My First Knowledge Management System Failed. Here’s What I Learned:
Introduction
Many of the people interested in productivity, self-improvement, and personal knowledge management have perfectionist tendencies, myself included. There’s not only a deep desire to nail the perfect system for all our use cases, but to get it right on our first try, instead of messily or incrementally. Otherwise, we might spiral or give up in the face of failure or initial resistance. These desires and anxieties often results in spending more time tinkering with and designing the ‘ideal’ system instead of doing the work we initially set out to.
I was one of those people until I bit the bullet and tried to design my own system and just test it, warts and all. Initially it worked, until I began noticing friction accumulating. Wanting to fight my perfectionism, I kept pushing ahead, until the increasing pain points of this workflow caused it to collapse. Despite this, the process was an incredibly valuable experience, and one I don’t regret. So I want to share my journey of failure and refinement. I’ll explain:
- Why I needed a system.
- What the first system I designed looked like, and how it functioned.
- What I learned from trying it out.
- How it lead to a much simpler & more sustainable workflow that I currently use.
The Problem
I have a lot of ideas.
They come from an overactive ADHD mind combined with a deep love for storytelling and media, in all its forms. For example, I have millions of pitches and concepts for the written word alone: novels, short stories, scripts, essays, blog posts, etc. Some of those blog posts could also work well as vlogs, too. Because I love media criticism, I also adore visual essays. So now in addition to writing, I want to make videos, too.
On top of that, I’m passionate about audio storytelling and am currently in school for audio journalism and radio specifically, so I have a bunch of podcast ideas too. In short, if a medium exists (👀), I probably have an idea for it.
Not only do I have a million ideas, I’m also constantly engaging in and fascinated with the ideas of others.
If you love storytelling like me, chances are you love the craft of narrative, and how those narratives intersect with our society. So you start reading about media or literary criticism. But then that pulls you into overlapping subjects like history, politics, and more. Depending on your own identity and experiences, you also might be engaging in ideas to make sense of who you are as well.
So for me, I’m an immigrant and not white: issues of colonialism, race, and politics interest me personally. I also have had formative experiences of trying to rebuild my life after a huge mental health crash and my ADHD diagnosis. So, like many of you, I also have been into books, articles, videos and podcasts on health, wellness, productivity, and finance. Therefore, my to-read/check out list is perpetually overflowing.
In short, my mind is buzzing with my thoughts, and churning on the thoughts of others. I need places to organize and put all these thoughts down.
At first, I used just paper, pen, and my default notes app. Pretty soon these ideas scattered everywhere, creating both digital and physical clutter. I was frustrated and overwhelmed. Then, as I delved more into the productivity world, I discovered Personal Knowledge Management Systems. Suddenly, there seemed to be a rope dangling right in front of me, offering me a way to climb out the mess I was in.
I could dump ideas and manage projects in Notion! I could take notes and link them in Obsidian! With each video I learned about the amount of integrations with these apps, their pro’s and con’s, and so much more. All of it became an overwhelming cacophony within my mind: I wanted a system that could do it all; write notes and documents, curate ideas, sync with Readwise for the content I was consuming, and do this all in a secure, seamless way.
After drowning in options, eventually I took a deep breath, and starting iterating. There were a lot of bumps to get there.
The Solution, Sort Of (Notion + Readwise + Drafts)
I started with Notion, because I was familiar with it through a previous job. Its database functionality is powerful, so it became a perfect place to dump ideas, tag them, and throw in links to any research and information. The only problem I encountered is that Notion isn’t great for writing and working on those ideas, especially offline.
So I looked at its main rival within this space: Obsidian.
Obsidian, with its ability to sync with Readwise and take notes on Podcasts and YouTube videos via PodNotes and MediaDB, combined with its database extensions, seemed like a perfect fit for both note taking and idea management. But it was such a pain to get all these systems running, and specifically to try and replicate my Idea Bank to Notion. Flipping back and forth between these two apps became a hassle. I abandoned Obsidian within a month of trying it out.
