I’ve only been a DEVONian for a few days, but I have thoughts, tips and interest in getting the most out the DEVONtechnologies apps, most especially DEVONthink, but am also interested if I’ve missed anything.
I won’t apologise for the length of this post (3,200+ words!) – I am, at heart, a long form writer. I wrote the Help Folder for Australian MacWorld for 10+ years plus many technical feature articles for mostly Australian Mac mags for over 20+ years, and was an independent Apple consultant for 20+ years, so I like deep dives and technical details. I’ve now been using computers for over 45 years, and Apples since 1982, so I have a lot of opinions 
Also, you may already know some, most, or all of this stuff, and you almost certainly know stuff I don’t, and many of you would have been using DEVONthink for years, so I’m interested if, based on what I write, you feel there might be something I’m missing.
I won’t be upset if it’s something I’ve already thought of (means I may be on the right track), I won’t be upset if I don’t think it will suit me. While I “have opinions”, I am already adjusting to a new way of looking at my files and processes, trying to optimise myself and my setup to get the benefits I know arise, so I’m considering everything.
Firstly, a few “bravos” from a newbie’s perspective*:
- No Discord or Slack! Thank you (!!!) to the DEVONtechnologies leadership for ensuring the availability of a searchable, non-transient community space for us all via Discourse, my favourite modern forum software.
- A real manual! When I started computing (yes, this is a “When I were a lad working down mill in Devonshire…" rant) manuals were standard, and when the Mac came out, Apple set a new standard in manuals. Over time, manuals have withered (even from Apple), sometimes reduced to a pretty dodgy looking help system which returns nothing useful when searching (if search is offered). Bah, Humbug! Get off my lawn! and all that. Anyway, I love that there is a comprehensive manual from DT to help guide our way, but not only that…
- A great help system! The manual, is available in a comprehensive Help system in DTP. It’s great presentation of the manual in an readily-onhand guide to what to do where.
- Direct support of an external (comprehensive) guide! @joekissell’s Take Control of DEVONthink 4 was my real introduction to DTP – it convinced me to download and start playing with DTP, and reading it got me enjoying getting into more of a deep dive.
*Those bravos are separate to any kudos for the app itself. I was only 3 days into my trial when I “pulled the trigger” (at a time when I’m between jobs, so it was not a done deal when I started the trial). I won’t gum up this already long post with my thoughts on the app itself – for now, suffice it to say I’m a big fan
OK, kudos for documentation aside, there’s already a new user’s perspective and some responses in this excellent post from ::checks notes:: 2016!
Maybe it’s time for another perspective almost 10 years later…
Right off the bat, you’re as paperless as possible, right? I’m guessing most here would be, but just want to note that the less paper in your life, the happier (and greener) you’ll be. Original PDFs are better than scanning something from your bank, or telco, or wherever. Of course, not everyone will be prepared to send you PDFs, but you should have already signed with as many as will already.
Consider getting the “Take Control of Your Paperless Office” book – while available when purchasing DEVONthink, it’s the same price directly, so you don’t lose anything buying it during the trial period if you want guidance on that topic. I’ve resisted buying it for now as I explore the app, using up my reading time with the Take Control book (see below).
While DEVONthink utilises some internal and OS features to take care of scanned documents, scanned PDFs tend to be larger than what I might call “true” PDFs (generated PDFs?), and you’ll want to OCR to get the greatest benefit from scanned documents in DEVONthink or any other paperless system.
Now, my first tip is, the best time to start using DEVONthink was probably 20+ years ago…but absolutely the second best time is now! Jump right in, explore as much as you can, as soon as you can. Absolutely just bring stuff in and start playing.
The sooner you get into an organisational mindset with your data, the better, and while you can be organisational in the Finder, the choices in DEVONthink are so much richer (although that can lead to a bit of feature paralysis, see below), so the sooner you start, the more benefits you will reap.
And while you’re exploring in those initial days/trial period, RAFM! Either one (official or Take Control), but read it well, and think about how you might use the info now, or maybe in the future.
For me, Joe Kissell’s guide has been invaluable, and I refer to it most frequently. I’m about half-way through reading the Kissell book cover to cover. I dip into the manual when I want a different perspective on a task or feature.
I’m lucky enough (i.e. on the spectrum) to already have a pretty comprehensive folder structure in place after 40+ years of playing in GUIs. I’ve sort of dabbled in OS and Yep tags (sorta-kinda-not-really) through their initial implementation in Classic Mac OS, removal from the OS, and not-so-triumphant return in Mac OS X, but I essentially have a folder structure and naming convention which are pretty regimented.
For general docs, and especially correspondence/notices/statements from organisations where I’m not generating much (or any) content, I have a “PDFs and Receipts” folder, which has some folders in it, but which is sort of my DEVONthink Inbox/tagged files equivalent.
Even more important than folder structure, though, is I’ve been stringent in my file naming conventions for a few decades now, relying on file search to help me find what I need, and to distinguish between similar files through “yyyy-mm-dd” (formerly “yymmdd”) suffixes on most filenames.
