Off the Top: Thinking Tools Entries

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29 August 2026

Markdown Apps Loosely Joined

I recently posted about the different web browsers I regularly use, My Browser Family, and it makes sense to go through my different apps I use for Markdown in a similar way. My use is very closely tied to my Small Apps Loosely Joined mindset (part of the Shift Happed series on Personal InfoCloud). “Small apps loosely joined” focusses on having a core adaptable data structure (like markdown) and use different apps with written content where the app has helpful capabilities that are needed in a workflow or to focus on a type of work as a step in a workflow. Much like a woodworker picks up different tools to perform different tasks and doesn’t use a saw or chisel for all tasks, the small apps loosely joined model is similar. This works and has worked insanely well for 15+ years that I’ve leaned heavily on markdown.

I end up in markdown discussions rather easily it seems. The way I have taken notes in text apps with asterisks or dashes for bullets and the octothorp (you know, this thing #) for headings goes a long way back for me (starting somewhere in the 1990s). When I came across markdown in the early 2000s, after I had looked at and tried Textile Markup, but markdown didn’t fully connect. It echoed what I had done and offered more, but at the time I didn’t see the advantage of the added capabilities.

In 2010 and 2011 I started to shift much of my note taking and writing away from apps that were siloed and lock-in models. The flow from notes from a meeting, to my personal notes and annotations, and on to writing that gets shared out was a series of less than optimal apps that all had lock-in and heavy friction. Microsoft products not only had intentional lock-in but were continually buggy. I loved (and still do) Scrivener for writing longer pieces in it due to its managing notes and scraps related to the longer writing piece, but getting things in, as well as getting things out into my various sharing / publishing workflows had a lot of friction. At this time my parents were sick and passed on. When my mom passed my laptop hard drive took it as a hint and it too left the living world. I had everything backed up and I was working off the back up drive hanging off my Mac, and was waiting on a hard drive replacement, but needed something for notes for meetings (with banks, lawyers, and so much more) that I could move across everything. I nabbed an iPad for that mobility to take to meetings have files move across and back to my Mac. This tipped me into a full markdown life.

Like Many, Not All Markdown Goes to the Web

Markdown started by John Gruber to be an easy means of writing with light structure, while maintaining decent readability and to fit his model notes, which Textile didn’t fully fit. John created markdown and the markdown conversion to HTML as a matched set. Over the years many write markdown that gets converted to HTML, but around 2010 I’d see people were using markdown that never was converted to HTML. Markdown was what they wrote in as it was highly portable and editable from any text tool or markdown app and not in buggy and lock-in software. I noticed this in San Francisco on a trip where I stopped in a couple law offices to visit friends and the receptionist and legal assistants were mostly using markdown. This surprised me, as it wasn’t something I expected. Largely markdown for writing has been in tech adjacent roles and organizations. Later year seeing high school kids and college kids using markdown for their notes and paper drafts, then pasting to Google Docs was really impressive with the deftness they worked and how they managed everything. (A funny sidenote is many who went through school this way were appalled that Microsoft Word didn’t natively understand markdown). Markdown isn’t the parent’s use case any longer.

Today markdown for me only has around 20% that gets turned into HTML. Most are notes and documents that stay in markdown or turned into Google Docs, PDFs, text in Keynote presentations, and much more. Markdown is incredibly flexible with just enough structure to get converted as needed.

At First Many Apps Only Sort of Joined

This 2011 timeframe was the heyday of small light markdown apps. I picked up many apps and found a few that worked well. I was knee-deep in the markdown matrix table that Brett Terpstra maintained that showed the markdown app and the capabilities and compared what seemed like well over 60 apps. I used Simplenote, Byword, 1Writer, Ulysses, and Bear notes quite a bit and have kept them around but don’t use them as much due to friction for where and how they keep markdown files and some interfaces didn’t evolve. I also have used Working Copy, Git on iOS on Mac and iOS (iPad) for working on larger documents across devices and with others.

Moving to Less Friction for Markdown Loosely Joined

Apps that stayed around and were added in respected where I kept my notes and work. Most of the notes and writing stayed in a notes directory, but also were in project work. My notes directory on my Mac was linked out to iCloud so I could have access from my iPad or other devices. For a long stretch my basic notes app on my Mac was NVAlt, which allowed for tagging the markdown files, which meant that while they lived in my notes directory, I could aggregate all project work in the project folders, other media, and notes all with a file tag on Mac. This was fine until NVAlt stopped opening.

My Menagerie of Markdown Apps Now

My markdown notes that NVAlt sat over (which also included a folder from Notional use) had a few thousand notes when it stopped opening. But, the markdown notes weren’t owned and controlled by NVAlt and I could use nearly any markdown app I had to open and edit them. I wanted something very close to NVAlt.

