Notes and outliner apps

krocnyc · September 19, 2026, 4:16pm

I rely on notes to 1) make all my “administrivia” less of a chore to manage and 2) to bolster research and learning.

Re item 1: I’ve divided the things I need to manage into “Domains,” each of which has a three-letter abbreviation (like airports and stock tickers). For example, “ADM” = Admin, “CSW” = Coursework. I’m on the board of two non-profits; each has its own Domain. I manage some family estates and trusts; each family group has its own Domain. There’s a Domain for my and my spouse’s professional matters. etc etc etc. Each domain gets its own folder in the Obsidian vault I use for planning and task management (I use the TaskNotes plugin). The notes in those folders contain information I need to have to hand—e.g. account numbers—as well as links to key documents stored in my digital document repository. My AI bots are fully up-to-speed on the Domains; they know where to look for things, where to file things, how to sort my email, etc. They also know how to create “session handoff” markdown documents for the Planner vault that recap what we worked on, what the outcomes were, what the next steps are, and, most important, my own ToDos to get us to the next phase of the project.

The notes exist for another reason: The day will come—and probably sooner than I’d like—where someone else will have to take responsibility for many of the administrative matters. I’ve learned from handling several estates that the very best gift you can give your loved ones is a clear map of what’s what and where to find it. I’m using Claude to help me build a document repository that someone else will be able to navigate from my notes.

I’m a lifelong learner: I also have an Obsidian vault for each of the things I’m learning or researching. It’s a place for my own notes, for links to key reference documents, as well as for relevant things I’ve extracted from the web. (I cannot recommend the fabulous Obsidian Web Clipper highly enough!) I’ve also started building LLM Wikis, which are entirely markdown notes-based.

beck · September 19, 2026, 5:17pm

I wanted to share an approach I’ve arrived at that feels very specific-to-me. The actual approach might not be helpful to anyone else, but it might inspire/allow folks to find a solution very specific-to-you.

It uses a surprising (to me) software choice (Apple Pages). Back when I was in high school, I was editor of my yearbook and I learned how to use tools like Aldus Pagemaker and QuarkXpress. Through chatting with Claude about my frustrations with notetaking systems (I’m sure many of you have done the same!), I learned that Apple Pages has two kinds of documents (Blank and Blank Layout). Blank is the traditional word processor, but Blank Layout is modeled after desktop publishing software and I can make it look exactly how I want, but also automate that layout so I’m not always having to fight with a layout, much the way magazines or books have a specific look and feel from everything else, but which is internally very consistent. For me, this is where a lot of outliner (and text editor) apps fall short. They may look very nice, but can’t do everything I need or want them to do. So, like a good Mac Power User, I made my own. Here’s a spread that features several of the things I needed in a notetaker that felt hard to make happen.

I can have annotations in the margins, paste images, quickly see quotes as distinct from my own thinking, embed links to websites or files, all the rest. At the end of the month, I export as PDF and also print out a physical copy so I can thumb through and have the sort of spacial sense I get from analog books/notebooks (but also have the digital to search).

I’m also able to finally do something sensical with the photos I take of my whiteboard sketches:

And I can note where AI has informed my thinking and find the chat again.

I think, for me, especially now, I need spaces to think. A friend of mine calls these types of spaces a “thinking gym.” Part of the friction of the system is intentional, and it’s also beautiful (to me) and useful, which motivates me to continue using it.

Bmosbacker · September 19, 2026, 6:25pm

This is not as unusual as you might imagine. I had an Air Force Academy professor colleague use Word for all notes and his projects and tasks.

I’m curious, how do you handle searching across related topics or is that not a need? Also, you mentioned outlining. Do you and if so, how do you approach outlining in Pages layout?

brookter · September 19, 2026, 9:14pm

This is very interesting, thanks @beck!

Would it be possible to explain a little more about how you automate the layout? Do you mean you’ve created a number of page templates with different configurations of text boxes and diagram spaces etc, and choose from them when you start a new page depending on the proposed content? (I don’t really use Pages, so I’m trying to imagine how it works in practice…)

Thanks!

beck · September 20, 2026, 1:53am

@Bmosbacker this was the same for me and one of my professors. He has a 500 page word doc (also printed in an enormous binder) and one of the most meticulous folders of pdfs full of books and articles collected over his career. I wanted to copy someone who had credibly stuck with something and found it useful.

Right now, I actually have four different notebooks. I consider each a “thread” of my work. There’s no cross/backlinking ability, which is a compromise.

I outline like you would in any word processor (organize my thoughts and indent as needed). I find Pages outline features similar to most word processors. It recognizes a line as a bullet if it starts with a hyphen (my bullet of choice) and a numbered list if it starts with a digit followed by a period.

Yes, I think you have it. I have created two master layouts (one for the right page and one for the left). They both have main content and annotations. Then, I have a slew of styles that I apply using keyboard shortcuts for headings, annotations, body, quotes, etc. Everything is on a baseline grid so the annotations and body text all line up. Some manual details: I have to “thread” the content from one page to the next (this entails clicking on the round handle at the top of a text box and choosing the thread it receives), insert a column break (keyboard shortcut) to get a “page break,” and manually tick the Drop Cap, which I like because it makes new days easier to spot. I have Typinator snippets for dates and times and that kind of thing. And if I make a tweak to a page or style it automatically propagates everywhere all at once, including reflowing the text.

