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Antifragile Writing

Designing a writing framework not just chaos proof, but that grows and gains from stressors. Come if you prefer jungles to gardens, freewriting instead of slip boxes. If you aren't afraid of disorder.

CurriculumAll CohortsFacilitators

How many notes and ideas get aisle, lost, or broken in what we write in our journal, notebooks, drafts, documents. or apps? How many concepts, stories, essays, not only survive the past of time but grow with it, get stronger, and generate new thoughts? Is there a writing capable to gain from the natural disorder of things?

This course explores how can we make our writing less fragile and more robust, even antifragile—the opposite extreme of fragile, according to the thinker Nicholas N. Taleb, author of Antifragile: Things That Gain From Disorder.

How Antifragile Writing was born.

In the middle of the year of living under uncertainty, I wanted a writing system, a writing workflow that not only could survive disorder but get the advantage of it.

Antifragile is a good term to use here. I wanted an antifragile writing to use in the middle of the chaos.

Things, systems that break or lose with stressors or disorder are fragile.

Some things and systems can be less fragile. Others can even have zero fragility against some stressors. We call these systems or things robust.

The interesting thing here is things and systems that not only aren't affected by stressors but grow, gain or get better with them. We call them antifragile, the opposite to fragile.

Bones need stress to stay strong or even to get stronger. If no stress is applied to them, they get weak and start to deteriorate. Bones are antifragile. Some particular stressors and in specific quantities, of course.

A model for antifragile things considers stressors as the trigger or detonator for growing or gaining. So, for antifragile writing, you have to find the stressors that make you write more and better.

It was obvious to me that some stressors can do that. The classic example is when you have a deadline that impulses you to do the work. Or the public comment to one of your posts that encourages you to write a reply or an answer.

Under that idea, I started to design a framework and test the hypothesis. I didn't try to reinvent the wheel, so I started to collect—or recollect because I already have most of them—techniques that could work with it this antifragile writing.

I even took some of the writing styles or processes of old and known writers and thinkers that, I think, fall down this category of antifragile writing.

That's how Antifragile Writing was born.

Course Goals

Each participant will develop a workflow for antifragile writing, a writing that embraces disorder, gains with stressors, and grows with optionality.

We’ll take advantage of the most outstanding and newest apps for note-taking and personal knowledge management, Roam Research, logseq, Athens Research, RemNote, Obsidian.md, especially suited for making sense of disorder.

We'll share a common Roam Research database (in multiplayer mode) for the course. But all the techniques and methods can be used in any of the last generations of personal knowledge system apps. You can use the database for practice, testing, and sharing with the class.

Each participant will develop a workflow for antifragile writing, a writing that embraces disorder, gains with stressors, and grows with optionality.


Every week is thematic, with a topic, resources, exercises, and writing prompts. Participants are encouraged to follow the writing practice around their own writing, ideas, or issues at hand. Those who choose to keep a particular project can work on it during the course.

There will be a shared database in Roam Research for all the participants to use as a sandbox, taking and sharing notes about the topics of the course, and for some collaborative exercises.

Every week we will have a synchronous session via video chat with a duration of 2 hours. Sessions are recorded in case you miss them. Another hour of asynchronous work—reading and writing, basically—with a total duration of 3 hours approximately is expected.

Every week there will be office hours available for shared writing sessions.

Every week there will be resources to read, check, listen or view in preparation for the topics of the following week.

Syllabus / Schedule

Week 1: Antifragile

What is antifragile? What are the advantages of being antifragile? What are the properties of antifragility? What makes writing antifragile? Why an antifragile writing?

PKMs basic walkthrough. Roam Research. Three basic elements to start writing on Roam: Daily Pages, outlining, linking. Differences between apps.

Week 2: Tools of Personal Knowledge Management (PKM)

What is a PKM? Tools for thought before and now. What makes Roam Research, logseq, Athens, Obsidian, RemNote, apps for antifragile writing? The two stages of writing. Note-taking, freewriting, drafting. Reviewing, editing, migrating.

The two stages of writing. Note-taking, freewriting, drafting. Reviewing, editing, migrating.

Week 3: The foundations of antifragile writing

Antifragile writing The principles of antifragile writing: a list for embracing disorder and welcoming stressors for the evolution and growth of your daily practice. Antifragile writing before Taleb: thinkers and writers that wrote antifragile text. How to use PKMs for antifragile writing.

Week 4: Techniques of antifragile writing I

Thinking and expressingNietzsche: aphorisms and rumination. Writing aphorisms. Define an idea, explain after. DaVinci's variations for expression. Write fast, explore combinations, subtractions, or additions later.

From simple to complexEuclid's ideas in movement. From simplicity to complexity, one step at a time.
The rhizomatic craft of Deleuze & Guattari. Cultivating and growing first, pruning after.

Week 5: Techniques of antifragile writing II

Learning from analog methodsBullet journaling basics. Logging, bullets, collections. The importance of migration.
Basics of zettelkasten. Write first, organize later. Index cards as an elemental unit. Nesting and linking.

Contemporary approachesTaleb's fractals or the craft of repetition. Layers and recursion. Fragments. The art of provocation.
Matuschak's evergreen note-writing. The writing inbox for transient and incomplete notes. Drafting evergreen notes.


Each participant will develop a personal workflow for antifragile writing with the preferred app, design and test their own templates, routines, tags, groups, etc.

Additionally, participants will follow the writing and project prompts during the course to develop a specific project for the course—book's first draft, essay, paper, etc.—, or take advantage of the techniques just to think deeper about their current topics.

Who Should Sign Up

Writing Lovers

For any kind of writing practice: note-taking, blogging, researching, journaling, authoring

Passionate Thinkers

Those who can see writing as the doing of thinking, as the essencial tool for thought

Tireless Learners

Problem solvers, brainstormers, mental modelers, seekers of algorithms of thoughts

5 weeksUp to 10 learners
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