File Placement - Distinguishing Location and Why

hey MPU,

I wanted to discuss the topic of ‘file placement’. What is your decision process for where your files sit?

Context - cleaning my computer, my NAS, DevonThink, etc - I am finding a few duplicates in some places, along with different folders. I am trying to unify the process, but I keep thinking of situations where it could get complicated.


  1. Lectures - 90% of them sit in Ulysses, it’s where I store all my sermons. However, there is maybe 10% scattered between DevonThink, Finder, NAS, iCloud because they have accompanying Keynote files. What’s the best solution to keep them all together? Is there 1 location that’s better than the other. A reason why it’s important, I was in a meeting and asked to give a talk on the spot, so I wanted to give the youth a list of topics I had prepared already. Jumping from app to app isn’t that great, would have rather consolidated it all.

  2. Accessibility - there is an ongoing storage problem we have in this world. Each time I buy a new iDevice, I always need to get the next larger size up to accommodate. Top Offenders for me are Photos, Messages, Day One, DevonThink.

  • Could they be dealt with? Yes
  • Do I want to deal with it? No
  • Why not? Because the solutions are’t that great. I’ll name a few.

Messages - Simply delete them (anything other than X days/months/etc - I can’t do that because there are times I will need to reference them and document certain conversations when asked.

Day One - I enjoy journaling, makes no sense not to be able to access it.

Photos - I have the option of storing in iCloud on there to free up space on my device. But also annoying trying to upload a proper photo into Day One

DevonThink - this has been debatable. If sync was faster, then maybe, remove it.


  1. Deciding on File Placement
  2. Accessibility of said file
  3. Space requirements

Except for the first sync for a database I do not find syncing slow. I use Bonjour and Dropbox. What do you use?

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I use iCloud for sync

Based on experience reported (e.g. on DEVONthink forum and forums for other apps) by so many others, Apple’s iCloud and CloudKit are unreliable and often slow. Try another method. That will probably cure the slowness.


It seems to me you have a “where’s my stuff?” problem. I’ve been using search to find my files since I discovered Evernote around 2009. I worked in I.T. and kept everything in EN, procedures, notes, manuals, scripts, etc.

Today my primary device is an iPad Pro and I keep almost everything in my Google Workspace account. When I need something I search for it and normally can find what I need within a minute or two. I have a business standard account which includes 2 TB of storage and a feature that allows me to search email, calendar, contacts, etc. and all of my files with a single query.

Older files, media, and sensitive files like bank accounts are stored in EagleFiler on my Mac.

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Keeping all your lectures in Ulysses sounds worth keeping going. Could you just link to the relevant Keynote file from within the Ulysses doc at the start or end? I use Hookmark so I’d be pasting in the Hookmark link to Finder/Devonthink/wherever, but you could also paste in the link for the presentation and present from there.

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I find that the Finder provides a solid base for storage and document management. The problems you mention happen when I work with apps that have to work with documents internally, e.g. importing rather than indexing in Devonthink. Alternatively, the problems arise when I fool myself into believing that I should never archive files but rather must keep them all with me all the time.

A few ideas …

  • I don’t use a NAS or iCloud to store a primary or current working copy of a file. I use the former solely as backup or archival storage. I use the latter solely to sync between my MBP and my iDevices.

  • What constitutes a proper photo? Is every photo you have taken from time zero until now a candidate to be a proper photo to add to DayOne?

Following on the mantra of archiving … suppose that you consider the document generating apps that you mentioned. Take of your lectures older than the last year or three years regardless of app (Ulysses or DT or KeyNote). Take your DayOne journals older than the last year or three years. Take your photos older than the last year or three years. Take your messages older than … How large would the storage need to be to archive all this “old” stuff?

Otherwise also …

  • What is your time limit on “keep it with me” versus “archive it”?

  • What is more annoying, a) agonizing over how to recover memory every so often to allow space to store more and more photos or b) searching for and uploading a photo in iCloud from three years ago to add to DayOne?



Files of specific types live only on one place. I have multiple backups nbut the home is a single source of truth for the file.

Some things that my husband also needs ready access to are located on the NAS system. Others are on my main mac (now a Mac Mini). Some things the truth is my laptop mac, and few the truth is my iPad or iPhone. Even if there are copies on another device the one true originals are in their one defined location. I decide where the defined place is base don where I most often use the files.

As fort accessibility, for me that is rarely an issue. I don’t try to have all files accessible on all devices. In your scenario of being asked to give a talk on the spot, unless it was a topic I could spout on without any preparation I’d have deflected by asking what they were interested in and how long and when and then defer to where the information on talks I have ready and gotten back to them later.

For your second one, photos. All original photos live on the iPhone until I get home. Then they are moved into a holding folder until I can eventually include them in my Lightroom catalog. So originals starton th phone, live for a while on my main mac (I use Photosync to get a copy of the photo onto my mac) and evnetually the one true source is the cataloged photos where the original files live on the NAS. Periodically if I need to I delete photos off my phone and I do have a few favorites in there I can refer to easily but by and large I go to the lightroom catalogn and then from there to the files on the NAS. I update my lightroom catalog with new photos about once a month or so.

