The Joy of Imperfection
Getting Messy with Personal Knowledge Management
Thinking is messy.
I tell this to my first-year university students every semester, but they look back at me with glossy-eyed stares, thinking that I’m giving them another lecture on why they shouldn’t procrastinate on assignments. But that’s not true.
I want them to procrastinate more effectively.
It’s a hard sell, like most of what I teach.
In Deep Work: Rules for focused success in a distracted world, Cal Newport argues:
“The key to developing a deep work habit is to move beyond good intentions and add routines and rituals to your working life designed to minimize the amount of your limited willpower necessary to transition into and maintain a state of unbroken concentration.”
Concentrating on a thought for any length of time requires a lot of willpower. And to preserve our precious mental clarity and focus, we need to develop habits of practice — rituals that help us overcome the anxiety that often keeps us from starting a challenging task.
You might be asking: What are your secrets, oh wise one? How can I think faster, smarter, and longer?
For the low cost of $29.99 a month, you can find out with my subscription-based…
Wait. Sorry. I got caught up in the spirit of the moment. The answer to your question is more complicated—and more personal—than a recipe.
The Productivity Trap
Personal Knowledge Management (PKM) is a newer buzzphrase in an already crowded field of productivity terms. Productivity itself is an expansive topic, complete with warring factions fighting on behalf of their preferred systems keyed to the vague goal of success.
Okay, yes, that’s a hyperbolic statement, and generally there’s recognition that no one productivity method is universally suited to everyone. We’re better off thinking of them as a buffet of options.
Most productivity systems focus on taking action as quickly and efficiently as possible. For example, Getting Things Done (GTD), pioneered by David Allen, aims to catalog all possible tasks and actions into an external database (either analog or digital), with the goal of prioritizing important actions that can be completed at the moment, while ensuring that the external system tracks everything that will need to be completed in order to free up mental space.
GTD makes action items the focal point of productivity, and it’s had a lot of staying power. Countless todo list apps on the market — OmniFocus, Todoist, TickTick, Amazing Marvin — aim to provide a framework for GTD and other action-oriented approaches to being productive.
These frameworks keep us from wandering off into the forest alone. They’re important. They provide focus, accountability, and stability in the day-to-day operations of our lives.
But they don’t help us think better. Not directly.
Remember, thinking is messy. And while you might be able to add a cognitive task like brainstorming to your todo list — and you might even be able to break that task into smaller items like outlining or mind mapping — nothing about that checkbox will help you do the mental work.
When it comes to thinking, you don’t need a checklist as much as you need a heuristic — a set of strategies or shortcuts to help you grapple with challenging questions, such as:
- What do I need to learn?
- Who is my audience?
- What do they want/need to know?
- How can I frame this idea in an interesting way?
- Why the hell does this idea matter?
Answering those questions calls on us to draw upon entire constellations of knowledge we’ve encountered in the past or have yet to investigate. So, while heuristics and task lists provide a direction, they don’t map a territory of knowledge.
This gap between regimented practice and messy thought is what Personal Knowledge Management systems attempt to bridge.
My students often think that research is a process of fact-collecting. It goes something like this:
- Receive the prompt for an assignment
- (Optional) Read the prompt for an assignment
- Google the topic of the assignment
- Copy and paste information from their search
- Reorganize and rewrite that information
- Report back findings
Typically, students start the semester feeling that they have nothing valuable to add to a conversation. They’re novices, after all, and even a simple Google search for information can turn into a labyrinth of concepts and models. That is, if they dig into the topic.
It’s much easier to treat any information out there on the first page of results as the Word of God passed down by the Almighty Algorithm.
But thinking isn’t linear. Understanding a new or unfamiliar idea doesn’t occur by reading one article or book.
Thankfully, there are many tools that help with this challenge. Tools far older than the internet. Early on, I teach my students to use a two-column research notebook for their research.
The concept is simple. Take a sheet of paper (or a page in a notebook) and draw a vertical line, dividing the paper into two columns.
I know. Thrilling stuff, this.
In the first column, record important ideas that you encounter in your reading. This can include quotes, but only if those quotes are the stuff of genius. It’s usually better to paraphrase to ensure you understand what you’ve read.
The second column builds connections and depth. Once you complete the preliminary research, you should review the material in the first column and ask yourself:
- Why does this matter?