Obsidian

In June 2020, after trying to find a replacement for how I worked with NVAlt I tried a few apps, but the one standout was Obsidian which slid perfectly into the exact role that NVAlt had for me. This role was to sit over the directory of notes and oversee them, but functionality on top of the markdown notes. Obsidian added even more capabilities (which most of my other markdown apps also adopted portions of over time). Obsidian is where my daily notes, drafts of longer pieces, meeting notes, and so much more go. Everything is relatively findable and refindable through backlinks (wikilinks) that are bridges between notes (but also with a plug-in Strange New Worlds - Obsidian Plugin I can see what other notes link to the note I’m linking to, and part of the magic is the note I’m pointing to doesn’t need to exist to see those links), tags to aggregate related notes with that tag, and search.

The other great advantage of Obsidian is transclusion, where one note can be added in as a view into another note. I can start a note in a meeting note or a daily note, then highlight a section and extract that section as its own note, but then transclude that note back in to show it where it was. This extraction and transclusion allows for that one piece of notes to mature and / or be included as a transclusion into other notes. The transclusions can also bring in a sub-heading into another note to show the section in the sub-heading. (I have a longer take on how and why I don’t use zettelkasten, which is similar to what I learned going into college for how to have far better study habits and write papers far more easily, but it also broke contextual understanding and really broke multiple contextual relationships).

iA Writer

My longer form markdown writing app is iA Writer. Often an idea for writing will start as something small in Obsidian (often in a larger note) and gets fleshed out a little there. But, when it starts getting longer I will extract it as its own note and then pick it up in iA Writer to take it farther. I love iA Writer as the interface is quite plain and it is just me and words and minimal structure. I often will create sub-headings early in longer pieces as outline structure to be filled in. Then it is just writing. The iA Writer app also has some light grammar checking (which fits my needs well), a quick preview to see your work as output that has some design and layout in the UI. It can be turned into a very minimal interface as well with focus on the line your cursor is on and just a few lines around that active line.

By and large, iA Writer replaced Scrivener and Ulysses as my longer writing app. The segmentation and notes capability in these other apps have made their way in as sort of similar forms into iA Writer (not everything, but enough for me). What largely caused iA Writer to replace the other two was very little friction getting my writing out into other outputs. Dragging the proxy icon to Marked (now Marked 3) is all that I need to get to HTML, styled PDF, or Word.

Marked (now Marked 3)

The Marked app, which is now in its 3rd major version, is the markdown conversion and clean-up app of choice. Marked has a lot of different capabilities, including proofing, writing statistics (like readability score and much more), writing support with proof reading, linting, and support for a wide set of markdown capabilities. Everything for using Marked for converting markdown to other formats is quite customizable and rather straight forward if you have some skills.

MarkEdit

The MarkEdit. app is one app I use as my default markdown file opener. It is like Mac’s TextEdit app, but focuses on markdown. It shows all of the markdown marks in plain sight. I find the showing everything raw is a good thing for review and understanding structure quickly.

I receive markdown files from others quite a bit, I also have access to other’s Obsidian vaults, and I have many markdown files that are spread all around my Mac and cloud environments. When opening one of these from search or a link I want to keep it outside of my Obsidian so they don’t get included and intermingled. This is really helpful reading and editing other’s shared Obsidian vaults as I can open, read, edit, and then close it while keeping clear of my Obsidian. If I want to copy something from my notes in Obsidian to another’s Obsidian, the two apps for two different environments look different, which helps reduce errors.

BBEdit

Another plain interface for markdown I use is BBEdit by Bare Bones Software, which supports markdown, but is the jack-of-all-trades text and basic coding tool. BBEdit is a go to for a lot of different text and coding needs where clearing out the cruft of an IDE or app is needed. I often open markdown documents in BBEdit when there are a lot of consistent text modifications I need to make. I have pulled in large outlines I have made in markdown and I need to do much work with nested levels in the outline.

Drafts App

I use Drafts for text and idea capture when I am away from my Mac. Everything from quick atomic notes (like where I parked, name of a book mentioned when at coffee, etc.). Drafts has long had solid voice-to-text for all Apple devices (iPhone, Watch, iPad, Mac) so it a great capture application. Drafts also has a highly adaptable capability for what to do with the note once captured, like sending it to my notes directory that Obsidian sits over. It is fully markdown capable. I can take a voice-to-text note on my Watch when driving, or invoke Siri and have it open Drafts to a blank not and tap the mic and leave a voice-to-text note that automatically is save and I can open it when I park and add some markdown elements and use and action to send it off to Obsidian, text message, or so many different end points.

iPad Apps

I started using markdown heavily, largely because my Mac hard drive crashed and I was taking notes on an iPad. I’ve gone through a lot of different iPad apps for markdown.

I have Obsidian, iA Writer, and Drafts, which I use pretty much the same way as how I use them on the Mac. Obsidian on iPad is a bit more limited, but still good for capture and modifications of notes in the directories I have it sitting over. I have Drafts always available as a slideover option off to the right of the screen.

I have Editorial for iOS as a relatively plain markdown editor. I don’t use it as much as I used to, but good to know it is there and it is quite capable.

The iPad also has small focussed apps for certain tasks. I use TextCase for changing capitalization in notes. I use Terminology by Agile Tortoise, which is the same developer as Drafts, as a really good reference tool when writing on iPad.

