A Bicycle for the Mind: An Odyssey

Not second brains, but mind bikes.

What a computer is to me is, it’s the most remarkable tool that we’ve ever come up with. And it’s the equivalent of a bicycle for our minds.

| Steve Jobs

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I’ve written a great deal about what others call notetaking tools and which I call workings: tools to think, create, and remember alone, in groups, or in communities. Indeed, it is the name of this publication. (I also use the synonym ‘work processing’, frequently.) These are tools like Notion, Obsidian, Roam Research, Dropbox Paper, and Microsoft Loop.

In this post, I will share my personal odyssey using all manner of note-taking tools on my path toward work processing nirvana.

There has been an explosive evolution of workings tools over the past few decades: from simple text editors, to outliners, to web platforms, to off-the-platform markdown tools, and quite recently to tools capable enough to be considered ‘bicycles for the mind’.

I am sidestepping various terms like ‘second brain’ or ‘tools for thought’ — they seem a bit grandiose — but I am influenced by the finding that human-power bicycles are the most efficient machine ever created. Converting human calories into the gas equivalent, a human-powered bicycle gets the equivalent of three thousand miles per gallon. A bicycle’s motive force — its motor — is the human on the seat, pedaling. The bicycle itself does nothing until the rider’s foot hits the pedal.

Just so with workings tools. We, the users, are doing the pedaling. Tools like Obsidian or Notion just sit there until we engage their machinery to drive our goals forward.

Sufficiently advanced context-centric workings tools are truly bicycles for the mind and the most advanced tower over the others, like a 20-gear graphite composite bike compared with a child’s tricycle. And I should know because I have ridden all manner of wheeled contraptions over the past decade, and now I feel like I am in the ‘thousands of miles-per-gallon’ echelon.

No more tricycles or training wheels.

My Odyssey

Over the past dozen years, I have used many workings tools, including some that I adopted and used for many months or years, including Evernote, Workflowy, Dynalist, Dropbox Paper, Typora, Notion, and Obsidian¹.

My odyssey was driven, in retrospect, by the belief that I would find a tool that could be the bicycle of the mind, that could serve a system of record and system of truth, a place where I could write today, recall tomorrow or next week, and create relationships between parts of my working set of content, inspiring insight, reflection, and synthesis into a network greater than the sum of its nodes.

I had preconceptions, even at the outset. I wanted text to be the principal element but needed rich media, PDFs, and other media types. I wanted to be able to create connections based on hypertext principles. I wanted tasks to be first-class objects. I wanted structuring elements like notes, folders, tags, and others.

I operate principally as an individual, not a team member working closely with others. But that is the core use case for any tool because, as I have written many times before, the individual is the new group. A tool must satisfy the needs of the individual user before scaling up to support groups or larger organizations. Social equals ‘me first’.

Evernote — I adopted Evernote not long after Phil Libin reoriented the former Windows-only tool in 2008, slowly migrating from my long history of paper-based note-taking. I quickly realized that the company was building very different tools on various operating systems, creating annoying silos. By 2010 or 2011, I was seeking a tool that was more than just digital notes in digital notebooks. During my time using Evernote they added — and in some cases dropped — interesting features, but it never came together to be more than a folio of notes.

Workflowy/Dynalist — I migrated from Evernote with a few thousand notes exported to my hard drive, and cut over to a new conceptual model: outliner. I started in Workflowy, but moved to competitor outliner Dynalist after a few months, because of a more aggressive product roadmap. In the earliest form, these offered a single gigantic file, but have later moved to support folders and files. The two share the fundamental model of nested outlines as the structure of all notes. At first, I believed that outlines would help structure complex information, but I quickly felt it was impeding a more traditional model of content creation. I am, after all, primarily a writer, not a list-maker. They did introduce me to markdown — incorporating that text-based formatting markup language a bit at a time — but I felt constrained by ‘every paragraph is an element in a bulleted list’.

Hackpad/Dropbox Paper — I transitioned to Hackpad prior to it being acquired by Dropbox in 2014, and when Dropbox announced it I joined the Paper release, with great borrowing from Hackpad. Paper is a collaborative editing tool derived from the ideas of tools like Google Docs, with a rich capability for collaborative editing, but not based on physical pages. It provided from the first a simple editing canvas with an integrated task model. It was from my perspective the first web-based content-centric work processing system. However, it never acquired the hypertext and advanced markdown, spreadbase² tables, and plug-in ecosystem capabilities that typify today’s ‘mind bikes’. Dropbox attempted to integrate Paper into its Dropbox file sharing, but that transition led to the loss of some capabilities. I grew disenchanted with Paper’s slow-roll product development and exported my documents in 2018 using Paper’s export-to-markdown feature.

