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Keeping a dual-Mac lifestyle in sync

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Relationships are a lot of work. You need to make sure you’re compatible, communicate well, and are on the same page for almost everything. Wait, you thought I meant personal relationships? Oh, sorry, I was talking about keeping multiple Macs in sync.

I was gifted a really nice 27-inch monitor a year ago. Connecting that to my 2011 15-inch MacBook Pro(s AAPL) essentially turned my laptop into a desktop Mac. Not that unplugging it and bringing it with me is a hassle. It’s getting it to recognize the monitor when I plug it in. I end up having to use GFXCardStatus to force the graphics card into Discrete mode (even if it’s there already) to get it to properly detect the external monitor. I also dual-boot this Mac into Windows 8(s MSFT) to play some games, so that just generates some extra hassles when reconnecting the monitor.

At the same time, I did need a mobile platform. I’m getting a band together, and need a laptop to bring to rehearsals to record with. Plus, I wanted something light if I was leaving the house to write with. I also didn’t want to pay a lot for this muffler, err laptop.

Fortunately, I still had my 2009 13-inch MacBook Pro kicking around. This is the tale of how I manage both laptops. Because everyone has two laptops floating around, right?


The Mac App Store

The Mac App store has really eliminated my “OK, where did I put that serial number?” issues. While software packages like Microsoft Office aren’t there, I’m finding that around 90 percent of what I need is available in the Mac App Store. Pages ($19.99), Things ($49.99) and Evernote  (Free) are key to my workflow, so being able to easily reinstall them from the Mac App Store (along with a 5-device license) is a blessing.

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Office 365

Sometimes (OK, often), iWork isn’t enough, and I need the full might and power of the Microsoft Office Suite. To make my life a lot easier, I just use Office 365, which gives me access to the Office suite on both OS X and Windows 8. It also comes with 20 GB of SkyDrive space (more on that later).

Usually, I need Office when I’m on a fast roundtrip collaboration with a person who does not have iWork. While Pages does handle Word documents fairly well, I’m more comfortable keeping Word documents in Word. Also, I loathe Numbers and much prefer Excel. My issues with Numbers are lengthy, but it sums it up with that it kinda plays at being a spreadsheet, but doesn’t have nearly the power of Excel. So, it’s just easier to handle those tasks in Excel.

The cloud

Keeping the same programs on multiple devices is one thing. The important part is keeping the data in sync. For that, I rely on a handful of cloud services: iCloud, Dropbox and SkyDrive.


iCloud has gotten kind of beaten up in the press lately, and to a certain degree, I admit the service has its good and bad points. So, I’ve separated out the pieces I have problems with (Documents in the Cloud) and instead focus on the parts that work for me (Bookmarks, iMessage, etc.).

The biggest issue I have with Documents in the Cloud is the walled-garden approach. Simply put, a file I start in Byword ($9.99) can’t easily be moved into Pages or Word, without cutting and pasting. I also don’t expect this to change, so I’ve looked for other solutions for document syncing. One problem I’ve run into is completely forgetting what program I even created a file in.

I also use quite a bit. Its interface for capturing notes quickly is a little easier than Evernote’s. As an example, I was recently watching a band perform. This band is the same style of music I’m playing, and I took copious notes on their stage manner, song list and the like. I just felt more comfortable doing this in iCloud and Notes. Evernote for me still remains a place to store large bodies of notes with lots of text.


My affair with SkyDrive started when I needed to edit Office documents on my Windows 8 partition. While Dropbox can handle this, I liked how it integrated natively into Windows 8. Also, it’s nice being able to edit Word documents in Skydrive’s web interface on a machine I might not have Office installed on. While I can use Google Docs(s GOOG) for this (and for one spreadsheet, my band’s songlist, I do use Gdocs), I prefer the Office web apps. With my Office 365 subscription, SkyDrive also comes with 20 GB of storage. That also means I can use it to move my GarageBand songs between machines. One conscious decision I’ve made is to only have production-type files on Skydrive. This is where most of my working files reside.