Trying a Couple Apps

There are a couple of apps that I’ve been trying on Mac, which may have a place. The first is Lettera, which is a markdown editor for Mac by the makers of Bear, which is currently in a limited beta. When I was using Bear notes app I loved the interface as it was clean, but what I didn’t like about Bear was the lock-in of notes in the app, as there was too much friction to use a note outside of Bear. Lettera is the markdown editor that is free of Bear. It still seems to default to a Lettera folder in iCloud, but opens markdown notes from anywhere. This may be a better reading and annotation app (it has easy to use callouts) for some of the uses I’ve used MarkEdit.

The other app is one I’m trying again as I used it 8 years ago (or so) when it was in beta and free, but became fragile, buggy, and would crash. It looked good and was rather simple. They changed from the free app to a paid app with the same name. I ended up with two versions with the same app with the icon and it was difficult to discern which was the flakey app and which was the good. Once the good version became pay, so I had neither working. This was Typora. In recent months many new to markdown have been talking about Typora and I get asked about it. Today I finally downloaded it again after deleting both of my instances of it a few years ago.

The current Typora has a lot of capabilities now, far beyond what it used to have. It has a similar interface, until you open settings then it has a lot of customizations. Typora can now cover a lot of ground. Much of it is covered in other apps I have, but I may find my current model of having different apps for different uses that are incredibly good for the purpose I use them is my preferred way of working. Having different apps helps me focus on what I am doing in that app to the markdown file and the task and focus needed from me for that task. To get to the same thing in Typora I would have to go to settings and make changes to keep that focus, but the context of the different app isn’t there. Moving between apps I will also keep the markdown file in multiple apps and see an edit in one instantly show in all the other apps (what good magic is this). Typora nice interface with additions for math UI (through LaTex) and charts (through Mermaid) may be a draw to keep it around.



12 August 2026

Thinking in Tools has a Category, Sort of

Posting more of what I’ve been only writing as notes for myself, but also things that start as intended posts, I’ve been updating and adding some categories. One category I thought I have had for a long time is Thinking Tools, which is for tools I think in. I have a regular set of tools I write, think, and research in and many have remained the same over many years.

Prior Thinking Tools Posts

Recently I posted about My Browser Family and I definitely think and work in Safari and Zen in different ways, which I outlined. Also in the Podcast Interviews and Presentations the Last Few Years I mention a little bit about my use of OmniGraffle by The Omni Group and OmniOutliner by The Omni Group. I have brought up Obsidian a fair amount since moving to use it as my regular note making app in June 2020, I got to the point of adding a category for it, Obsidian. But, my writing workflow has at least two markdown apps (including Obsidian) as I edit and work on longer writing pieces in iA Writer as it handles all the markdown I regularly use when writing and it is an interface that gets out of the way and lets me focus on words.

Some Tools I Write to Think In

My thinking tools also focus on adaptability so I can bounce between different markdown apps (adding in MarkEdit, Drafts, Marked, and BBEdit), but also can take outlines in OmniOutliner where I’m framing out ideas and export to OPML and import that OPML into a MindMapping app (my favorite is mostly gone (iThoughts), but mostly use MindNode that sort of fits the bill of need, but not as well). With MindMapping I can see the dimensions and gaps more easily and can relatively easily and rearrange the nodes. Sometimes I go back to OmniOutlines with that output, but either way it eventually makes it into markdown as an outline or headings and subheadings (and or export to Keynote as very rough slides).

See It to Think It More Clearly

When I need to see systems and map out flows and interaction points I often turn to OmniGraffle at some point as I know it like the back of my hand I can get it to do many things quickly. With layers and canvases I can turn things off and on to tell stories as needed or get a solid focus of people in a meeting of lawyers and leaders to get actual understanding and focus on decision points to get the best answers to move forward. Early on I’ll use Apple’s Freeform to roughly sketch things and capture rough ideas, as well as use it as a whiteboard or sticky board wall (I really wish there was a better means to bring the pencil and iPad into Vision Pro with Freeform as it is really close with the pencil shadows and bevel tip orientations, but it needs two more essentials). I also use Obsidian Canvas to lay out elements and components of plans and ideas to group them and understand and see flows and interconnections. Obsidian Canvas (Obsidian Canvas) is now its own Open Source offering, JSON Canvas. Canvas is something I’ll often throw on Vision Pro to work through large systems or flows using the Mac Extended monitor mode an ultra wide screen setup and reference materials on the same screen.

I have a couple others I dip into for visual thinking as well. Keynote is always close and often my Master Deck of 600+ slides is open to quickly reference something. I have nearly 600 keynote desks and I’ve been working on getting outlines of them to see what slides I used in which presentation or deck, but also the Master Deck has gaps and doesn’t have the fully fleshed out versions of idea sets. When I had 200 to 300 presentations the Mac search was quite good at finding presentations that would have a phrase in it, but now it finds a lot and I need to map the uses of a slide and the 25 minute version of explaining a concept or the 2 minute version.