Amontillado · September 20, 2026, 3:07am

Have you seen The Archive? It’s actively maintained, based on NVAlt and you can sync it any way you want. An archive is a directory with your files in it. The app itself doesn’t create indexes or anything else.

The Archive will recognize Markdown and media files in an archive directory and ignore the rest.

More here: The Archive (macOS) – Note Taking: Nimble, Calm, Plain.txt • Zettelkasten Method

You get a free trial. After that, it’s $20 to own it forever. Documentation is minimal, mostly because the app is minimal. How you use it is more important than what it does.

I don’t have any interest in The Archive other than an appreciation for minimal tools that work well.

brookter · September 20, 2026, 7:57am

Thank you for the detailed explanation! It does sound intriguing…

Bmosbacker · September 20, 2026, 10:36am

Thank you for the explanation. That is an intriguing approach.

He has a 500 page word doc …

I would be nervous to have important notes in a single document for fear of file corruption and losing that important information. I presume he has backups.

pencil · September 20, 2026, 12:10pm

I quite like using Bike as an outliner. It has this feature similar to workflowy where it allows you to focus on only a specific level of indentation. All the files are basically local html files with bulleted lists. But you can also export to OPML or other formats.

sridhar · September 20, 2026, 12:29pm

If you like Bike, you will love Kosshi.

MacDependent · September 20, 2026, 2:05pm

Yes I did! It’s super promising and the closest I’ve seen. The problem I ran into was that it was a bit laggy/slow.

svsmailus · September 20, 2026, 3:45pm

Thanks for sharing Beck. As always you provide some great insight. A few questions with Pages.

Do your files hit size limits that affect performance or risk corruption and how are you dealing with that, especially with images.
How do you deal with needing to migrate your data should the needs arise?
You said you print your notes. I’m assuming links are not important?

Hickz · September 20, 2026, 6:21pm

Doesn’t really hold a candle to Bike’s typing experience and in general. Plus, it’s a database outliner with only 1 global outline, you can’t create multiple workspaces/files.

It’s alright, but definitely not a “better” alternative to bike (except for mobile platform access for now, which is in progress for bike).

Bmosbacker · September 21, 2026, 9:59am

This morning, I stumbled across this article. This is not for me, but I thought Tasks.txt might be of interest to some.

sridhar · September 21, 2026, 11:13am

it’s a database outliner with only 1 global outline

ditto for Kosshi.

Hickz · September 21, 2026, 3:26pm

I was referring to Kosshi about being the database/1 outline app. Bike can create as many files as you want, and they’re a subset of html which you can browse/edit anywhere.

Kosshi is good, no doubt about it, but it differs heavily from bike’s approach. Kosshi does offer a trial, though!

beck · September 21, 2026, 4:09pm

Good point! And I should have mentioned, he has split them into five different files for this reason (after running into issues). He’s not, er, a MPU in the slightest, so I would dare mention Devonthink, but if he were a little less hesitant about such things, I think it’d be perfect for this.

Great questions and I’m not sure I have great answers, yet, but here’s my strategy. First, I am printing and exporting as PDF each month. Basically, I’m treating these documents as I would an actual notebook. I wouldn’t go and add things to a notebook, but I sure would like to be able to search this bookcart next to my desk digitally…

To be a bit verbose… a few months ago, I watched the movie Perfect Days (trailer embedded) and was really inspired by it. I started putting my glasses and watch and keys in the same place everyday, always, and it just worked so well for me. I realize this is silly because it’s obvious, but honestly I was always searching for those things and now I’m not and a part of my brain is quieter for it, and a part of my day is a little more satisfying. So then, I started hunting for other things I could do that would help… and I realized that while all this knowledge management rhetoric and guidance leans on the advice of a “garden,” I do better with a “tray” to put things on. And that’s true for me. I need things visible and dimensional, but I don’t really ever go back to “tend” just to reference. So, I am trying this out in an effort to have the thing just be a place I go to pick up what I need, instead of a place I visit to maintain.

I’m betting/hoping that it’ll help me more than all the efforts I’ve done in the past that frankly aren’t. I’m not sure if, coming up in the information age, we just think we can get on top of it but the fact is that we actually can’t, or if there are ways that we can. When my professor showed me his journal after having seen him use it during meetings, etc. and then the binder, etc. I got hopeful that it might be actually helpful. Time will tell!

Oh, and I think it’s probably clear now, but links are important but the system relies on me finding them in the digital files. Honestly, though, so much of the web is dying or being rewritten for AI that I’m not sure how long any link today will be good for. That said, so far I try to make a PDF of articles I read and make notes about. That’s what my professor does. Come to think of it, I don’t think he ever puts links. I’ll have to ask…

Bmosbacker · September 21, 2026, 5:55pm

Excellent information and response, thank you!

johnnyjohn · September 23, 2026, 10:00am

A good option for quick notes.

https://notchkin.app

geoffaire · September 23, 2026, 10:56am

This is the story of my life. If something has a “Home” (electronically or physically) that’s where that thing will live. If it doesn’t, then messiness will ensue.

It’s the difference between order and chaos in my life.