Beyond Blogging: Sketches for Social Longform Writing

I love blogging. I enjoy forum discussions. All too often, I relish Twitter banter. But these short-form formats are far from the only ways to write online. For certain projects, where I want to explore a subject in depth, it feels like the only answer is: go long.

I’ve been thinking a lot about blogs, writing and online networks, and have recently contributed to two blogchains on these topics (one, two). I also recently participated in the Friends as Force Multiplier workshop, thinking out loud with a small group of thoughtful folks about writing and connecting online.

Big projects are hard in all kinds of ways. Big online writing projects carry a particular set of challenges. I’d like to figure out a tack for two big writing projects I’ve had brewing. More on those below! But first…

Possibilities for Online Longform

What’s are some of the different ways to structure a writing project at scale?

A major theme we’ve been talking about in the Blogging Futures conversation is infrastructure for online writing, from many angles: technical, social dynamics, frameworks for thinking and for public dialogue.

Some structures may bring multiple blog posts together, as I explored in my post Proposal for Near-Future Blogging Megastructures. Other modes of longform may not fit the blogging paradigm at all:

  • Longform guides, e.g. Holloway’s bespoke deep dives into tech-meets-business topics
  • Chapterized works, as we see in serialized novels, or open scholarly monographs
  • Wikis, either massive collaborative ones (Wikipedia), or extensive personal wikis (Roam)
  • Online courses, whether paywalled multimedia courses, openly syllabi, or somewhere in between

As I mentioned, there are two specific projects I’m thinking about a lot right now, and I think each may require different approaches, both for how I structure the writing, and how I share it.

Project 1: Writing on Personal Librarianship


Antilibraries is a project arising from my relationship to books and reading — a hybrid of my own ever-multiplying book lists, and my urge to extend my curiosity in every direction at once. It’s currently a website where I both collect interesting books and host a small community forum. I’d like to also use the site to share in-depth writing about interesting approaches to reading and library-building.

Structure / Format:

I have in mind a series of essays or guides, each addressing a topic I’ve explored in my reading and independent library experiments. The length may vary, say 1k–5k words each. I’d like to focus on things that other readers may find practically useful: how to build your own antilibrary; how to diversity your reading; an overview of various book-related APIs. I have a number of topics in mind, and they’re loosely related but in no particular order, so I think I could publish one at a time.

Audience / Marketing:

I’m writing for bibliophiles with wide-ranging curiosity and a hacker mentality — anyone who wants to read and learn more optimally, experimentally, adventurously. I’ve started a small forum for talking about these themes, and I think there could be some good feedback potential with discussions feeding into more in-depth writing. I’d like to be in dialogue with great book-related newsletters and Twitter conversations as well. I don’t imagine charging for these essays directly, but I could see Antilibraries as a membership site in the long run.

Project 2: Guide to Indie Business Models


I’m fascinated by patronage, crowdfunding, ecommerce, and similar emerging approaches for making a creative practice sustainable. I have a lot of notes about this stuff, from ideas about climbing a “ladder” of indie growth, to audience and monetization strategies, to thoughts on specific platforms. I’d like to compile all I’ve learned about these topics into a big online guide that others can learn from.

Structure / Format:

I have one website that I could repurpose to house this guide, or I could make an entirely new standalone site. I think there’s a ton of stuff I could cover under this broad theme, and potentially expand in the future to more specific sub-areas (like media platforms, marketing tools, and so on). I have an outline started, and I think it makes sense to flesh out and publish the core of this all at once. From there I can iterate and expand, once I see what resonates. I could see the first iteration being in the 5–10k word range, and eventually expanding to double that or more.

Audience / Marketing:

I think this guide will be relevant to many kinds of creators: writers, internet artists, independent designers and technologists, etc. It’s intended as a practical resource for anyone looking to both foster a creative practice and make it financially sustainable, whether as a side hustle or (eventually) as a full-time business. I’d like to make the guide freely available; I also really like the idea of the “unlocking the commons” model, combining public goods and patronage, and I might eventually make this available in some kind of paid format.

Social Infrastructure

My goal is for these projects to be:

  • Meaningful, useful to many people, relevant for the long term (stock rather than flow)
  • Generative, something that can continue to evolve (not a static book; open and online)
  • Relevant to my own deep niche interests; a high-signal beacon for connecting with others who share those interests

One thing I’d like to explore is the sort of persistent infrastructure that enables us to sustain work on big projects over long periods of time. For this, the technical side is the least of my concerns. Much more important is the social aspect: how can I feel like I’m writing for and with others, even at the early, opaque stages? How can I write and share strategically to get others excited about the same things that excite me?

Just knowing other people, even one or two, are invested in seeing a project succeed is a huge motivator! And not only that, having active feedback is a great way to keep the quality high and the writing interesting.

I think what I’m seeking is a system for productively embracing risk, vulnerability, openness. A mindset that inclines me to put things out there, iterate, and respond to feedback. If I do this well, I think the writing will be better: feel more alive; elicit its own self-improvement, find its audience.

A few things I might try, in the service of this goal:

  • Publishing more iteratively (short-form as warm-up?)
  • Open outline (shared doc to start, but also public website, alpha version)
  • More frequent requests for comment e.g. via Twitter
  • Reaching out to specific people by email, for more targeted feedback

Request for Feedback

If you’re interested, I’d like to invite you to comment on notes for both the above projects:

Outline: Antilibraries

Outline: Indie Creator Biz

Please take a look and comment on anything that strikes you! And if you have your own big online writing project you’re working on, I’d love to hear what’s worked for you, or what you’re finding challenging. Let’s write in public together and make a dent on our mega-projects, one page or paragraph at a time.