Your questions answered: Why I switched from Outlook to Gmail

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.
Written by David Gewirtz, Senior Contributing Editor

A few days ago, I shared with you Why I bit the bullet and finally switched from Outlook to Gmail. To say that article generated letters would be an understatement. In addition to the comments from ZDNet readers in the article itself, I got a steady stream of email messages, Twitter comments, and Facebook opinions and questions.

Since there were so many different things discussed by all of you, I'm dedicating this article to addressing most of them (including those where you question my sanity). I expect to post some more detailed how-tos later on that go into specifics of what tools and solutions I'm using. But first, can we talk?

My mail system is better than your mail system

Are you saying you think Gmail is better than Outlook (client) or Outlook with Exchange?

Not at all. Outlook and Exchange are a brilliant team and I've benefited from using them for over a decade. However, as time has gone on, my daily usage patterns and workflow have changed, and the Outlook/Exchange combination may not be the best choice for me. I specifically documented some issues I had with rules, but it's also important to recognize that the organizations I work with are Google shops, so there's a natural fit there.

I still don’t understand why you switched to Gmail. Outlook is the Cadillac of emails, especially with Exchange.

Outlook is certainly a comprehensive package, but I don't think it's holding its place at the top of the heap anymore. For example, which Outlook are you talking about? Outlook on Windows is certainly excellent, but it's different from Outlook on the Mac. Outlook.com and Outlook Web Access could have been made by completely different companies. So, which Outlook is which? They're all workable, but that lack of cohesiveness has rough edges.

What about the Windows Phone? Isn’t Outlook and Exchange integration better?

This reader is commenting about my exploration of Windows Phone. In a perfect world, I probably would have finished my Windows Phone series before moving on to talk about email workflow. Here's the detail. After a few weeks of using Windows Phone, it's proving to be a fine environment.

That said, I have an Android Samsung Galaxy S4 on contract for nearly another year, and I'm probably not going to switch off of it, at least until the contract is up. As a product evaluator, I have to treat different systems as their own unique projects, and so while I'm using the Android phone as my daily driver (and it fits with the Google ecosystem), I am evaluating the Windows Phone environment.

I will give you one hint though: Windows Phone 8.1's integration of Outlook with Office 365 was... odd. You can't get to your email from the Office 365 icon. I'll discuss that more in a future article, but it's worth noting.

Desktop vs. Web client

So you basically moved from a desktop mail client to Web mail?

Mostly. I haven't completely given up on running a desktop client on one or more of my machines, but I'm finding the universal Web access extremely freeing. And it's really nice having a completely consistent UI for email no matter which machine I'm using at the time -- at least on PC-grade machines.

Why not use a local client, like Postbox or Thunderbird or Pegasus Mail?

I thought about Thunderbird, but the project is on hiatus, whatever that means. I've used Pegasus briefly in the past, and it's a heck of an email client, but I didn't find it as comfortable to use as I would have liked. It also feels kind of dated. The version update information lists Windows 2000, XP, Vista, and Windows 7, but makes no mention of Windows 8. It's certainly a viable client and if you like it, it's a solid choice. Just not for me.

As for Postbox, I was all ready to buy it (especially since it's based on Thunderbird, but with ongoing development support), but it doesn't do display scaling right on Windows 7. As a result, the text on my 1080p display is so small, it's unreadable. If anyone knows how to fix that, please post a note in the comments.

Gmail doesn’t work as well with non-Google devices since ActiveSync was disabled.

This is true. In fact, the Gmail app on my iPhone and iPad crashed trying to read my mail, while the native email app worked quite well. However, since I'm primarily using an Android phone, this isn't too much of an issue to me. I do wish, however, that Gmail would have continued to support ActiveSync fully. Interop is always a good thing -- at least for users.

Outlook techniques

Why not use both? You could use Google Apps for Outlook Sync, define rules in Google Apps, then read mail in Outlook

Yep, you could. I've done this sort of hoop jumping before. A lot. But I had this flash where I realized I was spending way too much time fiddling with coordinating accounts and keeping things all in sync. I wanted to simplify. One account. Simple.

Why wouldn’t you keep Outlook's signature files (which are local) on something like OneDrive so any device can look it up?

This pretty much tracks with the previous answer. Sure, I had a system that worked almost as well, using my daily backup syncs to move my sig files around. But who needs it? That's just more overhead and I'm at a stage where I just don't need that much overhead.

Signatures can be server based if defined as a rule with a template

Yep, that's a neat technique. Except I don't think it works. Inbound rules allow you to assign a template, but outbound rules don't. So you could do this if you were setting up an auto-responder, but not if you were composing a new message. Feature request for Microsoft: please add "assign a template" to outbound rules and allow users to replace or append the text.

Next up: Gmail vs. Outlook.com, privacy issues, and your migration questions answered...

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 Facebook.com/DavidGewirtz.

Outlook.com vs. Gmail

Outlook.com 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 Outlook.com interface to Gmail. Mostly. I don't like how the Outlook.com send mail interface seems to have subject lines hanging off in space away from the To field. But that's a nit. Outlook.com'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 Outlook.com?

I think the reader here is thinking about phones and devices, and most phones and devices do play nicely with Outlook.com (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.

Outlook.com 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 Outlook.com. You have to use Outlook Web Access, which is a completely different beast, with a completely different interface. Outlook.com 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 Facebook.com/DavidGewirtz.

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 Facebook.com/DavidGewirtz.

Editorial standards