Unproblematize

I’ve got 999 problems.

The essence of software engineering is solving problems.

The first impression of this insight will almost certainly be that it seems like a good thing. If you have a problem, then solving it is great!

But software engineers are more likely to have mental health problems1 than those who perform mechanical labor, and I think our problem-oriented world-view has something to do with that.

So, how could solving problems be a problem?


As an example, let’s consider the idea of a bug tracker.

For many years, in the field of software, any system used to track work has been commonly referred to as a “bug tracker”. In recent years, the labels have become more euphemistic and general, and we might now call them “issue trackers”. We have Sapir-Whorfed2 our way into the default assumption that any work that might need performing is a degenerate case of a problem.

We can contrast this with other fields. Any industry will need to track work that must be done. For example, in doing some light research for this post, I discovered that the relevant term of art in construction3 is typically “Project Management” or “Task Management” software. “Projects” and “Tasks” are no less hard work, but the terms do have a different valence than “Bugs” and “Issues”.

I don’t think we can start to fix this ... problem ... by attempting to change the terminology. Firstly, the domain inherently lends itself to this sort of language, which is why it emerged in the first place.

Secondly, Atlassian has desperately been trying to get everybody to call their bug tracker a “software development tool” where you write “stories” for years, and nobody does. It’s an issue tracker where you file bugs, and that’s what everyone calls it and describes what they do with it. Even they have to protest, perhaps a bit too much, that it’s “way more than a bug and issue tracker”4.


This pervasive orientation towards “problems” as the atom of work does extend to any knowledge work, and thereby to any “productivity system”. Any to-do list is, at its core, a list of problems. You wouldn’t put an item on the list if you were happy with the way the world was. Therefore every unfinished item in any to-do list is a little pebble of worry.

As of this writing, I have almost 1000 unfinished tasks on my personal to-do list.

This is to say nothing of any tasks I have to perform at work, not to mention the implicit א‎0 of additional unfinished tasks once one considers open source issue trackers for projects I work on.

It’s not really reasonable to opt out of this habit of problematizing everything. This monument to human folly that I’ve meticulously constructed out of the records of aspirations which exceed my capacity is, in fact, also an excellent prioritization tool. If you’re a good engineer, or even just good at making to-do lists, you’ll inevitably make huge lists of problems. On some level, this is what it means to set an intention to make the world — or at least your world — better.

On a different level though, this is how you set out to systematically give yourself anxiety, depression, or both. It’s clear from a wealth of neurological research that repeated experiences and thoughts change neural structures5. Thinking the same thought over and over literally re-wires your brain. Thinking the thought “here is another problem” over and over again forever is bound to cause some problems of its own.

The structure of to-do apps, bug trackers and the like is such that when an item is completed — when a problem is solved — it is subsequently removed from both physical view and our mind’s eye. What would be the point of simply lingering on a completed task? All the useful work is, after all, problems that haven’t been solved yet. Therefore the vast majority of our time is spent contemplating nothing but problems, prompting the continuous potentiation6 of neural pathways which lead to despair.


I don’t want to pretend that I have a cure for this self-inflicted ailment. I do, however, have a humble suggestion for one way to push back just a little bit against the relentless, unending tide of problems slowly eroding the shores of our souls: a positivity journal.

By “journal”, I do mean a private journal. Public expressions of positivity7 can help; indeed, some social and cultural support for expressing positivity is an important tool for maintaining a positive mind-set. However, it may not be the best starting point.

Unfortunately, any public expression becomes a discourse, and any discourse inevitably becomes a dialectic. Any expression of a view in public is seen by some as an invitation to express its opposite8. Therefore one either becomes invested in defending the boundaries of a positive community space — a psychically exhausting task in its own right — or one must constantly entertain the possibility that things are, in fact, bad, when one is trying to condition one’s brain to maintain the ability to recognize when things are actually good.

Thus my suggestion to write something for yourself, and only for yourself.

Personally, I use a template that I fill out every day, with four sections:

  • “Summary”. Summarize the day in one sentence that encapsulates its positive vibes. Honestly I put this in there because the Notes app (which is what I’m using to maintain this) shows a little summary of the contents of the note, and I was getting annoyed by just seeing “Proud:” as the sole content of that summary. But once I did so, I found that it helps to try to synthesize a positive narrative, as your brain may be constantly trying to assemble a negative one. It can help to write this last, even if it’s up at the top of your note, once you’ve already filled out some of the following sections.

  • “I’m proud of:”. First, focus on what you personally have achieved through your skill and hard work. This can be very difficult, if you are someone who has a habit of putting yourself down. Force yourself to acknowledge that you did something useful, even if you didn’t finish anything, you almost certainly made progress and that progress deserves celebration.

  • “I’m grateful to:”. Who are you grateful to? Why? What did they do for you? Once you’ve made the habit of allowing yourself to acknowledge your own accomplishments, it’s easy to see those; pay attention to the ways in which others support and help you. Thank them by name.

