In 1984, the personal-computer industry was still small enough to be captured, with reasonable fidelity, in a one-volume publication, the Whole Earth Software Catalog. It told the curious what was up: “On an unlovely flat artifact called a disk may be hidden the concentrated intelligence of thousands of hours of design.” And filed under “Organizing” was one review of particular note, describing a program called ThinkTank, created by a man named Dave Winer.

ThinkTank was outlining software that ran on a personal computer. There had been outline programs before (most famously, Doug Engelbart’s NLS or oNLine System, demonstrated in 1968 in “The Mother of All Demos,” which also included the first practical implementation of hypertext). But Winer’s software was outlining for the masses, on personal computers. The reviewers in the Whole Earth Software Catalog were enthusiastic: “I have subordinate ideas neatly indented under other ideas,” wrote one. Another enumerated the possibilities: “Starting to write. Writer’s block. Refining expositions or presentations. Keeping notes that you can use later. Brainstorming.” ThinkTank wasn’t just a tool for making outlines. It promised to change the way you thought.

Fargo: For “Outliner People”
Outlines are a kind of mental tree. Say level 1 is a line of text. Then level 1.1 would be subordinate to 1, and 1.1.1 subordinate to 1.1; 1.2, like 1.1, is subordinate to the first line. And so forth. Of course, outlines existed before software. (The philosopher Ludwig Wittgenstein composed an entire book, the Tractatus Logico-Philosophicus, as an outline.)

But with an outlining program, you don’t need a clumsy numbering system, because the computer does the bookkeeping for you. You can build hierarchies, ideas branching off ideas, with words like leaves. You can hide parts of outlines as you’re working, to keep the document manageable. And on a computer, any element can be exported to another program for another use. Items can become sections in a PhD thesis—or slides in a presentation, or blog posts. Or you could take your outline tree and drop it inside another outline, building a forest.

The years after the Whole Earth review of ThinkTank was published were intense ones for the industry and for Winer. He sold a company to Symantec, became one of the first bloggers (and makers of blog software), and was at the fevered center of the creation, standardization, and implementation of Web syndication. Now, 30 years later, he is again developing new software for outlining. He describes his new system, called Fargo, as “the culmination of my life’s work.” It runs on the Internet at Fargo.io.

At first sight, Fargo is a Web page with a smallish triangle icon below a simple menu bar. One writes in Fargo as one writes elsewhere, by clicking on the screen and typing: text appears to the right of the triangle. When you hit Return, a new triangle appears below, another line in the outline. If you hit Tab, that line will bump over a bit and become subordinate to the line above. Shift + Tab returns you to a higher rung of the hierarchy. Thus are built trees—and, Winer hopes, forests.

“I want a space that they can share,” Winer says, referring to the writers, designers, and programmers who he hopes will form a Fargo community; he talks respectfully about “outliner people.” “The people I really like,” he says, “are people who are aware of their own intellectual processes—those are the only people you can explain the benefits of outlining to. Normal people, even very intelligent normal people, don’t think in terms of wanting to buy a tool that helps them organize their intellectual work better.”

It’s an elitist view of software, and maybe self-defeating. Perhaps most users, who just want to compose two-page documents and quick e-mails, don’t need the structure that Fargo imposes.

But I sympathize with Winer. I’m an outliner person. I’ve used many outliners over the decades. Right now, my favorite is the open-source Org-mode in the Emacs text editor. Learning an outliner’s commands is a pleasure, because the payoff—the ability to distill a bubbling cauldron of thought into a list, and then to expand that bulleted list into an essay, a report, anything—is worth it. An outliner treats a text as a set of Lego bricks to be pulled apart and reassembled until the most pleasing structure is found.

Fargo is an excellent outline editor, and it’s innovative because it’s a true Web application, running all its code inside the browser and storing versions of files in Dropbox. (Winer also recently released Concord, the outlining engine inside Fargo, under a free software license so that any developer can insert an outline into any Web application.) As you move words and ideas around, Fargo feels jaunty. Click on one of those lines in your outline and drag it, and arrows show you where else in the hierarchy that line might fit. They’re good arrows: fat, clear, obvious, informative.