My basic pattern is:
[origin {company, person, etc}] [topic/subject] yyyy-mm-dd.[ext]
I’ve sort of got an addition where for some documents, the equivalent of a tag is prefixed (but those “tags” are limited in quantity) – so, for example, for documents related to my strata scheme (think HOA/Condo association) which is named “Strata Plan 87918”, I prefix “SP87918” to those filenames.
Or I might include my initials in the name if I’m trying to distinguish between documents relating to me or documents relating to my wife.
If you haven’t already, try to define your “best” naming system now and start using it. It is so hard to implement this retrospectively. If you can, travel back in time to the 1990’s and convince yourself to set a standard then and stick to it…you won’t regret it. You can use the batch rename feature of the Finder, or the equivalent in DEVONthink, if you want to modify your existing filenames on a bulk basis. Automation might also help with this.
As I’ve gotten away without tags for so long, I’m mostly (at the start, anyway), using Groups as replacements/equivalents for my folder hierarchy, but it doesn’t pay to be a slave to your existing dataset and its organisation for several reasons.
For one thing, don’t import everything. The temptation is to just have “One System to Rule Them All” and forget about the Finder, etc., but there really are valid reasons to leave some things out of DEVONthink, especially non-textual information.
I’ve either left out, or dragged back out, files such as extraordinarily large scans of books, movies, disk images for the Apple ][ (it’s my hobby), movie files, and most eBooks (for now). But compared to a week ago, my Desktop and Documents folders are much emptier.
Consider if you need/want more than one Database before you drag everything in – I spent some time wavering between one huge database with everything in it, splitting my folder structure into quite a few separate databases, and somewhere in between. In the end, what I think will work for me is a small number of databases, and for now it’s one for Archival information, and one for everything else.
Of course, “archival” is relative when you have files all over the place, some going back 40+ years (Apple ][s, remember?).
It’s a bit of a mantra for me that a document’s date should be “the document’s date” – I have a thing for changing the created and modified dates on PDFs, even those scanned, to the date the originals are from. A scan for my birth certificate has a date created and modified of mid-1968 (no, really!).
When I used Yep for my PDF management, I had a script which would change the created and modified dates to the date encoded in the filename. I’ll be doing the same at some point in DEVONthink, as DEVONthink sets the modified dates on files which are OCRed to the date and time the OCRed output file was created.
As you’re working through things, let processes finish before moving on. I find myself getting impatient sometimes, wanting to do the next thing after the one I just got going. I waited, however, for my Mac to finish syning my Databases to iCloud before I started the OCR process on my unOCRed PDFs (see below) – there were over 2,000 of them, and some of them are making DEVONthink’s UI pause or lose a character or two as I write this post (I’m drafting it as a MarkDown item due to its length)
The following statements all relate to a general view of motivation:
- Perfection is the enemy of done (“real artists ship”)
- Don’t try to do everything!
- Be kind to yourself while doing everything you can to support future you
We probably all want “the perfect system for us”, which is why we probably find ourselves becoming DEVONians in the first place. As a newbie, though, what we do now will never be perfect. So, look for the “good enough” sweet spot which allows you to organise the files you have so you can be productive now.
You might have scanned files with date-based numerical names, and think you should rename them ASAP so the list of files looks good (that’s certainly my first instinct). I have 70 or so of those sorts of files sitting in “PDFs and Receipts” at the moment (not bad out of 4,800 PDFs in my non-archival database), and I have a pile of another 10 or so documents waiting to be scanned.
I’m going to resist the temptation for the moment to rename them, and use See Also to file most of them into sensible Groups, and have a Smart Group (see below) to be able to find them all for renaming later.
That’s good enough for now as I have some more “foundational” tasks to do to get the system and my processes how I want them (see ToDo list below). But I’m being kind to myself by determining how I will deal with them in the future, finding the tools (See Also and Smart Groups) which will make the renaming task easy in the future.
And speaking of those tools, here are some I have definitely found some great benefits from as I do my initial sort/consolidation.
Smart Groups: Similar to the Finder’s Smart Folders, these have been great for me to collect together a lot of files of a type to do something to (e.g. I’ve switched from “SP 87918” to "SP87918” in filenames by having a Smart Group find all files with names containing “SP 87918”).
I used Smart Groups to look for any files (excluding Groups) larger than 30MB, then modified it to larger than 20MB, so I could export them then delete them from the database.
OCR to searchable PDF: This is probably worthwhile doing sooner rather than later to ease searching and other features of DEVONthink. To find candidate PDFs, I created a Smart Group which found PDFs with a zero word count. I then assigned “NoOCR” tag to PDFs which I didn’t want to OCR (floor plans, graphics, etc.) and excluded that tag from the Smart Group so the field would disappear from the Smart Group as I tagged them.
