A Mental Model for Personal Organization (Part III)

Cameron Flint
14 min readMay 9, 2021

This is a multi-part series on how to develop a system of organization for better personal productivity and growth. It’s an opinionated approach based on my own experience, so obviously take it with a grain of salt.

List of all articles in this series:

  • Part I starts with the core scenarios and requirements, and introduces the original 9-part model. Plus a quick aside on metadata.
  • Part II demonstrates three kinds of hierarchical taxonomies, and offers the “center of gravity” principle for dealing with information scatter.
  • Part III offers tool ideas for fundamental workflows, covering many apps and services. Discusses the intertwining of analog and digital workflows.
  • Part IV reflects on learnings from the original 9-part model, then evolves toward a more nuanced model featuring 5 major divisions and 15 minor areas.
  • Part V dives deep on metadata, providing a “3-axis” rule of thumb for ensuring your content can be rediscovered by you. Discusses a strategy for avoiding metadata rot.

In this third installment of the series, I will present a survey of systems and tools that can assist in implementing the mental model.

In keeping with the spirit of my previous articles, while I’ll suggest specific apps, software, and other tools that I like and make daily use of, I’ll also try my best to keep the recommendations that follow generally applicable to whatever your preferred “stack” is. If you’re not completely sure what that looks like yet for you, or if you’re not altogether happy with your setup, perhaps you’ll find some inspiration here.

A word of advice

As we dig into various tools, some of which might or might not be new to you, experiences you’ve had (or have not had) with these tools have the potential to cause you to react in one of two ways:

  1. One, you might feel motivated to immediately dive in, swapping out an app or service you’re already using. (The “ooh shiny” reaction.)
  2. Two, you might be tempted to dismiss a tool recommended here, on the basis that you’ve tried it before and it didn’t fit your needs. (The “didn’t work for me” reaction.)

I would challenge you to sit on any immediate reactions you might have to these tools and systems at first.

One lesson that continues to resurface for me, after trying hundreds of different tools and methods over a long period of time, is that frequently a new and shiny software package will fall short of being better than my prior “tried and true” solutions. Another phenomenon that occurs is that if I don’t spend enough time with a particular tool, I fail to realize just how powerful it can be and the depth of features it has.

Perhaps most importantly, I often lose sight of the truth that any given tool is less important than the system it’s used within. Consider keeping these rules of thumb in mind.

The digital hub: Trello

As I previously hinted at, my own personal “tools and systems” journey has taken a somewhat circuitous route. After having tried scores of the latest and greatest productivity apps — from task managers, to note-taking apps, to journals, wikis, and everything in between, and across many platforms — it is the tried-and-true Trello that now lives at the center of my daily system.

I use Trello for my daily “hub”, idea incubator, project workbench, and more.

Here are a few of the reasons why I believe that Trello is one of the best pieces of organizational software available on the market today.

  1. Trello is simple to use, but extremely powerful and flexible.
  2. Trello’s design language is clean, bold, and comfortable to use.
  3. Trello’s default Kanban (columnar) layout helps to engage the spatial/creative/associative parts of my brain better than more linear or hierarchical tools (like outlines).
  4. Trello’s “three-axis” navigational system (of boards, lists, and cards) helps my brain maintain a mental map of all my stuff. I feel the most organized and in control when inside of Trello.
  5. Trello can handle just about any kind of media I throw at it: including links, text, markdown, images, screenshots, file attachments, and more.
  6. Trello’s central unit, the humble card, is an incredibly underrated tool for capturing and developing ideas atomically (as opposed to my thoughts and research becoming buried in notes, documents, and outlines).
  7. Trello has additional organizational primitives besides the board, list, and card, including labels and metadata.
  8. Trello as a product is very mature. Its current owners, Atlassian, continue to invest heavily in Trello.
  9. Trello is a very high-quality application on web and mobile (I use iOS). It is secure, reliable, performant, and powerful.
  10. Trello is an extensible and open platform, with a marketplace of plugins (called Power-Ups), a comprehensive API, and more.
  11. Being as it is a long-running and popular product, Trello integrates well with many other well-known third-party services, such as Evernote, Dropbox, and Gmail.
The mighty Trello card: an under-appreciated note-taking and ideation modality.