- How does this connect to other sources I’ve found?
- How/why does this support or contradict other information I’ve found?
The second column is the most important because this is where new ideas are born through the mixture of information. But the work that happens in that second column is also work that’s often absent in novice research.
As a tool, the two-column notebook is a fantastic way for researchers and writers to find their voices. It helps us transition from collecting information to synthesizing information. In the space between the two columns, creativity is born.
On Zettelkasten and the Digital Tools of Thought
Of course, the two-column notebook is just one of many analog systems for organizing ideas. Lately, the Zettelkasten or “slip box” has grown popular thanks in part to Sonkë Ahrens’ book, How to Take Smart Notes, which focuses on a card-catalog-like system used by sociologist Niklas Luhmann.
Luhmann used small scraps of paper to create concise, meaningful notes that were assigned a catalog number that could then be cross-referenced on any other note to create analog links between ideas (much like the links connecting pages on a Wiki). The Zettelkasten allowed Luhmann to externalize his thoughts and helped him sort messy ideas into coherent essays and books.
In much the same way that todo lists could extract tasks from the mind, the Zettelkasten allowed Luhmann to work through concepts and knowledge that otherwise might not have been connected. While notes occupied a specific physical place within the system, links created between notes grew organically over time and connected ideas that might have been very far apart physically.
This is the barest explanation for a Zettelkasten, but so much has already been written about the method. Ahrens book is likely the best place to get started if you’re still curious about the analog method.
But the Zettelkasten also helps us to begin questioning one of the foundational structures of modern computing: folder-based file organization.
If you’ve ever spent time trying to organize your files on a long-used and well-loved computer, you know the process can be Sisyphean. Files have to be hierarchically structured in folders and sub-folders, and each user has the task of figuring out how to best organize and categorize those folders.
Sure, you can rely heavily on defaults like the “My Documents,” “My Music,” or “My Downloads” folders that come standard on almost every operating system. But when you hit a certain critical mass, there’s a need for subdivisions. And this can mean losing track of files. They might not disappear from your hard drive, but they certainly might disappear from your mind.
Platforms like Evernote can help by adding strong functionality for tagging, but it still requires some kind of hierarchical structure involving folders. Thus, in the shadow of the todo list productivity system boom, it was only a matter of time until a new wave of “thinking applications” hit the web.
Now, digital software for creating Zettelkasten are not entirely new. Some have been around for decades, but most existed outside popular consciousness and might not have been attuned to modern UX design. That changed somewhat with the release of Roam Research.
Roam Research is a web-based platform that seeks to eliminate the tyranny of folder-based organization. While an approximation of folders is possible, the goal of Roam is to create a flat structure where individual notes are all created equal. Instead of using folders, Roam instead creates networks of links similar to a wiki. Anytime a user creates a new page, they do so by creating a link to the new page, which means each page can be linked to at least one other, and a visual graph can show these relationships.
It sounds like a simple concept, but its implementation fosters connections between ideas that might not be apparent if a user’s notes all existed independently of one another. While the desktop metaphor of a computer requires a top-down structure where users consciously create the structure that houses their files, Roam Research operates from the bottom-up, with connections between files emerging organically as you create new notes and link them to others.
Designing systems can be incredibly fun. I once spent upward of two weeks building out a personal productivity system in Notion that made use of complex relational databases and kanban boards. It was powerful, but much more of my time went into creating the system rather than working on the projects that were being organized by the system.
I love tinkering with applications, but I needed to get past the system and get to work.
A Necessary Tangent: What Do We Mean by Productivity?
Productivity hacks are everywhere. You can fill your entire inbox with newsletters showing you the “best” way to get more work done with less effort. And for the low price of —
Sorry. Let me try this again.
As I’m writing this, I’ve been burned out for months. In the past few weeks, I’ve started to recover. But all this talk of productivity nags at me like a stubborn toothache.
Productivity systems are as fantastic as they are insidious. The tools and metrics we use to measure productivity privilege external actions. They might wrap wellness and mindfulness into their foundations, but the unspoken assumption is that a life without productivity — and specifically production for building capital — is unfulfilling.