Typora — I had searched for and tested ten or more markdown editors, sometimes for a few hours, and in some cases weeks, looking for a tool with more of the ‘mind bike’ kind of features I felt I needed, even prior to knowing what exactly those features would be. I wanted markdown, particularly for the capability now common in leading tools to reference a file B in file A by the use of double brackets: [[file B]]. This allows for the creation of a network of interlinked files, all in plain text files sitting on my Mac hard drive. I also wanted to be able to use both a folder hierarchy and tags to organize and search for information. And the leading markdown editors of the late 2010s all supported task management to one degree or another. Typora was the eventual choice, and I relied on it for several years, all the while knowing it was a fixie, and I needed a 20-gear touring bike.

Notion — I tested out Notion for a few weeks before migrating to that spreadbase-like, cloud-based, richly collaborative tool. I tried to take advantage of the capabilities of Notion’s spreadbase tables, where various views can be applied to the information managed, and new views can be generated by linking data from one table to another. However, I found that these capabilities were relatively heavyweight for a soloist focused principally on researching and writing. I needed dumb tables, not smart ones. So I fell back to a model of use quite like I had been using in Typora. Also, although Notion has a rich model of sharing — so documents could be collaboratively edited with others — I seldom found that others had experience with Notion, so even if I invited them to guest accounts, I had to walk them through the user experience at length. It was easier to simply share a Google Doc. I departed after a few months and went through a hellish experience exporting from Notion, and returned to good ole Typora until something more bikely came along: Obsidian.

Obsidian — My adoption of Obsidian had been shaped by my decades of experience using many, many tools: all those enumerated above and dozens more. But the most recent experiences — Paper, Typora, and Notion — had the most significant legacy impact. At first, I simply continued with the work patterns I had developed in Typora. Because both Typora and Obsidian operate on a collection of plain text files on the user’s hard drive, I was able to simply turn on Obsidian and manipulate the files and folders I had created in Typora: there was no import step involved. But because of the greater breadth and depth of Obsidian’s capabilities, I quickly evolved a different approach, and over the first years, Obsidian’s development team and extremely active user community have created a great range of capabilities not present in Typora or in earlier generations of Obsidian. In particular, I have come to rely on features like block references, where any paragraph can be assigned a unique address and, therefore, can be ‘transcluded’ to be rendered in another file. I can then, for example, refer to some quote or fact from a note I may have created by clipping an article from the web, and include it in a Kanban table (or in the new canvas capabilities), for use in an upcoming article. I can rely on sophisticated search queries using plugins like Dataview and Advanced Query Control to pull information into tables or lists based on tags, file names, or text search. I found a bike with twenty gears, at last.³

My experience is not general. As I stated, I am principally a writer, and most of my criteria for tool adoption are driven by that, along with necessary project-oriented task management to keep track of my ongoing work with clients. Others have significantly different goals, and my insights may be less relevant. However, the philosophy of using ‘mind bikes’ can be sliced a different way, not based on what we want to accomplish, but on how we think about organizing the elements of our thinking about the world and our work.

Minding Your Bicycle

I’ve spent a great deal of time on my odyssey, and I haven’t reached my home port yet, I don’t think. It could be that Obsidian will continue its explosive trajectory of adding new core capabilities, like the recent mind-map-like canvas that was rolled out in late 2022.⁴ I would like to see Obsidian develop core capabilities for shared access to notes, but that could be some time off. However, I am mostly operating as a soloist, with occasional collaboration with others, almost always channeled through a cut-and-paste into a Google doc because everyone is familiar with it.

But the use of ‘mind bikes’ is growing, and the concepts found in tools like Notion, Obsidian, and Dropbox Paper are becoming widely understood, even while the tools are innovating their way forward into the future.

I will keep trying new functionality — in Obsidian and other tools — and adopt new handlebars, seats, and derailleurs as they come into the market of ideas. I will keep minding my bike, so I can decrease the friction involved in my workings, as much as possible.

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1. Note that because of the dominance of Google Docs, I have continued to use that — and other tools — when collaborating on docs with others. Nowadays I am seeing a lot more Notion used in that way, as a means of content-centric collaboration.

2. Spreadsheet-like databases.

3. A complete exposition of Obsidian’s capabilities is beyond the scope of this article.

4. Again, out of scope for this article.