For a while, bloggers using Fargo could publish posts with a free hosted service operated by Winer. But this fall the service broke, and Winer said he didn’t see how to fix it. Perhaps that’s just as well: an outline creates a certain unresolved tension with the dominant model for blogging. For Winer, a blog is a big outline of one’s days and intellectual development. But most blog publishing systems treat each post in isolation: a title, some text, maybe an image or video. Are bloggers ready to see a blog as one continuous document, a set of branches hanging off a common trunk? That’s the thing about outlines: they can become anything.

Editorially and Medium: Divergent Approaches
“Everything we were using felt like it was against us,” says Mandy Brown, a designer and editor with long experience of the Web, who produces books about Web design and user experience for the publisher A Book Apart. “Nothing had the right set of features. We were stuck in this print world.” At the same time, “there was something about the mental model for how you collaborate on a product that mapped in my mind to how you collaborate on a text.” To scratch this itch, she led a small team to create Editorially—as stripped-down a text editor as you could want. Like Fargo, it runs in a Web browser. The focus is unequivocally on the words, and the product is organized around collaboration, with many people working on many successive versions of a document.

Whereas in Fargo the core functionality is the outliner, in Editorially it is a document editor. The emphasis is rigidly on composing; the editing screen is one huge blank field with only a few options. You can have any kind of document you want as long as it’s plain text (albeit with a few codes to indicate formatting). An Editorially user invites collaborators; the program e-mails the collaborators and gives them permission to manipulate the text. Every change is tracked, and a slider timeline allows one to return to past moments in a text’s creation. It works backward from deadlines and defines documents in terms of a process, with “Final” as the goal.

Editorially is an editing platform, not a publishing platform. It lets groups manage words over time. It encourages teams to take large risks with big projects. A document in Editorially is not a fixed thing so much as a pancake stack of states. If one pancake gets burnt, it’s easy to throw it away. The goal is to keep cooking, until the product—the book, article, or business plan—is finished and ready to send off to the printer, or to post on a website.

If Fargo is about outlines and Editorially about text over time, Medium favors easy Web writing. Medium was created by Ev Williams, the former chief executive of Twitter and one of the founders of Blogger. (Full disclosure: I am an advisor to Medium.)

Williams describes his new software as having “just the right amount of formatting to tell your stories without getting in the way.” In practice it means that Medium suggests the structure for a piece: a headline, subtitles, spaces to be filled with body text, images, or video. And while it also handles collaboration, the focus is more on the writer and less on the group. A Medium user drafts a post and then can share that draft with friends for “notes”—feedback. There is no box to fill out; rather, a Medium post looks the same while it’s being written and when it’s published. (It’s a hallmark of all these new systems that they directly manipulate the structure of the Web page, making the page itself the medium of composition, saving as they go. The old text box is dead.)

Once a Medium post is published, the public can leave notes, too. These are like blog comments but are not displayed by default (they are also marginal notes, rather than comments at the end of a post). Instead, the author decides whether or not to show a given comment. The result is that Medium promotes a particular process of composition where the author is in control. Medium is a tool for public writing, for individuals. It provides mechanisms for feedback, both before and after publication, but it also sets boundaries around font use, image sizes, and layout. Medium maintains an editorial team and has hired well-regarded journalists to write and post on the platform. The “Medium post” is emerging as its own sort of thing—not quite a blog post, not quite an article, but something in between.

The Eternal Quest for the ­Perfect Document
Right now, there are so many platforms and tools for words under development that it’s difficult to keep track. Svbtle is a new writing platform, still by invitation only, that offers users a minimalist interface and encourages readers to give “kudos” to good posts. Marquee (online at marquee.by) is a “flexible platform that’s perfect for telling stories.” Scroll Kit is “a new type of content editor that allows you to own the page in one click.” Quip is a collaborative writing application that runs as an iOS app, built by an ex-CTO of Facebook. Ghost is another new blogging platform, a sort of modernization of WordPress.

