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Q: I was wondering if I made the change from a Windows PC to a Mac how difficult it would be for me to recover and access my files such as word, excel, powerpoint and outlook mail.

– John S.
Niceville, Florida

A:  Like so many questions that I get asked, there is no one simple answer to this one, especially when the heart of the issue is the subjective and unquantifiable question “how difficult is this?”.  The answer relies on several things, such as your knowledge and skill level, and whether you are willing to spend money on software to facilitate your needs.

Apple has done some interesting things with Macs in recent years.  Their systems are actually capable of running Windows itself, and so any Windows-compatible software, such as the various components of Microsoft Office that you mentioned.  That is one possible option, but if you’re moving to a Mac, it would seem to me that you’re trying to get away from Windows.  Microsoft also publishes a Mac-compatible version of Office, which would give you MacOS-native versions of the Office Suite which should be perfectly compatible with your files.  Finally, there are MS Office-compatible products such as Apache Open Office that are essentially available for free.  Open Office is cross-platform, meaning there are versions available for Windows, MacOS, and even Linux.

I’m not sure what you mean when you speak of needing to “recover” your files.  Assuming they are still intact on your existing PC, it can be as simple as backing them up to a cloud account from one machine, and downloading them to the new one.  You can also accomplish this with CD or DVD media, thumb-drives, or an external hard drive.  If you have the Windows machine and your new Mac resident on your home network simultaneously, you might even be able to do a direct file transfer from one machine to the other.

You have similar options for your e-mail.  Outlook is a component of MS Office, so if you choose one of the routes where you end up with outlook running on the Mac, you’ll be pretty good to go.  If you’d rather use the Mac’s native Apple Mail, that’s entirely possible, but requires a few gyrations.  Now, Outlook keeps your downloaded e-mail messages (plus Notes, Events, and other Outlook-related items) in a Personal Storage Table (*.pst) file.  If you’re using any of the versions of Outlook on the Mac side, you can simply move this file over using the same method you chose to move over your other Office files.  If you’re going to go with Apple Mail, your PST files will need to be converted.  You can do this using the version of Outlook for Macs.  Even if you’re not going to use Outlook as your final e-mail solution, you can download a 30-day free trial of it using the “Try it Now” link on the Microsoft Office 365 home page.  Once you have a version of Outlook, all you have to do is choose File->Import from within Outlook, select “Outlook Data File”, click “Next”, select “Outlook for Windows Data File” and click “Next” again.  Then navigate to wherever you put the PST file that you copied over from your Windows machine, select it, and click “Import”.  When the operation is complete, you’ll find the messages filed under the “On My Computer” heading.  Drag the containing folder to the desktop, and it will be automagically converted directly into an Apple Mail-compatible mbox file, ready for import.

Hope this helps you out, John!  Good luck with it, and Happy Computing, no matter which platform you land on.