Elliot Jay Stocks is a designer, speaker, and author. He is the Creative Director of Adobe Typekit, the founder of typography magazine 8 Faces, one half of Viewport Industries, and an electronic musician.

The cloud-centric Mac set-up: 8 months on

Posted on 10 April 2012 27 comments

Article illustration for The cloud-centric Mac set-up: 8 months on

Recently, quite a few people have been asking me how I’ve been getting on with my MacBook Air and iMac set-up, which I got about eight months ago after blogging about my plans for ‘a cloud-centric Mac set-up’ way back in April last year. In short: I couldn’t be happier. If you’re thinking of doing the same or simply want to read a bit more about this set-up, read on…

The definition of the cloud

When we say ‘the cloud’, we tend to think of Dropbox, and whilst it’s true that Dropbox is very much the key to keeping my two Macs in sync, there’s more to it than that. The thing that many people forget is that we’ve actually been living in the cloud — to some degree — for quite some time: IMAP email, for example, is one of the oldest and most common examples of data being stored on servers to allow access from multiple devices. So if you’re thinking of going to a two-or-more Mac set-up, you’ll be pleased to know that you’re already a fair way there. (Unless you’re using POP3, of course, in which you case you really need to get out of the 16th Century.)

There are many other elements of the cloud that we’re already using on a day-to-day basis that have nothing to do with Dropbox; activities such as reading our Google Reader feeds with an app like Reeder; or using online (as opposed to local) services, like listening to music on Spotify or Rdio. Taking your entire set-up to the cloud doesn’t actually take that much more effort.

The check-list for a cloud-based set-up

If you’re thinking of going the same route as me and getting two (or more) computers with the intention of keeping them in sync, here are some steps I recommend you take:

  1. Use IMAP email. It pretty much goes without saying, but as I mentioned just a moment ago, it’s probably the oldest and most essential bit of cloud technology you’ll need.
  2. Buy the biggest Dropbox account and put everything in it. I keep our photo library, music, TV shows, and movies on an external drive, but everything else is in Dropbox.
  3. Set up as many apps as you can to sync using Dropbox. Sometimes it’s as easy as storing your library (like, say, for an app like LittleSnapper) in a folder within your Dropbox, but every app is different. See my note on the potential pitfalls further down the page.
  4. Get an iCloud account. You don’t need to worry about email because you’re already using IMAP, but iCloud will sync iCal and Address Book, which is essential not just for multiple Macs, but if you have iPhones and iPads, too. You can also sync your photos via iCloud, but I choose not to as we manage our photo library separately. Oh, and you could also use Google Calendar and Google Contacts if you’d rather not pay for iCloud, but iCloud is so deeply baked into OS X and iOS that personally I find it’s easier to just have it all running automatically.
  5. Work out what you’ll have to sync manually and remember to do it. Again, see my note below about the pitfalls.
  6. Invest in an online back-up solution such as CrashPlan. It’s not just about being diligent in case you lose the data in your Dropbox; I also use my CrashPlan account to back-up the data from our external drives, such as our photo library, music, TV shows, and movies. And in the unlikely event you ever find yourself on another machine and are unable to access the Dropbox servers, you can restore selected files from CrashPlan.
  7. It’s not essential, but I personally found it a lot easier to set up both new Macs at the same time, so that everything had a fresh — and equal — start. If you’re using an existing computer or computers, make your life easier and do clean OS installs on both.
  8. Minor pitfalls of cloud-based syncing

    Every application is different and will therefore each will have its own nuances when it comes to cloud-based syncing. In my experience, I’ve only experienced very slight hurdles with two applications: FontExplorer X and TextExpander.

    Font organisation is something of a dark art at the best of times, which is why I use FontExplorer X in the first place, but syncing via Dropbox does unfortunately add another layer of complexity. Initially I’d thought I could simply store my FEX fonts folder within Dropbox, but for some reason this caused some conflict issues where FEX thought it couldn’t find certain files even though they were there, possibly due to the application preferences not being synced. After some fiddling around that lead nowhere, I eventually opted to store the fonts folder within my default user folder; in other words: outside of Dropbox. Unfortunately this means that syncing is a manual procedure, which involves me making a semi-regular back-up from the app’s preferences panel and storing that back-up in Dropbox, ready to be launched by the app on the other Mac. It’s not as bad as it sounds, because although it’s not automatic, the back-up can contain all of your fonts as well as your preferences. But yes, of course I’d like FEX to implement some proper Dropbox syncing.