I noticed through Ali Abdaal that Notion also worked with Readwise, but again, I didn’t want to write in Notion per se. Moreover, Notion on mobile is miserable: I was capturing my ideas on the go in Apple Notes, and then having to create pages for those ideas in Notion later. Digging through blogs, forum discussions, and more, I found Jordan McMahon’s helpful posts on using technology to manage ADHD. His write-up on Drafts, in particular, caught my eye. I downloaded the app, and felt immediately confused by the simplicity of the writing combined with all the clutter around the text box. It took me further digging and looking at Christopher Lawley’s set-up to grasp the power of Drafts. Suddenly, a light-bulb went off in my head.
Drafts could be the place I captured my ideas and wrote notes. Notion could be the final destination for both, via Draft’s actions.
In hindsight, the integration between the two apps was a little convoluted, but made sense in my head at the time. Ideas could be quickly sent to Notion via the ‘add to Notion page’ action in Drafts. I could then just drag that new page into my Idea Bank. I had a separate database for Knowledge, aka my notes. That’s where I rewrote Readwise highlights and tagged them with the appropriate area of knowledge. So I would copy these highlights from Notion, dump them into Drafts, rewrite them into notes to revisit, trigger an action, and then drag that page into the Knowledge database.
While I loved Drafts for its distraction free writing environment and powerful integrations, it still felt limited to dump research in Notion, and then flip back and forth between those pages and Drafts. Surely there was a better way.
Enter Bear.
The Solution, Version 2
Bear had been on my radar for a while, and I briefly tried it out years ago; I vastly preferred it to Apple Pages or Microsoft Words, but didn’t see a point or place for it in my system back then. When I found Drafts could also integrate with Bear, my brain lit up.
I could do the heavy lifting for projects in Bear, and then have the actual ideas and research in Notion. Drafts could be the messenger boy, the first point of capture for both: allowing me to quickly capture ideas or bursts of writing inspiration, which I could then send to the appropriate places. Here’s an example: I have an idea for a video or a blog post. I use Drafts to quickly capture it and send it to Notion. Any research, links, or inspiration I could dump in that Notion page. I could then write the scripts and other things in Bear, drawing on its useful tagging system to have multiple notes corresponding to that project. Here’s an example below:
Again, hindsight is 20/20 and the complications of all these apps, which lightly touched each other but did not fully integrate, didn’t hit me until later. At the time, I drew the process out on my iPad to keep track of how it worked:
The Solution Becomes The Problem
For a time, this system did work. It got me out of my head fixating on the ideal workflow, and focused on doing the actual work instead. However imperfectly, I had places to store the ideas I was coming up with and a place for notes on the ideas of others, and a distraction free place to write. The main problem was that this workflow wasn’t as seamless as I thought it would be. Worse, it actually became a project in and of itself to manage this system. Here’s why:
First, Notion does not work well with Bear. Bear’s wonderful x-callback-url system doesn’t register in Notion. I had to manually use this shortcut from Kevin Jalbert to turn Bear links into TinyUrl links for Notion. This is because I also used Notion to track the statuses of my projects, and wanted a link to where I was working on the project in Bear.
Second, while I love — and still use — Drafts, it became increasingly unnecessary. Keyboard shortcuts combined with Bear’s quick note widget on mobile meant I didn’t need a middleman between me and capturing inspired bursts of writing. Drafts, over time, simply became a mixture of a digital scratchpad (which I still like to use over, say, Apple Notes¹), and a place to talk to Notion. But I could just write Knowledge related notes in Bear, too, and send them to Notion via copy and paste, or import as Markdown. Really, Notion became an idea dump, but at an increasing cost. I began to re-examine why I was so committed to Notion in the first place.
Initially, I wanted to keep my research and my actual projects separate from each other (in Notion and Bear, respectively). This was to avoid digital clutter and overwhelming my brain. But the more I used Bear, the more I realized that a good tagging system, opening notes in a new window side by side, and linking notes meant I could have a clean and useful division between information and project-related notes all in one app. Worse came to worse, was using the search function within Bear really more time-consuming than going back and forth between two apps? In other words, did I really need Notion?
