Failing upward

"That means we lose. And lose, and lose, and lose ... Until we're ready." - Luthen Rael, Andor, season 2

As I type this, I am sitting on my couch. Across the room, there is an entire bookshelf filled with my notes from graduate school. By that, I don’t mean just the notes I took in class. Those are part of it, of course. But the much greater volume of papers there, both in bound volumes as well as various composition notebooks, are my own thoughts. Pages and pages of ideas, copied quotations, diagrams, and marginalia.

I’m an academic, and I spent years doing this sort of work. A lot of my thinking has been captured on paper through the years. There’s a certain romance to that. This is one of the reasons I keep these notes ready to hand, and on a sort of display on the shelves here in our living room.

But there is a problem with this sort of notework. As you go from one notebook to two, to four, to (eventually) dozens, it becomes basically impossible to use these thoughts effectively. What started as a library, or perhaps a zoo, quickly becomes a morgue. The notebooks became where ideas when to die, not to thrive.

Why? The answer is simple. Ideas live in conversation. They live not just in writing, but in public writing. If you have the best ideas in the world, and you keep them stuffed in a drawer in your cabinet, they might as well not exist, so far as meaning goes. I like the way that Michael Short, who is a professor of nuclear engineering at M.I.T., once put it in one of his lectures. I’ll paraphrase it here: “If you discover the neutron, and the paper you write up that discovery on goes into your desk drawer, and no one else ever sees it, did you really discover it?”

So this is what was happening to my ideas. I got the joy of having them, but they quickly withered on the vine, because they were not reaching my other ideas, and they weren’t reaching anyone outside my own skull.

So about 15 years ago, I started exploring various styles of note taking and productivity systems. Some of them were pen and ink, analog systems. Others were based on the computer or the web. Some were glorified to-do lists. In each system I tried, I could feel what I was looking for — not because I found it, but because using the system helped me sense another edge to the whole that wasn’t getting filled.

Probably the most famous system I tried was David Allen’s Getting Things Done (GTD), which is not so much a system as it is an entire lifestyle. Reading his book, the promise was that my life would be radically transformed, and I would become a much more productive person. I loved the idea of it all, and the far shore of productivity it showed to me sounded so exotic and beautiful. I wish I could live there.

What I quickly discovered, however, is that the GTD system takes a tremendous amount of time. First of all, it takes time to get the system in place (Allen recommends setting aside several days to reorganize your files and to get things up and running). Beyond that, however, the sheer amount of mental energy it took for me to maintain the system, once I got it in place, was exhausting.

You see, as I have gotten older, I have become confident that I have some combination of neurodivergent traits. I have been formally diagnosed (I don’t yet have the money for that), but it seems clear I have some mixture of ADHD and level 1 autism, simply based on observing members of my family who do have formal diagnoses. Anyway, the trap for me with GTD ws that I had to spend so much time thinking about the system itself, and maintaining it, that I had very little time left over to do actual work.

The next solution I tried was Evernote. This promised to be the solution to my “one thousand open browser tabs” problem. See, I would want to remember something (or, more accurately, I would want to make sure I didn’t forget something), and so I would open a browser tab, and then keep that open until I could “come back to it.”

Only I never actually came back to it.

Coming back to something takes time - and all I seemed to have was forward motion. All I seemed to be able to do was plunge ahead toward the next task, which usually meant the next crisis or the squeakiest wheel. I was not good at circling back (never have been). So eventually, my computer would just start running really slow and crashing.

Evernote promised to fix all that. I could just dump things there, and then go back and organize them later. Nothing would be lost.

It didn’t work like that, though. Instead, this became an electronic version of the bookshelves where my notes would go to die. Disconnected, unused, distant, dark.

It was frustrating.

For years, I tried out system after system, and each one was not right for me. Either it was too disconnected, or it was too high-maintenance. I saw these systems working for other people, but I couldn’t get them to work for me.

Longtime readers of The Late World will recall that I am not really afraid of failure. In fact, failing in public is a core part of my creative process. Nevertheless, this was a really demoralizing period for me. I spent more than a decade going from platform to platform, from fad to fad. I almost gave up hope.

Then about six years ago I learned about a method called Zettelkasten, which is a very labor-intensive method that involves managing physical notecards (the German word basically translates to slipcase). It sounded like a monstrous burden, and yet the pepople who used the Zettelkasten system sang its praises, claiming amazing leaps in creative thought and productivity.

I filed that away, and continued looking.

For a long time, I had my eye on a platform known as Tinderbox. From a distance, it seemed kind of like the Cadillac of these sorts of systems. It promised to be incredibly powerful and super flexible. After months of research, I bit the bullet and paid the fees to get access. I installed it, played with it a bit, and then … nothing.

Again, it was clear that this was going to take a lot of work to learn, to set up and to maintain.

It didn’t bring me to the edges of despair, exactly, but it was frustrating to have tried so many solutions and not found … a solution.

On our refrigerator I have a magnet with a quote from Thomas Edison: “I have not failed. I have successfully found 9,637 approaches that do not work.” I like this magnet because, in many ways, that is the embodiment of my mantra about productive failure. If you can learn from it, a failure can be your greatest tool of success. As my beloved Samuel Beckett once put it: “Fail again. Fail better.”

