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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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It’s been a while since I’ve blogged about productivity tools. With all of the (continued) seismic changes in technology, it seems like a good time to update the list.

As always, my desire for tech is that it as transparent as possible so that productivity is accelerated.

To this end, here’s what I’m using:

1. I cannot stress enough that if you have a pre-Flash based MacBook, you should immediately, swap out your old Solid State hard disk for a Flash drive. It sounds hard, but it’s not, and this hack alone will boost your productivity by leaps and bounds. I detail the process here: Weekend Project: New Mac for ~$200 — Upgrade from HDD to SSD

2. Alfred. I still do miss my beloved Quicksilver, but it’s really gone unsupported in any meaningful way for so long now that (for me at least), it’s just not stable. Alfred fills the void nicely (if not freely when you add the sort-of-necessary Power Pack), and allows you to customize its functionality fairly well (the new Workflows in the Beta version show a lot of promise). Even if you don’t ever customize it to any degree, having an app launcher, calculator, iTunes controller, etc. all at your fingertips does save time.

3. 1Password. We’re bogged down with passwords. Wired recently ran a story about how we need to kill the password, and I couldn’t agree more. Until we get there, however, we’re stuck with the boogers. Therefore, having a great app that not only stores your passwords (across your devices), but also generates random passwords when you have to create new ones, comes in super handy. I use 1Password every day, and it saves me time and stress.

4. Google Drive. Sort of crazy to me that I have to even mention this, but I run into enough people who still aren’t familiar with how great and efficient this tool is that it merits inclusion. Google’s play at dethroning MSFT is at its most articulated in their apps. As companies move from an Outlook-based email solution to a Gmail solution, it stands to reason that the bloated, unreliable MSFT apps are next to fall, and the Google apps are ready to fill the void nicely. Combine the web-based Google apps with the Google drive on your phone/tablet, and you’re pretty well set in terms of content creation/sharing.

5. Speaking of content creation, as we move to more tablet-based content creation, having the right case/input method is crucial. As for me and my iPad, we’ll stick with the Touchtype iPad case (which I reviewed in detail for Paste) and an Apple bluetooth keyboard. Increasingly, I leave the laptop at home.

6. Cobook. With respect to software, Apple seems to be going the way of Microsoft. Apple’s Mail app sucks (replace it, of course, with gmail both on your desktop/laptop and your mobile devices), and so too does their Contacts/Address Book. Unusable, unreliable. Nightmare. Cobook is the first innovation in contacts since…ever. It pulls your social contacts in as well as your contacts from Google, Apple’s iCloud, etc. Their iPhone app is great, too.

7. Tweetbot. One of the biggest issues we face in a world of many screens is synchronization. Viewing Twitter on your home device, and then having to scroll through a bunch of tweets you’ve already seen when you check on your mobile device is a waste. Tweetbot, in addition to its many other great features, keeps your Twitter feed in synch irrespective of whatever screen you happen to be on at any given time.

8. Evernote. Everyone knows and loves Evernote, but it just gets better and better. You MUST install the Chrome Extension in order to really enjoy its full power. Clipping images, web articles, etc., pretty much eliminates the need for bookmarking. Of course, its mobile apps are killer too. Its Skitch integration was a bit rough at first, but the two now seem to play nicely, which makes grabbing and notating screen grabs (with Skitch) as easy as archiving them (with Evernote).

9. Reeder. I still enjoy RSS feeds, though, admittedly, my usage has gone down. In terms of best of breed, there’s no single choice for both laptop/desktop and mobile. While people love Flipbook, it’s never done it for me. On my iPad I use Mr. Reader, on my MacBook I use Reeder, and on my phone, I use the Google RSS reader. I’m hopeful that a more unified solution will emerge (Reeder does have mobile apps, but I haven’t felt compelled to switch). In the mean time, this solution works in so far as that – like Tweetbot – each does synchronize with your Google Reader streams, and therefore marks items as read universally.

10. Notational Velocity and Simplenote. Notational Velocity is, hands down, the simplest, fastest way to take quick notes, and keep them easily organized on the desktop/laptop. It synchs (relatively) seemlessly with the Simplenote app for mobile. I use them both multiple times a day.

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