  • “I’m lucky because:”. Particularly in post-2020 hell-world it’s easy to feel like every random happenstance is an aggravating tragedy. But good things happen randomly all the time, and it’s easy to fail to notice them. Take a moment to notice things that went well for no good reason, because you’re definitely going to feel attacked by the universe when bad things happen for no good reason; and they will.

Although such a journal is private, it’s helpful to actually write out the answers, to focus on them, to force yourself to get really specific.

I hope this tool is useful to someone out there. It’s not going to solve any problems, but perhaps it will make the world seem just a little brighter.


  1. “Maintaining Mental health on Software Development Teams”, Lena Kozar and Vova Vovk, in InfoQ 

  2. Wikipedia page for “Linguistic Relativity” 

  3. “Construction Task and Project Tracking”, from Raptor Project Management Software 

  4. Jira Features List, Atlassian Software 

  5. “Culture Wires the Brain: A Cognitive Neuroscience Perspective”, Denise C. Park and Chih-Mao Huang, Perspect Psychol Sci. 2010 Jul 1; 5(4): 391–400. 

  6. Long-term potentiation and learning, J L Martinez Jr, B E Derrick 

  7. The #PositivePython hashtag on Twitter was a lovely experiment and despite my cautions here about public solutions to this problem, it’s generally pleasant to participate in. 

  8. As we well know. 

Announcing Pomodouroboros

I wrote my own pomodoro timer which is also a meditation on mortality.

As I mentioned previously, I’ve recently been medicated for ADHD.

Everyone’s experience with medication, even the same medication, is different, but my particular experience — while hugely positive — has involved not so much a decrease in symptoms, but rather a shifting of my symptom profile. Some of my executive functions (particularly task initiation) have significantly improved, but other symptoms, such as time blindness have gotten significantly worse. This means, for example, I can now easily decide to perform a task, and actually maintain focus on that task for hours1, but it’s harder to notice that it’s time to stop, and still somewhat difficult to tear myself away from it.

I’ve tried pomodoro timers before and I’ve had mixed success with them. While I tend to get more done if I set a pomodoro, it’s hard to remember to set the timers in the first place, and it’s hard to do the requisite time-keeping to remember how many pomodoros I’ve already set, how many more I’ll have the opportunity to set, etc. Physical timers have no associated automation and data recording, and apps can be so unobtrusive that I can easily forget about them entirely. I’ve long had an aspiration to eventually write my own custom-tailored app that addresses some of these issues.

As part of a renewed interest in ADHD management techniques, I watched this video about ADHD treatments from Dr. Russell Barkley, wherein he said (I’m paraphrasing) “if I don’t put an intervention into your visual field it might as well not exist”.

I imagined timer that:

  1. was always clearly present in my visual field;
  2. recorded the passage of intervals of time regardless of any active engagement from the user; the idea is to record the progress of the day, not give you a button you need to remember to push;
  3. rewarded me for setting active intentions about what to do with those chunks of time, and allowed me to mark them as successful or failed.

So, last weekend, leveraging my newly enhanced task-initiation and concentration-maintenance abilities, I wrote it, and I’ve been using it all week. Introducing Pomodouroboros, the pomodoro timer that reminds you that the uncaring void marches on regardless of your plans or intentions.

I’ve been using it all week and preliminary results are extremely positive.

This thing is in an extremely rough state. It has no tests, no docs, and an extremely inscrutable UI that you need to memorize in order to use effectively. I need plenty of help with it. I contemplated keeping it private and just shipping a binary, but a realistic assessment of my limited time resources forced me to admit that it already kind of does what I need, and if I want to enhance it to the point where it can help other people, I’ll need plenty of help.

If this idea resonates with you, and you’re on macOS, check out the repo, make a virtualenv somehow, install its dependencies, I don’t know how you make virtualenvs or install dependencies, I’m not your dad2, and run ./runme. If you’re on another platform, check out the code, ask me some questions, and maybe try to write a port to one of them.


  1. I cannot express how alien the sensation is to have conscious control over initiating this process; I’ve certainly experienced hyperfocus before but it’s always been something that happens to me and not something that I do 

  2. If I am your dad, come talk to me, based on your family history it’s quite likely that you do have ADHD and I’m happy to talk about how to get this installed for you offline. 

Diagnosis

I got diagnosed for ADHD, and you won’t believe what happened next. At least, I didn’t.

On August 4, I received a clinical neuropsychiatric diagnosis of ADHD.

Squirrel squirrel on gold
Brunetto Latini, Li Livres dou Trésor, Rouen ca. 1450-1480
Bibliothèque de Genève, Ms. fr. 160, fol. 82r

I expected this to be a complete non-event. I’ve known I have ADHD for the last 16 years or so, so in principle this should not have been news to me.

