I asked the two women if they had heard of Lean In. Randall said she had seen a couple of Sandberg’s TV appearances, but didn’t quite understand the message. I told her that Lean In argues that women need to break down “internal obstacles” within themselves that are preventing them from moving up the work ladder. “There are a lot of barriers women face,” Randall said. She ticked off a few: lousy pay, no benefits, no sick leave, no unions, sexism, and a still highly sex segregated workforce. “There are lots of jobs that are still considered women’s work,” she said. “In one of the mills, I was actually referred to as ‘the girl.’”

What Randall described is what most American working women face. And they are also the sort of problems that the advocates of Lean In and its sister impulses must address if they are not to be seen as individual women empowering themselves by deserting other women—if they are to be called, as Sheryl Sandberg calls herself, feminist.

What about “internal obstacles,” I asked Randall—the sort of obstacles that cause women to curb their ambitions because they’re afraid they won’t be likable? She pondered the question for a time. “I don’t know,” she said finally. “That’s just not the world I came from.”

Every once in awhile, though, you’ll run across some decent practical advice on LinkedIn. A post about avoiding frequent-flier miles scams—another one of LinkedIn’s top “influencer” posts of all time—has some unwittingly trenchant advice for aspiring thought leaders. “First,” author Christopher Elliott explains, “only a few people at the top of the scam benefit in any meaningful way. And second, many of those elite program apologists will do anything to defend the system that has rewarded them.” You don’t say.

[...] On first impression, O’Reilly seems like a much-needed voice of reason—even of civic spirit—in the shallow and ruthless paradise-ghetto that is Silicon Valley. Compared to ultra-libertarian technology mavens like Peter Thiel and Kevin Kelly, O’Reilly might even be mistaken for a bleeding-heart liberal. He has publicly endorsed Obama and supported many of his key reforms. He has called on young software developers—the galley slaves of Silicon Valley—to work on “stuff that matters” (albeit preferably in the private sector). He has written favorably about the work of little-known local officials transforming American cities. O’Reilly once said that his company’s vision is to “change the world by spreading the knowledge of innovators,” while his own personal credo is to “create more value than you capture.” (And he has certainly captured a lot of it: his publishing empire, once in the humble business of producing technical manuals, is now worth $100 million.) [...]

[...] O’Reilly confessed that, as a young man, he had “hopes of writing deep books that would change the world.” O’Reilly credits a book of science fiction documenting the struggles of a young girl against a corporate-dominated plutocracy (Rissa Kerguelen by F. M. Busby) with helping him abandon his earlier dream of revolutionary writing and enter the “fundamentally trivial business [of] technical writing.” The book depicted entrepreneurship as a “subversive force,” convincing O’Reilly that “in a world dominated by large companies, it is the smaller companies that keep freedom alive, with economics at least one of the battlegrounds.” This tendency to view questions of freedom primarily through the lens of economic competition, to focus on the producer and the entrepreneur at the expense of everyone else, shaped O’Reilly’s thinking about technology.

It was the growing popularity of “open source software” that turned O’Reilly into a national (and, at least in geek circles, international) figure. “Open source software” was also the first major rebranding exercise overseen by Team O’Reilly. This is where he tested all his trademark discursive interventions: hosting a summit to define the concept, penning provocative essays to refine it, producing a host of books and events to popularize it, and cultivating a network of thinkers to proselytize it.

It’s easy to forget this today, but there was no such idea as open source software before 1998; the concept’s seeming contemporary coherence is the result of clever manipulation and marketing. Open source software was born out of an ideological cleavage between two groups that, at least before 1998, had been traditionally lumped together. In one corner stood a group of passionate and principled geeks, led by Richard Stallman of the Free Software Foundation, preoccupied with ensuring that users had rights with respect to their computer programs. Those rights weren’t many—users should be able to run the program for any purpose, to study how it works, to redistribute copies of it, and to release their improved version (if there was one) to the public—but even this seemed revolutionary compared to what one could do with most proprietary software sold at the time.