More Thinking in Tools Posts to Come

I have many more categories that are regular parts of my thinking tools and framings that let me go broad and deep, as well as pull on my own work from across the years.

I’m thinking I may do deep dive posts on one tool and/or a set of tools / apps. Also layout my app use that map to long standing concepts like the The Elements in the Social Software Stack, which has a build order that helps social tools for use in organizations, but also personal tools that follow the same pattern are vastly more helpful than those that have some things out of order. The “Action” and then “Share” is essential and the Drafts app became a great example of this process order. Action is capturing an idea or writing and framing something out fully. Then figure out what you want to do with what you just created and captured. This allows you to think and capture fully with out thinking about the social context of where it can go. You can push the full content to your working notes and ideas and then create sub-notes from copying paragraphs into new notes and send those as text messages, post to Mastodon (or Twitter), as well as share in Slack and/or a text message and so much more.

Having this category of Thinking Tools gives me a wrapper to post this and some may also cross post to Personal InfoCloud as well.



11 August 2026

Did I Leap on Mac Developer Beta Too Soon?

I’ve been following along with this year’s round of Apple Operating System updates (OS 27) and had jumped on the iPad and visionOS developer betas in the first round or two. With iOS and ipadOS 26 with Liquid Glass if I turned it down and turned much of it off it wasn’t horrible, but it didn’t seem like a finished product. Since some of the inspiration came from visionOS for Liquid Glass it was mostly fine. The updates to the OS 27s are solid improvements for the most part, with odd bugs (mostly in YouTube app and some Meta apps). The iPad has been far more performant on the ipadOS 27 than the ipadOS 26 and fewer odd bugs.

On the Mac the OS 26 experience was poor with bugs, performance issues, UI design decisions seemingly made by people who had no understanding of interaction nor digital design. Hot mess would be too kind. My Mac is my core beast and my backup brain. I was tired of bugs and was pestering those I know whom had jumped on the macOS 27 betas if things were fine. The one oddity I didn’t want to run into was the menubar not working with menubar managers.

Yesterday the macOS 27 Developer Beta 5 was released and I ripped through the developer notes and saw the menubar had an update and claims it should work like it did on OS 26. That was enough for me to give it a try. After updating the other two devices I put in harms way, I finished a fresh back-up of my Mac and took the plunge.

First Impressions

The macOS 27 first impressions are it is more responsive and quick like it was prior to OS 26. Also OS 27 seems like it is what should have shipped last year as it has a finish and more design cohesion and relative purpose. Things in settings have been somewhat easier to find. Nothing seems broken.

I did hit an oddity and bug in Apple Music where the sound profile for hi-res lossless tracks was noticeably different when using my usual DAC/Amp and good headphones that are open back and resolve things really well. The sound stage seemed wider and the spatial separation of voices and instruments was much more pronounced, and the resonance of metal sounds (acoustic guitar strings, cymbals, and upper register piano (like an open grand piano)) were all really pronounced and forward. Something in the equalization had changed in the upper registers. I tried the track in other apps as hi-res and they sounded as they did. I also plugged in my DAC/Amp into my iPad and Apple Music like it did the day prior before the update. So I filed a report. I also found trying to edit a playlist in a playlist by clicking “edit” would crash Apple Music, so another report filed. Other than that Apple Music is much improved, but I’m not sure it is fully on par with the iPad Apple Music, which is really well done and has music content with production notes and more, but favoriting a song or album doesn’t beach ball the app.

To Test

One of the reasons I took the leap is I like using Apple Freeform for quite digital whiteboard and quick sketching of idea and there are some features with it that have improved that I want on my Mac and not just iPad (even though I largely use it on iPad and Vision Pro).

I also want to give Keynote a solid run through as that is also one of the tools I think in. I’m doing a few things in Keynote lately around folksonomy, Model of Attraction (as I’m walking new generations of product and engineer folks through it they want to know why they didn’t know about it before as it would save time tying to work through problem sets the model frames more easily to think through) with the four InfoClouds, and various Complexity Lens / Social Lens frameworks for seeing and thinking through problem sets.



8 August 2026

Single Page PDF Option for Webpage Capture

Every now and then I get a bee in my bonnet about something. Often it is about something that has been long brewing. A current one, is PDF pagination. It is incredibly rare that I print anything. I regularly store / archive webpages in PDF, using DevonThink / DevonThink and for much more than a decade that PDF has been a “single page, continuous PDF”, which has no page breaks.

There is no reason (for the last 10+ years) to only offer multiple-page pagination for a PDF. It can be an option, but it’s driving need is the printer and rarely do PDFs get printed, as they are consumed on screens that we easily scroll.

A friend, Tantek, pointed me to Firefox (or derivative, a week ago I moved my work and research browser from Arc to Zen Browser to handle my spaces and capability to easily handle an abundance tabs) as it has good PDF capabilities built in. Firefox does have a lot of really good PDF tools (I deal with a lot of academic papers and related texts in PDFs). Firefox also has a full page screen capture, which is insanely helpful, which makes is really strange that there isn’t a similar single page PDF or “Print to PDF” option for one continuous page PDF capture of a web page.