The formal diagnosis was also unlikely to affect my treatment. Prior to testing, I’d had an initial consultation with a psychiatry provider and based on that was prescribed Buproprion. While this medication is more commonly used for depression, it’s increasingly commonly used off-label for ADHD. Good evidence of its efficacy for ADHD has emerged in the last few years. It has fewer side-effects than stimulant medications. I’ve been tolerating it well — almost no experience of side-effects. More importantly, it’s helping to manage my symptoms. Doctors are unlikely to switch treatments if the one with fewer side-effects is working well. Furthermore, my extremely offensively named, specific subtype of ADHD1 is correlated with somewhat poor performance of methylphenidate specifically and sometimes stimulant medication more generally, so I have low expectations of improved performance if I take something stronger. And I certainly wouldn’t look forward to the much more annoying process for managing the prescription for those medications.

And yet.

One of the quirks of the particular way that I went about getting a diagnosis was that I had a battery of neuropsychiatric psychometric tests to go along with the traditional interview-based evaluation process for ADHD. At the time, this was just a huge annoyance. I was subjected to a lot of psychometric testing in my early childhood, and given the circumstances of that testing2, I have very negative associations with the experience. Moreover, since these tests were all administered remotely due to COVID, they were on a website, and unfortunately, as you probably already know, computers. JavaScript almost stopped me from getting critical mental health care.

I already knew what the interview portion of the testing would say, more or less. I’d been roughly aware of the diagnostic criteria for many years, I knew what my childhood was like, I knew how the symptoms still affected me today, so there wasn’t a whole lot of variation that I’d expect there. However, I’d never self-administered any neuropsychiatric evaluations, and when I’d been subjected to psychometric testing as a child, I’d never gotten to review the results in detail, just given a high-level summary.

So, given this quirk, included with my diagnostic results was clear evidence of additional ADHD symptoms, such as a gap between general intelligence and cognitive performance explained by a deficit in working memory.

I already knew many of my issues were caused by ADHD. I knew that I have a neurodevelopmental disorder that affects roughly 3% of the adult population; i.e. fewer than 1 in 20 people. I knew that despite public perception of this disorder as something frivolously over-diagnosed and “not real”, it’s been possibly the best-researched condition in clinical psychiatry for decades.

And yet.


Reading through my diagnosis, after the fact, I was surprised to discover that despite having known this for years, despite having written extensively about how this specific paradigm about ADHD was both incorrect and unhelpful, there was still somehow a part of me which subconsciously believed that it was just a collection of character defects. That neurotypical people must feel like this all the time as well, and that they just try harder than me somehow.

One can easily believe that any behavior out “in the world” is simply a result of character. Failing to complete assignments in school, blowing through estimate after estimate at work, needing 3 different “upcoming meeting” reminders on every device to ensure that one doesn’t miss appointments, having a slavish dedication to to-do lists so intense that it literally borders on an obsessive compulsion... one can believe that these are all just quirks, responses to things that everyone must struggle with to some degree, and that one’s behavior in these areas might be colored a little bit by a disorder but ultimately it’s down to choices.

But what influence could “character” have on the performance on totally synthetic psychometric tasks? “Repeat this string of numbers backwards.” “Sort the numbers and repeat them in descending order.” “Describe the relationship between these two words.” “Describe some property of this baffling arrangement of shapes and colors, then do it again faster and faster.”

These are completely value-neutral activities. They take a few minutes each. They couldn’t possibly require sticktoitiveness or will-power, ambition or drive. They’re just arbitrary test results. And from the aforementioned childhood experiences of psychometrics, I know that I am hilariously, almost pathologically competitive about these sorts of things, so there’s no way I’m not going to give these brief tests my full attention and effort.

And yet, the raw data that these tests produced are consistent with my diagnosis. I really can’t help it. It’s not a choice.

I knew I might feel externally validated by receiving an official-sounding clinical diagnosis. I know that I crave validation, so I expected this to feel a little good. What I didn’t expect was the extent to which this would subtly allow me to align my subconscious, emotional self-concept with the one that I’d rationally accepted a long time ago.


The medication that came along with the same process has been life-changing, but I’ll cover that in a separate post. The diagnosis itself (along with the medication changing my symptom profile somewhat) has also lead me to re-investigate coping strategies for ADHD, and to discover that quite a bit of useful research has been done since I last checked in on this disorder. There are new strategies, techniques, and medications to use since the last time I read a book on it. As annoying and tedious as the whole process was — the first step to getting treatment for ADHD is to prove you don’t have ADHD — it has absolutely been worth it.

So fine, I had a non-intuitive but ultimately positive experience with a psychiatric diagnosis, but why’d I write this? There are a few reasons.

In part, I just needed to work through my own complex feelings. I wanted to have something long-form written out that I can refer to which explains the journey that I’ve been on for the last couple of months, instead of haltingly re-deriving the explanation in every personal conversation I have.

I also wanted to “normalize”, as the kids say, talking about struggles with mental health issues. I’m too self-conscious and private to lay out the full extent of my struggles in public, but I can at least gesture towards the fact that I have struggles, and thereby give people some comfort.