    TextExpander syncing is in a remarkably similar position, but is slightly more confusing in that TextExpander does actually offer Dropbox syncing out of the box. The problem with that, though, is that it uses a folder than has to sit in the root of your Dropbox, which slightly frustrates a pedant like me who wants everything stored neatly in its designated place. The solution, thankfully, is pretty close to what I do with FEX: I generate back-ups to a folder that lives wherever I want it to live inside Dropbox, and then launch those back-ups on the machine that needs to sync. Again, not that graceful, but one advantage is that TextExpander can generate those back-ups automatically.

    There’s one other application-related downside: the rather arduous task of having to install apps twice. For most apps it’s an easy task, but the doubled time spent installing Creative Suite was something of a chore, to say the least.

    The downsides mentioned above paint a very clear picture of where cloud syncing needs to go: we need to stop worrying about files alone; we need preferences, installations, and in fact every type of data to be transportable. The recent update to Tweetbot is a great example of that, from keeping muted settings synced across devices to remembering your place in the timeline. As I said back in my original post about moving to a cloud-based set-up: you’re effectively only changing the chassis. The device itself is becoming less and less relevant.

    (As an aside, quite a few people have asked me how I feel about security, since Dropbox has been hacked in the past. Personally, I’m not concerned at all. If my account was ever hacked and someone got access to my PSDs, it’s not the end of the world. If you have particularly sensitive information on your computers, you might disagree.)


    Lastly, on a non-cloud-related point, one of the questions I get asked again and again is: ‘how does the Air perform with Photoshop or [insert name of another processor-intensive app]?’ And my answer is the same every time: amazingly. In fact, I’ve yet to notice a performance difference between the Air and the iMac, even though the latter is significantly more powerful in terms of spec. They both run on SSDs, which is possibly the biggest contributor to speed. Even my old MacBook Pro was like a new machine once I’d put an SSD in it. If you’re buying a computer today, make sure you pay the extra to get an SSD because it really is the best upgrade you can perform.

    Both computers are a joy to use and even more so for sitting at the extreme ends of the spectrum: the iMac for its ridiculously huge screen and connectivity; the Air for its über-portability. This is — without a doubt — the best computer set-up I’ve ever had. If you’re thinking of doing something similar, do.


  1. Justin


    10 April 2012 @ 05:52PM #

    Great writeup! Can the Air not be hooked up to a cinema display though? If computer performance is comparable, I would think this setup might be easier and then you wouldn’t have to worry about syncing everything. Just curious if that was an option when you were first getting set up…

  2. Aaron Bassett

    Aaron Bassett

    10 April 2012 @ 06:30PM #

    I think symbolic links could solve an awful lot of your “folders can’t be moved” woes. In terminal use `ln -s /path/to/local/folder ~/Dropbox/path/` to create a symbolic link between the two directories, that way when one directory is updated so is the linked directory, and Dropbox follows symbolic links just fine. For more information type `man ln` in terminal.

  3. Matt


    10 April 2012 @ 06:42PM #

    @Aaron We use symbolic links at work in our local dev environment, but I didn’t realise that could also be applied to directories and Dropbox – Nice tip! :)

  4. Raph


    10 April 2012 @ 09:20PM #

    Great article – I really like the approach!
    I’m using CodeBox for snippets, which can be synced via Dropbox.

    @Aaron: Yep, I’m using symlinks to link my git repos with my local server folder. My vhost picks them up and voila.

  5. Brendan Dawes

    Brendan Dawes

    10 April 2012 @ 05:51PM #

    Great stuff. Coda is another one that’s a bit of a bitch when it comes to syncing via Dropbox. Whilst there’s no built in support it is possible to some extent using symlinks. Search on the web to find out more (on a train at the moment so sketchy connectivity)!

    I’ll also chime in here for Backblaze as an alternative to CrashPlan. Been using it for years and saved my hide many a time.

  6. Stéphane Lambion

    Stéphane Lambion

    10 April 2012 @ 09:41PM #

    Ah, so we got news about that article you wrote eight months ago … great! As far as I am concerned, I don’t use a cloud setup like the one you are describing in your article since I am used to softwares like Sublime Text (instead of Coda), etc., which don’t allow any backup on Dropbox (unless I have not seen something in the software’s settings), and also because the problem of the Internet connection sounds rather annoying (I work, sometimes, without any connection, not to be disturbed by new mail notifications and this kind of stuff) … besides, I must admit I may be a bit exagerating, but I feel concerned about the data security problem … even if I have no sensitive information, I don’t want my files to be stolen).

