Everything in its right place: Migrating and synching files to OneDrive and Google Drive

With Apple’s recent announcement of forthcoming new (MacBook) and updated (MacBook Pro and Airs) machines, I was prodded to examine how I wanted to migrate my data to one of these new machines.

I’ve been holding off on upgrading my old faithful late 2008 MacBook Pro 1, for a looong time now in anticipation of these new machines.

Along the way I’ve been pretty diligent about backing up 2. Nevertheless, a 7 year old machine will get some kruft happening, and I didn’t want to transport this to a new machine via restoring from a TimeMachine backup or using Migration Assistant, as it doesn’t offer enough flexibility in determining what to bring over to the new machine.

So, this leaves one with … what?

Amazingly, where it leaves someone – with a very minimal amount of set up – is in a place of not having to worry about it.

Let me explain:

You can, and should, download Microsoft’s OneDrive (nee SkyDrive) product. I know what you’re thinking: “Microsoft?! That dinosaur monopoly that hasn’t innovated since 1982?! C’mon, George.”

I understand this emotion, and I – for years/decades – would have agreed with you, but things have changed.

I’m going to write a longer, more academic piece on how Microsoft is – finally – resisting the Innovator’s Dilemma soon, but, concisely: With the (free) release of the mobile version of Word, Excel, PPT (which are GREAT), and when combined with OneDrive, you really do have a viable cloud-based system for ALL of your work-related files.

The logical question at this point is, why not just use Dropbox or Google Drive?

With respect to Dropbox, it’s fine for having access to files, but it’s not a document creation tool.

With respect to to Google Drive, it too is fine for having access to files (more on this below), but, while better than Dropbox in terms of document creation, Google’s productivity suite (Sheets, Docs, and Slides) really just don’t compete with Microsoft’s.3.

That said, I’m NOT suggesting you abandon Google Drive, but rather, create a system where your Google Drive is synchronized with your files on your desktop and on your OneDrive. Doing so is truly the best of all worlds.

Here’s how to make it work:

1. Download OneDrive

2. Move the OneDrive folder to some place prominent and not overly nested on your hard drive. I put mine right in my User Folder, and add to the Favorites side bar:

onedrive screen shot

3. Here’s the rub. It’s a little scary at first, but bear with me. Take ALL of your folders that you currently have in your Documents folder and drag them into the OneDrive (do not copy the files; just move them). This means you have NO files in your Documents folder. Essentially, you’ve made the OneDrive folder your Documents folder.

4. Synchronize your files that are in your OneDrive folder with OneDrive. To do this, open the OneDrive app, and, under preferences, select “Choose Folders” to synchronize, and de-select Music and Photos (unless you want those synched. I do not, as mine are all on external drives).

Depending on the size of the files in your OneDrive folder on your Mac, it may take a while to synch. It took me about 7 hours to synch about 38 gigs.4

5. At this point, you have a mirror image of the files in your OneDrive folder on your Mac with those on the OneDrive cloud service.

Importantly, you ALSO have access to all of these files on your iPhone/iPad. And, as above, using the fantastic MSFT apps, you can create/edit, etc., and everything will stay in synch. For instance, if you create a new doc on your iPad, and save it to your OneDrive folder, this doc will also be created (synchronized) on your OneDrive folder on your Mac.

6. As above, I’m not discarding Google Drive. I have too many collaborative projects on Google Drive, and while, OneDrive does allow for shared files, etc., it’s not going to displace Google for this any time soon (if ever). But, what I wanted was a unified approach. This is where CloudHQ comes in.

CouldHQ will – among other things – synchronize OneDrive with GoogleDrive. This is precisely what I did. I mirrored the file hierarchy on OneDrive with Google Drive (meaning I have exactly the same folders (“Work,” “Personal,” “Writing,” etc.)) in the folder on my Mac (in my OneDrive folder) as I do in my OneDrive folder in the Cloud, and on my Google Drive.

To get there, I first did a one-way push of the folders on my OneDrive (which were the same as those on my Mac) to Google Drive. There were of course lots of other files on my Google Drive, and I had to manually organize those into the file hierarchy created by the push from OneDrive.

Once this was done, however, I just turned on two-way synch on CloudHQ, and now all the files that had heretofore been only on my Google Drive are now synched with my OneDrive, and, thus, my Mac.

This now means that if I create a document on my Mac, my mobile devices, the web version of OneDrive, OR Google, they will be synchronized across all my devices.

This is something approaching magic for me, and completely changes the way you think of file storage generally. It’s unbelievably easy to locate files, access them, and create them from anywhere, and no where they all are.

Importantly, you now also have a redundant backup of every file on your mac (first on OneDrive and second on Google Drive).

The above process may seem a bit involved, but once you get through it, it takes zero effort to maintain and the benefits are huge.

Beyond the backup, it absolutely made getting set up on my new Mac painless. I downloaded the OneDrive app to my new mac, hit synch, and about five hours later had all of my files on my new mac. Of course, I was able to work with whatever I needed during this time either via OneDrive’s online apps or Google Drive.

Optional step: Evernote

I love Evernote. I use it constantly to capture articles, etc. that I find online. However, much like my Google Drive, it had become an unorganized disaster full of Notebooks (their version of folders) that I don’t use anymore etc. So, I deleted and consolidated all of my Evernote Notebooks so they mirrored the files I have on my Google Drive and OneDrive (mac and cloud). I now use tags to sort the articles into “subfolders” on Evernote.


I’m not entirely clear how I did it, but I have 1T of space on my OneDrive, and if I’m paying anything, it ain’t much (I think it may be an educator discount).

I do pay for extra space on Google (because I never want to delete emails, mainly), and for Evernote premium.

CloudHQ is ~$10/month, and I may be overpaying, as once everything is synched for the first time, there’s not too much data transfer on an ongoing basis.

In total, it’s likely under $15/month, which is pretty close to what you’d pay for a cloud backup from Backblaze or something, but without NEAR the functionality.




  1. I’ve added an SSD drive and RAM to this machine.

  2. TimeCapsule and external drive connected to an AirportExtreme and periodic Carbon Copy Clones

  3. I do a lot of redlining of docs, and create some fairly detailed spreadsheets; the Google version of Word and Excel, just don’t give me what I need.

  4. One MAJOR source of annoyance: OneDrive will not recognize or transfer files that have a slash “/” character – you must change all of these to an underscore or remove – this is a remnant of the old MSFT that needs to go. NOW.

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