As a consequence of my particular … idiom … I guess, it seems to have taken the form of an essay. Every good essay has a call to action, so here’s one: consider that getting help might be worth it. If you believe you’ve got a mental health condition—whether it be ADHD, anxiety, depression, or anything else—and you believe that you’ve been managing it on your own, I think it’s worth considering: maybe not. Particularly after this hellish 18 months. I really was managing my disorder on my own reasonably well, until one day, I wasn’t. Maybe you could really use a little help, too.3 If you can afford to, seek therapy. Seek treatment.

Good luck, and be well.


  1. The psychiatrist apologized when they delivered the results, prefacing it with “I know the name is offensive, and it’s not very accurate, but please forgive me since this is the clinical term”. 

  2. But that’s a story for a different day. 

  3. I haven’t yet had the opportunity to check it out yet, but given the likely audience for my blog generally, and for this particular post, I would be remiss if I did not mention that Open Sourcing Mental Illness might be a good place to start for that particular audience. 

Lenses

Squinting harder never cured my ADHD.

I suffer from ADHD.

photo of a man with his head in his hands Photo by Taylor Young on Unsplash

Update 2021-08-22: Almost exactly a year after this post was written, I sought and received a clinical neuropsychiatric diagnosis of ADHD (predominantly inattentive, sluggish cognitive tempo), so I’m no longer self-diagnosed.

I want to be clear: when I say I suffer from this disorder, I am making a self-diagnosis. I’ve obliquely referred to suffering from ADHD in previous posts, but rarely at any length. The main reason for my avoidance of the topic is that it still makes me super uncomfortable to write publicly about a “self-diagnosis”, since there’s a tremendous amount of Internet quackery thanks to amateur diagnosticians.

This despite the fact that I’ve known for the past 15 years that I have ADHD.

I am absolutely not trying to set myself up as a maverick unlicensed freelance psychiatrist here. If you think you might have ADHD, or any other ailment, whether mental or physical, call your primary care physician. Don’t email me.

At the same time, for me, this diagnosis is not really ambiguous or in a gray area. This is me looking down and noticing I’ve only got one arm, and diagnosing myself as a one-armed person. I’ve taken numerous ADHD screening questionnaires and reliably scored well into the range of “there is no ambiguity whatsoever, you absolutely have ADHD”, so I feel confident to describe myself as having it.

Terminology aside, this post is about a set of cognitive and metacognitive issues that I have, and some tools that I found useful to remedy them. I think others might find those same tools useful in similar situations. So if you’re also uncomfortable with the inherently unreliable nature of self-diagnosis, or the clinical specificity of the term “ADHD” — and I absolutely don’t blame you if you are — I invite you to read “ADHD” as a shorthand for some character traits that I informally believe fit that label, and not a robust clinical analysis of myself or anyone else.

With that extended disclaimer out of the way, I’ll get started on the post itself; and where better to do that than at the start of my own challenges.

The ‘Laziness’ model

photo of a cat relaxing on a couch Photo by Zosia Korcz on Unsplash

Throughout my childhood, I was labeled an “underachiever”. I performed well on tests and didn’t do homework. I was frequently told by adults — especially my teachers — that I was “brilliant” but “lazy”.

Was I lazy? Is there even such a thing as “laziness”? Here’s a spoiler for you — “no”1 — but I didn’t know that at the time. All I knew was that I couldn’t seem to do certain things — boring things: homework, long division, and cleaning up my room, for a few examples. I couldn’t seem to do the things that my peers found routine and trivial.

This is a common enough experience that it shows up clearly even in systematic reviews and meta-analyses of adult sufferers of ADHD. Everybody tells you you’re lazy, and so you believe it. It sure looks like laziness from the outside!

In retrospect, that’s the interesting problem with this false diagnosis: “from the outside”. Assuming for the moment that laziness does in fact exist and is a salient character flaw, what would the experience of the interiority of such laziness actually feel like?

It seems unlikely that it would feel like I what I actually felt at the time:

  1. Frequently, suddenly remembering, in contexts where it wouldn’t help — walking to school, in an unrelated class, while walking to work — that I had to Do The Thing.

  2. Anxiously, yearningly, often desperately wishing I could Do The Thing.

  3. Trying to Do The Thing at the responsible time, finding that my mind would wander and I would lose several hours of time... sitting for hours, literally bored to tears, while I attempted and failed to Do The Thing.

  4. At long last, finally managing to start. Once I was truly exhausted and starting to panic, I’d drink a gallon of heavily-caffeinated and very sugary soda at 2 in the morning and finally finally find that I suddenly had the ability to Do The Thing, and white-knuckle my way through an all-nighter to finish The Thing. (This step was more common after I got to my late teens; before that, The Thing just wouldn’t get Done.)

Sitting up night after night destroying my mental and physical health, depriving myself of sleep, focusing with every ounce of my will on tasks that I absolutely hated doing but was forcing myself to complete at all costs: it doesn’t seem to line up with the popular conception of what “laziness” might be like! Yet, I absolutely believed that I was lazy. If I were not lazy, surely Doing The Thing wouldn’t be so difficult!

