How best to organise and backup information on my Mac?

This not about how to optimise storage, but about the way I organise information so that it's both safe and easily and intuitively accessible.

How to name files and folders

But before we look at organising files in folders, it's best to look
how to name files and folders.

HFS+, Apple's journaling file system, uses Unicode for naming items such as files, and permits filenames of up to 255 characters. There is a lot of discussion on what is accepted or not in OS X and in APIs, so the best idea is avoid naming folders and files with forward-slash "/", back-slash "\" and colon ":", and also avoid starting files names with a NUL "0" or with a dot ".". In addition, files names may be a problem when trying to share files between Mac and Windows computers.

More generally there are some
good practice rules for naming files:-
  • It's vital to be consistent, and I have a 1 page "naming conventions" sheet to remind me how I name files.

  • It's good to keep file names relatively short (<25 characters), but I often go beyond this for both folder and file names, etc. For example I might name a folder "[persons initials] Medical Scans waiting to be submitted to XXXX" or "[persons initials] Medical Scans [sequential numbering] [ISO date format] [doctors name] Visit Ord+Med", and I've standardised on filenames along the following lines "[ISO date format] [persons initials] [doctors name] [act such as visit, medication, prescription, etc.]".

  • I avoid special characters in file names (e.g. * : \ / < > | " ? [ ] ; = & £ $), but I do use empty spaces and ".", and occasionally "&" and "+".

  • I never start or end filenames with an empty space, ".", "-", "~" or "_".

  • I will add "version [number]" at the end of a filename, as needed.

  • All dates according to ISO date format, e.g. 2021.11.15.

  • In my above examples, one of the key requirements is to be able to define a useful term that can be searched on my local hard drive, e.g. [ISO date format], [persons initials], [doctors name], etc.

  • I don't use number 1, 2,…9, but 01, 02, …09, 10, 11, …

  • For file names on my websites I use only standard English words and numbers, all lowercase and all spaces are "_", e.g. filename_and_folder.

There is a lot of advice to avoid using empty spaces, "&" and "+" in files names. But modern operating systems all support filenames with empty spaces. So, it's an old habit, but one that is still advisable if the filename is used in a command line or script. Plus if you intend to post a file for download, it's best to use "product_list.pdf" and not "Product List.pdf", however "product_list.pdf" might not look right in an underlined link (i.e. the "_" will almost disappear in "product_list.pdf").

For completeness there are numerous webpages hosted by many prestigious universities that tell us to avoid a whole string of characters including # < $ + % > ! ` & * ' | { ? " = } / : \ "blank space, and @. I'm not sure why this type of list does not also included ± € £ ¥ æ Ω or any other special symbol. And Wikipedia has a whole webpage on
naming conventions including technical restrictions and forbidden characters.

Interestingly, one of these lists "to avoid" mentioned that using "-" and not "empty space" or "_" actually improves search engine rankings. And Google's developer style guide recommend to use only standard ASCII alphanumeric characters and "-" and not "_", although they accept that "_" is "sometimes OK". Yet my hosting service will replace any empty spaces in file or folder names with "_".

Even more so than with files, I try to
name folders so that they are very easily understandable, e.g. "Out-of-Date Passports, Documents, Cards, etc." or "Health and Travel Insurance".

Good practice rules for organising folders

Organising files

Apple tells us that there are different
ways to organise files on a Mac desktop.

The first step is to
put files in folders. I'm not a fan of 'Stacks' simply because I want to see what's on my desktop. So my interest is more focussed on how best to organise folders.

Files can be in many different formats, ranging from .doc, through .jpg to .pdf, etc., and sometimes it's sufficient to organise files by file type (although often this is not the best option). Another way is to organise files by date, but perhaps the most obvious way is to organise files by client, project, topic, etc.

You can of course mix things up, e.g. within a client folder you can organise files in sub-folders by topic, by date, or even by year. You can put all clients in a higher-level 'Clients' folder.

Date-based folders is another way forward, e.g. with sub-folders for year, month, and even week or week number.

One good piece of advice is that there will always be somewhere a little 'mess', and it's important to be honest about how to accept and manage those little 'messes'. You can even use a sub-folder titled 'mess', or perhaps 'waiting', rather than invent a sub-folder with an incomprehensible name and containing only one or two infrequently used files.

I don't like folders that contain a lot of files or other folders.
I don't like folders that contain a mix of folders and files.
But above all I don't like folder structures where you have to open several nested folders to get (finally) at the files.

If the folder contains a lot of files or other folders, I name the 10 most important files or folders, "00 name", "01 name", "02 name", etc. so they sit at the top of the list and are always visible when first opening a folder.


Name files, and organising information in folders is one thing, but backups is as important, if not more so.

The first message is that any conventional storage medium is fragile and inevitably subject to failure, so anything that's valuable, important, useful, unique, needed, etc. must be backed up, preferably in at least two different ways.

Is there a foolproof plan for backing up a Mac?

The first rule is to have multiple backups in multiple locations, e.g. at least one local and one remote.

I actually use two local backups and one remote backup.

first local backup is an external 5th-generation Apple AirPort Time Capsule, running Time Machine.

Originally the Time Capsule was a router with a built-in hard drive, however I now have a different router, but still use the Time Capsule for Time Machine. In fact Time Machine will backup a Mac to any external hard drive, provided it's as big or bigger than the hard drive on the Mac.
Time Machine works by backing up every file on the Mac to the external hard drive, including applications and preferences. The only thing not backed up is the operating system. Time Machine stores hourly backups for twenty-four hours, daily backups for a month and weekly backups indefinitely, limited only by the capacity of the storage being used.
In addition Time Machine also has a versioning system, so as well as backing up every file, it backs up a snapshot of file structure. It can find an individual file or folder, back to exactly how it was an hour, a week or even months ago. For example, the most recent Time Machine snapshots won’t show a deleted file, however, snapshots from a week or a month ago will still have it.

second local backup is a LaCie 1TB HD with a USB-C connection (so works with Thunderbolt 3).

On this second local back up I create a backup by hand, copying across a selection of folders and files, namely:-
  • Desktop

  • Music with the latest version of 'Music Library.musiclibrary' and the Media folder

  • Pictures with the latest version of 'Photos Library.photoslibrary', and including any photo collections waiting to be uploaded

  • Documents

  • Passwords exported as a .csv file

  • Safari>Files>Export>Bookmarks

  • And a collection of third-party apps, for example, including my RapidWeaver websites, etc.

In addition I have a set of custom built "Access" pages,

remote backup is the cloud storage, using the iCloud Drive, which is part of the Apple iCloud offering.

Perhaps the only real criticism of iCloud Drive is that it is tied to a specific hardware environment, so something like DropBox Pro might be a good alternative for some people.