Cal Newport (Deep Work), David Graeber (Bullshit Jobs), Anne Helen Peterson (Can’t Even), and Jenny Odell (How to Do Nothing) are just a few of the authors writing about the hazards of the modern push for ever-increasing productivity. Many of them have found that our current notions of productivity are counterproductive and potentially harmful. If we measure our worth only in quantitative metrics, we risk the messy processes at the heart of creativity and nuanced thought.
If you’ve ever read an interview with a visual artist, you’ll hear a few familiar refrains. It’s important to establish habits and routines that make doing hard work easier. But equally — maybe more important — is carrying and filling sketchbooks with rough, unpublished drawings.
Sketchbooks, especially those of masterful artists, can be incredibly beautiful, and they do occasionally become “finished texts” of their own for fans of the artist, but they’re not meant to do public work. They’re meant to be blank canvases that encourage experimentation and development. They’re avenues for play that might lead to novel compositions in the future. They also might lead to nothing, and that’s just fine.
That’s the point.
Rather than focus time on crafting the perfect productivity system, I’ve become a fan of embracing the imperfect system. The system that can grow and change, leaving behind ragged messy edges, which retains its value over time.
Perfect systems look nice, but perfectionism has been the death of far more ideas than laziness or lack of motivation.
On the Perils of Min-Maxing
I first encountered the idea of min-maxing in Massively Multiplayer Online games like EverQuest or World of Warcraft. In these games, players would spend a lot of time figuring out how to create the strongest character builds by doing detailed analysis on how certain equipment could boost various stats. The goal was to create the ideal and most effective character using all the resources at hand to be more successful at the highest tiers of these games.
To me, this mindset looks similar to the practices in many productivity circles. Now, not everyone subscribes to this, but a quick Google or YouTube search will point you to videos claiming to have developed the most efficient, effective, and rigorously tracked system for boosting your output.
More than a few of these will send you to a digital shop where you can purchase all the secrets of these systems or enroll in a specialized course.
And this is fine.
Like I said, there can be enjoyment in crafting a good system. Investing time in productivity can be quite unproductive. And again:
This is fine. Do what you love, and I know that I love an elegant system.
I mean, I probably won’t use it for long, but I do enjoy tinkering with it.
For me, the sweet spot of productivity (order) and creativity (chaos) is a tool like Obsidian.
Obsidian and Imperfection
Obsidian is an application that functions much like Roam Research. Oh, and it’s free.
I use Obsidian for writing, and I’ve begun thinking of it in the same vein as an artist’s sketchbook. In the program, I can experiment and play with ideas by linking together different notes. I can throw almost any kind of written information into this beautiful system and link ideas together easily.
And while it might lack a few features that a premium service like Roam Research can provide, it also has some benefits. It can work as a flat hierarchy, but you can also arrange files into folders and sub-folders.
It also makes use of plain text markdown files, which means that everything you write and build through Obsidian can be opened on any computer built in the past three decades or so.
How’s that for longevity?
But let’s be honest here: the tool doesn’t matter. There are other fantastic free alternatives out there, from logseq to Zettlr, that do similar things.
In my mind, there’s only one useful metric for evaluating a system: how much do you use it?
I used to be so focused on ensuring the consistency across my system that I’d focus more on document structure than I did on document content. Everything looked pretty, but it was also shallow.
When I came back to my Obsidian system after months of burnout, I might not have remembered all the specific templates I’d constructed. But it didn’t matter because I could jump back in and make messy notes that still link up to those I made back in my perfectionism phase.
Thinking is messy. And it takes time.
No system can make the process of developing new ideas easy. It can spur serendipitous connections, but it can’t get rid of the sometimes painful process of putting incoherent thoughts onto the page. And the process that works one time might fail the next.
But that’s the joy of it. Embracing messiness means we’re free to treat thinking like play. Some paths might lead to amazing destinations. Or they might be equivalent of staying at home and meditating. Both things are meaningful.
By all means, if you like to tinker, min-max to your heart’s content.
But I’d also encourage you to look for the joy of imperfection. Throw together words and ideas to see what kinds of odd combinations you can create. It doesn’t matter if you use Roam Research, Obsidian, RemNote, Zettlr, Notion, Evernote, OneNote, Word Docs, or physical index cards.
It doesn’t matter if you step away for weeks or months when you’re burned out.
It doesn’t matter if you hack your ideas together inelegantly.
You can’t simplify life into any one system or tool. Instead, make messiness your friend instead of viewing it as an obstacle to efficiency.