How To Stay On Top Of Your Shit As A Flawed Human

rhetoricize
10 min readApr 1, 2019

I can probably thank the motivating factor of chronic recurrent distractibility that I’ve spent the majority of my adult life constructing elaborate organizational systems and safety nets to prevent my intractable attention span from wandering at every split second into a bottomless hole of distraction fodder, whether externally or intrinsically generated. Since I’m already maintaining this elaborate system at all times in order to achieve just baseline functionality, it’s easy to throw just a little more into my daily routine to up “baseline functionality” to “super on top of my shit, mostly”. I still donk up, but apparently infrequently enough to fool some people into believing that I have inaccessible, mystical, logistical superpowers that they cannot also achieve.

The truth is that I am as flawed and forgetful a human meatblob as any, but I have constructed a variety of simple logistical prosthetics to directly compensate for my personal weaknesses, largely held together by the twin adhesives of sticky notes and Google Calendar. It takes a bit of detective work and trial and error, but unblocking yourself so you can decide to get shit done and then actually do it is one of the raddest catalysts you can gift to your own self-fulfillment trajectory.

Occam’s Razor for safety nets

You are a flawed and, to varying degrees, somewhat irresponsible human. It’s nothing personal; it’s just true for everyone. This will not change by chanting “i will be more responsible, i will be more responsible”; that is the indulgent trap of hubris.

However, foreknowledge, understanding, and acceptance of your tragic flaws allows you to build effective safety nets around them. Foreknowledge, understanding, and acceptance alone don’t change anything; it gets old pretty fast if you keep showing up late to commitments with the excuse “well, I’m just not one of those people who’s good at being on time.”

Analyzing your historical behavior is merely the prerequisite step to designing a safety net to target your weaknesses so that they are more difficult to fall into. Rather than trying to bum-rush your weaknesses head-on while chanting to yourself “I will not forget to do this I will not forget to do this” and then inevitably forgetting to do it, you can more easily circumvent them by strategically flanking and trapping your irresponsibility so it has nowhere to escape to.

Coming up with rules that work

  1. AWARENESS: Make a brutally honest list of ways you personally suck at being responsible. Accept them and accept that they are difficult to change directly.
    (for me: losing track of time, getting distracted whenever I check my phone, forgetting things 10 seconds after thinking about them, letting lists pile up, forgetting meetings, overcommitting)
  2. DEBUGGING: When are you most and least likely to successfully complete your goal?
    Identify favorable and disfavorable conditions. Would it help you to have a written reminder? An alarm? A physical box that you organize similar things into? Is it too much energy when you have to go dig a specific notebook out of your desk before you can do a task? What do you need in place in order to do the thing?
  3. CREATE A HABIT: Identify the simplest possible habit you can form which will negate your future irresponsibility lapses.
    By “simple”, I mean something you can do the instant a task presents itself to you; something that doesn’t require any creative thoughts, fresh action plans, critical evaluations, or having to locate an object that’s not in your pocket. Simple, repeatable, mindless behaviors are key to forming automatic habits.

Related reading recommendation: The Power of Habit by Charles Duhigg is a nice read into the cue-routine-reward loop of habit formation and repetition, accompanied by illustrative anecdotes.

Example scenario

(1) AWARENESS

Let’s say I want to tackle my forgetfulness about tasks I need to do in the near future. (This includes such mundanities as getting the laundry, checking on a boiling stove, going to a meeting, remembering to take something out of the oven, or taking the tea strainer out of the teapot before it overbrews.)

Trying to remember to do these things by myself has repeatedly ended in comic tragedy, overboiled pasta, overbrewed tea, smoking ovens, and mildewy laundry. Let’s accept the assumption for now that I am incapable of remembering to do something more than 30 seconds in the near future.

(2) DEBUGGING

However, I am quite capable of doing the things with a loud alarm. What’s the easiest way to make sure I set and hear this alarm? My wristwatch’s alarm is kind of a pain to set and easy to miss, but my phone’s alarm is very loud and easy to set. But sometimes I walk around the house without my phone and miss it. So I need to make sure I keep the phone near me.