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Dropbox takes the place of flash drives for moving my files between computers. If I get a PDF in the mail I want to have on all computers, I put it in Dropbox. One exception to having work files on SkyDrive is most iOS text editors save to Dropbox, so I use that tool for any text files I’m working on. For the most part, these files are notes from meetings, or stories I’m working on that are in very rough draft and I don’t need to worry about niceties like formatting.

Final thoughts

A few months ago, I wrote about how I use Dropbox for some of the iCloud-type storage. Since then, I’ve started using SkyDrive quite a bit, and I like the separation between the digital junk drawer that’s my Dropbox folder, and the more organized, work environment in SkyDrive. While Dropbox would handle this well, the appeal to me is easy editing in a web interface via SkyDrive that I enjoy.

7 Responses to “Keeping a dual-Mac lifestyle in sync”

  1. Gustavo Domínguez

    I had this same issue–working with more than one Mac–so I just went to the Mac App Store and installed OS X Server, pointed a DDNS subdomain to home and everything is now in sync without going to the hassle of relying too much in so many third-party services.

    The first sync was made over Ethernet and syncs from there on are over Wi-Fi or my slow 3Mb/s uplink back home. As it turns out you don’t even need a fast connection and it works even when there is no Internet connection. Eventually the computers catch on with each other.

    Everything is automatically kept in sync and the desktop is the same no matter where I log in.

    If you’re interested is very easy to setup, just follow the instructions given by Server and share your home folder. Don’t set everything up with the account you’ll be working with but set it later as a network account not a local account (even though it will be local in the server) and then you’ll be able to access it as a roaming account in the same server.

    As for Windows, well, I don’t use Windows except for Windows Media Center in just one computer; you can set up File Server in Server to access it remotely, use something like WebDAV so you’ll be able to work with it as if it were a local folder on Windows. If you go FTP, as I remember windows has native support for FTP, just type in your IP address or domain name after “ftp://” in Windows Explorer…or mount it. :)

  2. I’ve been using symbolic links via Dropbox to sync my two mac desktop and downloads folder. Very handy. Check out Aayush Arya’s article titled: “How to use Dropbox to sync your Documents folder between Macs for free”

  3. Google Drive allows my business partner and I to sync documents across our Macs, PCs, and iOS devices. But trying to sync Contacts and Calendars amongst my Mac, iPhone and iPad has gotten so difficult, I’ve taken to manual updates.

  4. I use SugarSync also. I have a DropBox account, but I am completely underwhelmed by its massive limitations, so I don’t use it.

    I have designated about a dozen pre-existing folders to be sync folders. That is nothing special in itself, except that they include the Templates folders for iWork and Office, as well as the corresponding folders for BBEdit. It makes my computers functionally interchangeable. The folders don’t have to be the same on the two computers, which is handy. I could set up ~/users/me/folder on the Mac to sync with c:/users/me/directory/subdirectory on the PC.

    SugarSync lets you choose any number of pre-existing folders and make them into sync folders, while DropBox mysteriously limits you to a single folder. On the other hand, DropBox can sync bundles, while SugarSync mysteriously cannot. For me, DropBox has massive limitations while SugarSync only has a smudge. So SugarSync it is.

  5. Ecrah

    I use SugarSync’s folder syncing feature to keep my ‘Documents’ folders in sync between my iMac and Macbook Air (you are able to choose any number of folders to keep in sync).

    Not only do I always have access to exactly the same documents on both my Mac, but is also works as a backup solution. A copy on my iMac, a copy on my Macbook and of course a copy on my SugarSync cloud space.

    Magic. I love the cloud!

  6. Gee Deezy

    I manage a six Mac, 20 Windows, 30 iPhone /iPad company, and have had so much trouble syncing Contacts between devices, I finally gave up on iCloud. Can’t wait for Apple to get its act together on this long-overdue piece of tech.

  7. coryxjklatik

    Great write up Mark. I actually take this a step further and have nearly identical Macbook Air 13s… One strictly for work to meet IT infosec guidelines and one for everything else I do at home and on the side.

    One thing to note in this case is hardware – I’ve found one major way to reduce the head ache of multiple macs in *multiple* locations is to match your USB hub + mouse + keyboard + monitor setups as closely as possible. This also gives you the added bonus of a consistent workspace regardless of where you are working that day – home or the office.. ☺