Doctorow, Swartz envisioned a strategy that would allow a passionate independent to get elected to national office. First, the candidate uses a “vote-finding machine” to ask all of his or her social-media friends for support. Each supporter is then asked to do the same with their contacts, and so on. The vote machine constantly deploys A/B testing to optimize its persuasive strategy. TV spots, web ads, and events are all likewise tested and optimized according to voters’ GPS locations. The whole system is “built into a larger game/karma/points thing that makes it utterly addictive, with you always trying to stay one step ahead of your friends.”

The campaign sounds a little bit like The Manchurian Candidate meets Candy Crush. But it’s also reminiscent of Facebook’s widely hated experiment in “digital gerrymandering,” altering users’ newsfeeds to successfully influence voter turnout. Swartz signed off his e-mail to Doctorow writing: “anyway, i could go on, but i should actually take a break and do some of this…” It’s unclear if he was kidding.

One of Swartz’s most successful efforts as an activist was his work with Demand Progress to help kill SOPA, the Stop Online Piracy Act, a bill that would have authorized Congress, using the framework of copyright law, to censor parts of the Internet. He told the story of these organizing efforts in a keynote speech delivered at the Freedom to Connect Conference in May 2012, printed in the collection. “There’s a battle going on right now,” he said, “a battle to define everything that happens on the Internet in terms of traditional things that the law understands.” Despite the victory over SOPA, and anticipating the coming battle over net neutrality, Swartz warned his audience: “It will happen again. Sure, it will have yet another name, and maybe a different excuse, and probably do its damage in a different way. But make no mistake: the enemies of the freedom to connect have not disappeared.”

At the conclusion of his address, Swartz reflected on its form with a sort of political parable. He noted that he had chosen to narrate the events that led to SOPA’s demise as a “personal story,” one that he compared to the two-sided Hollywood structure of Transformers. “But that’s kind of the point,” he conceded. “We won this fight because everyone made themselves the hero of their own story. Everyone took it as their job to save this crucial freedom. They threw themselves into it. They did whatever they could think of to do. They didn’t stop to ask anyone for permission.”

His meta-commentary is telling: Swartz never stopped believing in the power of small groups of people to collaborate for change, but he also never stopped dreaming about leaving his own radically individual mark. It’s one way to explain the oddity of both designing Creative Commons and hacking JSTOR. But if everyone makes themselves “the hero of their own story,” as in Transformers or Swartz’s beloved Batman trilogy or, indeed, The Boy Who Could Change the World, it becomes impossible to organize collectively, to orchestrate social movements, to struggle against the social injustices that blockbusters and databases are not designed to capture.

* * *

From an early age, Swartz learned to “just live his life without asking for permission,” as he wrote of The Trial’s Josef K. He left high school after ninth grade, college after one year, and the moneyed offices of Condé Nast, which purchased Reddit, in a matter of months. (“I couldn’t stand San Francisco,” he explained in a 2007 speech. “I couldn’t stand office life. I couldn’t stand Wired. I took a long Christmas vacation. I got sick. I thought of suicide. I ran from the police. And when I got back on Monday morning, I was asked to resign.”) The criminal-justice system was simply the last of Swartz’s encounters with a series of frustrating bureaucracies. It also happened to be the only bureaucracy from which he couldn’t walk away.

Swartz saw himself like K.: “an individual in a world of bureaucracies,” fighting against impersonal, inefficient systems. He didn’t want his contributions to be replaceable. This made it difficult for him—despite his stated commitment to collaboration, collective action, and free information—­to exist within institutions designed to understand workers, students, or collaborators as interchangeable. He urged managers to understand an organization as a “machine made of men and women,” but he didn’t want to be a cog in one himself.

Although Swartz circumvented traditional schooling, he took education—his own and that of others—seriously. He wanted to create structures in which everyone had a fair chance to be curious. Despite his distrust of bureaucrats and his faith in algorithms, he deeply believed in people and trusted their ability to disrupt the status quo. “Too often, people think of schools as systems for building good people,” he wrote. “Perhaps it’s time to think of them as places to let people be good.”

Nor was Swartz interested in reforming a failing educational system through high-stakes testing and privatization, but rather by showing how the system itself had been set up to fail. After researching the history and philosophy of American education, Swartz concluded that the system was working exactly as it was intended to: inducing compliance and boredom in order to pre-empt future labor agitation, and teaching everyone very little in the process.

As an adolescent, Swartz subscribed to “unschooling,” an educational philosophy based on the idea that “kids want to learn.” When he blogged about his own adventures in unschooling, he addressed the clichéd question of how children would make friends if they didn’t go to school by explaining the appeal of online communities. Proving his own point at the essay’s end, he thanked the friends who had contributed to the online discussion from which his essay emerged.

This was the upside to Swartz’s self-education. He thrived in the chat rooms and collaborations of the early Internet, where appearance, age, hierarchies, and social norms didn’t matter. Compared with the inane rituals demanded of kids in a classroom, the “magic” he called coding must have seemed limitless.

The “downside,” as his friend and Creative Commons collaborator Lawrence Lessig told The New Republic, was that Swartz “never had to…learn to live with the failings of bureaucracy. He was always just free to just walk away.” According to friends and family, Swartz never did anything he did not want to do, including dishes. He told his girlfriend that he would rather spend his life couch-surfing than working an office job that he didn’t want merely to pay the rent. In the case of his lawsuit, he didn’t want to ask friends for money, didn’t want to go to trial, didn’t want to be labeled a felon.

To Swartz, walking away was the only way to get somewhere.

“I realize it must seem like the greatest arrogance to think one could escape life’s mundane concerns, like asking to live on a cloud, floating above the mere mortals,” Swartz reflected at 22, after taking a month-long vacation from the Internet. “But it was that arrogance that made me think I could contribute to adult mailing lists when I was still in elementary school, that arrogance that made me think someone might want to read my website when I was still just a teen, that arrogance that had me start a company as a college freshman. That sort of arrogance—not bragging, but simply inwardly thinking I could do more than was expected of me—is the only thing that’s gotten me anywhere in life.”