    Anyway, I may give it a try … got to see, now.

  7. Zaiman Noris

    Zaiman Noris

    11 April 2012 @ 12:35AM #

    Nice read. Altho I don’t use Macs but I live in the cloud. I have yet subscribe to premium packages but I managed to live with the free plans until now!
    The trick is to distribute your files across many providers based on categories. Photos on Picasa, settings on dropbox. Snippets on evernote. Others not so big, I lump into SkyDrive

  8. Martin Helbo

    Martin Helbo

    11 April 2012 @ 01:10AM #

    Hi Elliot, nice article.
    I use Fontcase to manage my fonts. It has a feature to move your ‘Vault’ to a specific location. I have stored mine on Dropbox, and on my MacBook I have located the Vault so the two Macs use the same library.
    So if you’re not totally in love with FontExplorer you should check out Fontcase.

  9. Neil Sweeney

    Neil Sweeney

    11 April 2012 @ 09:00AM #

    Great setup, I’ve been doing it this way for a number of years now (about four years, that was across two machines, but now I do it across three/four). It originally started as I used to work with a Mac and Win machine equally and needed a way of getting files working across both machines without thinking. Syncing has dramatically improved as well as cloud storage solutions; I’m at the point now where I can get a new machine, install my two storage/sync apps (Dropbox and SugarSync) and I’m ready to go. The only bugger when it comes to web dev is local development and MySQL; the data file changes are difficult to capture by SugarSync so I’ve opted for using a remote solution (actually, it’s a hosting company that sit behind me at work with the data centre not 20 feet away).

    I’ve also setup a NAS drive in my home where I sync my larger media to, typically my iTunes library, so both machines get the same local access to movies and music that I’ve archived as well as any DLNA devices in my home (just need to make sure both machines aren’t running iTunes at the same time as it can cause issues to the library files).

    On a note that STÉPHANE LAMBION was saying, Dropbox doesn’t make it easy to backup certain files or folders outside the Dropbox directory, this is why I use SugarSync as it does. Also, with programs like Sublime Text, rather than syncing the files with a program like that, I use Github to store the settings that I’ll typically have across my machines.

  10. Andrew Hall

    Andrew Hall

    11 April 2012 @ 10:03AM #

    I have been considering doing this for a while and more recently, due to a house move, this has come up again.
    Recently, I threw away lots of old CDs and DVDs from 1998-2005 and I wondered if I should back up any of the data to the cloud (Dropbox specifically) In the end, I decided it was too much hassle to go through each disc individually so I just get rid of them.

    If I had a system where content (movies, music, images, work etc) were automatically backed up and stored centrally, it would make my life a whole lot easier. I can see this issue coming up again in another 5 years, so unless I get on with it and sort it out soon, it might be an issue.

    Thanks for the original articel and this followup one to remind me!

  11. Ed Lea

    Ed Lea

    11 April 2012 @ 12:36PM #

    Don’t you find that saving working files in dropbox often leaves you with lost, flattened, old, corrupted versions of files?

  12. Rob Knight

    Rob Knight

    11 April 2012 @ 09:19PM #

    I just want to plug Aaron Bassett’s symbolic links solution. I actually use it with TextExpander and Dropbox and it works great. You install TextExpander and open it once so it creates its .settings file in ~/Library/Application Support/TextExpander. Then quit the app and run the symbolic link command Aaron mentioned and then TE settings are located in Dropbox. In my case, I put my TE settings file in ~/Dropbox/Apps/TextExpander.

  13. Jelmer de Maat

    Jelmer de Maat

    11 April 2012 @ 09:38PM #

    There is a small typo here: “it uses a folder than has to sit in the root of your Dropbox”.

    Thanks for your info, I’ll look into FontExplorer to start organising my stuff.

  14. Jimmy


    13 April 2012 @ 02:55PM #

    Nice to see how you’re getting on with your setup Elliot. I’ve recently gone to using a single 13" Air for work and relegated my old MBP to become a central hub/media center. Like you I have all my media stored on drives connected to the MBP and then run Plex Server to manage it all. Using myPlex, I can access my media on both the Air and my iPhone from anywhere I have a connection. It’s a bit of a pain to setup at first, but once you’re up and running, it makes accessing a centralized media Library so much easier. You should check it out.