When I am away from my computer and I suddenly happen to think of something important — which happens often — I open the Email Me app (iOS, watchOS), dictate my note, and hit “send.” Since I’ve already configured the app to point to my private Trello email address, the note shows up within seconds in a list on my “Global Inbox” board. It works with images and screenshots, too.

There are many products on the market that offer Kanban-like views of tasks (including Todoist, TickTick, Firetask, and MeisterTask), but I find that most of most of Trello’s competitors lean more toward pure task & project management than Trello does, and thus are less generally useful than Trello. If, however, you want to use a full-blown GTD-style task manager & database apart from your ideas, pinboards, and projects, look no further than OmniFocus, Things, or one of the aforementioned options. (TickTick is my personal favorite.)

If Trello is too visual or free-form for you, then consider trying Dynalist or Workflowy, two highly powerful and flexible tools for managing all kinds of information in a hierarchical manner. If on the other hand Trello feels restrictive and not free-form enough for you, then Milanote might very well be your jam. Notion is a very popular choice for the “personal hub / workbench” use case that also supports long-form documents, wikis, and databases, though I personally find it a bit too fractal and easy to get lost. Finally, Walling is a newer competitor on the market that feels like a cross between Trello and a daily planner.

The constant companions: a bullet journal & other paper products

I will freely admit that I have an “app” problem. I’m not proud to admit that I have easily maintained 20+ premium subscriptions at a given time, in addition to purchasing permanent licenses to dozens of productivity-oriented products. For all this time and money investment (well into the $1000's), the impact on my productivity has undoubtedly been negative more than positive. (That said, I have a lot of fun playing with all those shiny app-toys.)

A journal/diary from Peter Pauper Press. Image: Amazon.com

Perhaps it’s inevitable then, that at long last I would come to the realization that an old-fashioned, paper-based, analog system is an inescapable part of my real system: that is, if I am to get anything done in a given week.

At the heart of this “analog half” of my system are:

  1. A bullet journal. I don’t strictly adhere to the official methodology, but for the most part I do. I use the bullet journal for writing month- and week-ahead summaries, making daily agendas, and performing periodic reviews. I use it to take meeting notes, keep track of conversations and 1:1’s, track habits, and keep lists. In the past I used Agenda for this. Others swear by NotePlan.
  2. A scratchpad. Many folks recommend Drafts for quick capture of text, but for me, I always have a pad of blank tear-off sheets of two different sizes and a smooth ballpoint pen next to me at my desk. I like having a place to scribble down quick memos, brainstorm lists, etc. where I can be messy and unconstrained. When I’ve filled up the sheet and I’ve transferred anything worth keeping into my journal, I tear the sheet off, crumple it up, and throw it in the wastebasket. (Crumpling up paper is quite satisfying, try it!.)
  3. A diary. While most of my daily notes get written into my journal, my private thoughts and reflections belong in my diary. I have used apps like Day One, Everlog, and Journey in the past, but I prefer a well-bound paper diary the most. Since I tend to write slowly and intentionally in my diary (and to a lesser extent my journal, too), I like to use a felt-tip pen which I find to be more enjoyable to use on the higher-quality paper.
If you only keep one analog product on hand, make it tear-off pads and a smooth ballpoint pen. Image: Amazon.com

The reason the paper products are more effective for me — even if less enjoyable than software and apps — is, I believe, twofold. First, I find thinking on paper to be inherently less distracting and more intellectually freeing than using a computer, phone, or tablet. Second, the act of habitually rewriting my tasks and lists (known as “migration” within the bullet journal system), while mundane, is very effective at reminding me of what I need to do and forcing me to cull unnecessary tasks from day to day.