(3) CREATE A HABIT

I create a very simple, minimal, yet powerful habit: any time I have to do something in N minutes, I will set a timer on my phone and put the phone back in my pocket.

(Related yak shaving anecdote—I realized my oft-pocketless women’s pants were holding me back in life because pockets are the exception rather than the norm. A few months ago, I donated all my pants whose pockets could not comfortably contain a phone or wallet, and went shopping specifically for pants with deep pockets. This was an almost comically impactful unblocker in my life for many layers of productivity, happiness, and streamlined-decision-making, allowing me to constantly carry useful daily tools, and freeing me of the need to confront the dilemma between functionality and style every morning. Get it together, fashion industry.)

More boringly effective examples to prod your thought-juices for inventing habits

Some more habits I’ve built to flank my weaknesses.

Weakness: getting distracted whenever I open my phone
+ <one-time prep, not a habit> make my phone deeply unengaging
+ if I am bored, look at the beautiful mundane world around me, rather than at my phone. (pet a moss, listen to a bird, talk with a stranger, etc)
Weakness: forgetting things 10 seconds after thinking about them
+ if I would like to remember something, write it down in my pocket notes
Weakness: my todo lists have piled up
+ if starting a new sticky note, write date and context at top
+ star the 2 most critical items on each sticky note
Weakness: being late / forgetting events
+ as soon as I become aware of an event, immediately put in calendar
+ if event involves traveling somewhere, add an event named "transit" before it that lasts 15m + travel time
Weakness: overcommitting
+ if presented with potential commitment, don't immediately say yes by default
+ if the answer is not obvious or if I lack information, write down opportunities in my pocket sticky notes to consider later
Meta-unblockers
+ <one-time prep, not a habit> only own pants with respectably spacious pockets
+ any time I put on pants, put sticky notes, pen, and phone in my pockets
+ when getting dressed, put on my watch

The sheer quantity of habits here might look overwhelming, but I’ve built up this internal habit repository over many years of debugging my own personal failures to live the way I want to live, and each individual habit is super simple and mindless. You can do it too if you start one habit at a time!

The key is that these habits require no critical evaluation (“if obvious cue happens, do habit”), and they each involve a single, small action that doesn’t require me to go out of my way, so long as I habitually keep four small items on my person: a watch, a phone, sticky notes, and a pen.

Exobrains

Human brains are great at some things, but not so great at storing random information in verbatim format. Augment yourself with an exobrain!

Exobrains are all different and subject to some trial and error. An exobrain is not merely a planner notebook, or a productivity app, or sticky notes in a pocket. That’s just the raw data. An exobrain is also a network of habits and preferences you carry within your own mind — an interface customized to your weaknesses, if you will, for how to most cognizantly access and store the raw data.

For example, I could tell you the concrete tools that make up my exobrain — sticky notes and a pen that are always in my pocket, a 3x5 notebook that I transfer todos into, Google Docs to dump longform information. But simply using those tools and apps would not work for you. Without the associated habits, the habitual structure you impose on information to make it more readable, the reasoning for using different tools in different situations, and the tailoring of your writing formats to the way you think, the physical tools are no better than any random word processor or random notebook.

That said, an exobrain must have certain features in order to be effective.

  1. easy to write in (low activation energy)
  2. easy to read (not overwhelming, easy to search, contextual)
  3. low-distraction
  4. difficult for items to slip through the cracks and be forgotten forever

1. Easy to write in.

Accessibility is important. Ideally, your exobrain is always at hand and easy to open.

Mental activation energy is as important as physical accessibility; you need to be able to write without hangups. For example, a cheap-ass replaceable pocket notebook that you habitually jam into your pocket every morning is an easy entry point. A large notebook with a gorgeous embossed cover that makes you scared to write in it, and that you keep in a box on a high shelf, is a terrible entry point.

2. Easy to read.

It’s easy to write loads of notes you never remember to look at, so make sure your exobrain is easy to skim, easy to purge, and easy to identify context. I always write the date and context on the top of notes.

When organizational schemes are too complex, they often fail by being too overwhelming to maintain or too overwhelming to look at. Keep it as simple as you can.

It may help you to group similar things together. I frequently think of home improvement todos, hear of educational content or musicians I want to look up, etc, so I have a Frequently Used Topics section in the front of my notebook where I stash these items. I originally tried an elaborate tagging scheme where I colored tags along the sides of the pages and it was too much effort to maintain, so I quit. Again, your mileage may vary.

I find it helpful to write a short contextual manifesto to my future self in the top of all my digital longform notes. Examples:

  • “I am building awareness of my material possessions because I would like to be more cognizant of my consumption patterns and stop owning things I don’t need.”
  • “I am keeping track of my movement workshop notes to make it faster to apply to teach workshops and to optimize the content teaching order for learners.”

This helps me stay on track with my intentions, instead of spewing out notes for no reason other than to have them. This way, when I come back to my overflowing digital notes after some time, I can remember my overarching goals and the original problems I was addressing, instead of getting distracted by the proposed solutions or the fine details in a zillion bullet points.

3. Low-distraction.

I think this frequently comes down to analog vs. digital, although your mileage may vary.

My notes tend to funnel into two categories: quick todo lists, and detailed long-term notes.

For any notes I want to scribble down quickly and then get out without any lingering — daily todo lists, fun facts, music my friends have recommended, grocery lists — I use only analog entry points. Computers are distracting as hell. (I once tried using Evernote on my phone as an exobrain entry point, and it ended in several hours of Facebook newsfeed scrolling. I don’t remember the original thing I was trying to do.)

Pocket notebooks or sticky notes are a great low-distraction entry point. They are a blank slate serving little purpose other than the containment of your thoughts. (Said thoughts may or may not include origami.)

For long-term exobrain management, I rely heavily on Google Docs because I find it useful to share notes, make spreadsheets, and type out massive amounts of structured information. This is great if I’m compiling longform information that I’m going to be bashing on for an hour or more (such as reading notes for research papers, rundowns of applied sourdough science, or workshop teaching notes).

For more general tips on reducing digital distraction, check out my 2017 article on making your devices deeply unengaging.

4. Difficult to lose track.

Exobrain items love nothing more than getting lost forever. It’s important to continually expire todos lest they pile up and become overwhelming. For events and plans, I avoid losing track by habitually entering them into my Google Calendar the instant I consider going to the event or executing the plan.

“Plans” include incredibly mundane events such as breakfast because I am a trash person who is bad at remembering to eat breakfast, which I inevitably regret three hours later when I have become a zombie. No item is too embarrassing to enter in your calendar or alarms, because guess what: being automatically reminded about things you want to do more often results in you remembering to do them more, no matter how basic the thing is.

behold my glorious recurring breakfast reminder and also recurring reminder of my unsupervised inability to actually get myself out of bed in the morning without rolling around in my cozy grave of blankets for about 30 minutes

Notes and todos are tricky to stay on top of because organization is far more a function of mental customization than tool choice. You could use a webapp that purports to have developed the perfect organizational scheme, but if you are obsessive enough to have read this far, your brain structure will probably mesh imperfectly with it and let things fall through the cracks. (My purely anecdotal understanding is that pre-made organizational systems tend to work better for people who do not already have major distraction problems.)

One major reason I prefer analog todo lists is that I’m forced to address them when the pile of paper gets too big, while digital notes can invisibly hide forever without being addressed. In Google Keep and Evernote, I have graveyards of random todos stretching back years that I will embarrassingly find 5 years later. The lost souls of these todos will wander this plane for eternity.

As usual, I hope these metrics and pitfall-avoidance-tactics were vaguely useful to you; drop me a shout if you have questions or suggestions and otherwise go forth and live your best life.

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rhetoricize

autotelic polymath with an overwhelming compulsion to reverse engineer things I’ve never tried before