Update 11/12/24: You may not be surprised to know the below system didn’t stick in its original form. I basically took the philosophy and ditched the formalised system. But I think the philosophy was well-intentioned, and still carrying through to the freeform way I am approaching my life today. I have removed a couple of details from this blog that felt too personal/confessional to me.

This blog was written as a response to a challenge in Struthless’ Discord. The original goal was to make an ‘analogue’ computer: a physical, external brain to keep track of projects and goals. My attempt certainly bends the rules of the challenge, as we are indeed using a computer-based method. But I would say we both made ‘analogue computers’ - just with opposite interpretations of the phrase. Struthless’ board puts systematic methods and trackable goal data into a creative, physical format, while I am carrying analogue and creative approaches over to the digital world, where efficiency is typically king… albeit often at a human cost.

What I’m chasing — and have never found — is a forever-system. A system for Doing Stuff that is infinitely interesting, and flexible enough to reshape when I get bored.

I’ve done paper-based methods, which tend to have the most opportunities for creativity and flexibility, like bullet journalling, using printed planners, and yes! Having a big board on the wall (both a corkboard and a whiteboard). Unfortunately, I don’t find these work long-term for my brain. The bullet journal probably stuck the longest, because it did have the flexibility I needed, but it eventually died off because of the high amount of maintenance month to month, and needing to remember to take it with me everywhere.

Likewise, I’ve done digital methods that promise maximum efficiency — trying to collect my entire life in Notion databases, and using TickTick to set up complicated recurring task schedules. But the databases got overwhelming, and as much as I know roughly when x, y, or z periodic task might need doing, the arbitrariness and requirement to reschedule tasks that didn’t necessarily have a deadline made my actual deadlines blend into the background, and irritated me to the point I dropped it altogether. I also experienced performance problems with both those apps, making them much less reliable than digital methods often promise (though it was a few years ago that I was using them actively — so if they seem up your alley, don’t let that discourage you from giving them a try).

what do we want to organise?

I’m fortunate that my job is pretty compartmentalised and ad hoc, so we are just focusing on my personal life for my system.

The tasks I need to organise fall into two important categories:

1. Personal projects and hobbies

I have a lot of dreams! Most of them have a degree of ‘boring work’ to them that I am liable to avoid, but sometimes I even struggle with doing the fun parts. Keeping everything straight in my head is super difficult. I like the idea that a system will help me to do those things, but not burn myself out on them.

2. Basic survival.

I struggle with ADHD + some complex mental health problems. As a result, there are days that I struggle to do very basic survival tasks, like feeding and cleaning myself. When I’m doing well, these actions fade into the background and are simply part of my day, on autopilot. But intermittently, they become insurmountable or easy to forget about. The amazing KC Davis calls these kinds of tasks ‘care tasks’, and I try to keep her advice in mind when I try to make these tasks easier for me - but I have made a modification.

Because I have problems with workaholism, I try to afford these tasks a greater sense of urgency, reflecting the way they get diminished in my head when I’m doing worse. For me, these mundane maintenance areas are an alarm system - they are the first thing to flag up when I am doing worse, though I may otherwise ‘appear functional’. So, for me, they are urgent; they are ‘survival tasks’! And the consequences are also directly linkable to my survival. When my system fails, it is materially expensive, and it makes my illnesses much worse and harder to manage. If associating these tasks so directly with survival fills you with anxiety, you might prefer calling them ‘care tasks’ - this is just what works for me.

There’s another reason I’m referring to these tasks as survival, which I’ll come to (you have probably guessed it, if you read the title of this blog).

digression: what about different types of task? tasks with no deadlines? tasks with deadlines?

To me, no previous system has provided a sufficient answer for this. Task systems are typically quite inflexible. Digital to-do lists encourage the creation of deadlines that are arbitrary and make no sense for the kind of task being carried out.

Tiago Forte makes a distinction between projects and areas of responsibility - projects are finite and can be ‘completed’, while areas of responsibility are ongoing and neverending. Most of my survival tasks are areas of responsibility, and most of my personal pursuits are projects… but not all.

I find that the ‘areas of responsibility’ attached to my hobbies are the hardest to do consistently. Building a habit because it has a material consequence is a lot easier. The pain of not eating is worse than the pain of getting something to eat, even if complicated food prep is by that point off the table. But the pain of not practicing my musical instruments is not worse than the pain of practicing, because well, there’s always tomorrow (and the next day and the next day and the next day), and I will really do it tomorrow, I promise!

