Notes / 5 min read

Some Thoughts on Open-Ended Writing

Open-ended writing connects ideas and identifies new questions. It encourages conversation instead of presenting a polished argument.


Writing online, especially for a blog, can feel difficult. Especially for a (recovering) social media and content marketer like myself. Yes, it’s easy to make a blog. It seems like there are constantly new tools popping up promising to help you blog, build a newsletter, or post on social media.

But writing is a different matter. Today it seems like blogging is focused on producing capital “C” Content for consumption. Everything becomes an “ultimate guide to X,” even if you try to use slightly more tasteful titles. With the arrival of Chat-GPT and other AI tools, the world is faced with even more bland and repetitive capital “C” content as the “dark forest” of the web expands, to borrow a term from Yancey Strickler.

This isn’t inspiring. And it’s rarely enjoyable to write these types of articles.

Digital Gardening and Small b Blogging

When I started writing on this website (again), I wanted to treat it more like a digital garden. I’d like to expand my thoughts on digital gardening sometime, but I think Maggie Appleton has the best working definition for now:

A garden is a collection of evolving ideas that aren’t strictly organised by their publication date. They’re inherently exploratory – notes are linked through contextual associations. They aren’t refined or complete - notes are published as half-finished thoughts that will grow and evolve over time. They’re less rigid, less performative, and less perfect than the personal websites we’re used to seeing.

This approach resonates with me. Mainly because producing exhaustive articles is, well, exhausting. This definition of the digital garden is similar to the concept of “small b blogging” introduced by Tom Critchlow:

Small b blogging is learning to write and think with the network. Small b blogging is writing content designed for small deliberate audiences and showing it to them. Small b blogging is deliberately chasing interesting ideas over pageviews and scale. An attempt at genuine connection vs the gloss and polish and mass market of most “content marketing”.

I recently read another note by Tom Critchlow that was the direct inspiration for this line of thinking, entitled “Writing, Riffs, and Relationships.” There are lots of good concepts in the article, but the idea of making writing small stood out to me. In particular

People’s first instinct with content is to try and make it polished and closed. To be useful by solving something or creating the ultimate guide to something. Those pieces of content can be good - but they’re very hard to write, and even harder to write well! Instead I prefer to take a more inquisitive and open-ended approach….

And then:

Closed writing is boring writing. If you’ve fully explored and put to bed the topic you’re writing about then there’s very little left for someone to react to. “Nice post” someone might say.

But if you deliberately leave some rough edges, some threads that the reader can pull on, then you’re inviting the reader into the conversation. You’re saying (possibly explicitly!) - “Hey, what are your thoughts on this topic? How do you think about it?”

Critchlow goes on to recommend ending a blog post or “riff” with more questions that encourage you (and your audience) to explore other topics. Altogether, this made me think about the difference between open-ended and closed writing and how they are different modes of writing altogether.

A Brief Definition of Open-Ended Writing

Open-ended writing seeks to connect ideas and identify new pathways of inquiry. It explores a topic by connecting sources and identifying tensions, conflicts, or missing information. Open-ended writing invites conversation and debate.

In practice, open-ended writing is defined by three basic activities: free writing, summarizing, and questioning:

  1. Free writing introduces sources, ideas, and questions and starts to connect them together.
  2. Summarizing organizes the information into a statement of what is known so far and what has been covered.
  3. Questioning identifies tensions and gaps that could be explored further in the future or invites areas of conversation.

Some Spring Cleaning

I started this blog to write small, informal blog posts. So far I’ve fallen back into the trap of writing “articles” that don’t really encourage conversation or provide new threads to pull on. While it’s not critical for doing the actual writing, I decided to re-classify my digital garden to encourage myself to focus more on riffs and notes.

Previously, I had two categories: Notes and Essays. Notes were supposed to be objective and focused on single topics; essays would pull together multiple notes to present a specific point of view. Obviously, neither category encouraged exploratory writing. I generally wrote less and focused on polishing my notes, which were supposed to be the rough form of writing. I seldom got around to writing essays.

I now have my digital garden organized into three categories:

  • Notes– Open-ended, exploratory riffs that connect 2-3 ideas or sources together. These are the heart of the digital garden.
  • Articles – Closed writing that thoroughly explores a single topic from a mostly objective point of view.
  • Essays – Utilizes either open-ended or closed writing to explore a single subject from a personal point of view.

How do you practice open-ended writing?

This particular post might be my first true note. It’s not meant to be comprehensive and it’s mostly my attempt to work out (in public) an approach to open-ended writing.

  • What do you find hard or challenging about writing?
  • Does changing the purpose to open-ended writing encourage you to write more? Or does it scare you?
  • Do you use a public platform or a private one? Is one better than the other, or are they just different?
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