583: The Obsidian Deep Dive

I am using both and will likely continue to do so. As someone mentioned, they are really rather different tools. Craft is for…crafting documents and personal wikis. Obsidian is for note-taking and thinking. I don’t know how else to summarize it, but for me, that’s how it works!


So so so happy to see this in my podcast feed today! Sunday’s are usually my nerd out on Obsidian day but I wasn’t able to do that much. Glad to see I’m going to get some extra Obsidian time today :slight_smile:

I found Craft a couple of months ago and loved it a lot but quickly ran into things I didn’t like and stopped using it quickly. I probably wouldn’t have stopped using it if I hadn’t found Obsidian.

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Before I download Obsidian or listen to this episode, is Obsidian strictly for text files? I’m wondering out a system that’s more like a digital filing cabinet, where I can shove PDFs of articles and emails that may be part of a similar topic.

@tjluoma, you may have some insight: I’ve found an article for a sermon, and I don’t really want to print it out, and I may not even want it for this week, but three years from now, when this text surfaces again, I might want to go back to this piece.

Anyway, that’s where I find myself and wondering if Obsidian is good for that (Bear is out; that’s siloed off for completely different tasks for me).

Obsidian isn’t “strictly” for text files – though it is built on plain text markdown files, one can store PDF or image attachments within Obsidian and insert them into markdown files within Obsidian. But Obsidian is not a “digital filing cabinet” in the sense that DEVONthink, or Keep It, or Eagle Filer, or Yojimbo are. You might want to check out one or more of those four – at least the first three are discussed here often. I don’t see people mentioning Yojimbo much, but it’s pretty good.

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The only thing I would trust for something that far away would be my calendar. I would save the PDF with a specific and meaningful name, and then look for approximate date in 3 years’ time, and put a note that says “Re-Read (article name here)”.

Calendar items can have attachments, so I would attach it to the calendar item, but I would not let that be the only copy of the article that I have.


Excellent point @JakeBernsteinWA


I disagree with such a firm distinction between the two (I’ve used both quite extensively now, building the novel I’ll be publishing next year in Obsidian, and training myself to code in Craft). Obsidian is terrific for thinking, it’s what it does best, but Craft is also very good at linked-based thinking.

They are really two vastly different takes on the fundamentally same paradigm, and both have the exact inverse strengths and weaknesses by choices of design.

You can design a wiki with Obisidian: that’s the very goal of Publish. You can think in links with Craft: its block references are even better. What will set your choice is the subset of features and global approach of both apps: are you adamant with not having any kind of friction when thinking in links? Obsidian. Does the formatting help you to think and curate your notes? Craft. Etc.

These tools are so personal that I really don’t think one can choose before extensively testing them on a real project.


@MacSparky — curious as to how you (or anyone else) that threw an existing plain-text/MD “library” into Obsidian, got going initially?

Did you do any curation at the get-go (working through entries/files and adding/creating links etc.) — or did you just let it be, and then allowed that integration to happen organically?

Really enjoyed today’s show. As a heavy DT user, my biggest challenge is conceptualising how I should go about using Obsidian. I have had an itch to scratch on this side of things for a long time — but think that (similar to Hook) I haven’t got my head around how/where to use it because my usage has been shaped by what I have available in my current tool belt, rather than kitting out those tools to match the usage scenario…

Today’s show has given me some much needed impetus to jump in!


I’ve mentioned before my own integration between Obsidian and DEVONthink. I really just conceive of the relationship as Obsidian being a editor that works with some of my data, and, now, gives me access to a collection of markdown notes on iOS that is better than the markdown editing on iOS that DEVONthink provides.

There are features Obsidian specializes in and does better: the graph, the backlink and unmentioned link displays, the large and growing library of community plug-ins, tagging, less friction with editing, faster sync, etc. And there are features that DEVONthink specializes in and does better: scripts and templates, “see also and classify” for finding related documents, etc.

In my own integration of folders between Obsidian and DEVONthink, I used Obsidian 95% of the time to access those files and DEVONthink 5% of the time.

Obviously, this is all dependent on what files you share between the two apps, how you do it, and what their content represents for you.

And, you’re right, just jump in. You are not going to break anything.


Is there any way to bring DT’s classification into Obsidian, so Obsidian shows probable connections between documents in addition to the more literal unlinked references?

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Note-taking has been an important part of my workflow going back into the mid-1990s. At first I simply used word documents to track notes, but eventually moved into OneNote. When Evernote launched around 2007 or 2008, I started to use Evernote as my catch-all and continued to use OneNote for structured notes.

At some point, I added TheBrain to the mix. This helped me make connections and links between concepts.