I took pains at the start of this post to point out that mental health diagnosis is usually best left to professionals. I think that at this point in the story I should emphasize that “I’m lazy” is also itself a self-diagnosis, and — at least in every case where I’ve ever heard it used — a much worse one than “I have ADHD”.

If you are not a licensed psychologist or psychiatrist, any time you decide with certainty that someone (even yourself!) has an intrinsic, persistent character flaw, you’re effectively diagnosing them. If you decide that they’re inherently lazy, or selfish, or arrogant, you’re effectively diagnosing them with a sort of personality disorder of your own invention.

So, although I didn’t see it at the time, laziness didn’t seem to describe me terribly well. What description fits better?

The ‘Attention Deficit’ model

photo of a squirrel in a grass field Photo by Tom Bradley on Unsplash

In my late 20s, my Uncle Joel gave me a gift that changed my life: the book “Driven to Distraction: Recognizing and Coping with Attention Deficit Disorder”2 by Edward M. Hallowell. The life-changing aspect of this book was not so much that it showed that there were other people “like me”, or that my problem had a name, but that it gave me a different, and more accurately predictive, model to understand my own behavior.

In other words, it allowed me to see — for the first time — that the scarcest resource limiting my efficacy wasn’t the will to do the work, but rather the ability to focus. With this enhanced understanding, I could select a more effective strategy for dealing with the problem.

I did select such a strategy! It worked very well — albeit with some caveats. I’ll get to those in a moment.

Although my limiting factor was the ability to pay attention, the problem that prevented me from recognizing this was one of metacognition — the way I was thinking about how I think.

My early model of my own mind was that I was a lazy person who just needed to do what I had assumed everyone else must be doing: forcing myself to do the tasks that I was having trouble completing. If I really wanted to get them done, then what possible other reason could there be for me to not do them?

The ‘laziness’ model didn’t generate particularly good predictions. For any given project at school, it would predict that I would not try very hard to do it, since the very dictionary definition of ‘lazy’ is “unwilling to work or use energy”. The observed behavior, by contrast, was constant, panicked, intense (albeit failed, or at least highly inefficient) uses of significant amounts of energy.

The main reason to have a model of a thing is to make predictions about that thing. If the predictions that a model gives you are consistently wrong, then the model isn’t directly useful. At that point, it’s time to discard it and find a better one. At the very least, it’s time to revise the model in question until it starts giving you more accurate, actionable information.

The ‘laziness’ model is wrong, but worse than that, it’s harmful. What it routinely predicts, regardless of context, is that I need more negative self-talk, more ‘motivation’ in the form of vicious self-criticism, more forcing myself to “just do it”. All of these things, particularly when performed habitually, cause real, significant harm.

If I gave myself the most negative self-talk I could muster, the most vicious criticism, and really put Maximum Effort into forcing myself to do the thing I wanted done... if it didn’t work, of course that just meant that I needed to engage in even more self-abuse! I could always try harder!

This is the worst way that a model can be inaccurate: an unfalsifiable, self-reinforcing prediction. I could never demonstrate to myself that I’d really been as unkind to myself as was possible; there was always room for escalation. Psychologically, it’s also the worst kind of behavioral advice, which is the kind that generates a self-reinforcing negative feedback loop.


Once I started putting my newfound knowledge into practice, the difference between interventions predicated on an understanding of the problem as “lack of usable attention span” and those based on “lack of willpower” was night and day. I stopped trying to white-knuckle my way through all of my challenges and developed non-judgmental ways to remind myself to do things.

I knew that I, personally, was never going to spontaneously remember to do things at the right time, so I developed ways of letting computers remind me. I knew that I’d never be able to stick with routine, repetitive tasks, so I made a unified list of all the tedious administrative tasks I need to perform. I can’t keep important dates and times in mind, so I rely completely upon my calendar.

Even given these successes, “it worked!” is a colossal oversimplification. Today, it’s about 15 years later, and I’m still sifting through the psychological rubble wrought by the destructive, maladaptive coping mechanisms that I just described, and still trying to find better ways to remain effective when I’m feeling distracted... which is most of the time.

Simply having a better model at the coarsest level is just the first step. Instantiating that model in a working, fleshed out technological system is a ton of work in its own right.3 But it’s work that starts having little successes, which is a lot easier to build on and maintain momentum with than the same failure repeated day after day.

Given that I was starting — nearly from scratch — at 25, and had a lifetime worth of bad habits to unlearn, constructing a workable system that addressed my personal organizational needs still took the better part of a decade.

So as I move into the next, slightly more prescriptive section here, I don’t want to give anybody the idea that I think this is easy.

Don’t give up!

Listen up, Simon. Don’t believe in yourself. Believe in me! Believe in the Kamina who believes in you!

Kamina, Episode 1,
Tengen Toppa Gurren Lagann

At the start of this post, I specifically mentioned that I hadn’t wanted to write at length about ADHD due to my discomfort with self-diagnosis. So, you might be wondering: what was it that overcame this resistance and prompted me to finally write about my own experiences with ADHD?

