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How to Migrate to a New PC Without Losing Your Mind

How to Migrate to a New PC Without Losing Your Mind

Both gadget geeks and normal humans can find a lot of joy in unwrapping a new PC. I won’t go as far to suggest you ought to love the new computer smell (it’s real), but the initial burst of happiness can quickly turn sour if you realize how much work you have when switching from Mac to Windows, or vice versa.

There are valid reasons to move across the Windows and Mac divide, but knowing why and what you’re in for can make for a smoother transition.


Changing ecosystems can be just about as pleasant as moving in real life. It might even take longer depending upon how much stuff you have saved across multiple hard drives or buried deep in your system. But if you do it right, switching can be an opportunity to do some digital house cleaning that will make such future moves easier.

Everyone has their own reason for jumping from Windows to Mac, or the other way around*. You may be making the move to a Surface Book, Studio, or Pro 4 because you’re intrigued by Microsoft’s sudden hardware prowess. Or perhaps the Touch Bar or deep iOS/Mac integration has you tempted to jump on the Cupertino train.

I bounce back and forth between Windows and macOS myself, so this is a well-worn path for me. Here are some insider tips to survive the journey.


Whether it’s that elusive TouchBar or the ultra-thin build, MacBooks are definitely laptops that may encourage you to turn to the OS X universe.

And Apple has taken notice. The company offers an official migration tool that handles just about everything - mail, contacts, photos, and even bookmarks (if you’re using Microsoft Edge and want them to go into Safari).

If you want a quick transfer, it’s a pretty solid choice. However, perhaps you don’t want to go all-in with the world of Apple. For example, if all of your files are in a service like Dropbox, OneDrive, Google Drive, or Box then you may want to stick with those services. Or if you already use Chrome (despite some bloat, still the best browser in my opinion) just download it and sign in.

In general, I’d advise that if you like the close ties between an iPhone and the desktop, embrace the integration. The iCloud Photo Library both keeps everything in sync and supports edits and Live Photos.

The Windows Migration Assistant is designed to suck in your content from the PC in one, fell swoop.

But when it comes to moving, one thing you can also count on is that your Microsoft services will work just fine. In fact, Office on Mac finally has feature parity with the Windows version - something that wasn’t always the case. It’s most apparent in OneNote, which still offers many inking tools even though Apple will never introduce touch to mac OS. Microsoft is even supporting the TouchBar, a sign of how committed it is to the platform.

Outside of work files, I always find that consumer services like photos and music tend to cause the most consternation when it comes to some type of ecosystem switch. Keep in mind that if you go with the Apple transfer tool (you’re going to need a USB-C dongle if it’s the new MacBook), you’re probably going to be using the dreaded iTunes. There are alternatives, with Spotify being another way to just sign in, download, and get to playing music. Apple’s services work well if you’re staying in the company’s world, but enough alternatives exist so that you can rely on the rock-solid hardware and operating system while going with different application offerings.


This is the journey I took recently, going through a slow metamorphosis from a MacBook user to opting to make my Surface Pro 4 my daily driver. While the device got off to a rocky start, continuous improvement and all of the unique Windows 10 features have won me over.

But that means making some tough decisions. If you’re an all-in with Apple, there’s definitely going to be a downside.

No more iMessages on your desktop.

Good-bye Siri, hello Cortana.

You can access iCloud files with the iCloud for Windows application, but you don’t get the same magic of having files that are saved to the desktop magically available on your iPhone.

The upside, however, is that Microsoft makes every key service available for iOS. Office, Cortana, OneDrive, the new Teams application, and more are all there. It’s been a key reason that those who use Apple’s mobile platform have been able to explore the Windows side without suffering too many pain points.

Microsoft is just fine if you want to bring your iPhone along for the journey.

Microsoft is aware of this, offering you a handy guide to making your iPhone play nicely with a Surface (the tips work with Windows 10 in case you’re not moving to the company’s hardware). The only place I would deviate from where Microsoft is taking you is to consider where you want your services to land.

Personally I find when it comes to cloud connectivity and a smarter way of working, Google services are often the way to go. Your Gmail feeds into Google to help you remember key events. A small example of many that makes you life easier: being able to perform smart searches like “my reservations” or “my trips” and Google will pull them right up.

Your Google life can follow you whatever desktop platform you’re using.

The point is that these type of services are fairly platform agnostic (not all of what Google does is, as Android is obviously going to succeed at this in more ways than iOS). Google Photos can keep all your images in the web and integrated with the Chrome browser. This helps me stay sane in moving across different PCs, and this could be a smart strategy, as long as you’re willing to live with sharing that information with El Goog.

In the end, this strategy can play out well for other services. Dropbox is rapid-fire syncing, and if you have the 1TB Pro service you’re going to have an easier time keeping everything up to date and moving across the ecosystem chasm. OneDrive isn’t as feature rich, but it’s a better value as you get a free terabyte with an Office 365 subscription. The options are there as long as you’re willing to invest the time to best fit your workflow.


Moving ecosystems is nowhere as near as challenging as it once was. Both Apple and Microsoft continue to try and roll out the red carpet for you. Google continues to make its ecosystem rather sticky, making it the place you want to hang out no matter if you land on Windows or Mac (or as the company hopes, even a Chromebook).

Nonetheless, being aware of the pain points and finding ways to minimize them is always a smart strategy, given how it may just take one piece of new hardware to give you serious thought about switching teams.


* Chrome OS is great, but this piece will focus specifically on Windows 10 and MacOS Sierra.

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