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.

Google complaints

I would never use Google because of "literally zero customer support."

That is an extremely valid concern and it's one of my biggest. I have no idea what to tell you here, although I do address some offline security issues below. It is a problem and I'd sure like it if Google would add better security. For that matter, I wouldn't mind paying $50/year (about what Google Apps costs per seat) just to get my regular Gmail account quality support. Google, I know you're listening...

What riles me sometimes is Google changing things without first telling users.

Yep, but that happens on all Web-based SaaS services. QuickBooks recently completely changed their interface and I logged in one Monday morning and had no idea at all how to work it. A few weeks went by, and I'm pretty much up to speed. The good news is I didn't have to code or even install the upgrade.

Offline security

How do you access your Gmail data while offline?

Google does have some offline services, and you can certainly use an email client with IMAP to download a copy of your mail. I haven't explored this yet, because I still have all my mail in an active Office 365 account and on local copies of Outlook .OSTs, but that's definitely something I'm going to look into in the coming weeks.

What about backups?

There are some backup services, and Google does let you do an entire dump of your account, but I'm not convinced that's an elegant approach. I'll look into this, too. If I come up with anything good, I'll let you know.

You R stoopid

You just proved you are stupid

It took you this long to figure that out? Have you not read the comments posted on my previous articles?

Your wife stayed on Outlook? Proving once again she is smarter than you

There is no proof needed to know she's smarter than me. She's brilliant, beautiful, and amazingly tolerant. I'm a very lucky guy.

Why didn’t you go to a guaranteed, 100% uptime Exchange provider, since Google has outages?

I've been using Office 365. That's about as good as it can get. They've had a few rocky days, but generally they've been rock solid. I have no complaints about Office 365 reliability. I didn't look at switching because of reliability. I looked at switching because I needed to be more personally efficient.

If you were a real technology journalist, you’d run your own mail servers on your own machines

Been there. Done that. Starting in the mid-1990s, I was the editor of a newsletter about cc:Mail. Back then, cc:Mail wouldn't run on just one machine. It required a set of DOS machines all to work together, one as a mail store, one as an inbound mail exchanger, one as an outbound mail exchanger.

I then went on to found ZATZ, and we had an email list of more than a million opt-in subscribers. Not only did I run the mail servers, I wrote a mail server, including all the list serving components, VERP confirmation, and more. I ran multiple Linux-based mail servers, some Windows-based servers, and my own Exchange server.

When we moved down to Florida in 2005, the T-1 line that came in through my bedroom, over my bathroom window, down through my clothes closet, across the hall, and into the linen closet where the stack of servers lived wouldn't do... because I was moving out of that apartment. So I signed up with an Exchange hosting provider, who did a great job. Then a year or so ago, I moved to Office 365.

So yeah, not only have I run mail servers, I've written them. I am SO over running mail servers. And at this stage in my career, I don't need to. So why should I?

As a computer scientist, why wouldn’t you run Linux?

The two are unrelated. In fact, one of the strongest lessons that you learn in engineering school is to use the right tool for the right job. Yeah, you also know how to crowbar the wrong tool into the job when you're stuck, but that's not a best practice. The point is, I can choose from any environment I want. At this point, I want whatever is the easiest and gets me through my administrivia work the fastest.

At least, from the few days I've been up on Gmail, that's Gmail. But it wasn't always the case. I've also run Linux servers for years. And, for the record, I was also the product manager for one of the first UNIX RISC-based servers, back when servers cost a quarter of a million bucks per CPU. So, again, been there, done that. Don't need more T-shirts.


When do you have time to be productive? Seems like you spend a fair amount of time "attempting to refine my workflow."

Fair question. Keep in mind I write the DIY-IT column, so all these projects are fodder for articles I can share with you. But I actually have a formalized process for this I call "side projects."

I've talked about side-project time before, but I spend the bulk of my time (like now, when I'm writing this article) on my main doing-my-job work. However, I usually have a small percentage of time (sometimes more, sometimes less) that I always try to allocate to something future looking. A few of my side projects resulted in my books. One of my side projects resulted in migrating an old CMS. Another was spending a month writing iPhone apps .

This month, my side project is to do another spin on refining workflow. It's how I manage to get all this done and meet all my responsibilities. Once a year or so, I look at how I work and tune it, turn whatever I can into a repeatable system, and tweak things for efficiency. It doesn't always pan out, but it often does.

These things broaden my horizons, keep me in touch with technologies I might not otherwise have the chance to use, and help keep my skills from going stale.

Why do you have to get government approval to switch phones?

The government works with certain professionals who have expertise in infrastructure emergency management and sometimes calls on us when there are situations needing attention. In order to be responsive to those situations and to be able to respond and coordinate emergency activities in troubled circumstances, our phones are encoded with certain access credentials that allow us to get our jobs done.

As a result, if I choose to change phones, I need to check and make sure those models are supported and then go through the paperwork process to migrate the necessary credentials to the new phone.

While the details of the situations and credentials can be confidential, there's no restriction on being able to share with you that some phones need to have interlocks to get them into emergency and federal systems when the situation warrants it.

I'm like a fireman who's on call, except that my area is our cyber-infrastructure and its security. Nothing Big Brother. Just keeping citizens safe from some nasty bad guys out there.

There you go. Many of your questions answered. Stay tuned. I'll be writing hands-on tips and providing my picks for some great Gmail add-ons.

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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