It’s the now/not now problem of timeblindness. Instead of affecting me immediately, the pain spills over into the rest of my life. I feel unfulfilled, and I can’t do the things I want to do. If I don’t practice my instruments, I can’t learn or perform the pieces I wanted. If I don’t study drawing fundamentals consistently, my artistic output stagnates, and I hit more roadblocks when I need to draw something I’ve not practiced before. If I don’t read frequently, my writing begins to feel stale and uninspired. I need a system that will help link those areas up and make it clearer how they are all part of a symbiotic system.

I eventually had the brainwave that areas aren’t individual tasks, but containers for projects. I envision them as the gateway to entry. I barely acknowledge all the things in the way of getting started, so they need to be externalised somewhere so I don’t have to think about it so hard. There can be physical areas, like keeping a particular part of the house clean so it can be used for a particular project. There can also be mental areas, like doing stuff that reminds me I actually do enjoy drawing and making music. And, of course, my survival tasks are the gateway to doing anything that’s ‘productive’, sustainably.

Realising this is crucial because I want to do so much, all the time, but I know that project-hopping and task-switching is pretty bad for people with similar brains to me. Having a bunch of unfinished projects will create mental noise and dissatisfaction, while task-switching is mentally exhausting. If I’m insistent on doing it all, and I am, I need rituals - areas of responsibility - to grease the wheels and switch naturally between them.

I carry no less than 6 areas connected to creative output (visual art, fiction writing of all forms, poetry/songwriting, music, coding, nonfiction writing). It is simply not an option for me to put any of these on the backburner, even temporarily (e.g. ‘I can’t take on any art projects until I finish my novel’… reminds me of ‘if you finish your homework, you can have your dessert’). I want to do it all, and restricting myself is just going to frustrate me, and associate doing the things I actually want to do with discipline and suffering (and not the fun kinds). It’s sort of like intuitive eating, needing to trust my body and mind to know what it needs, instead of falling into patterns of restriction and punishment (again, not the fun kinds).

For more on juggling hobbies, I would highly recommend Barbara Sher.

This long ramble is basically to say: we will be using the concepts of Projects and Areas to help build a sustainable system.

our chosen medium: obsidian.

Obsidian is a notetaking app with an extreme amount of customisability, the capacity to make your own layouts and mindmaps (‘canvases’), and the ability to mod the app using your own code. It is so incredibly flexible that I couldn’t imagine storing my life anywhere else at this point. It has the same appeal as paper, because it’s so easy to just ‘start a new page’ and root through my notes later, and canvases have a paper collage quality to them. But equally, it has digital non-negotiables that I need, for accessibility: text search, the ability to link notes like a wiki, and it syncs across all my devices so I can access it anywhere. Most crucially for a ‘forever-system’, if I ever want to move it to a different app, it does not use a proprietary format. Text files are stored in markdown, and the canvas format we’ll be using is open-source, so it can be transferred to other apps if I ever want to leave Obsidian.

Basically I am a little obsessed. And I’m already storing notes on my projects here. (In fact it’s a wonderful metric for whether a project should be continued, based on how many notes accumulate about it, or how frequently I reference it in other notes.) It’s a natural fit to put my task management for those projects here too.

We’ll be using Obsidian Canvas.

gamifying a digital system

This post is actually a response to two separate Struthless videos. Last year Cam made a video on gamification, its potential power and drawbacks, and it got me thinking about why gamification has previously not worked for me as a productivity strategy.

The easiest technical methods to apply gamification to productivity are game mechanics that personally bore me. A very popular to-do/habit app, Habitica, uses RPG stats and levelling systems. But I dislike the kind of turn-based RPGs that rely solely on numbers, so why would this ever motivate me? Another of Habitica’s positive aspects, having an active community with groups for shared goals, is not personally helpful for me. Social accountability can often be stress-inducing for me and lead me towards unsustainable habits and workaholism. And being quite a solitary person, I’m not the biggest fan of multiplayer games anyway!

So, we’re going to try and make a new organisational system instead, one that applies game mechanics I know I enjoy.

but which game mechanics to choose?

I spin a million plates at once, and carry numerous creative identities. I love games that allow me to do this, too. Two in particular: open worlds, like Grand Theft Auto, Yakuza/Like A Dragon and The Elder Scrolls, and roguelikes/roguelites, like Rogue (of course!), Hades, Dead Cells, and Slay the Spire (as you can see from this list, I like roguelites the best, which are looser in definition and adherence to the mechanics of the original Rogue, but we’ll call them all roguelikes for the sake of simplicity).

Well-crafted open worlds scratch my itch for exploration and completionism, a desire to see and do everything in the game, and often offering me many ways to do just that. You can often become an ‘expert’ in literally every skill in the game, if you are so inclined.

