Your questions answered: Why I switched from Outlook to Gmail

Summary:We got a ton of reader comments and questions when David Gewirtz told us he was moving from Outlook to Gmail. In this article, he tries to answer most of them. vs. Gmail has a nicer interface than Gmail, which is dated and The Gmail interface is terrible

I'm going to address these two together. I prefer the interface to Gmail. Mostly. I don't like how the send mail interface seems to have subject lines hanging off in space away from the To field. But that's a nit.'s interface is more attractive.

That said, after a few days working with Gmail, it is possible to tweak the interface to be less disturbing. I'm actually finding I kind of like it now.

You said everything integrates with Gmail. What doesn’t integrate with

I think the reader here is thinking about phones and devices, and most phones and devices do play nicely with (and any mail service that supports POP3 or IMAP). However, there is a rich market of add-ons and plug-ins for Gmail that doesn't exist (yet) for Outlook. integrates well with desktop Outlook. What do you you mean you can’t use it?

This is true, but oddly enough, if you have a business Office 365 account, you can't use You have to use Outlook Web Access, which is a completely different beast, with a completely different interface. is rather sophisticated. Outlook Web Access doesn't even let you set many of the desktop type rules from the Web environment. *Corrected*

Migration questions

How did you migrate everything?

That's a lot to explain. Okay, I'll start by saying I was planning to use YippeeMove again , but after I bought the migration instance (for all of fifteen bucks), nothing happened. I got no sign of life from them for more than 12 hours. So I started my move by connecting Gmail to my Outlook client using IMAP and moving each folder.

Let me state that before this move, I had consolidated my Outlook folders. A few weeks ago, I had 439 folders, including hundreds going back to before 2005. I hand-moved the contents of hundreds of folders into a few big ones, so by the time I was done, I had about 20 folders, instead of 439. Then I IMAP connected and let them copy. That took a few tedious days.

I moved the contacts using a program I bought called gSyncIt. I suppose I could have used gSyncIt to move my notes, but instead I used the Evernote add-on to Outlook and just added my complete Notes folder to a newly created "From Outlook" folder in Evernote. That was a little nerve-wracking because it opened a ton of windows, but it actually went quickly and smoothly.

Did you migrate your old email and folder structure to Gmail?

Yep, once I consolidated it down to a manageable number of folders.

I’d use Gmail, but I can’t get my mind off of not having folders.

Gmail has labels. I use them exactly as I'd use folders. They're really tags, and you can have multiple labels per message, but 99.9 percent of the time, they feel like plain ol' folders. Don't sweat it.

Privacy issues

You know Google will scan and sell your personal information, right?

Yes, but you all know everything about me, anyway. Look at it this way. Last time I bought a phone, half a million people read about it. I switched email last week and more people read about it than fit into Yankee Stadium. I've been online, writing about my life for almost 20 years. For me, it's not a concern.

That's not to say the privacy issue isn't a concern for others, but for my life, at this point in my life, ain't no big thing.

Not only that, Google builds predictive profiles and predicts your behavior. Doesn’t that freak you out?

No. My behavior is entirely predictable. I like coffee. I like to cuddle my wife. I have a muscle car I drive on cruise control so I don't break speed laws. I like steak and cookies and baked goods. I can't wait until the next Game of Thrones comes out. I dislike both political parties and mock both houses of Congress. There you go. Now you can have my profile, too.

Again, though, my life has been something of an open book since the first days of the Internet. Others will need to think long and hard about how privacy issues will impact their choices.

For doctors, psychologists, patent lawyers and others for who professional confidentiality is important, I'd consider Gmail unacceptable.

I don't know if I'd call it unacceptable, but HIPAA (for health care) is an issue. On the other hand, I teach at UC Berkeley, which is extremely conscious of FERPA, and they're a Google Apps site. So I'd say that if you do have compliance and confidentiality issues, you should certainly consult your organization's attorney. For me, it's not a problem.

I do -- sometimes -- send extremely confidential email, but I do so only to people I work with in the government, using a hardened and classified government email account that's been assigned to me. That account never goes near Gmail (or anything else).

Next up: Google complaints, offline security, you R stoopid and WTF?

By the way, I'm doing more updates on Twitter and Facebook than ever before. Be sure to follow me on Twitter at @DavidGewirtz and on Facebook at

Topics: Cloud, Google, Microsoft, SMBs


In addition to hosting the ZDNet Government and ZDNet DIY-IT blogs, CBS Interactive's Distinguished Lecturer David Gewirtz is an author, U.S. policy advisor and computer scientist. He is featured in The History Channel special The President's Book of Secrets, is one of America's foremost cyber-security experts, and is a top expert on savi... Full Bio

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