Thinking tools (Overview)

This is a public Zettelkasten overview (see FAQ) of the concepts surrounding "thinking tools", aka "second brain".

Intro: why this overview?

I first came across the interrelated concepts overviewed here after launching myhub, and realised I'd been developing similar ideas as far back as 2013, when I first piloted this Hub on Tumblr (see Why you need a Personal Content Strategy). My ideas for MyHub evolved as a result - I now see:

  • the user's public hub as the part of their Second Brain which they share with the outside world using the ActivityPub open web standard for decentralised social networks (aka Fediverse - see related Overview)
  • the underlying MyHub content management system evolving into a Thinking Management System, with content productivity and creativity tools integrated within it. 

As far as I know this hasn't yet been done: creators are currently supposed to do their thinking in Obsidian, Roam or some other "thinking tool" software, and then publish their content using Wordpress, and then share it via Twitter. Why not make your public website - and the writing on it - a seamless extension of your second brain? And why not network it with other second brains via the Fediverse?

Why not make your public website - and the writing on it - a seamless extension of your second brain?

To turn these ideas into reality, however, I need to do a deep dive into thinking tools. I'm using my current personal content strategy - ie:

  • refocusing my Priority Sources (newsletter filters, Highlights Twitter List, etc.) on sources of high-quality content about thinking tools
  • queueing the best content they publish on a daily basis
  • reading and annotating it on a daily basis
  • reviewing that content on a weekly/fortnightly basis, and updating this Overview as required
  • developing my own ideas in the form of notes, newsletters and posts.

More: Simplifying Zettelkasten by working out loud

This Overview is therefore a crucial part of this process: it provides both a summary of what I have discovered in this space so far, and (below) a search result of the content I read when developing this Overview (stuff I Like), and the content I wrote and built as a result (stuff I Think and Do). In other words:

  • I'm using my personal content strategy processes to explore directions for MyHub's evolution
  • I'm using my current Hub to test how well its features support those processes today, and how they evolve
  • the rest of this Overview is a continual work in progress, written primarily for myself. If you want to see what I've written, then jump straight to All the Stuff I Do or Think about Thinking Tools, Anytime.

Key concepts

(Last update: 31/10/2021): When I created this overview I identified 10 pre-existing tags to use as a baseline: inbox zero, spaced repetition, 2ndbrain, fedwiki (for federated wiki), mindfulness, mindhack, (information) overload, roamresearch, weekly review and zettelkasten. That pulled in 44 resources, each with at least one of those tags. Of course, each had other tags as well, so I took them all and created a tag cloud to get a first picture:

thinkingtools: initial tag cloud

(Feature idea: AI & visualisation tools integrated into my backoffice to help better surface concept clusters and the explore links between them).

Some notes on the major concept (bundles):

  • Second Brain (2ndbrain): essentially a synonym for thinking tool (which I use, as I prefer verbs over nouns)
  • Productivity, GTD, Mindfulness: while a lot of the resources tagged mindfulness paint it as a racket, I still want a thinking tool that replaces FOMO with the serene confidence that my thinking tool has (a) captured the content I need to read, the stuff I have already read & the ideas I've already had; and (b) will easily surface it when I need it. It must support personal Getting Things Done (GTD) processes rather than become a GTD tool: it'll have a reading queue, for example, and hopefully provide a stream of ToDos to external task management tools.
  • Zettelkasten, Knowledge Management, Creativity, Ideation: the Zettelkasten personal knowledge management (PKM) technique will be a building blocks of the MyHub thinking tool, which is why I created an entire overview on it. My zettelkasten is currently distributed across several IT tools: this Hub (public bibliographic notes and other public content - i.e., the stuff I Like, Think and Do); Pocket (my reading Queue): Asana (ToDo mgt) and fleeting/permanent notes (Roam Research). While it works as a whole, it's hard to connect the dots between these different siloes, so I'll be exploring other tools as I develop this overview.
  • (Personal) Content strategy: content strategy is itself an important tag on my Hub (188 resources and counting) as it's a major element of most of my professional consulting gigs. In this context, however, the focus is on personal content strategy: what sorts of content are important to you, where do you put that content, how do you manage it, which types do you share, and how? While there's a major overlap with personal knowledge management, you need a personal content strategy first, as it defines the needs.
  • Annotation, Curation: If you annotate (make notes on) what you read as you read it, you're more likely to absorb the knowledge within it and apply that knowledge to your life. If you curate it (tag it) as well, you're more likely to find it again when you need it (assuming you have a half-decent knowledge management tool), alongside your own ideas and other notes (also tagged). Most people tag these notes in their thinking tool, which is private. By integrating thinking tools into MyHub, users will be able to keep some notes private and share others as part of their personal content strategy (next).
  • Progressive summarisation: successively summarising knowledge to better improve understanding and memorisation. This and other Overviews provide a simple example: after summarising each resource as I annotate it into my Hub, I summarise the knowledge of multiple resources in an Overview.
  • Fediverse: a "collection of interoperable social networks built on Open Web standards... [including] Twitter-lookalike Mastodon and YouTube-lookalike PeerTube", according to my dedicated Overview. It's here as well because linking Hubs together via Fediverse standards would allow users to expand their thinking tools to include the notes publicly shared by other Hubs, Mastodon & PeerTube accounts, etc. Moreover, those accounts would also be able to follow Hubs.