Why Single-Continuous Page PDF?

Why is single page PDF such a need for me? Most of our interfaces around the web, or even our tablet note taking and beyond are one long page. PDF has long been, and still is, a great archive mechanism for holding onto and sharing things of interest that work across time. PDF is better than saving a web interface in its native form, as every 8 to 10 years there is a large enough change accreted that break web view files that are older and assemblages of components that they don’t consistently work in a browser. Having a colleague share their hand written notes from GoodNotes or Notability as a PDF often have pagination breaks in the middle of text, formulas, diagrams, etc. that have no need to be paginated at all. Most digital information and knowledge workflows don’t ever hit paper, nor have a need for multiple-page pagination. Multiple-page pagination as the only option is more than a decade outdate, but it seems only DevonThink offers a modern option by default.

Having the option and setting a preference for continuous single-page pagination printing to PDF (just like DevonThink has been doing for more than a decade) is needed in browsers and most of our digital applications. It is long past time to catch-up to this past decade, if not farther past.



My Browser Family

Browsers come up often in discussion. But, in a recent MacSparky Labs meetup, one of the discussions started going deep on browsers. I mentioned how and how much I abuse my browsers. Also, how I manage the volume of what flows through.

My Browser Use

I have four browsers open on my laptop nearly always. I use Choosy to route links coming in to the browser I want it to go to. I don’t count my RSS feed reader, NetNewsWire as a browser, but see it as a pre-browser. I use Safari, Google Chrome, Zen Browser, and DEVONagent Pro as my core and are always open. I also use regular Firefox, but not as much.

Safari - The Triage Workhorse

Safari is my browser that takes a beating and often where I open a tab for general reading. I use quite a few extensions, which all work well in Safari. The regular extensions are for passwords, Readwise (for local highlighting extraction and full page capture for future lighting and annotations), Instapaper (this is less for reading later, but capturing and sending a link to my personal Slack instance as well as feeds DevonThink RSS aggregation), Choosy (used to push a link to another browser for a focussed task), Obsidian web clipper, screen capture for full page capture, Stop the Madness, and Wayback Machine.

The biggest advantages for Safari are how well ad blocking works from extensions, the Reader view, and having an insane amount of tabs open at once (I’ll often find I have 1,000 tabs open after 60 days, which it is so easy to open the left sidebar, click tabs, command+A to highlight all open tabs, copy, and paste into a markdown document as a good bulleted markdown list of title and link lists - then commit “tab bankruptcy” and close the window and start a new one).

Chrome

I use Google Chrome mostly for things Google, like YouTube, Google Maps, Google apps, some social networks which get JavaScript heavy. Chrome can handle some heavy use, but nothing like Safari can handle. There are a lot of sites that only work properly in Chrome, which feels like poor development practices of the late 90s and early 00s are back again.

Zen Browser

Zen browser is built on Firefox and replaced my use of Arc browser for its Spaces (compartmentalized browsing sections with their own tab collections) and left sidebar tabs. Zen is my browser I work in (other than the first Space, which is more fun regular access). I have 12 Spaces with one with productivity focus for things around Obsidian, note making, my vanderwal.net related resources, Personal InfoCloud site related resources, Apple Developer, techno-social cognition research, O’Reilly Media related research, one for grad student mentoring, and others for focussed related reading and notes.

I really like the Firefox foundation with all the extensions offered, good security, good privacy, and incredibly good PDF resources built-in. There is a lot open at once in the Zen browser as well and it just keeps chugging.

DevonAgent Pro

DevonAgent Pro is one I use mostly for one purpose, capturing pages as single continuous PDFs and directly add them into DevonThink and easily annotate the metadata. When in Safari or Zen I use the Choosy extension to open the page into DevonAgent and click command+option+P to capture the logged-in page easily. There are extensions for DevonThink, but it is a bit buggy at times and often doesn’t capture my logged-in state, so DevonAgent Pro becomes my go to. I will also use it for research as it has nice features to easily capture assets and its direct connection to DevonThink.

Firefox

While I keep the four above always open, I also use Firefox as my Facebook browser when I go there as it does a really good job keeping Facebook’s creepy privacy tendrils at bey along with a plug-in that is a Facebook fence.

I also use Firefox for a handful of Streamlit • A faster way to build and share data apps browser-base data analysis web apps. Firefox does a good job keeping things contained and the interactive data builds in Streamlit won’t impact anything else.



6 August 2026

Podcast Interviews and Presentations the Last Few Years

The last few years I’ve been on a handful things that have been shared out, but I’ve not posted about them. I’ve started to add them to my homepage, about page, and an old media pages. Posting things here, sometimes slips my mind.

The first two are for a company I’ve long been a fan of The Omni Group as I’ve used OmniGraffle and OmniOutliner around the time I picked up my first Mac for myself in 2001. The two products may have been included with the purchase of Mac and were great apps that have been a have been a central part of "the tools I think in" and communicate using. They asked if I would be on to talk about my use.