Once I’d reviewed the 3,000 unOCRed files (as large icons with minimal Preview), I was able to exclude 1,000 of them from my bulk OCR task which is still running (it will take 9 hours, roughly, so I’ve saved 4+ hours of processing time by culling the list of files to OCR).
Note: there are trial period daily OCR limits (I don’t know what they are), so you may not be able to complete this during the trial period. After a few days of playing, this was the tipping point for me to stump up for DEVONthink (and DEVONthink To Go, and DEVONagent, and DEVONsphere).
Replicants: A great feature which many Mac OS users might equate with aliases (especially as they share the key modifiers to create them in other places when dragging), but they’re more akin to Unix hard links. Replicants are effectively all direct pointers to the same file data on disk (or in the DEVONthink database).
Unlike aliases, you can delete the “original”, and the replicant will still function and act exactly like the original. Only deletion of the last replicant deletes the file forever. Replicants are a great way to reduce version control issues between copies of files, and also saving space. Duplicate a file if you need different versions of it.
Get an automation companion: I know from posts here that some people use Alfred in their system, I happen to use Keyboard Maestro. Each one will suit different users (I’ve been creating and using macros for decades) – I found it easy to create a function key command to select the “Convert Duplicates to Replicants” menu item, then did another for “OCR to searchable PDF”.
I’ll develop others in conjunction with DEVONthink’s AppleScriptability, which is also a great feature of the app.
Categorisation is always your friend: There are so many layers/types of categorisation in DEVONthink that it’s a bit dizzying. Not only Groups and Tags, but also Labels and Flags! And don’t forget metadata, both standard and custom!
Your brain works your way, so select the mix of categorisation tools which suit you, between fixed ones like Flags and customisable ones like metedata fields, groups, and tags, you’ll be able to find a great mix.
Deep links are easy: This is one I’ve only just started exploring, but deep links into file contents look so useful. While I’m putting off a deep (haha) exploration of them for now, I have toyed with, for example, linking to a meeting item in an agenda for consideration of the prior meeting’s minutes directly to the file containing those minutes.
Similarly, I could link from one part of one file to the relevant part in another (for example, between related topics in the DEVONthink manual and Joe Kissell’s book). Try them out so you’re familiar with them, and maybe let them stew in your head as you get more pressing things attenedd to.
Don’t try and learn everything at once: There’s simply too much, and you’ll end up losing productive time if you think you have to become a DEVONthink expert in a few days (or even in the trial period) – or you’ll get paralysed trying to choose between alternatives (see Categorisation above). Like all good apps, there’s lots to get started with, and you’ll always have new features to find over time.
Don’t be afraid to cull or exclude: As you may have surmised, I’m a digital hoarder. The financial cost to keep any given document is effectively zero these days, but cognitive load or time cost to maintain a large set of documents can lead to operational paralysis (or, at the other end, overwork!).
While I’ve developed things already in a way which minimises the time and cognitive load to import and sort any given document, I am looking to put as many files into my Archives database as possible. It’ll be a change of mindset, but one I think worthwhile embracing. However, whether I actually ever delete the files or not…
Wow – still with me? I’m not done yet!
Not long to go, though, I promise – here are some general tips, rather than tips specific to DEVONthink.
- Get a big screen (or three!): I find the Widescreen view on my iMac’s 27" screen (XHD, 2560 x 1440) an absolute joy – so much so that when one of my two external HD monitors died last week, I bought two 27" XHD monitors whose panels are pretty well exactly the same size as the iMac’s. Space is a great resource to have when working with and categorisiting documents and information, so if you can afford the money and space, try and get as much screen real eastate as you can.
- Be prepared to change your mind: mental flexibility is a great attribute to have, and one I’ve been working on over the last few years as I’ve come to understand my profile on the spectrum. I’m more accommodating of change these days, and for less enjoyable change, better able to cope. Flexibility while you settle into working in DEVONthink is crucial to you finding new tools you may never have imagined you needed!
- Listen to others: there’s a wealth of knowledge here in the Forums – tap into it. Ask questions (after researching if they’ve already been asked, of course!). Engage in conversations where you can.
- Keep learning and exploring: Browse the topics here as a discovery tool not only on features but also how people are adapting DEVONthink to their processes, and vice versa. Put things you’d like to explore in a ToDo list to remind you to go back to them.
And lastly (hooray!), speaking of ToDo lists, here’s mine (so far [Updated 2025-07-16 14:55 UTC+10]):
- Reorganise Groups
- Explore Graphs, especially when sorting
- Consider additional Databases
- Set up automated OCR of incoming scans, possibly renaming files as they come in if feasible
- Tidy up existing tag use, and work on a new heirarchy
- Archive as much as possible
- Explore custom metadata fields
- Plan e-mails in DEVONthink (a biggy: 31 years = 170,000 e-mails!)
- AppleScript to change .rtf file’s page print margins by editing the underlying RTF markup
So, what do you think - what can I improve? What have I missed? How do you do any (or all) of the above?
Can’t wait to delve into this stuff even more.
Sean