Meanwhile, roguelikes force you to start (almost) from scratch every playthrough. This rewards adaptability, and gives you a massive amount of flexibility in how you can beat the game. Equally, minmaxing your character in the hope of getting a specific set of items and abilities is quite a risky strategy. (Minmaxing is how I’d characterise a lot of productivity tips, especially for neurodivergent people - often you will be encouraged to exploit your hyperfocus at the cost of your general wellbeing.) Taken together, these two provide quite a powerful set of mechanics for existing, more flexibly than an RPG of hard numbers and unnecessary quantification could allow. They abide by the rhythms of life.

what to steal from the roguelike/roguelite?

the randomness, of course.

I find roguelikes incredibly addictive. It’s a gambling high that I don’t have to pay for. I want my system to be able to ‘pick for me’, when decision-making is too hard that day, but also just to add a degree of novelty, playfulness and spontaneity to my day.

getting better at a roguelike is a closer match to ‘serious’ real-life skill acquisition.

I am strongly motivated by mastery and learning, so this must be a key part of any system I use. While I do enjoy levelling up in open worlds, there can often still be a lot of ‘number go up’ mechanics, so that isn’t going to help here.

In a roguelike, learning to maximise your success in a run is much more 1:1 to the actual experience of improving at a particular skill. You never quite start from scratch, even though each run (project, subarea of whatever skill I may be learning) may be a blank page - the principles stay the same, and can be practiced. You will have learned something from every success and failure, and each run will give you a broader, ever-expanding understanding of the game. This reflects how I feel about learning and acquiring new skills in real life. Everything sort of feeds into each other. What I have learned about writing craft affects how I compose music and make visual art.

roguelikes map onto my emotional experience.

Roguelikes reflect an experience I feel pretty much every day: the strain of burnout and depression. Permadeath mechanics, where gear must be re-earned and abilities must be relearned, and runs may begin with random penalties, is very evocative of my experiences of depression, which often seems to strike randomly. Everyday responsibilities can suddenly become newly challenging if not impossible.

Roguelikes often explore Sisyphean narratives that gradually evolve into something genuinely radical - fighting a seemingly insurmountable status quo, doing so through gradual, incremental, and often painful steps. It’s reassuring to know that failure is, in fact, expected - that the odds are stacked against you, and can only be gradually rebalanced through not giving up, through keeping on putting one foot forward.

Consider those slower first levels after dying and respawning - a time where essentials must be exploited, and ‘dying’ is actually much easier, until you manage to scrape some decent gear together. This reflects my experience of burnout, where even simple tasks become a struggle. If my ‘analogue’ app could reflect my experience the way that these games do, I think that would be a gentler way to incorporate recovery tools, rather than my usual strategy of burying my head in the sand and ignoring what usually makes me feel better. It needs to accommodate me when I am sick and need scaffolding to take care of my basic needs, not just when I am ready to do a million things.

I don’t think I’d have thought so deeply about this until I encountered Ryan Sheehan’s writing, particularly their doctoral thesis, and this article with Gavin P Johnson. Trying to craft a productivity tool that would feel ‘natural’, that would promote my weird brain instead of punish it for straying off in 20 directions, seemed difficult, and I don’t think I have necessarily cracked the code on doing productivity in a way that doesn’t serve late-stage capitalism. But I have to live here and feed the beast for now.

a reconciliation with grief.

I am terrified of missing something, of forgetting, of letting go, of abandoning. I hoard ideas and aspirations. I’m so scared they will just disappear if I don’t store them somewhere. I’m scared of the process of narrowing down. This is the joy of the roguelike. Nothing is sacred. Something you worked your ass off to get may later be discardable, or abandoned when you die. But the more you practice and keep going back, the easier it will be to get and utilise the next time you encounter it.

Living in a mortal body with memory problems, we can’t do everything. We will forget. But the key is to keep coming back anyway, and rekindling memories, and making that ‘resurrection’ easy.

what to steal from open worlds?

geographical exploration, nonlinear travel, and worldbuilding.

Originally, my system was going to be purely based on roguelikes. But something wasn’t quite right.

As I was building my system, I realised it was still too linear to accommodate life.

Ultimately, as I tried to tweak the system, I wound up creating a ‘map’, where each domain of my life had its own ‘realm’ or location associated with it, with specific purposes. I could either follow a preset path to that domain, or I could ‘fast travel’ to that domain if I know exactly what I want to do.

I don’t think this is any surprise. It feels very natural to treat life as an open world, as something exploratory, possessing a spatial geography. And, I suppose, my real world has narrowed so dramatically thanks to the pandemic - my real-world explorations are limited almost exclusively to my city. Envisioning my life as having a metaphorical geography helped alleviate some of my grief.

an aside: life domains!