Journals: All of mine are now in Obsidian. before theat they were paper and pen. I do not include photos in my journals but will include references to them.

Space requirments: That’s one reason things live where they are now. Photos is fairly large, about 320GB so far and grows rapidly. It also takes big jumps when I finish a chunk of scanning old negatives and slides. So that’s why they are on the NAS. Moving most other reference out of formatted text systems into plain markdown has dramatically reduced the amount of space it needs. For about 6000 notes right now my Obsidian vault is only just over 620 MB of space. I anticipate it will at least double in size as I am finding it can replace several other systems I had (Scrivener for one) so I am converting documents into that. All my research PDFs are on the NAS and comprise about 1 GB of space so far. When I need to have some on my iPad for review and annotation I use Zotfile to get them there but the originals and ground truth versions are on the NAS.

No matter the location of the true original I do keep a robust set of backups of all the systems.


I’ve always found this a difficult one.

I think as has been mentioned keeping all lectures/sermons in Ulysses looks like it’s already working for you. The challenge is how and where you store supplementary data like keynotes related to lectures/sermons. You could store them in devonthink and link to them or similarly in icloud. The benefit with devonthink is that links to an item will also open in ios.

An alternative is something like Omnioutliner. I have 10+ years of sermons in there and you can embed other files like keynote. I have however stopped using it as it is too proprietary and development seems to have ceased.

I still tend to use a naming convention on all files to find them no matter where they are:

yyyymmdd-major category-minor cat-title.ext

This has worked well for me in over 10 years, but can be a pain on smaller screens as you never get to see the title as it gets truncated.

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I second using one system of organization across applications and devices. I just recently adopted this along with the PARA system which hold that applications should conform to your system, not the other way around.

So, pick your applications wisely. iCloud , Apple Mail, etc are pretty flexible on making folders, but apps like Reminders are not as flexible.

The advantage of having one system is not having to guess where you stored something, and also you only need to store one copy of each document as it only makes sense to store it in a single location.


Carl Pullein just released a course on this that you may find helpful. It’s not free and about an hour in total, but I found it gave me some good tips I hadn’t thought of. You can find out more here:

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Did you find it worth $25? $25 is inexpensive; I ask not because of the price, but the content. I certainly don’t consider myself having “arrived” when it comes to file management but I think I’m pretty good at it, mainly because I’m so OCD about such things. :slightly_smiling_face:

I’m tempted by this course by Pullein, from his “Working with” series in YouTube, he seems to be good explaining things. Given how important it is to manage files, if the course just drops a tiny bit of wisdom that I hadn’t seen, that’s a great return on investment.

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Ok, I’ll spend the $25. If I don’t profit from it, I’ll consider it a “donation to a good cause.” :slightly_smiling_face:

I found it worth it. It’s about an hour and he’s very good at explaining. There wasn’t alot that was new, but it’s given me some fuel for thought in tweaking my filling system. I really liked his use of tags which I hadn’t even thought about and his integration with notes. $25 for an hour is good value for me.

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Thanks, I purchase and watch the course.

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If it gave you fuel for thought it surely is worth the price! Instant purchase!



I don’t keep photos in the Photos app. I just find the endless stream of unsorted images untidy. Nowadays it’s very easy to save an image to Files straight from the Photos app, and I do that. I have a folder in iCloud with lots of subfolders and I file the images I actually want to keep in there. (Sidenote, many of my photos are actually screengrabs, so they don’t get saved, I just extract what I need and save that info wherever.)

Occasionally I feel guilty about not renaming the files (they’re called IMG12345 or whatever) and do a little flurry of renaming, but mostly I can’t be bothered and my folders are well named so I can mostly find what I need. You can sort by creation date.

Day-to-day this means that my Photos app only has pending items in it. (Don’t think I’m super-efficient, there are many items in there currently that I’ve been ignoring!)

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I purchased and watched the course as well. I was already following the file naming convention before hearing it from him. The new idea that I have to play with and see is the use of tags, I haven’t really considered that. But there’s a part that I wish he touched upon a bit more, but I think it’s up to a person’s individual workflow.

Today’s real world situation.

  • Received a PDF recommendation form I need to fill out for someone via iMessage.
  • Started on the computer, but realized I can fill it faster on an iPad/Apple Pencil.
  • Imported PDF into PDF Expert, opened it on iPad.
  • Found many other PDFs in there I had forgotten about :see_no_evil:
  • Finished filling out PDF form

At this point, does the PDF stay in PDF Expert Folder (iCloud)? Or would this PDF be sent to DevonThink, or stored in NAS/Hard Drive/Finder

  • My gut is telling me DT, because I have a folder in there that stores ‘recommendation letters’ and DT has been more of my ‘archive’. But it doesn’t help that my NAS is also my ‘archive’. Of course, the NAS is a bigger long-term archive, whereas DT is storing items that I may come back to frequently (all our house measurements, manuals, etc). DT was my transition from Evernote a few years ago, my catch all bucket

I tend not to receive documents through messaging apps, only email. This makes it easier to deal with.

All files go in a file system not app (except databases like devonthink). That’s the weakness of ios. Save it in finder, rename it with your naming convention and stick it in your archive.

Delete copies elsewhere to avoid duplication.

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