The original inspiration was a pattern of complaints about suffering from ADHD I see periodically — mainly on Twitter — that look roughly like this:

  • “ADHD means never being on time for a meeting and having no excuse, forever.”
  • “It’s great to have ADHD and never be able to complete a routine task. Sigh.”
  • “I can’t take out the trash and my roommates just can’t understand that this is just part of who I am and I will never get better.”
  • “Why can’t neurotypicals understand that I’m just never going to “get stuff done” like they can. It’s exhausting.”

These are paraphrased and anonymized on purpose; I really don’t want to direct any negative attention towards someone specific, particularly someone just venting about struggles.

Of course, no blog post in mid-2020 would be complete without some reference to the ... situation. The original inspiration for this post predates the dawn of the new hell-world we all now inhabit, but, to say the least, COVID-194 has presented some new challenges to the coping mechanisms I’m writing about here. (Still, I know that I’m considerably better off than the average American in this mess.)

The message I’m trying to get across here is hopeful — others suffering with executive-function deficits similar to mine might be able to do what I did and fix a lot of their problems with this one weird trick! — and the constant drumbeat of despair all around us right now makes that sort of message feel more urgent.

Posts like the ones I described above seem to represent a recurring pattern of despair, and they make me sad. Not because I can’t identify with them; I have absolutely had these feelings. Not even because they’re wrong, exactly: it really is harder for folks with ADHD to handle some of these situations, and the struggle really is lifelong.

They make me sad because they’re expressing a fatalistic perspective; a fixed mindset5 that precludes any hope of future improvement. The through line that I have seen from all of these posts is a familiar, specific kind of despair; a thought I’ve had myself multiple times:

When somebody that I care about asks me, ‘Can you do the dishes later?’, I want to say ‘yes’ and have them believe me. I want to be able to believe myself, and I don’t think I will ever be able to.

Unlike myself when I was younger, the authors of these posts already have a name for their problem: ADHD. Sometimes they’ve even tried some amount of therapy or even medication.

Even so, they’re still buying in to the maladaptive strategy of “just try harder”. Since they already know that ADHD is, at least in part, a structural brain difference, they despair of ever being able to actually do that though, which leaves “giving up” as the only viable strategy.

Don’t give up! I believe in you!

Different problems, different tools

I have had another lifelong problem since when I was young: I am severely nearsighted. Yet, I never developed any psychological hangups around that; nobody ever told me that I needed to buckle down and just squint harder. This problem was socially quite well understood, so… I got glasses. Then I could see, as long as I consistently used those glasses.

Nobody ever expected me to be able to see without glasses.

photo of a pair of eyeglasses resting on a book Photo by NordWood Themes on Unsplash

Calendars, to-do lists, and systems like Getting Things Done are the corrective lenses for the ADHD brain.6.

If a to-do list is a corrective lens for ADHD, one of the major issues around understanding how to use it is that the mass-market literature around to-do lists assumes a certain level of neurotypicality. Assistive devices may frequently be useful to non-disabled people, but their relationship to and use of such affordances is very different.

Through the Looking-Glass ...

Let’s stretch this lens metaphor into absurdity.

In our metaphorical world, ADHD is myopia, and so most — or at least many — folks are “sight-typical”. Productivity systems are our “lenses”.

If nearsightedness were as poorly understood as ADHD, and you were nearsighted, you wouldn’t be able to pop on down to Lenscrafters and pick up a pair of spectacles. You might realize that the problem was with your eyes, and think, “lenses might help me see farther”. Many kinds of lenses might be commercially available in such a world! Lenses for telescopes, cameras, microscopes...

The way that someone with 20/20 vision might use a lens to see farther is to use a telescope to see something really far away. But you, my hypothetically-nearsighted friend, don’t need a powerful zoom lens to take surveillance photographs from a helicopter. Even if you could make such lenses work to correct your vision, you wouldn’t want to carry a pair of 2-kilogram DSLR zoom lenses everywhere you go. You want eyeglasses, which are something different.

photo of a picture of a giraffe with DSLR lenses over its eyes Photo by James Bold on Unsplash

The lenses in eyeglasses are — while operating on fundamentally the same principles of optics as the lenses in a telescope or a microscope — constructed and packaged in a completely different way. But most importantly, the way you use them is to wear them every day, not to deploy them on special occasions in the rare event where you need to do something extreme, but all the time, every day, in the same way.

... and What I Found There

photo of a to-do list written in a notebook Photo by Glenn Carstens-Peters on Unsplash

A person with nominal executive function might use the occasional free-floating to-do list to track a big, complex project with a lot of small interrelated tasks. Most folks in the modern information-driven economy routinely need to do projects that are too complex to easily memorize all the required steps. Even doing your own personal taxes has enough steps to require at least a little bit of tracking.

Such a person could make a to-do list for that one project — their telescope, if you will — put it in a place where they’d remember to look at it when they’re working on that project, and then remember to check things off when they’re done.