    Thanks for the update, your first post helped me decide on my current setup.

  15. Derek


    12 April 2012 @ 01:53PM #

    I’m about to upgrade to some sort of setup. Whether it be a Macbook Pro + External or an Air + iMac I’m unsure. Trent Walton talks about his similar setup here if you are interested. http://trentwalton.com/2011/11/18/workspace/

    I’m still not 100% sold on trying to sync files, although I’m not sure it’s it’s even necessary that they contain the same files. What exactly do you use your Air for? Going mobile with a current project or does it act as an exact mobile replication of your iMac so you can perform the exact same duties?

    Thanks for the article.

  16. Vincent


    17 April 2012 @ 04:11PM #

    Interesting Article with good examples, thats why I love Reeder soo, because of the cloud sync. But Dropbox is the main thing for a good sync between other computers

  17. Tony C.

    Tony C.

    19 April 2012 @ 03:04PM #

    @Aaron is exactly right about symlinks. Before iCloud, that’s how I kept my Address Book data synced between 3 Macs.

  18. Carlo


    19 April 2012 @ 05:38PM #

    Do you know how to get the LittleSnapper library file to update/sync without having to quit the app?

  19. Matt Vickers

    Matt Vickers

    20 April 2012 @ 06:29PM #

    For programs that won’t backup settings, like Sublime Text 2, I’ll usually just setup a GitHub repo and push all the settings files there. If I make a change on one computer, I just push the new changes and pull it down on the other computer.

  20. Zeno Popovici

    Zeno Popovici

    25 April 2012 @ 07:36PM #


    I sync FontExplorer X with Dropbox, no issues. You just have to move the folder that contains it’s database (fontexplorer x.fexdb) to Dropbox and create a symbolic link instead.

    All works fine for me, and it’s been months since I did this.

  21. Tyce Clee

    Tyce Clee

    26 April 2012 @ 02:15AM #

    Hi Elliot, great article – I read your previous one 8 months ago.

    Have you considered using Google Drive to replace your DropBox setup? I’m about to step off on some remote travel, and will be employing something similar. However, I’ll be storing our iPhoto library as well as a majority of a content in DropBox / Google Drive to sync entirely.

    The pricing scheme for Google Drive is excellent.. I’m interested in whether the issues with DropBox you’ve listed above could potentially be resolved with Google Drive?

  22. Peter Rees

    Peter Rees

    29 April 2012 @ 02:58AM #

    Enlightening as always Elliot. I too store and sync working files via DropBox though I think bundled cloud storage could well become a standard feature in many design applications. Already seeing this in packages like Adobe’s Creative Cloud and it’ll be interesting to see how this evolves.

  23. Steve Brown

    Steve Brown

    30 April 2012 @ 07:05PM #

    Hi Elliot,

    What do you mean by “Sometimes it’s as easy as storing your library in a folder within your Dropbox”? Do you mean you are getting apps to sync by moving their respective folders from the ~/library folder on your mac? Or are you just referring to a ‘library’ of apps?

  24. Andrew Wilkinson

    Andrew Wilkinson

    03 May 2012 @ 12:47PM #

    I wouldn’t touch google Drive with a bargepole. Read their Terms & Conditions. You are transferring ownership to them of all your files.

    Dropbox is great as is Codebox. Will look into CrashPlan as that looks really useful for a Home/Office setup with multiple PC’s. The dilemma is always the movies and where to back them up to!!! Terabytes!!

  25. Brando


    03 May 2012 @ 05:40PM #

    If you’re worried about the security of sensitive files on Dropbox, you can store and sync encrypted volumes (a la TrueCrypt) rather than flat files. I sync an encrypted password database between my computers via Dropbox.

  26. Shaun


    10 May 2012 @ 07:08AM #

    Hello! Interesting read Elliot. I have one question, you mention you keep movies, music etc on an external drive. Is it… a NAS drive connected to your router? and if so… do you keep your iTunes library on it?…if so, how do you find it performs? (a lot of "if"s in there!)

  27. Fred Blogs

    Fred Blogs

    13 May 2012 @ 11:35AM #

    this is a fantastic section displaying the quality factors of the cloud feature. Love it!

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