So what did matter about open source? Not “freedom”—at least not in Stallman’s sense of the word. O’Reilly cared for only one type of freedom: the freedom of developers to distribute software on whatever terms they fancied. This was the freedom of the producer, the Randian entrepreneur, who must be left to innovate, undisturbed by laws and ethics. The most important freedom, as O’Reilly put it in a 2001 exchange with Stallman, is that which protects “my choice as a creator to give, or not to give, the fruits of my work to you, as a ‘user’ of that work, and for you, as a user, to accept or reject the terms I place on that gift.”

This stood in stark contrast to Stallman’s plan of curtailing—by appeals to ethics and, one day, perhaps, law—the freedom of developers in order to promote the freedom of users. O’Reilly opposed this agenda: “I completely support the right of Richard [Stallman] or any individual author to make his or her work available under the terms of the GPL; I balk when they say that others who do not do so are doing something wrong.” The right thing to do, according to O’Reilly, was to leave developers alone. “I am willing to accept any argument that says that there are advantages and disadvantages to any particular licensing method. . . . My moral position is that people should be free to find out what works for them,” he wrote in 2001. That “what works” for developers might eventually hurt everyone else—which was essentially Stallman’s argument—did not bother O’Reilly. For all his economistic outlook, he was not one to talk externalities.

To weaken Stallman’s position, O’Reilly had to show that the free software movement was fighting a pointless, stupid war: the advent of the Internet made Stallman’s obsession with licenses obsolete. There was a fair amount of semantic manipulation at play here. For Stallman, licenses were never an end in themselves; they mattered only as much as they codified a set of practices deriving from his vision of a technologically mediated good life. Licenses, in other words, were just the means to enable the one and only end that mattered to free software advocates: freedom. A different set of technological practices—e.g., the move from desktop-run software to the cloud—could have easily accommodated a different means of ensuring that freedom.

In fact, Stallman’s philosophy, however rudimentary, had all the right conceptual tools to let us think about the desirability of moving everything to the cloud. The ensuing assault on privacy, the centralization of data in the hands of just a handful of companies, the growing accessibility of user data to law enforcement agencies who don’t even bother getting a warrant: all those consequences of cloud computing could have been predicted and analyzed, even if fighting those consequences would have required tools other than licenses. O’Reilly’s PR genius lay in having almost everyone confuse the means and the ends of the free software movement. Since licenses were obsolete, the argument went, software developers could pretty much disregard the ends of Stallman’s project (i.e., its focus on user rights and freedoms) as well. Many developers did stop thinking about licenses, and, having stopped thinking about licenses, they also stopped thinking about broader moral issues that would have remained central to the debates had “open source” not displaced “free software” as the paradigm du jour. [...]

“Open” allowed O’Reilly to build the largest possible tent for the movement. The language of economics was less alienating than Stallman’s language of ethics; “openness” was the kind of multipurpose term that allowed one to look political while advancing an agenda that had very little to do with politics. As O’Reilly put it in 2010, “the art of promoting openness is not to make it a moral crusade, but rather to highlight the competitive advantages of openness.” Replace “openness” with any other loaded term—say “human rights”—in this sentence, and it becomes clear that this quest for “openness” was politically toothless from the very outset. What, after all, if your interlocutor doesn’t give a damn about competitive advantages?

Unsurprisingly, the availability of source code for universal examination soon became the one and only benchmark of openness. What the code did was of little importance—the market knows best!—as long as anyone could check it for bugs. The new paradigm was presented as something that went beyond ideology and could attract corporate executives without losing its appeal to the hacker crowd. “The implication of [the open source] label is that we intend to convince the corporate world to adopt our way for economic, self-interested, non-ideological reasons,” Eric Raymond noted in 1998. What Raymond and O’Reilly failed to grasp, or decided to overlook, is that their effort to present open source as non-ideological was underpinned by a powerful ideology of its own—an ideology that worshiped innovation and efficiency at the expense of everything else.

[...] Following the open source model, citizens are invited to find bugs in the system, not to ask whether the system’s goals are right to begin with. That politics can aspire to something more ambitious than bug-management is not an insight that occurs after politics has been reimagined through the prism of open source software.

It’s clear from all these accounts of the sensibly pragmatic exercise of power in Washington that the “center” is where corporations go to pick up their free cash. But at least there are no extremists at that center. [...]