Sorting through what stays in the Finder vs what goes into DevonThink and sorting out my mess

So I’m running into a dilemma that I could use some thoughts on. I have DevonThink version 2 (whatever the latest version 2 is). I can’t afford the upgrade to version 3 at the moment. I’m trying to fix my file structure and get more organized. Currently, I have the following basic folder structure in my Finder.

Then here are some of my inner folder items in my “Docs Archived” folder.

Of course, this isn’t all of them but what I could fit showing the folders on my 13" Mac.

I have the following separate databases in DevonThink…Screenshot 2020-04-19 10.29.03
Also within a few of the various databases, I have similar folders/groups to what I have in my Mac Finder. For a while, I was thinking about having DevonThink as a sorta souped-up Finder replacement, can’t quite remember if that’s recommended or not. I tend to manipulate files and move stuff around using FokLift as I find the viewing panes and allowance for multiple tabs make things super easy. I also understand this is something I’m not going to have done overnight.

So my questions are the following:

  • How do I sort through this mess?
  • What is the best way to tackle this?
  • If having this many databases is overwhelming to me right now should I condense stuff down?
  • What DevonThink databases do you have?
  • What’s your file structure either in DevonThink or the Finder?
  • Do you index Finder folders into DevonThink to make things easier?

To start things off I’m going to tag some people I trust to jump-start the conversation. @OogieM, @bowline @nlippman and @FrMichaelFanous

I think the key question is “What are you doing with which files?”

Keeping everything accessible and searchable is paramount for me, so everything is in DEVONthink. At the same time, I do a lot with apps that need files to be accessible in the file system, so I need them to stay on disk. Ergo, practically everything is Indexed in DEVONthink.

The point of a database is to use features like See also, Classify, and wiki linking. Keep files together in a database in DT if those are important to you. If not, it doesn’t really matter. I have found smaller databases sync more easily, though.


Trying to organize everything all at once, compounded by trying to organize Finder at the same time you’re organizing DEVONthink, compounded even more by trying to make a global decision about when to user Finder and when to use DEVONthink — well, that can lead to endless frustration.

My advice:

  1. Don’t organize history – at least not for now. Start your "re-"organization with what you collect going forward. Got some invoices coming in? Then make a folder for invoices and do not try to make a hierarchy for now – that will come later. Work with that evolving hierarchy for a month or so, then gradually set aside time to add some older documents from your older hierarchy to the new set of folders. Above all – take your time – if you spend 6 months organizing yourself then that will be time well spent.
  2. You have Spotlight. That means you are not likely to lose anything. Just search.
  3. Organize Finder first. After a while, you can index folders into DEVONthink. Perhaps even import those folders into DEVONthink. Again, above all – take your time – it’s your stuff, no need to race through to some deadline.

Finally, use DEVONthink for the documents you need to work with now or soon, or documents that you need to take notes about, or documents you want to annotate. If you are like most folks, then 90% to 95%, or more, of what you own is irrelevant most of the time. So don’t waste time organizing databases around archival material. Don’t build a database that you’ll never use.


I agree with @anon41602260, and will add:


Your folder structure looks really flat (at least the Docs Archived), more like I would think tags would look. That may just be the nature of your archive, and could be fine if it’s just a dumpster to put things in.


When you go looking for something in Finder, make note of the first place you look. More than likely, that should be where it is filed. When you find the thing, you can move it to its more likely location. If you don’t want to move things around too much, you can also use aliases and put the alias where the thing should be, and leave the original wherever it is.

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Yes I agree, like @anon41602260 has said I think I’ll start with new stuff first. Indexing will be key @ryanjamurphy so things are accessible outside of DevonThink. It is strange to thing of this is something new that will take a long time but it is what it is. Biting off more than I can chew will frustrate me later.

The first things I can think of to have organized would be my credit card statements and tax document information being in the same place. I’m thinking of making a running list of things to document and keep track of the changes I’m making or at least my observations of things I want to include in DevonThink. Aside from working on the credit card statements and tax information, I’ll organize stuff in Finder first using ForkLift. Keeping only what I’m working on in the present or soonish is something good to consider too, I think that’s where many including myself get overwhelmed. I do like the quote of “don’t build a database that you’ll never use”. This is huge!

