5 Rules for a Second Brain You’ll Actually Use

JA Westenberg, an essayist and creator of tools like Kerouac and Distributism.ai, outlines five rules for building a practical 'Second Brain' knowledge archive, emphasizing manual curation over automated ingestion and organization around problems rather than subjects. Westenberg argues that automating collection leads to overwhelming noise, citing a past experience where a month of automated ingestion nearly caused a panic attack. The rules, drawn from sources like 'The Craft of Research' by Wayne C. Booth and colleagues, aim to transform personal archives from hoarded warehouses into usable gardens.

5 Rules for a Second Brain You’ll Actually Use Tend a Garden, Don't Fill a Warehouse 🍕 I’m JA Westenberg. I write essays about technology, philosophy, productivity, and what it means to be human. If you like ideas that take their time, you’re in the right place. While you’re here, a few things I’ve built: Kerouac, a writing app | Post Through It, a solo microblogging tool | Distributism.ai, my MCP platform | Laterware, all the AI news you need | Studio Self, a thought leadership agency for founders x VCs. You can buy my book Permissionless here. The central anxiety of the Second Brain builders: if we don’t hoard every digital scrap, any possible gem could be lost for all time. But that fear can only produce one thing: a large, overpopulated archive in disarray and decay, rarely visited by its owners, rarely more than admired, and never actually used for any practical purpose. The reality is that collecting information is incredibly easy. Anyone and everyone can save anything and everything. Every single day we’re exposed to vast amounts of information that could - technically - become insightful at some point. Blog posts and videos, tweets and graphics, screenshots and quotes, links upon links upon links, constantly being surfaced and retweeted and shared on every feed and timeline. It’s a firehose of potentially relevant s t that never quite goes anywhere. The skill to actually judge this information is a good deal more scarce. I’ve been skeptical of Second Brains for a while now, but I don’t reject the entire concept out of hand. I’d rather try to get to a set of rules that can govern a personal archive - proactively - and turn into something that can actually be used. Rule 1: Never Automate Ingestion I have a hard rule against automating my knowledge collection. I’ve done it before, and it’s easy to get pulled into feeling like you’ve developed superpowers; piping the world’s best bloggers and thinkers into Obsidian or Notion via Readwise, running RSS feeds via Zapier, etc and giving your knowledge base free rein to grow . The last time I did this, I left the automation alone for a month, and when I came back I almost had a panic attack trying to sift through the immense volume of noise that had accumulated in every single folder and tag. The goal had been to reduce the friction and see what emerged on its own. But friction, as it turns out, isn’t always a bug. These days, I manually choose everything that enters my system, forcing myself to exercise agency in an act of judgment and aim for a higher bar of ingestion. It’s not enough for a blog post to come from a source I’ve pre-approved. It has to be a good article on its own. I only save something if I can articulate to myself why I’m saving it; why it matters; what it changes; and where I expect to use it. If I can’t be f ked to spend 30 seconds writing a single sentence about the object I’m stashing, it probably has no place at all in my notes. Rule 2: Organize Around Problems, Not Subjects This comes from a book called The Craft of Research https://en.wikipedia.org/wiki/The Craft of Research by Joseph Bizup, William T. Fitzgerald, Wayne C. Booth, Joseph M. Williams, and Gregory G. Colomb: When beginning researchers start to organize their material, too many sort it under the most obvious topics, arrange those topics into a plausible sequence, and start writing. Unfortunately, the most obvious topics may be the least useful, because they probably reflect not what you discovered through your own hard thinking, but only what your sources gave you. And even if those topics do go beyond the obvious, they are likely to constitute only a linear sequence A + B + C + ... , a rhetorical structure rarely strong enough to support a long and complex argument. The worst result is that you just summarize someone else’s ideas. It’s a great read, and the Kobo 5th edition is worth the $20. We tend to assume that knowledge should be organized into filing-cabinet categories. We put everything into neat boxes and folders marked “Psychology,” and “Marketing,” and “History.” But these are top-of-funnel markers; they’re not reasons to think, and they’re not catalysts for thought. I’ve replaced my Topic folders in Obsidian with tags focused on either questions or highly specific, time-bound projects. Questions in particular have a stronger sense of momentum and direction, and I find I can pick out a thread a good deal faster and with more depth to boot. “Why do people abandon good habits?” is one recent tag; and it’s a far more useful place to collect scraps of research instead of shoving anything that vaguely pattern matches to “habits” into a folder marked “Behavioral Psychology.” Rule 3: Save Notes That Disagree With You You’ll never think differently if you compile reasons to think the same. When your archive is a shrine to the things you already believe, you’ll never break out of your bubble or have the information you need to push back against your weakest ideas or your least interesting assumptions. But isn’t that the point of expanding your knowledge in the first place? If you’re not running headlong into yourself, you’re really just collecting shiny rocks. And they may be nice to look at, but they won’t make you a better thinker, writer, or founder. A good knowledge base isn’t actually a single coherent worldview. It contains multitudes, and it preserves productive tension, until your own experience and // or evidence clarifies, disproves, or erases it. Rule 4: Delete, Don’t Just Add Growth is a bad way to measure most things. It’s an exceptionally poor measure of a knowledge base. Having 10,000 beautiful notes in one of those gorgeous graph views people love to share on Twitter is meaningless if those notes don’t contain value, information you need, connections that are worth making, etc. Celebrating compost heaps of notes, links, and highlights as evidence of your Great Thinking is like claiming to be a brilliant software developer because you’ve generated more lines of code. The two might go hand in hand, but there’s no actual causality. Outdated and duplicated, vague and unused notes just create huge amounts of cognitive noise, and they turn your “PKM” into a hulking mass that gives you enormous anxiety and actively discourages you from poking at it. My attempt to counter this has been to actually spend at least an hour a week pruning - reviewing notes, removing and merging items, and either processing or deleting at least one object for every five I add. I aggressively delete anything my brain marks as “someday useful.” If there’s a helpful analogy, it’s probably to think about your own knowledge as tending to a garden, rather than filling a warehouse. Rule 5: Never Review Without Producing Something ...which brings me to the last rule. I never finish my weekly review without producing something. Every review has to result in an external output. It could be a single paragraph, even a single sentence, an experiment, a question, an idea for a blog post, something to change my own behavior. But for the review to mean anything at all, it has to change something in me. I enter a review session with a goal and a purpose in mind - it’s never “sort through my notes”; it’s “find something to write about,” or “find an idea for an app.” A knowledge base as proof of how much you know is a waste of your energy and your mental space. It gets you nowhere, and it impresses nobody worth impressing. Instead of existing as a tomb where you pile in dead knowledge, it should be an active tool that gives back to your life and your work in some measurable way. The better knowledge base is slower to fill, harder to wrangle, smaller than Wikipedia, and accessed and interacted with as often as possible. It’s constrained rather than given endless agency to grow and mutate on its own, until your knowledge becomes something you no longer even recognize. There’s nothing particularly wrong with saving things you like. But the things you save should save a part of you, or at least your time, or at the very least your capacity. “Knowledge is of two kinds. We know a subject ourselves, or we know where we can find information upon it.” — Samuel Johnson