OmniGroup Podcast

In 2023 I had an invite to talk about my over 20 years of use of OmniOutline and OmniGraffle for the Omni Group’s podcast. (I also have used OmniFocus heavily, but haven’t been using it for a while due to work limitations and I got out of the habit and I haven’t restarted the habit). The interview by Andrew J. Mason with me talking about, How Thomas Vander Wal Uses Omni Software. I really enjoyed this interview as I’ve deeply enjoyed and used OmniOutliner and OmniGraffle for a very long time. I have my full set of Complexity Lenses and sub-elements (Complexity Lenses – An Overview – Personal InfoCloud) (there are now over 100 lenses with over 1,500 nodes altogether). I use OmniGraffle a lot for explanations, diagrams of systems and processes, but also quick graphics to put into Keynote presentations.

OmniGroup Podcast 100th Episode and 30 Year Celebration

100th Episode Celebration with Ken Case - In this I have a short snippet to offer thanks and congratulations to the 100th Episode of the podcast, but also to Ken Case for 30 years of OmniGroup. I was deeply honored to be asked to contribute to this and to be included with so many other wonderful people whose work I’ve deeply appreciated as well for many years.

Seeing Clearly Through the Fog of Complexity - on the Complexity Lounge

In February 204 I did a two hour presentation and Q&A with the The Complexity Lounge to present my Seeing Clearly Through the Fog of Complexity talk. This is a good group and having this available to share is a wonderful asset to have. This is a decent intro to the Complexity Lenses and contains around 12 to 14 lenses touched on during this talk.

Sustainable AI That Has Our Backs interviewed by Jane McConnell

Also in February of 2024 I was interviewed by Jane McConnell for his Imaginize World podcast talking about sustainable AI - Sustainable AI That Has Our Backs — Thomas Vander Wal | Full Podcast Episode - YouTube. This touches on the balance of assistance it can offer, but also some of the troubling areas around it. I started working with AI/ML (along with NLP) in mid–2008, and that background comes into this discussion.

MacSparky Members Only - DevonThink Power Use Overview

I did a deep dive on my DEVONthink use, which I’ve used since 2003 and now has roughly 180,000 objects (in one database) with David Sparks for one of his groups in MacSparky Labs. I don’t have access to it, but it is out there as well. Since 2003 I have tucked away anything I think I may have potential future interest to me in into DevonThink. I’ve been amazed that DevonThink’s incredible search on what is in its database is still solid and quick. But, its most amazing feature to me is the “See Also” tab in its insights button, which when looking at a document it will show you other documents related and its strength of confidence on that relationship. This See Also is incredibly good and has not only found things I wasn’t looking for, but it has drawn connections to things that have been massive lightbulb going on moments and started new idea and paths of exploration.



7 July 2025

My Writing Process with Obsidian

A few times lately my writing process has come up as it relies heavily on markdown for portability, longevity access, flexibility, and using the Shift Happened – Part 2: Small Apps Loosely Joined – Personal InfoCloud. The Small Apps Loosely Joined concept is something I use heavily for many things, but for writing the use of markdown I use the concept quite heavily.

Recently in a IndieWeb gathering, James who runs and writes James’ Coffee Blog shared his process and workflow for writing through to posting on his site, which was similar to my own process, but uses different tools along the way. He had something in his process he was looking to improve upon so I walked through my process.

My Process has Morphed Over the Years

My current writing process is an extension and evolution from my initial processes that trace back to college. But, it was in the late 1990s and early 2000s that my current process formed iterated upon. My early writing for blog posts and articles all start in markdown, which years back was well structured text and sometimes HTML for the structure.

My notes prior to formal blogging (started at the tail end of 2000) that I posted to my site were all hand coded HTML (or raw coding). If a note was going to turn into a blog post it quickly was marked up, and often as I was making the note or post.

Automate Early

One of the core elements I learned in the 1990s was to automate early for anything you can automate, use the tools you have at hand to help yourself be more productive. Most of my writing up through around 2010 was text and then quickly turned into HTML markup, as it is simple to do. But, the tough part is connecting related content, which is why I created my personal content management system (CMS) to run this vanderwal.net blog in 2000 and fully put it to use in 2001 (I used Blogger for a bit early on). Taking rote patterns and automating them was a great addition to help my process in 2000 to now.

In 2010 I shifted all of my note taking to markdown as moving across apps and devices made using other note making methods difficult to access and use. This shift to full markdown for notes, helped my writing move from notes to posts and articles much easier.

Markdown Workflow Process

Today and the last 5 years my notes start most often in Obsidian (and on mobile in Drafts, which is great for the good practice of get it out of your head and then sort out what to do with it). I have many notes flagged as “blogfodder” and track those through the writing process and moving them from a stub of an idea, to draft, not posted but ready, and posted (which includes a link to where it was posted). I’ll have another post about my new blogfodder process, which I’m really liking.

The writing starts as a note and gets fleshed out, if it is needed. If it is a short item I may stay in Obsidian and then grab and drag the markdown file in the Finder to the next step (I will get to this shortly).

