I had planned to spend a couple of weeks this summer migrating all my notes from the various systems where I keep them, into Notion. If you’re anything like me – laying awake at night thinking about the optimal productivity setup – you know of Notion. It’s been in the making since 2013, but seems to have became an overnight success a couple of years ago, when all of a sudden Youtube was flooded with productivity gurus hailing its superiority to apps like Evernote and OneNote.

One of the gurus was August Bradley, who proselytised fiercely for his “Life OS” which revolved around a concept he calls PPV, short for Pillars, Pipelines and Vaults. I was one of the thousands who signed up to his channel, spending hours and hours studying the crazy complex implementation of PPV in Notion. I was sold and felt that no matter what, migration would be worth the effort.

Fast forward to a week ago, when I finally had timed blocked in my calendar to begin doing actual work on this momentous task. I meant to start by checking out a few bookmarked videos for reference, when to my great distress I discovered that there’s now a new kid on the block. It’s called Obsidian, and in many ways it is kicking Notion’s butt. Where Notion is slow to load, has privacy issues and a capped free tier, Obsidian is free forever, lives locally on your hard drive and is lightning fast. Also, it does a type of graph representation of all your notes and how they relate to each other. It looks really science fictiony. Clearly next level.

So alas, I need to dive back into the rabbit hole and spend countless more hours watching online walkthroughs. I’m hypnotised by Morganeua, the Canadian PhD-student who explains why Obsidian is the perfect tool for implementing the Zettelkasten method of knowledge management. The what!? Another deep dive ensues. It turns out this system for organising knowledge dates back to the early 16th century, and has been used by everyone from Roland Barthes to Henri Cartier-Bresson and Eminem. At its core, it’s a highly structured way to do bi-directional linking of informational tidbits. Even when done with pen and paper, its proponents argue that the value in terms of support for associative and linked thinking the Zettelkasten system brings, well outweighs the huge amount of time you have to put into making it work. Of course now with a digital tool like Obsidian, which seems to be tailored to fit the the Zettelkasten model, much time can be saved. But in order for the system to start creating real value, you still need to put in thousands (some would say tens of thousands) of entries and you have to be mindful of how to tag and link them all to each other.

That’s looking at a huge investment in terms of time and discipline. Still, lots of people out there seem to think it’s worth it. Rachel Madrigal is as convincing as she is charming as she describes at length why she – who was once obsessed with Notion, still considers it a no-brainer to migrate all her personal information from the painstakingly well designed Notion databases, into Obsidian and its far superior data views.

Then I stumble across Nick Milo of Linking Your Thinking. He’s charming too, looks like someone out of a Wes Anderson cast. I spend yet more hours. Now I feel I could actually start using Obsidian, which is installed and warmed up on my machine. But Nick is selling me a slightly different implementation than the one built on the Zettelkasten model. He calls it the PKM Planet, where PKM is short for Personal Knowledge Management. It has several sub-sections. One for managing your memory, one for skills, another one for productivity, also one for relationships and so on. As I’m trying to wrap my head around this I’m interrupted by my dog who seem to have gotten something stuck in his paw.

Dog dealt with, I pause to think.

I instinctively understand that there are methods and tools out there that could provide me with superior ways of getting organised. After all, my current state of “personal knowledge management”, if you can call it that, is fractured over many different platforms each of which imposes its own data model. I’ve poured hundreds of hours into taking and organising notes on every single book I’ve read in the last five or six years, and that’s great because now I can see exactly what I thoughts have been provoked by different reading experiences. But that’s not just it, I can also explore what themes I’ve touched on over time; what the ratio have been between fiction and non-fiction; between reading in different languages, and many other exotic bits of metadata. That’s absolutely great and I wish I’d have started earlier, but there are of course inherent limitations with my setup. If I want to cross reference that book I read on, say, semantic web (back when that was the thing), with design sketches I made for some old project, then I’m stranded because they live in different systems.

So it would make sense to take on the gargantuan task of reorganising. But that would mean spending weeks tearing down what I’ve already invested so much in, and by the time I’d be done I guarantee that there will be a new new kid on the block that everyone’s raving about. Perhaps a contender that fuses the best of Notions visuals and team functionality (two of Obsidian’s current week spots) with the best of Obsidian’s data model. And then what do I do?

So at the end of the day I’ll probably spend this summer reading a few good novels rather than locking myself into a dark place shovelling data. I know it means my systems will remain outdated and imperfect, but I also know that there’s no such thing as perfection when it comes to knowledge management.

Coming out at the other side of this thoroughly unproductive productivity fever, I’m left with the feeling that Freud called unheimlich. The word connotes a particular flavour of unease which originates in living through a situation that on its surface seems unique, but resonates with some prior experience that you can’t exactly put your finger on.

After pondering what my subconscious is trying to tell me, I realise that my own decision making process over the last week perfectly mirrors that of untold numbers of potential customers whom I’ve met with over the years, trying to sell my own software (a sort of b2b productivity platform for publishers). It explains how again and again the people who seem to have the most acute need, seldom ended up being the ones to push the buy button. They love what I present and see how it would clearly solve problems for them in a much more efficient and elegant way than anything that they’ve been able to come up with themselves. Yet the patchwork of makeshift solutions they’ve built to keep the ship from sinking is exactly what makes it so hard for them to invest in a new platform.

There’s at least two ways to think about what’s at play here. Traditionalists would claim that this is the dynamic that allows new entrants to disrupt the incumbents. Others hold that while the dominant players in any given industry might be reluctant to invest in new third-party software solutions, they’re busy plowing billions into building their own proprietary solutions, since they’ve come to understand software as their main competitive edge (something I’ve written about before).

Whoever turns out to be right, it probably won’t help out of my spot. But that’s a concern for rainier days.

There’s more where this came from