Key elements

Different tools have different elements, but here are some of the most important and/or common ones.

Flexible/difficult vs. inflexible/easy (aka 80/20 rule)

The 80/20 question (aka the Pareto principle) is central to productivity, and applies to many software tools - do you design it:

  • to be used in only one way: this makes it really easy to get started, but difficult/impossible to customise to your needs
  • or as a toolbox: each user can customise to its specific needs, but only after a lot of work?

The flexible/difficult approach is IMHO best illustrated by roamresearch: it's enormously powerful and flexible, but to take advantage of that you need to dive deep and geek out on templates and other plug-in code developed by 3rd parties. If you don't - like me - you end up with a lot of notes, but you're not harvesting the true power of your second brain. For me it fails the 80/20 rule: too much effort to get something useful out of it.

Bidirectional links

Extremely powerful feature. In essence, it means that linking from page A to page B adds a link from B back to A, but there's a lot more to it than that. I'm currently most familiar with Bidirectional links from roamresearch, where every page is designed like a Zettelkasten overview, and there's a page for every tag.

To be continued.

Blocks vs. pages

Does the tool use pages to manage knowledge? Or is a page simply a collection of blocks, each with its own unique identity, allowing you to find and manipulate it separately from the page in which it was first created?

Again, I understand this question principally through the optic of roamresearch, which takes the latter approach. To be continued.

Tools to explore

See: resources tagged ~2ndbrain and #tool. I am currently migrating from RoamResearch to Obsdian, but you can't throw a stone without finding another one being launched.


Automated links to recent, relevant Highlighted Resources follow. All resources here.


Stuff I (Really) like

Here are the latest 9 resources I've Highlighted about Thinking tools (Overview). There's more reading over here.

The Road from Roam to Obsidian
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After covering the "bullet train" trip (hubbed elsewhere), this provides a detailed elucidation of all the issues you need to address on "The road from Roam ... to" by summarising and linking to dozens of other posts, threads etc., creating "one place to look and minimize the pain of flipping through numerous p…

From Personal to Social Knowledge Graphs: a vision statement
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I've been invited to write a chapter for an upcoming book on Personal Knowledge Graphs (PKG). My chapter will encompass each user’s PKG, the Social Knowledge Graph created by networking them together via the Fediverse, Solid hosting, AI writing tools and Decentralised Autonomous Organisations.This post provides a first draft of its Introducti…

Obsidian, Roam, and the rise of Integrated Thinking Environments

Covers "a new class of apps called “Integrated Thinking Environments (ITEs)”... [and] NOTE framework, used to describe the specific feature sets ITEs provide... examples and some future directions".The term ITE riffs off "Integrated Development Environments... provide developers a comprehensive set of tools ... a kind of augmented c…

Personal Knowledge Management is Bullshit
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"the underlying problem is stubbornly intractable"Great piece, although I'm unsure that "a great proportion of the variance in “knowledge management” effectiveness across individuals is genetic", it is true that:productivity geeks exist, develop their system and then try to sell it.speaking from experience, it is really, r…

Wiki as a Commons | Gordon Brander

Wikis are like Minecraft for thought — very simple, very open-ended... can generate complex living systems, from personal notes, to collaborative fansites, to Wikipedia.While open-ended, there's scarcity: there can be only one page for each name, forcing "negotiation, communal norms, communal goals, communal meanings... Open-ended meanin…

Evergreen notes, outlines and executable writing strategy | Andy Matuschak

Having fun using Andy Matuschak's wonderful site to explore his innovative ideas on note-taking, zettelkasten, writing, etc. This link opens a number of his interrelated notes, displayed horizontally using his innovative 'stacked notes' information architecture.Key ideas from this stack:the importance of 'task division' in…

About these notes | Andy Matuschak

Andy Matuschak's working notes "are mostly written for myself: they’re roughly my thinking environment... But I’m sharing them publicly as an experiment ... [see] Work with the garage door up... Write notes for yourself by default, disregarding audience)... there’s no index or navigational aids: you’ll need to follow a link to some start…

The Garden and the Stream: A Technopastoral | Hapgood

I suspect this will be a canonical text for me moving forward with Caulfield in 2015, when my first hub was only about 2 years old, had also "been experimenting with another form of social media called federated wiki... instead of blogging and tweeting your experience you wiki’d it. And over time the wiki became a representation…

The Memex Method. When your commonplace book is a public | Cory Doctorow
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One of my favourite writers (offline and online) on his personal content strategy, first taking aim at the "tawdry and mercenary" version of "“why writers should blog”... the story goes, “and build a brand ... to promote your work.” Virtually every sentence that contains the word “brand” is bullshit, and that one is no exception.&qu;…

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