I knew I wanted to incorporate life domains into this system. My own are based on Rachael Stephen’s witchier implementation, the constellation system. (Rachael’s blog for patrons also introduced me to Tiago Forte’s projects/areas distinction!) I have 7 domains corresponding to a life aspect: self (mind/body/wellness), others/the world (existence as a social creature), creativity, learning (theoretical, as opposed to practice-based), home, leisure, and money. Now they have actual geographical spaces in my imagination.

getting to be all the barbies.

A lot of open worlds don’t have, like… hard cutoffs, closing you off from a part of the world. Some do, but you will generally always be able to 100% complete and do everything that is available to you. This is quite exciting to me, because, as above, I experience not being able to do absolutely everything I want to do in life as an eternal loss. But, to a point anyway, time is limitless in an open world, and exploration of every nook and cranny is encouraged. We want to harness this encouragement to seize the moment, instead of remaining stuck and scared.

being necessarily a little convoluted and complicated! or: the ability to create shiny new subsystems that are independent of the whole.

Open worlds often try to simulate parts of life, so it makes sense to use them as a template for gamification, right? Done right they are like Life But More Fun. This can often make them very complex, easy to bog down with decision paralysis. Some, like Yakuza, are well known for their minigames, which sometimes wind up being complex enough to be entire separate games.

A system, designed for novelty and flexibility, should allow you to get as complex as you want and do what works for the project. Provided we’re at a granular level, complexity shouldn’t be feared. That is, there’s no reason to add extra friction to the top level of the system, deciding what domain to focus on and what to do in that domain. But for specific and complicated projects, I’ve found it helpful to have specific subsystems and data collections, and the capacities of Obsidian to link notes together makes that very easy to implement while not interfering with the main system’s comparative ‘simplicity’. Like my notes in Obsidian, the system can grow organically when I take on bigger projects.

the code and paper prototypes that failed

I started off trying to build a fully coded JavaScript app, and had a big learning curve teaching myself how to work with a cloud database. I realised the pursuit of the full tech prototype would take months if not years to do as a hobby! And at the back of my mind, I fretted that I needed to make sure the theory worked first. So when I got stuck, I turned to paper instead.

The paper prototype took… a lot of repetitive setup. It sort of reminded me of the most exhausting aspects of bullet journaling. Each day I would draw a tarot card to help me think through some problems in my life metaphorically. I would then roll physical dice to determine what to do with my day. I’d plan it out without even consulting a list beforehand. It worked for a little while to tackle the inertia… but deciding what to do, even with my options reduced, was still too heavy on my decision making, and it also felt like overkill when my executive functioning was doing better. I needed a system where deciding what to do - and how to PICK UP and CONTINUE an existing project - felt effortless, no matter how I was feeling.

the final system: a continued work in progress.

My system is currently a bunch of Obsidian notes that are all embedded on a single canvas. I can start off at the centre, roll for an area if I can’t decide what to do, and then zoom in on the section.

In the back of the system is the ‘undreamt dreams’. These are inaccessible and not directly visible on the canvas on purpose: they are a rolling inventory of future ideas, tasks and projects. I am very serious about not accessing or doing these until I have a free spot on the canvas. This turns my ‘now/not now’ time perception to an advantage, clearing my head of the ‘not now’ until it’s time to pick one (which I may also randomise, if I struggle to pick).

Borrowed from struthless’ board, there is a finite amount of space. I decided that each subsection of the map should only have one area of focus at a time.

The act of building this system has been therapeutic. I feel much less terrified by the prospect of losing everything. My life feels more holistic; I feel like I am paying attention to the whole because I am not utterly paralysed by decision all day. In that way, it is functioning in a more ‘analogue’ capacity. It has led to surprises, like picking up books I forgot about, enjoying the act of walking around my town, taking up exercise again, and… also writing this blog post, which is one of the tasks under ‘amduscias’, the creative domain.

I still don’t have a perfect solution for ‘areas’, those non-project-based but still important tasks. I think that area upkeep is required when a project feels intolerable, but I’m still not sure how to get myself to do it. And some domains are nothing but ‘area’. For instance, I think I would get pretty annoyed to have music listening goals. Basically, it depends! This is definitely the ‘in progress’ part. That’s fine. We’ll get there.

Thanks for joining me on this journey! This challenge finally got me to set a blog up and learn a little version control, which was in fact a distraction from setting up the system. But, fortunately, I am running on a system that encourages those kinds of detours and productive procrastination. I’m excited to see what this helps me do, but most of all how this might provide a fun scaffolding for my life.