583: The Obsidian Deep Dive


Having just fully committed to Craft, I am not going to want to listen to this week’s episode, huh? :slight_smile:


Having just used Craft and Obsidian a little, they both seem like different tools to me.


Listening to the episode now, and they directly talk about the differences between the two. It sounds like the apps overlap a lot (not that I have used Obsidian). I believe Craft is trying to be a writing app, but it also seems like a good notes app. I am mostly using it as a notes app for a very specific purpose and it is working really well for this project. I am really happy with Craft, but I am still using Bear for my everyday stuff.

I think I am like @ismh, since he is coming from Apple Notes. I could move all may Bear stuff to Obsidian, but I am not sure I need the back-linking. I use back-linking in Bear, but not heavily.

I do really like the idea of a daily note in Obsidian that @MacSparky talks about though. I will have to give it a try.

The lack of mobile apps would be a problem, but everything starts in Drafts anyway, so it isn’t that big of a problem. So, I guess I will give it a try.

Edit to add: Trying it out, and the Linking your Thinking YouTube channel, listed in the show notes, is extremely helpful. Plus, he’s a right side dock person, so you know he is a smart person.


Dear @MacSparky,

Should you make a SparkyOS Field Guide, you’ll have my money as quickly as I can fork it over.

That is all.



@tjluoma Are you using both Craft and Obsidian currently?

Like @MacSparky , I’m using Obsidian closely with DevonThink and my task manager (for me it’s Things rather than OF). I work on a half-dozen or a dozen projects running concurrently, and I create a folder in Obsidian for each project, index the vault to DevonThink and replicate each folder to an appropriate location in my primary DevonThink database.

This is not recommended by DevonThink’s developers. And yet I do it anyway.


At some point I’m going to stop indexing the entire Obsidian vault, and instead index each folder individually, which is the way DevonThink’s developers recommend doing it. I really need to do that sooner rather than later; the task is only going to get bigger the longer I put it off.

Obsidian handles my Markdown documents, DevonThink handles everything else — Word documents, PowerPoints, PDFs, web pages saved as PDFs, videos, and audio files. By indexing the Obsidian vault, the Markdown documents appear in DevonThink and the other file types appear in the Obsidian vault — at least on the Mac. I have not explored whether they also cross-populate on the iPhone and iPad. Neat!


That is what I do. For example, I index my Obsidian daily note hierarchy (year/month) in DEVONthink. have a script that creates my daily note in DEVONthink, and places it into the relevant year/month folder in that hierarchy, so that it is immediately available to Obsidian on macOS and iOS/iPadOS.

My script is a personal hybrid of the Daily Journal - Markdown template that ships with DEVONthink 3. (It’s really a total rewrite of that script, FWIW.)


Only very lightly. I like Craft but haven’t been captivated by it. I’ve downloaded Obsidian and used it a few times but haven’t had time to really use it much.


I started with Obsidian a couple months back but a funny thing happened. My primary computer is the iPad, so, with no mobile app (at that time), I started experimenting with a couple apps, 1Writer and Taio for creating/editing the markdown files from the iPad. I figured I’d just hop onto the Mac occasionally to use Obsidian. A couple months in and I’ve hardly touched Obsidian but I’ve been much more proactive in writing of daily notes (a new practice that I’d long pondered) and more writing generally as a result of starting the day with daily notes.

Another result is that it’s got me thinking more actively and critically about what/how/where/why I save files. Ryan recently started a thread about pdf files compared to html which also got me thinking about file format as it relates to what I do with stored files. As a part of considering my intent, I’m also considering the saving process and the information I actually want to save. To put it plainly, I’m trying to be very deliberate about my accumulation of information I may never need. Be it whole files, text, or images embedded in pdfs, etc. For example, I happened upon a recipe last night and rather than just save to pdf I used a shortcut to save a markdown/text file to Files in my 1Writer folder. I hop over to 1Writer and open the new document, clean out any cruft and tag it both in the text and also in the Files app. Within just a minute or two I have a very tidy, portable text file that works in 1Writer and Obsidian and also fairly easy to find in Files/Finder.

So, rather than dive into DEVONthink as a catch-all tool my plan is to go the opposite way. Thinking about what I currently have saved and the work I do, I don’t think I need it. It’s also got me looking at how I use Apple Notes… largely, I’ve been far too lazy and sloppy in throwing stuff in there and not cleaning up after myself when notes are no longer needed.

All this to say that it’s great that we have so many apps/tools but I’m recognizing how easy it is to get lost in them, jumping from one to another looking for the perfect tool with all of the exact features we need or think we need. It’s easy to focus on the new shiny tool rather than actively engage with and use the information in a meaningful way. I suppose that’s one of the pitfalls of being a geek.

I guess that was a bit of a sidetrack but I think in looking at the bigger picture it can be helpful to ask what it is we’re hoping to do with apps. I expect I’ll get around to actually using Obsidian more often and it’s feature set will prove helpful when I need them. But for the most part I’m currently just enjoying the focus on writing and more active engagement with information processing for a more tidy and deliberately curated set of open, accessible files.


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?

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.