Quite often I will leave Obsidian and from it click to open the Finder with the markdown file highlighted and then open that file in iA Writer - iA Writer, which is a nice focussed writing app for markdown, with additional capabilities. I often use the old journalism marker for needs attention (tk!) or “to correct” for things that need links, fact checks, or reference notes. Once I’m happy with the writing and structure in iA Writer (or Obsidian) I move to the next step.

Move to Prep for Posting

In years past I would take the markdown and quickly take the markdown structure and convert it to HTML markup by hand. Around 2013 or so I started scripting this transition, but the script was fussy. I’m not sure when, but it wasn’t long after this, I ran across Marked 2 - Marked 2. I think I started using Marked to convert markdown to PDFs and Word documents (for things that need to be sent out for formal article transformation in publications from Word). But, I realized Marked 2 had really good markdown to HTML conversion that was as good as my script, but not fussy. As I moved to Obsidian with properties in front matter and a footer with blogfodder tracking, it can remove all of that with ease, translate external links very nicely, and remove all backlink notation.

It is often in Marked 2 that I find markdown problems or the tk! marks. Marked 2 also includes some light grammar checking, which I appreciate and I’ll work through those suggestions. Then I flip to the HTML markup view and make edits, if needed, there.

Open My Blog Entry Form

Once I’m happy enough with the post I open my blog entry for for vanderwal.net or Personal InfoCloud and paste the HMTL into the form for the body of the post. On vanderwal.net I add in the title, location, type of post (these days everything is a weblog, but in the past it was more diverse), then select the related categories and submit it. Then I just to look at the post and review it again. If it needs an edit (up until July 5th) I would go into the database and make edits to the post there, but now have an edit process in my CMS (after 25 years, I figured it was about time). Once that is done, I go click to generate the RSS feed for the site, and send out alerts to services that share out links and summaries farther.

Wrap-up of the Workflow

This workflow is now done, except for seeing spelling errors or things not right and needing tweaks.

The process that starts in a markdown note, then progresses through to a more formal writing process and flow. I replaced a lot of manual steps that I didn’t think were difficult nor took a lot of time and automated the steps that do exactly what I had been doing with the same level of care, but saving time and reducing errors.

I don’t use AI in any of this writing process. I run across too much AI written content that is lifeless and doesn’t sound like the writer any longer. I’ve stopped reading many colleagues who used to have great ideas and a great personal voice, but are now just bland slop through the use of AI that tilts at, but doesn’t achieve mediocrity.

I have my own quirks and writing patterns, which I am fine with. I don’t write to impress, but to get honest ideas and understandings out. I blog and write to find connection with others of like or similar minds.



3 October 2020

Rebuilding My Note Taking and Management System and Model

The past many weeks I have been digging into a better note taking and management method, while also embracing what I have and my core underlying principles. A continual genre in YouTube I watch is around productivity, particularly around personal knowledge management methods and tools. A couple years back I ran into Zettelkasten Method, that comes from Niklas Luhmann, which focuses on his prolific reading and his card catalogue and related note taking system. Then a few months back I heard Jorge Arango’s interview with Beck Tench it drew Zettelkasten back into focus. The interview with Beck focussed on Tinderbox, which I love, but I also want mobile access to my notes from phone and tablet.

Early Exploration

I have been using Notion a little bit, but my only use the last few months is as an interstitial capture for YouTube and some other rich media. [I like Notion and it seems like a modern take on Podio and has a similar downfall of not sorting out an adaptive data structure for interoperability and consistency.] But, the communities that are interested in Notion became obsessed with Roam Research, so I looked at Roam. Roam and Notion are two vastly different approaches, which can complement each other but in to way replace each other. But, each has a similar faults, no API, no standard export for structured information, and fully cloud based. That is too many common failure points wrapped into one product (Notion is working on and API, which is really good). Roam bugged me most because it relies on an outline format but has no clue about OPML exporting, but worse has no good export model. The cloud based, which requires being connected and online is a model I really don’t like as, particularly if their isn’t a local sync nor standard data format model. What I really like about Roam is its block focussed format, that is akin to purple numbers model of small chunks that are addressable and reusable.

In this time of looking what a next generation of quick note taking would look like, but long used tool, NValt failed spectacularly, in that it would not find my directory where my 1,200+ notes were stored, nor could I add new notes. Fortunately all of my notes are in plain markdown text files, so all I was missing was my tagging of the files in NValt (Brett Terpstra who created NValt has been working on a new tool that can replace NValt but has been taking forever to show up and my need became immediate). This is one of the common reasons for owning my own notes and having them locally and not using somebody else’s model and framework. But, also using the [small apps loosely joined] model where many tools pointing at well formatted / structured data / information can function to their best ability and can use their strengths without breaking anything with the information / data.