So, for over ten years I have worked with a combination of OneNote (structured notes), Evernote (catch-all), and TheBrain (connected thinking). While there are rudimentary ways to connect notes between these apps, it is not efficient. Typically, thoughts move from OneNote into the Brain with a link back to the source in OneNote. Evernote is nothing more than a collection point.

I have worked on-and-off with Obsidian for the better part of a year. I have trouble wrapping my brain around Obsidian. I feel it is like Tinderbox, an app I have wanted to love. I have purchased several licenses for Tinderbox over the years, watched the video series, read the forums, and yet simply cannot reach a place where it all clicks. I watch videos like the one @beck recorded, and I am inspired by the connectivity and creativity she is able to draw from Tinderbox. For me, I just don’t get it.

As I have thought about this whole concept of note-taking, PKM, etc., I think I am struggling with how native the linear, structured format of OneNote seems to just fit. It’s native for me. Plus, I have not discovered a simple process of transferring decades of notes and thinking into Obsidian.

This post is probably meaningless to most of you, but it has helped me clarify in my own mind the conflict I have felt in the area of note-taking for the past couple of years. I love the power of connected thoughts, back linking, and watching ideas emerge from previously unseen connections, but it seems overwhelming at the same time. Moreover, I question whether this is a true game-changing innovation in research and knowledge development or if it is simply a fad.


Within Obsidian – no, not in any significant way.

But … you can index Obsidian folders in DEVONthink and then “see all and classify” will take into account not only the Obsidian documents but anything else in the currently opened databases.

I would never recommend trying to do that. You have a corpus of notes that, I assume, has made sense to you over several decades – so, unless you are dissatisfied with that library, it would be very frustrating to try to, in essence, redo those years of effort.

I strongly feel that anyone who feels overwhelmed by software should step away. Either for good, or for a long while. Don’t boil the ocean to make a cup of tea.


I really enjoyed hearing the thinking behind David’s linking. I just started with Obsidian about 2 months ago and have less than 100 notes. I have not created many links yet and haven’t quite grasped the idea of linking yet, though I do know how powerful it will be. I’ve watched Nick Mylo’s intro video on creating links a few times, but until I get more notes, the concept is still pretty abstract.


Good advice, and I completely agree. What I am trying to discern is whether or not the connected thinking the recent wave of apps like Craft, Obsidian, and Roam bring to the table is a paradigm shift in research or if it is a fad. Moving from a collection of Word documents to OneNote was a paradigm shift and well worth the transition. It is too early to tell if connecting thoughts at the block level rather than the document level represents a true innovation.

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I guess it depends on what you do. For huge creative endeavours, which work by emergent layers and constant sense-making, it is indeed a game-changer. I would never want to go back to anything that does not allow flexible linking.

If your work functions more in fixated areas, then folders absolutely represent a more readily accessible paradigm. Even though I would venture that link-based thinking, that is, working through analogies and not categories, is the natural way of the human mind.

It’s not an early revolution by any means; the Zettelkasten method is decades old, but it’s all, deep down, a fancy word for… hypertext. It’s been tried and true at the Internet level.


This is why Tinderbox keeps bubbling back up for me. Eastgate and the overall TBX community has been engaged in research into hypertext for decades. They see it for what it is. I’m not convinced that many other companies do (but I’m equally convinced that it probably doesn’t matter), however, it’s often helpful when the individuals developing a tool are also steeped in the theories behind it.

All of this linking truly isn’t new: it’s as old as the first HTML experiments (at least on a computer) and the concept of cross-references, of course, goes back centuries (at least in legal texts and academia). In any event, it’s definitely not a fad–these tools are just trying to make Wikipedia available to everyone, in their own personal way.


I would love a MacSparky Field Guide to Obsidian…just sayin’!


Yes, you’re absolutely right, I actually wanted to mention TBX (but didn’t). It’s probably the first app that really got it, especially when reading how it came to be with The Tinderbox Way: many of the concepts Bernstein talks about in the book, sometimes describing his own thinking that is several decades old, predate spectacularly Roam, Obsidian and such. It was (and sort of remains still) extremely ahead of its time.

(I wish I would have been able to make it work for me, because on the surface it was supposed everything I was looking for. That’s an app I really wanted to love, but I clicked a hundred times better with Obs and Craft.)


I second that! @MacSparky

I brought the two apps a little closer together with the DEVONlink plugin. It provides a way of opening or revealing the current Obsidian note (providing it’s indexed) in DEVONthink. It also includes an “insert related notes” feature that uses DT’s “See Also” list to insert a list of related notes to the current note in Obsidian.

There’s a companion AppleScript that lets you jump from an item in DEVONthink to the note in Obsidian. It’s handy to put that in your toolbar/hook it to a keyboard shortcut.

Here’s an MPU thread on the DEVONlink plugin:

The official write-up on my blog is here:

…and the GitHub repo is here, because why not: