Taming My Organizational Tornado

Thinking about and exploring how I should organize my life.

The Teardown

Thursday :: May 8th, 2024

👋 Hi, this is Chris with another issue of The Teardown. In every issue, I cover how we evolve in concert with the technology that enables our day-to-day lives. If you’d like to get emails like this in your inbox every week, hit the subscribe button below.

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I previously wrote about using Todoist to create habits and maintenance procedures in life. I described what worked in Do You Buy From A Slob:

• Simple to-do set-up: As a start, write a task name. That’s it. I use due dates to keep myself honest too. There are more advanced features, some of which I've used, but I’m not doing a deep dive right now.

• Nudges: The app sends push notifications and reminder emails. The reminder email is great as it highlights what I need to do - once per day. It is. So far, this combination works effectively as it’s not overwhelming but also not letting me off the hook.

However, Todoist is just one of many tools in my life. A family member asked me about my system for data collection. Do I keep records? Do I collect data? If so, where? How?

I said something like yes, but not quite that word. There was smirk on my face when I wrote the response in our WhatsApp chat.

Flashing back to that moment today had me laughing: am I organized? And, maybe by extension and consumption, you might figure out if you are.

Man uses right tool for the job, and one screen per job

First, Right-Angle Obsessions

Before you read this section, I’ll come right at a condition that might criss-cross your might through this post: obsessive-compulsive disorder, or OCD, or colloquially something like dishwasher (if you have one) dictator.

My life as a semi-organized individual started with my love of angles. Or obsession. You be the judge.

I played with rudimentary architecture applications on the family computer during the late 90s and early aughts. I was in a drafting class in high-school. And, at some point, my brain decided that most things needed near-perfect physical placement around me.

A piece of paper needs to be on a desk with perfect parallel edges. I place my knives on cutting boards either parallel or perpendicular to the cutting board edge closest to me. That edge is, of course, parallel to the counter edge. Pots and pans on the stove have handles pointed in the same direction or in some angular and organized way to maximize space. My dishwasher organization system should be on display The Met.

I care a lot about this system in my kitchen. Do I belong in some local insane asylum with other suburban dads that complain about their disheveled dishwashers during weekend days at the park? Probably!

My kitchen and other high-interest physical areas are still just that: tangible, physical things around me. What the intangibles? What about email? What about important files for home renovation? What about notes about my house? What about a calendar?

All of these things should be organized, right?

One Approach: Algorithmic Czar

Let’s come back to that question in a moment. Let’s instead focus on the concept of a messy desk for a moment.

The book Algorithms To Live By covers a computer scientist’s approach to daily life and decisions. Chapter Four focuses on caching, the art (and science) behind storing something for later retrieval. A comment on Hacker News caught my eye:

I read the book a while back and realized I do the caching one automatically. I have a pretty messy work bench where I build rockets and play around with microcontrollers. I purposely didn’t try to organize it because, over time, it organizes itself. All the stuff that has my attention gradually drifts to arms reach where the stuff I don’t currently need gradually drifts to the back of the workbench.

What an overachiever! This person tosses a calm bomb of intelligence to the audience, claiming to build rockets and play with microcontrollers. Yes, of course, don’t we all?

They also say that they don’t organize their desk because it naturally sorts itself. Stuff they use frequently is close by and laying in peace parallel or perpendicular to other things. Items that decrease in importance drift away, unmoored but in calm water. Things of little relevance over some span of time gather fine age and dust elsewhere.

So, there is a system of caching here that might look like this:

• Level 1 - Don’t Forget It / Need It Soon: You need to do something by the end of the day and make a note. You keep that note close by. It might be the classic sticky note on a computer monitor. Or, a to-do in an app with extra reminders and alarm bells.

• Level 2 - Likely Irrelevant In Foreseeable Future: There is some pile of things that might have relevance at some point. Nothing in that pile is urgent today. Nothing needs attention right now. You’ll pick through it tomorrow or next week or next month.

• Level 3 - What Are You Talking About?: If you’re asking, you care. But I don’t care. Remind me what we’re talking about? Oh, is that the huge pile of things in the attic, basement, secret room (yes, remarkably - my house has one)

Level 1 stuff is at arms-reach but probably ephemeral in some sense. It’s important only in the near future. Level 2 has valuable material but is a pile. You spend or waste time finding the thing you want and picking it out of the pile, perhaps depositing the thing in Level 1. Level 3 may or not be a mess but is a true archive of lots of crap that rarely see light, oxygen, or love. Retrieving something from Level 3 is very time-consuming.

In a computer, the first level is a small but very fast blob of storage that contains things that the processor and/or GPU (graphics) chips need in short order. Storage size often increases as you move into the second and third levels, but those storage blobs are slower. After all, the chips don’t need those things too often, so retrieval speed is less important.