Seriously Looking at Note Taking and Management Tools

I started looking at about five or six different note taking tools. I was building out a rough attribute model of tools to help see what each offered or didn’t. I am needing to write this up, but it started with watching Mike and Matty’s, Notion vs Roam vs Obsidian vs Remnote - How to best fit note taking app for you and using their criteria as a base, then building on it. Obsidian and Remnote were already on my list, but also included Zettelnote, Zettlr, and a couple that extended Tidlywiki for a Zettelkasten type model. I also included OmniOutliner as that has been (and will be) my core outlining tool that interplays well with OPML and I can back and forth with good mind mapping tools that also output and import OPML data standard. I also included DevonThink Pro as it is my long used (since 2005) note and information storage and smart search tool (it already was indexing my notes directories) that there is no chance I’m going to give up, but also knew it didn’t have the core functionality I was seeking, wiki-style back linking.

I did a quick test or Roam and ruled it out as it broke rules I try not to break, and it broke many of them (biggest one is know now you are going to exit before you enter anything and a lack of any structure nor API made it a giant risk I’ve been burned by too many times, but the developers have a lot of arrogance about their approach that far too often leads to disasters - sometimes the kindest, smartest, and solid planning people end up with disasters that I feel very badly about but arrogance and ignorant I don’t).

Zettlr and Remnote were next. But the setup took a bit more of me managing and building things and I know when I lose focus those may not be best choices for myself (my past self 15 years ago or more would have loved it and done well with it, but those days are not now).

Obsidian Ticks the Right Boxes and Adapts to My Existing Model

Obsidian is where I put some time. I pointed its “Vault” to my notes directory (and sub-directory) where I had my 1,200 markdown notes already (some of them were .txt extensions, which I did bulk extension swap on) and it could read everything perfectly. One of my first tests was adding backlinks to some of my social lenses and social scaling notes, which worked really well by making related elements connected. I started capturing my notes about what I was doing in Obsidian and the ease of not only connecting things with backlinks, but having the ability to set empty node wiki links (many notes with the same link to a note / page that doesn’t exist yet, but have the same link to it) and then being able to use backlink following from that non-existent notes link list of things pointing to it was insanely valuable.

I have quite a few book list and book note pages already and I started linking them and linking authors and making author pages. I also found I was wanting note page templates for simple book pages in a Zettelkasten model, a book notes template, author / creator template, and a few others. I created these from existing structured notes I’ve used for years and put the outlines in TextExpander using a simple input line or two to label all of the headers with author name or other name.

I started typing out my notes and highlights from books I’ve read and annotated over the years and after the first three or so books I was deeply hooked.

The Use Where Obsidian Showed I was Hooked

Where I knew I was sold was this last weekend I went back to one of Matt Webb’s blog posts on Small Groups that is dense and has links out to great resources. I captured my initial notes on Matt’s post, and annotated relating to his sections. But, I also quickly dug through the linked materials and created and filled out structured note pages for those as well. The James Mullholland post on Small Groups was fantastic and it spidered out to more related resources, so I followed those and took notes. All of this was cross-linked and back-linked and fleshed out small group notes that I have been building as part of social scaling I’ve been writing on and presenting (talks and workshops) for years. The small group size they focus on is roughly team size, but not a team. Both of these are cooperative social models, which scale from teams, groups (small to large groups with similar social interaction models, but the dynamics shift quite a bit around 75 people and break fully about 300 to 500 people), community (everybody inside a firewall or inside an walled off construct), and network (inside and outside a firewall - so for business it is customers, contractors, consultants, vendors, etc. where there needs to be a safe model for sharing information with shared goals as different roles with their purpose come together for back and forth exchange) - more can be found in my related write-up 5 Core Insights for Community Platforms Today.

This note taking and contextualizing and cross linking to rip through and gut a series of related and interrelated pieces has been something I’ve long looked for and wanted. Many dog years ago in college I took reading notes on note cards with citations and context. When writing a paper / essay I would assemble the note cards in an order that could tell a story. Then I would build an outline in WordStar and type in the quotes. Then I would write the narrative and wrapper. Obsidian is starting to get at that, but ripping through a resource to pull out highlights, quotes, annotations, and notes is utterly fantastic. It gives me a solid resource to easily pull together ideas and supporting information.

Other Obsidian Capabilities

Obsidian can show two note pages at once so to easily copy book citation information from the structured book note file into the book note page. The multiple notes in panels also works well for copying quotes to quote pages and cross linking.

Using Obsidian and Still Working from Mobile and Tablet

The mobile use essential had been broken for a bit after Dropbox stopped supporting softlinks in Mac and requiring that to be native in Dropbox and doing the softlink from the Mac to Dropbox. I moved the directory to Dropbox, which leaves a copy locally usable should something happen to Dropbox and added a softlink for local backups. I pointed DevonThink to this directory to index and I was back running. Now I can use Drafts to take a quick note from my iOS devices and push it to the notes directory (later go back and fix the file name) and I have good inbound notes and can use backlinks (which I test later). This method also works for share sheet to Drafts from Overcast or YouTube and having the link to the media and the notes all pulled in.

Happiness with notes has been missing for a while, perhaps happiness has returned.

Resources


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