In a counterintuitive sense, the two major ostensible disadvantages of using paper to take notes, make lists, and form agendas are actually their great hidden advantages. The fact that handwriting is slow means that my thoughts have time to collect & order themselves as I write. The fact that migrating tasks and lists by hand is tedious means that I remember them better and only focus on the things that matter.

My bullet journal and diary put away for the day.

When I’m not actively using my journal or diary, I store them upright toward the back corner of my desk in a minimal file organizer. Any loose papers, letters or envelopes are kept in a file tray on the other side of my desk until I can deal with them.

The internet directory: Raindrop.io

Previous readers will be familiar with my usage of Raindrop.io as a bookmarking service. Raindrop remains a core part of my system and toolkit, used mostly as a directory of online resources, documentation and databases that I might need to access but can’t or don’t need to maintain a local copy of.

I frequently experiment with the organization of my bookmarks within the sidebar. The astute reader will notice that I’ve deviated some from my strict “collections,” “reference,” “interests,” etc. layout from the mental model introduced before.

I continue to use Raindrop.io as my personal “internet directory.”

I also use Raindrop.io as a personal internet archive as well, since the paid version takes full-text backups of any link that I throw at it. The fact that Raindrop can also handle images and PDFs makes it especially handy for this purpose.

I pair Raindrop with Pocket for reading articles.

Usually when I discover a new article or blog post of interest, it doesn’t immediately go into Raindrop.io, because I might finish reading the article and archive it without any desire to store a permanent copy. For this reason and also because Pocket is a better reading service, articles go to Pocket first.

Sometimes I do complete an article and decide it’s worth keeping. In that case, I will “star” the article in Pocket. A simple Zapier trigger that I have running in the background will automatically pick up the starred article, then send it Raindrop.io where I can organize it later.

The impenetrable vault: 1Password

1Password is one of those pieces of software that has become ubiquitous within my workflow because it performs its job so well in doing exactly what it’s made for: storing, generating, and auto-filling passwords; tracking licenses; and generally keeping any kind of secret I have a need to protect.

1Password is my password vault & more.

While we’re on the subject of utilities, let me just sneak in a mention of two I use heavily: CleanShot X for screenshots, and TextExpander for text snippets. If you’re satisfied with your system but want to improve efficiency, these are fantastic arrows to have in the quiver.

The filing cabinet & the stockpile

For keeping official records and documents of various kinds, I use Box.com (previously Dropbox) as my digital filing cabinet. I also use my cloud filesystem as a place for all my reusable assets and materials, including templates, fonts, design files, stock photography, and so forth.

Box.com functions nicely as my digital filing cabinet.

I changed from Dropbox to Box because I found that on both my Mac and my iPad, it is easier to directly open and edit files without having to download, modify, then re-upload them. This comes in handy when I need to read and highlight the occasional PDF with something like the Highlights app, though I admittedly don’t read this way very often (preferring to put excerpts and summaries from books that I read into a Trello card, instead).

I also have a small physical filing cabinet next to my desk, but it doesn’t actually store files or documents. Instead I use it to keep frequently-accessed gear (cables, mice, headphones, keyboard) close to hand, and it’s stocked with replenish-able office supplies (screen wipes, sticky notes, pens, etc.) that I might reach for throughout the workday.

While many use a “shoebox” application like Evernote, Keep It, or even a full-fledged personal information manager like DEVONthink to store their files and documents, my use cases are simple enough that these tools mostly get in the way more than they help. It’s easy enough to get scans of receipts, documents, etc. into Box using Scanner Pro by Readdle on my iPhone or iPad. Once they’re there, I rarely-if-ever refer to them again.

Boxcryptor works on top of many cloud filesystems, providing end-to-end encryption.

The main downside that I’ve found to using Box.com as my digital filing cabinet is that it doesn’t do automatic OCR of PDFs and images such that I’m able to perform full-text search on the contents of my digital “office.” And for particularly sensitive documents, I feel safer using Boxcryptor as a layer of total encryption over certain folders inside my Box.com account. (Boxcryptor works with other cloud providers too, such as Dropbox, iCloud Drive, Google Drive, and more.)