@JohnAtl yeah absolutely is flat, I’ll be the first to agree. Maybe I’ll mind map it of what basic structure would make sense for it. Kinda like what I was saying about the running document, taking note of where I first look is good to observe and record, making the creating of databases or new folder/file structures more intuitive.

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Sorry for being so slow to respond, wanted to have time to answer in depth.

I have 6 main DT databases, Android_Development, LambTracker_Queries which is an index of the Git repository where the clean query text files are located, Oogie_notebook for my small notes, Filing_Cabinet_Index which is he index of my main digital filing cabinet folder, Mail_Archive_Curated which the the database I moved all my emails into and Reference_Files_DT_Only which is hte archive of stuff that was in my notebook but I only need irregularly.

Looking at your top level in your first picture. For me that looks confusing. I prefer to separate my own structures from those that the system does for me. So my top level looks like this,

Screen Shot 2020-04-22 at 1.42.13 PM

Then I go down into Documents, again apps and the system set things up in there so I try to keep my personal filing in a more confined space. Looking at this level the real filing I do is in the folder DWA_Data

Here is where I have filing folders for organizations I am part of, folder for my active projects which are like my project support documents for things I am actively working on right now and the biggie, my File_Cabinet.

File_Cabinet is my archive of digital stuff, my reference files, my inactive or someday/maybe project support materials and more. That is the folder I index in DEVONThink. Changes I make to it will eventually be synced to my DT systems where I need them. File_Cabinet is very flat, much like your Docs Archived but in my case it also includes stuff you’ve separated out earlier. I don’t think to look for things based on what they are (notes, outlines, transcripts) like you appear to do but instead by what their subject is so I have folders like these in my File_Cabinet


That level is flat, things in those folders are just files almost never a second layer of folders.

Personally I’d set up a whole separate structure and slowly move stuff into it.
I agree with @anon41602260 to start with new stuff and refile as you need or access things, to use Finder first and only after you are comfortable with the new structure create an indexed DEVONThink Database.
I do think it’s useful to have a database for archived material though so I would have that as the end goal.
Set up your naming scheme first and then keep to it.

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As an alternative to a category-based hierarchy, you might also consider Tiago Forte’s PARA (Projects, Areas, Resources, Archives) system based on current actionability — basically Projects are things you’re working on right now and need most at-hand, Areas are things that are not immediately active but that you use frequently and know you’ll need soon, Resources are things you’ll probably need again sooner or later, and Archives are things you don’t really expect to need again but don’t want to delete altogether. Using Finder folders you might have Projects on your desktop, Areas somewhere on your internal drive or iCloud documents, Resources on an attached external drive, and Archives in zip files on a detached drive or archival DVD (do people still use those?) in your closet. Tiago recommends replicating these four classifications across all your systems, i.e. in your case maintaining a parallel structure in the Finder and DEVONthink along with any other systems you might be using.

Sorry getting this to later than expected. Finally getting to breathe again.

A lot of the suggestions listed above are really good already. Other items I would possibly add is the following.

  1. Use a system that works for you, your style, your personality. It took me forever for this as I bounced around from app to app style, etc.
  2. As mentioned by @anon41602260 you are organizing many things at once, start off small and work your way out. Keep in mind things change, this isn’t set in stone.
  3. Hazel would be helpful in the future for you in terms of sorting things out.
  4. Framework/Mindset - As @ryanjamurphy mentioned, what are you planning to do with the files, what is the overall goal. Keep that focus as you plan your steps.

Hope that helps!


Hi all, as a first step I’ve decided to gather up and download my financial documents from my savings accounts, CC accounts, and checking accounts and have it broken up by Institution. I have it organized in DevonThink from importing but I’m thinking about indexing it instead. Not sure yet though. The important thing is I found a problem (having my financial archives in one place) and took the first step to a solution. Glad I’m not overwhelmed or biting off more then I can chew.

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