Again, Notion was where I did rudimentary project tracking as well. But during this time period, I began to manage most of my life in Things 3. So I’d use a link to Things within Notion as well, via that aforementioned TinyURL shortcut. When Bear 2 became closer and closer within reach, I realized that even a rudimentary table was all I needed for project tracking. It wouldn’t be as sexy as a Notion Kanban board, but it would get the job done.
There were three final nails in the coffin for me using Notion, and therefore Drafts.
Breaking Up With Notion, Then Drafts
First, I realized Bear and Things 3 work well together, being able to copy and accept links into the other app, no URL shortcut required. This combined with tables in Bear 2 meant I didn’t need Notion for project tracking, and therefore could stop managing links between 3 different apps.
Second, as I committed deeper to Things, I realized it was actually a faster place to store ideas than Notion, and didn’t need Drafts as a middle-man. I could simply create an Area in Things called Idea Bank, create my ideas as tasks, and tag them with the appropriate format for later filtering. I could even dump links and initial notes in the task, and then convert that task later into a project when I started working on it. Widgets meant I could literally just press a button on my phone, or keyboard shortcuts on my laptop, and send ideas to Things immediately. So I didn’t need Notion for an idea dump any longer. My Idea Bank in things isn’t as sexy as a database, but it’s faster and frictionless. For example, recently I wanted to write about Celine Song’s film Past Lives after I saw it. I quickly jotted something down in Things, and added it to the Idea Bank. Later, as I’ve started writing, I put in the appropriate Bear link in as well:
There was one last reason to keep Notion: its integration with Readwise, which Bear officially lacked. But then, recently, Ben Bailey made a shortcut that syncs Readwise highlights into Bear. Is it as automatic and effortless as Notion? No. Does it get the job done? Yes.
In fact, this entire process of slowly parting ways with Notion and Drafts, and whittling down to a few key apps left with me the following lesson:
A system whose core pieces are integrated and work well together, reliably, is much more valuable than a system whose core components are perfect in a silo, but do not speak each other without pain or friction.
In the end, I realized all I needed to use was Bear, Things 3, and Readwise.
Roving Realizations
Despite the complications of this journey, I’m grateful my first system eventually broke down and failed. There are so many valuable things I learned about productivity and perfectionism from this process. Here’s the 3 key takeaways for me:
1. A system doesn’t need to be perfect, it needs to work.
This system had setbacks and bottlenecks since day one.
But still, using an imperfect system for a time had me writing, creating, and reading far more than the days I spent pouring over YouTube videos, blog posts, and sketching out the Ideal PKMS on paper. It got me out of my head and into the world. But eventually, the reason this system broke down wasn’t because it failed to live up to an ideal: it just didn’t work well anymore. This failure gave me a way to cut through the noise of my own head and daydreams of being the next Ali Abdaal: do I really need a bunch of cool apps, or do I need to get stuff done? This has now become the sole metric behind adopting and testing new tools: they need to work, period. This lesson should’ve been obvious, but I had to learn it for myself.
2. The value of failure & iterative progress
I really enjoy the simplicity of my current system.
But in order to have my present creative process stripped down to its bare essentials, I needed to do a test run, have it fail, identify its sore sports, and redesign it appropriately. I now think ‘sprint’ type thinking is incredibly valuable to fight perfectionism and actually figure out what works, and what doesn’t.
3. The system behind the system
This is arguably the most important takeway I’ve gained from this process: learning how my own mind works. That is, the meta system of knowledge and project organizing my brain already does, that I can then map onto apps and tools appropriately. This process can be neatly summed up as Thinking, Planning, and Doing.
I’m going to do a longer write up on this current system and how the three tech tools I’ve settled on work with it. But in short, I need places to capture my ideas and the ideas of others (Thinking). I then need to turn these ideas into manageable projects with clear steps and tasks (Planning). And then I need reliable tools to work on these projects (Doing), tools that let me engage with the other phases of the process as well.
Conclusion
I hope you enjoyed this in-depth breakdown of my first PKMS. I think there’s stigma around failure and learning in productivity ecospheres on the web, which is a shame since failure is the cornerstone of self-improvement. I’d love to hear about your own iterative learning with tech and PKMS in the comments below. If you have questions, you can drop a comment or shoot me an email at hussain_khan@berkeley.edu.