My term for this is failing upward.

I’ll do another post sometime with more details, but here’s the brief conclusion to this saga of failing and failing until I found a way to succeed. In the wake of my somewhat expensive Tinderbox disappointment, I once again went online to see if there were any alternatives left I hadn’t tried.

In that search I came across a platform called Obsidian. It seemed to have all the strengths of Tinderbox, but with some core differences. For example, where Tinderbox was a fussy development project spearheaded by one man and a small team, Obsidian was an open source development project. Moreover, where Tinderbox was somewhat expensive, Obsidian was free.

This might have been another recipe for disaster, but in my research I stumbled on a short video from a graduate student who described how he had used Obsidian to develop a simple and light implementation of the Zettelkasten system I mentioned earlier:

This changed everything.

What Obsidian allowed me to do, once I had configured it more or less in the manner that Artem Kirsanov suggested, is to implement a completely anarchic approach to my notes. I didn’t need to do a lot of planning on the front end, and I didn’t need to do a lot of organizing on the back end. All I had to do was capture thoughts and ideas as soon as I had them. Using a very lightweight markup protocol (basically the same architecture used by Wikipedia) I could quickly generate hyperlinks that connected these ideas to other ideas I had already captured.

It was as fast as paper, and almost as effortless, and yet it allowed every idea to continue to be available and present in real time, rather than locked away on a shelf.

I started using this system in earnest at the start of 2022, so just about exactly four years ago. Over that time, I have generated thousands of notes. Each one is just a little atomic thought, at least. Some notes are more substantial, involving a few paragraphs.

Over time, this project has not just captured my ongoing ideas, but I discovered that taking conected notes in this way was helping me to see new connections, and therefore to venture into new thoughts along the way, in a manner kind of like a snowball rolling down a mountain, gathering mass and momentum.

For a long time, it was all focused inward. I was having fun thinking in a new way, generating connections and seeing patterns.

Over the past summer, though, something changed.

I decided to start a new blog, David Dault is Writing Things, as a place where I would be able to write whatever I wanted. That sounds silly at first — all blogs are like that, right? But in fact, no. In every blog I have done up to this point (Including The Late World), I’ve placed thematic restrictions on myself. Each blog was focused on a certian sort of research or around a certain sort of social moment. But here, this new blog was going to simply be a regular, weekly forum for what I wanted to write.

Since it got started in August, I have managed to post an essay every week. These are not just short blurbs, but substantive think-pieces, between 1,500 and 5,000 words. As a result, the total work I did in 2025 was just over 50,000 words. That’s about the length of the book I have coming out with Bloomsbury later this year (The Covert Magisterium). That’s pretty astonishing, given my near-decade I spent with writer’s block, after I got out of grad school.

So I think I have finally found a system that works. All this recent productivity is coming directly out of these swirling ideas and notes that I have been gathering in Obsidian for the past four years. It doesn’t seem like the well is going to go dry anytime soon.

So here are some ket takeaways I have learned in this litany of failures leading up to my recent “overnight” success:

1. The system has to work for you, not make you work for the system. So many of the paths I tried were predicated on the idea that I would have to completely remake my brain or my habits to conform to their particular system. After years of trying, I had to admit I just couldn’t do it. instead, I finally found a “system” (not even sure that’s the right word here) that started where I did, in the midst of my messy mind, and didn’t demand that I pretty anything up.

2. The wool-gathering is an essential part of the process. I keep wanting to beat myself up for not writing essays like this sooner. But looking back, I have to keep in mind that it took me almost four years to figure out what I wanted to say in the first place. That’s only really come together very recently. Once it did, I realized I have all these connected ideas. Now, as I write that week’s essay, I am realizing that I am discovering new ideas that can then be followed up in the next essay, or one.a few weeks down the line. None of this would be possible if I hadn’t taken a lot of time (a LOT of time) to just meander and build little thought structures and to explore connections.

3. Writing leads to writing. I now find myself almost in the opposite state to writer’s block. I am now able to turn around essays of a few thousand words (like this one) in relatively short order. Using Obsidian to build my research muscles also helped to strengthen and condition my writing muscles, because in the Obsidian environment those are the same muscles. As Sonke Ahrens has noted, writing is thinking, and thinking is writing. As you take time to trust your thinking, there is a scaffolding there that can help you trust your writing, as well.

So, as I regularly say, work on trying to not be afraid of failing in public. Maybe, like me, you’ll try out a half-dozen or dozen possibilities, giving each the ol’ college try, only to leave each one abandoned on the junk pile. You may court despair long before you achieve wonder. Nevertheless, if you fail in public, and analyze each setback so you can learn from it, you might discover that you have made a compelling case, to yourself and others, for the path that leads to actual success.

But this path must be grounded in the ways you think and operate. There is not a “one size fits all” approach here. Each traveler on this road must find their own way of doing things. That’s kind of what keeps things exciting and surprising. Don’t you think?

So Obsidian works for me. It manages to be on my brain’s wavelength. One of these platforms that didn’t work well for me might work for you. Or you might discover an entirely new path, or you might even discover that what you needed all along was just pen and paper.

Whatever it is that will work for you, don’t give up until you find it. Keep going.

Courage.