Why are so many creative software developers building tools for composition? Because the Web is growing older, and its authoring tools seem increasingly unsatisfactory to larger numbers of people. Much of the writing on the early Web was short, ephemeral, weightless. Bloggers would write about where they went, who they saw, what they ate. Content creation tools evolved to support brevity, with Twitter and Facebook as the logical end point for that style of expression. In contrast, entrepreneurs like Winer, ­Williams, and Brown are building tools for reflective thought. They expect their users to contemplate, revise, collaborate—in short, to work more the way writers historically have written, and as the pioneers of the digital revolution expected people to continue to write. What all these new tools for thought must prove is that there are enough people willing to give up the quick pleasures of the tweet or Facebook post and return to the hard business of writing whole paragraphs that are themselves part of a larger structure of argument.

Not long ago, Ted Nelson, a complex and influential thinker who carried the flame of hypertext for decades before the Web existed, gave a talk at MoMA PS1 in Queens, a satellite of New York’s Museum of Modern Art. It was a melancholy reflection upon the failure to realize the humanist ideal of computing.

“I don’t know anybody from my generation of computer people that has adapted,” he said in his talk, “because we all had original visions.” Nelson’s vision is of a system called Xanadu, composed of interconnected documents; any part of any document would be able to connect to any other part, and writers would be compensated with tiny payments as their work was read. He loathes the now-­dominant formats—HTML, PDF, and Microsoft Word—for aiming so low.

“I think every quotation should be connected instantly to its source,” he explained. He was thinking of something more than mere links, which go in only one direction, pointing from one document to another. Instead, he wants documents to be directly embedded into one another—”transcluded,” in his language—so that the original source of an idea is always there.

Nelson has a radio announcer’s voice and the bearing of a beleaguered prophet. “For this,” he said of his vision of connected quotations, “the conventional computer people call me crazy, or a clown, or a pariah.” Then, for a painful moment, he struggled with his computer, unable to launch a demo of his hypertext system. It was as if the computer industry was having its revenge.

It’s easy to scorn products that don’t ship and the people who don’t ship them. But it’s also possible to look at Nelson’s body of work—his many self-published, self-assembled books, his demos, his talks—and see a system of thought that exists outside computer-consumer culture, and to appreciate it for what it is: a kind of art that informs the thinking of those who come across it.

Doug Engelbart, a friend of Nelson’s, who died in July, was described in obituaries as the pioneer of hypertext and one of the inventors of the mouse. But the programmer Bret Victor, an inheritor of the Engelbart ethos, has described him differently.

If you attempt to make sense of Engelbart’s design by drawing correspondences to our present-day systems, you will miss the point,” he wrote in his own remembrance, “because our present-day systems do not embody Engelbart’s intent. Engelbart hated our present-day systems.” The mouse was only a means to an end: a tool for navigating the two-dimensional space of NLS, which offered the world then-barely–fathomable concepts such as teleconferencing, hypertext, and real-time collaboration—all in order to “augment human intellect,” or make it possible for human beings to think new kinds of thoughts. 

The man who filmed Engelbart’s Mother of All Demos was coincidentally Stewart Brand, who went on to found the Whole Earth Catalog. In the 1984 Whole Earth Software Catalog, Brand wrote as clear an explication of the power of software as ever has been offered: “Software, when it is used at all intensely, comes to feel like an extension of your nervous system. Its habits become your habits. The reason the term ‘personal’ got stuck to these machines is, they become part of your person.”

Then, almost as a postscript, he added: “Buyer beware.”

Paul Ford, a writer and computer programmer in Brooklyn, is working on a book of essays about Web pages. He reviewed Facebook’s new interface for smartphones in the July/August issue of MIT Technology Review.