They could have one to-do list on the fridge for groceries, a note on their phone for stuff to get for their spouse, and a wiki page outlining some tasks at work. They would probably have enough free-floating executive function to remember which list maps to which project and when each project is relevant, and remember to check each one at the appropriate time.

I spent a lot of time trying to make disconnected to-do lists like this work for me. They never have. Even when I’m feeling particularly productive there is a cycle of list-generation, that goes like this:

  1. When I want to work on the project in question, I can’t remember where the to-do list is, but I need to figure out what I need to do again.

  2. So I go and write a new to-do list, spend a bunch of time rewriting the one I’d already written but can’t quickly find. Then I do some work on the project, check off a few things, and put the list away.

  3. Later, I’ll find both lists, both half checked off, and now I waste a bunch of time trying to figure out which one is the right one.

  4. Repeat this process a few times, and now I have a dozen lists. The lists themselves start generating more work than the actual project, because now I am constantly re-making and finding lists, trying to figure out which one is the most up to date.

This is the simplest case, but the real problem happens at a higher level: one of the biggest problems caused by any executive function deficit like ADHD is the difficulty of task initiation.

The more irrelevant distractions I can see while I’m trying to work out what to do next, the harder that decision becomes. And there’s nothing quite so distracting as the detritus of a thousand half-finished to-do lists.

One List To Rule Them All

What I’ve found works for me is a single, primary to-do list that I can obsessively check in with every minute of every day, which subsumes every other list related to every other project in my life.

I’m hardly the only person to have this insight — if you start engaging with the “productivity” noosphere, reading all the books, listening to the podcasts, this is a recurring theme. You don’t just have an ‘app’ or a ‘list’, you have to have a System. It has to be reliable; you have to know you’re going to keep checking it, or it’s worthless for storing your commitments. But unfortunately this is frequently buried under a lot of other technical complexity about the fiddly details of how to set up one system or the other. It’s very easy to miss the forest for the trees.

Having ADHD means that I routinely forget what I’ve decided to do over the course of only a minute or two after I’ve decided to do it. Just this week, I had to remind myself no fewer than three times to write down “buy more olive oil” because I kept remembering that we were running low when I was in the kitchen and by the time I finished washing my hands to put it into my phone I’d already forgotten why I did that and went back to making dinner.

I need to write everything down. I’m not going to remember five or six, or even two or three places to check for what to do next. I need to have one place to check what comes next, and then build the habit of constantly going back to it, both to add new things and to see what needs to be done.

Technology can help. Technology might even be necessary — it is for me.

But if you’re considering trying this out for the first time, be mindful that piles of to-do apps can be just as distracting as piles of paper. The important thing is to clearly, singularly decide on the one place which is the ‘root’ of your task tracking system.

You can even do this with a pen and paper. Carry the same, single notebook with you everywhere, and make it absolutely clear that it is your primary list, which is where you have to put any references to other lists. Some people have a lot more success with something tactile, to engage all the senses.

For me personally, the high-tech portion of this strategy is indispensable. I use a combination of OmniFocus for things that have to be done and Apple’s built-in calendar application for places I have to be at a particular time.7

OmniFocus8 defines the core gameplay loop of my life. Rather than having to cultivate and retain an elaborate series of interlocking habits and rituals to remain functional, I have a single root habit which triggers every other habit.

That habit? Consulting the unified “what should I do next” perspective in OmniFocus. Every time I am even marginally distracted, I check that view again.

Any time I have trouble initiating a task, I start breaking down the top task in that list into smaller and smaller “next physical action”. I don’t even rely on myself to do this; since I know I’ll forget to break things down, I frequently make tasks that look like this:

  • thing I want to do
  • plan the thing I want to do
    • break down the planning task into tiny actions and write them down here
    • break down the task itself into tiny actions and write them down here

To reduce distraction, I routinely close down any windows that are not necessary for whatever I’m currently working on. Particularly, I routinely sweep to get rid of browser tabs, asking (as I would with an email) “does this window represent a task I should do?”. If yes, it goes in the task system, if no, I close it so it won’t distract me further.

To facilitate this clean-up, on every computer that I use, I have a global hot-key set up to turn the thing that I’m looking at — some selected text, an image, an email message, a browser tab, a chat message at work — into a task that I can look at later.

Everything I have to do on a regular basis is in this system as a recurring task; for example:

  • taking out the trash
  • doing the dishes
  • logging in to Jira at work to look for assigned tasks
  • checking my email
  • brushing my teeth

Yes, even basic personal hygiene is in here. Not because I’ll necessarily forget, or that it takes a lot of energy, but I don’t want to waste one iota of brainpower I could be devoting to my current task to worrying about whether I might need to do something else later. If I don’t see ‘brush teeth’ in my “what should I do next” view, then I know, with certainty, that I don’t need to be thinking about tooth-brushing right now.

The “what should I do next” view is available on all of my computers, on my tablet, on my phone, and it even dominates my watch-face; I check it more often than I check the time:

screenshot of an apple watch face displaying a to-do item saying “write ADHD blog post”

No single feature is a hard requirement of my system; I could get along without any one of them in a pinch. However, the way that they combine to constantly reinforce what the next thing I need to do is in any given context, at any given time, means that I need to expend less energy trying to consciously hang on to all the context.