The filing and retrieval operations are also important. In simple terms, there are techniques focused on how to organize things in the caches, and how to search and pull things out. Everything is tidy, organized, and searchable.

There’s one last level: the hard disk, or maybe Level 4 to continue with our example terminology. It hold a vast number of things, but takes much longer to search. And, sometimes that vast collection is a bit ragged around the edges, requiring a helper to move things into more optimal location or, in solid-state disks, to do a little surface cleaning.

So, this all sounds like a well-oiled machine. What about me?

Partial Organizational Paralysis

Here are a few statements about my organization systems. I’ll focus more on digital organization:

1. I keep a tidy desk that functions a bit like the rocket guy’s desk I mentioned earlier. Most things on my desk are Level 1 items, or at most Level 2.

2. My personal computer is similar. The “Desktop” is where lots of things live that I think I need soon. I file other stuff into various local folders or cloud folders depending on their importance.

3. My cloud storage looks a lot like Level 3. I stuff away lots of digital assets that I really don’t need any time soon. Examples: documents from purchasing my house (4 years ago). I reference them once a year or so, maybe.

4. Lastly, there is a trove of information on an old spinning hard drive and a handful of USB thumb drives (and, yes, a few writable CDs). Looking through these archives often produces a thought like I really should really get rid of this stuff. But, then I don’t. Storage capacity isn’t a limiting factor. It’s easier to keep everything and not spend time pruning. Long live small-dollar cloud subscriptions!

In shorter words, there are four basic storage bins:

1. A desk

2. A local digital drive (in my computer)

3. A cloud (one or more) digital drive

4. Various local plug-and-play disks and drives

There’s one last puzzle piece that’s somewhat harder to categorize: thoughts

Where I lack proper structure is in the documentation of my thinking.

Too Many Tools?

I think the answer is yes. What I’m exploring and motivated me to write is the process of cleaning up my digital life and how I paint my thoughts onto digital paper. These days, I’m often using some combination of these tools.

Gmail, Google Calendar, Hey (email), Notion, Todoist, Google Drive, Microsoft OneDrive, 1Password, iPhone voice memos, Apple Notes, Dropbox Paper, Microsoft Excel, Google Sheets, and Substack Drafts. I’m probably leaving out five to ten others.

So, about that data collection I mentioned? Let’s say I want to centralize stats about all of my blood tests over time. I might do that in Google Sheets to enable data-oriented operations. Or, I could download all the tests in their various formats and store them together in a local or cloud folder.

Then what? Is this action accretive to my time or is it a total waste of brain cells? The possibilities trap me between thinking that I won’t use the data and should toss it vs. building some sort of dashboard to satisfy my over-analyzer personality.

My recent usage suggests some improvements to the above tool cacophony, narrowing my day-to-day work to just a handful of apps:

• Notion is my reference library to construct and store recipes, notes, home instructions, and etc. I don’t love populating this sort of stuff in a platform I don’t control, but it does the job well for now. Also, it’s where I document lots of professional things like notes about conversations, business ideas, etc.

• Excel and Google Sheets are my data-centric portals. Why both? Excel is for local-only tracking of sensitive things (e.g. budget) whereas Sheets is for other data points - like car mileage, or drink counts. I like trends, measurements, and accountability.

• Todoist is for tracking things I need to do, and methodically ticking through those things. Notion has to-do lists as well, as of course, you can construct a simple checklist in Excel and Google Sheets. But, Todoist is built for the concept of to-dos whereas the other products integrate the concept. Use the best tool for the job.

Also, let’s not forget two critical puzzle pieces: email, and a calendar.

I switched from Gmail to Hey for person-to-person emails within the last two years. My Gmail looked like a traffic hub for everything - ads, personal emails, newsletters, reminders, etc. Algorithms To Live By suggested I was waiting my time with pruning, labeling, and sorting. Instead, I needed to empower my brain with search, the foundation of Google itself. And, sure, I search Gmail and usually find what I need without wasting too much time.

But Hey was missing a calendar, something tied for better or worse to email. 37Signals recently added a calendar to Hey to blunt the inconvenience of using one address for email and another for calendar scheduling. Alas, Hey’s calendar is just too weird for me, for now. And, it doesn’t include built-in conferencing that I’m so used to using via Microsoft Teams in Outlook or Google Meet via Google Calendar.

I referenced Hey because I wanted to reduce the strain of digging through loads of emails in Gmail, but the resulting additional strain of flipping between email addresses because of calendars isn’t working well. So, I’m likely to flip back to Gmail.

There are also loads of files and other archives in my various cloud storage sites like Google Drive and Microsoft OneDrive. On one hand, I’d like to centralize important stuff from both clouds in just one of the two, or move everything into a secure enclave like 1Password.

And, my existential/meta-thoughts? I’m tossing them in Notion. I have another Notes About Notes post in the works that will go into more detail.