If you are managing more than a filing cabinet, for example a library of academic papers for research or writing, then a dedicated research tool like DEVONthink or Zotero might be worth investing in.

Long-form writing and permanent notes

When I wrote parts I and II of this series, I was using Nimbus Note for various note-taking and writing needs. Since then, I’ve stopped using it mainly for two reasons: first, I unfortunately ran into some stability and quality issues with the app, such as it being slow to load notes, and buggy to export them to PDF. Second, as my use of Trello increased, I found less and less reason to use a traditional note-taking app for most of the ways I used to use a note-taking app for.

The hunt for a personal wiki solution is far from over.

Within my personal O.S., the lack of a dedicated note-taking app does leave a few gaps. To be completely honest, I am still experimenting with this corner of my system the most. I would like to find additional tool(s) to meet the following extra use cases.

  1. A personal wiki. For keeping how-to’s, guides, checklists, snippets, templates, and “runbooks” that I build for myself over time. Some of the apps I’m evaluating for the purpose include: Bear, Craft, Notion, Notejoy, and Nuclino.
  2. A long-form writing tool. For writing articles and blog posts like this one, outside of Medium itself. Ideally I’d be able to embed a handful of Trello cards with the raw ideas, materials, or outlines that I’d be drawing from, right into the document itself. Candidates are: Craft, Ulysses, Dropbox Paper, Whismical Docs, GitBook, and Milanote.
  3. A digital “note garden.” All the rage these days with emergent apps like Notion, Obsidian, Roam Research, Dendron, Contextualize, and others gathering large followings and pushing forward the field of “connected notes.” I’m not 100% sure I’m ready to commit to a heavy-duty system like this yet, though.

The creative toolkit

This category is the most “fun” of the categories. It includes tools that I love to use for scenarios where I need either a) a more free-form tool (than Trello) during the early stages of ideation, or b) I need a tool to work or manage complex or highly-connected topics (such as when I’m taking notes on a sprawling codebase at work).

Whimsical is great for flowcharts, mind maps, and other free-form ideation.

Whimsical is a very nice tool to use for mind mapping and diagramming. If I need to use Whimsical, Lucidchart, or any other app that stores data in its own service or “container,” I will make a point to link it to a Trello card in my hub so that it doesn’t get orphaned or fade into the background once I’m done with it.

Dynalist is an extremely-capable outlining tool that has many powerful features hidden behind its banal interface.

The two outlining web applications previously mentioned, Dynalist and Workflowy, can also be excellent tools for complex idea development. Of the two, Dynalist is arguably more powerful and complete, with the ability to quickly move or “send” bullet items to other parts of the outline in a few keystrokes, format text, organize outlines into multiple documents, and more.

Milanote lets you be as messy or as organized as you please.

I mentioned Milanote in the first section, but I’ll refer to it again in this context because it’s really a first-rate tool for free-form personal brainstorming, whiteboarding, and pinboarding. Miro is a popular alternative built mainly for teams, but unlike Milanote, Miro feels heavier and a bit enterprise-y, in my opinion. Jira vs. Trello might be an apt comparison, or Confluence vs. Notion (in terms of comparative look and feel).

On the other hand, if you stick mostly to the Mac and don’t mind spending money, you may find the combination of OmniGraffle and OmniOutliner to be all you need.

There’s a lot more

It took me a long time to write this article — far longer than I planned — because there truly is no end to the infinite combinations of tools, methods, workflows, and opinions out there. It was a huge challenge to narrow down the options into something manageable, both for my own daily use, and to be able to succinctly write about. I hope that you nonetheless find the suggestions here to be a useful springboard for your own experimentation.

As always, if you have thoughts or feedback for me, feel free to drop a note to feedbackforcameron {at} fastmail.com. Cheers!

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Cameron Flint

Diving deep on topics related to note-taking, personal information management, and software engineering, with occasional diversions to less nerdy things.