Limitations and Risks

I don’t want to give an overly rosy view of this strategy. Getting a single unified to-do system that works for you is not the same as getting a brain that can remember to do stuff. So here are some caveats:

  1. Implementing and maintaining such a system is never easy. It just takes tasks like ‘making sure I renew my passport before I need to travel’, ‘show up on time for the meeting’ and ‘buy a gift at least a week before the wedding’ from totally impossible to possible to do at least somewhat reliably with a sustainable level of effort. The main thing that I believe is possible for everyone is being able to commit to simple future tasks.
  2. Building enough data about one’s own habits and procrastination triggers also takes time, and to make such a system effective, one needs to do that work as well. (A passive time-tracking tool like Screen Time on your phone or RescueTime on your workstation can be quite illuminating — and surprising.)
  3. The initial wave of relief I felt when I started tracking tasks masked a gradual increase in my general anxiety over time. Checking and re-checking the ‘what to do next’ list can become a bit of an anxious compulsion, a safety behavior that doesn’t always help me plan my day. As one builds the habit of routinely checking the list, it’s important to avoid developing constant anxiety about the list as the only motivation to do so.
  4. Similarly, it is important to learn to under-commit. Not only does one need to avoid putting an unrealistic amount of stuff into the system, everybody (but especially everybody with ADHD!) needs non-trivial chunks of unstructured, unplanned time, where the system will clearly say ‘nothing to do now, just relax’. The “poor self-observation” and “time blindness” symptoms of ADHD ensure that properly estimating things before committing is a constant challenge that never really goes away either.
  5. This strategy definitely won’t be sufficient for some folks. ADHD is a spectrum and there’s no precise mechanism to calibrate where you are on it. Some folks will respond really well to this strategy, some folks will need medication before it helps to a useful degree.

Finishing up (about finishing up)

If you’re suffering from ADHD and despairing that you will never finish a task or be on time to an appointment: you can. It’s possible to do it at least pretty reliably. I believe if you commit to one and only one task tracking system, and consistently use it every single day, all the time, you can commit to tasks and get them done.

If you do it consistently enough, it will eventually become muscle memory, and not something you need to consciously remember to do every day.

It’s still never going to be easy to Do The Thing, even if your digital brain can perfectly remember what The Thing is right now.

At the very least, it was possible for me to learn to trust myself when I say that I will do something in the future, by designing a system around my own limited attention, and if I can do it, I think you can too.


Acknowledgments

This was a big one! I’d like to particularly thank my Uncle Joel, without whom this post (and many of my other achievements) would not be possible for the reasons described above, as well as Moshe Zadka, Amber Brown, Tom Most, and Eevee for extensive feedback on previous drafts of this post.

Additionally, I’d like to thank David Reid for introducing me to many of the tools and techniques that I still use every day, and Cory Benfield, Jonathan Lange, and Hynek Schlawack for many illuminating conversations over the years about the specifics and detailed mechanics of the tools whose use I describe in this post.

Any errors, of course, remain my own.


  1. The broader topic of the nature of “character”, fundamental attribution error and the extent to which the entire concept of a “character flaw” is a cognitive illusion that arises from the expedient but cruel habit of ignoring the context in which someone is making decisions is more than enough fodder for another post, but here are some good articles covering a newly-emerging psychological consensus that laziness as we understand it doesn’t really exist, and that there are always mitigating factors

  2. Paid link. See disclosures

  3. It was 54 years from Einstein figuring out the photoelectric effect in 1905 to the first MOSFET in 1959; and another 45 before we got MicroSD cards out of the theory of quantum mechanics. 

  4. Hello, future archaeologists! If you’re reading this in the far-flung future, as of this writing, shit is just incredibly fucked up right now. Just incredibly, horrifically fucked up. 

  5. Growth Mindset is a useful concept, but it definitely has a lot of problems, and has been a particularly pointed casualty of the replication crisis. This is a pretty good post outlining its remaining utility, even in the face of its relatively small remaining effect size. 

  6. This is to say nothing of medication, which is also quite useful. More or less necessary, in fact, for some of those suffering from ADHD. One thing I want to be very careful to point out is that in this post I’m talking about my own experiences with ADHD here; without a proper diagnosis, I haven’t had the opportunity to try a pharmacological solution, so I can’t comment on its efficacy for me. However, there’s a school of thought that since some people can resolve some of their ADHD problems with non-medicative interventions, therefore all people should refrain from medication. I want to be as clear as possible that I do not endorse this point of view. 

  7. I’m not going to get into what I use for email here, since I’ve written about that before, and you can just go read that. 

  8. Since I know many of my readers are not in the Apple ecosystem, and might be motivated by this post to put some of these ideas into action, there are plenty of cross-platform apps with similar capabilities. You might check out Taskwarrior, Todoist, or Remember The Milk. There’s definitely something out there that can work for you!