Your questions answered: Why I switched from Outlook to Gmail

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.

SHARE:
TOPICS: Cloud, Google, Microsoft, SMBs, DIY
60

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.

WTF?

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.

Topics: Cloud, Google, Microsoft, SMBs, DIY

About

David Gewirtz, Distinguished Lecturer at CBS Interactive, is an author, U.S. policy advisor, and computer scientist. He is featured in the History Channel special The President's Book of Secrets and is a member of the National Press Club.

Kick off your day with ZDNet's daily email newsletter. It's the freshest tech news and opinion, served hot. Get it.

Talkback

60 comments
Log in or register to join the discussion
  • Switching

    I recently did a reverse switch from Gmail to Outlook.com. My old phone was a Galaxy Nexus (no letters or numbers) so the email account I used was my gmail account. Because Android has hooks to all Google Services (*cough*). My home computer is a Windows 8+ laptop. So the email account for this machine is, of course, Outlook / Hotmail.
    Now, that I've finally got a Windows 8 phone, I could finally consolidate my email houses into one.
    Oh, by the bye, you could do well to get with your compadre Ed Bott regarding the Outlook 365 for business conundrum you've run across and he's previously documented; he may have a workaround, or three, for you to try!
    Crashin Chris
    • Yeah well

      If he does go back to Windows Phone, he won't have those Gmail contacts because the Sync feature is horribly broken!
      slickjim
  • Pointless justification, even an 8 year could do better.

    Outlook.com capabilities are unparalleled.

    You should think of getting trained in using modern email systems.
    Owl:Net
    • I am guessing you didn't really read the article

      As he goes over why Outlook.com was not going to do it for him - (a) he can't (he has Office 365), and (b) there are certain plugins he uses for Gmail that don't exist for Outlook.com.

      Reading the article - always a good thing to do!
      Mac_PC_FenceSitter
    • more troll nonsense

      You need to get trained in how not to be a self righteous dick then learn how to read then get your head out of your ass and learn t hat people have different needs Just because you prefer outlook and it works for you doesn't mean everyone else has to be the same.
      I don't know why you trolks even bother to come here as you just slagg off everyone else's opinion all the time.
      If you don't like other opinions then stop using the internet.
      Capt Obvious
      • Your comment will probably be removed soon

        Like the other 100 or so comments that were on this piece until today.
        Boothy_p
      • hey cap.

        fowlnet doesn't prefer outlook, he prefers microsoft, doesn't matter what it is.. if Microsoft are in a field.. they are fowlnet's choice.. before he considers or looks at any alternatives, then he tells everyone as if he knows about all of them and "chose" microsoft.

        If he was in high performance computing, he'd be pushing HPC windows, and it wouldn't matter that the worlds top 500 supercomputers only has 1 windows machine and it's nowhere near the top..

        It's just how he rolls, you get used to it after a while. it's actually kind of entertaining.
        frankieh
    • Even an 8-year old could...

      ...post better comments than Owl:Net.
      helloTekWorld
  • Good luck

    I'll give you a few months to discover all the shortcomings of Gmail and related services such as Google Contacts. I've had a Gmail account for many many years. So long that I'm one of the users who got grandfathered into the ActiveSync support. However, that didn't save Gmail and I migrated to Outlook.com a couple of years ago.

    The primary reason I migrated is the severely lacking Google Contacts. For example, Google Contacts cannot aggregate contacts from various sources such as Facebook, LinkedIn etc. and unify your entire universe of contacts. Outlook.com can aggregate all your contacts from all these services and even from Gmail btw, unify them and if it can't automatically unify a contact because one of your friends uses a different email address on Facebook vs LinkedIn for example, you can manually link those contact records together.

    The secondary reason is that the structure of how Gmail manages and stores emails really clashes with everything other than Android and the Gmail web interface. I'm not married to a single platform. I use PCs w/ the Outlook desktop client, I have a Mac and Windows Phone, several Windows tablets and many other devices that sync with my email, contacts and calendar. Outlook.com does it all w/o requiring an awkward mapping of the email structure. Gmail's conversation structure was unique when it came out, but over the years it has proven to be more of a headache unless you exclusively use Google products.

    Another great feature of Outlook.com is that it can use your SMTP server to send emails. I actually have my own personal email domain. Had it for years. I'm not running it myself, though. I never really wanted anyone to know my Gmail address. I wanted that my emails always come from me@mydomain.com. With Gmail that doesn't work so well. While you can change the From in Gmail, the email header still contains the actual Gmail address and if a recipient uses Outlook they'll see the from as my@mydomain.com in behalf of me@gmail.com. Furthermore, when sending emails from a non-Android phone, the From address is the Gmail address. Not so with Outlook.com. Because Outlook.com sends all emails through my domain's SMTP server, regardless if I send them from the Outlook desktop client, my phone or any other device they always originate from me@mydomain.com and the header shows that they came from my email domain so reverse lookup etc. works properly, so there is less of a risk that emails end up in people's spam folder, because they get interpreted as being spoofed.

    Don't get me wrong. Google has some great services. I use their search all the time. I love Google Maps and in fact all my emails still run through my Gmail account, but now get forwarded to my Outlook.com account. I keep Gmail as a middle man for several reasons. One reason I have to admit is that it has probably the best Spam filter ever. The other reason is that Google search can search my emails and inform me about upcoming flights, reservations, deliveries etc, but having everything aggregated in Outlook.com makes life with different devices so much more productive.
    superswiss
    • Most people work off of phones these days

      and your phone is already doing all that unification for you.

      In the gmail web client, gmail knows about every person you've ever emailed, or been emailed by. I can't think of anyone I've tried to reach in the last 4-5 years where it didn't just autocomplete whoever I was trying to email.

      So while your point is a valid one, there are a lot of factors that mitigate it to the point you'd never really notice the difference.
      Mac_PC_FenceSitter
      • Missing my point

        If you indeed only use a single device (phone, tablet) than you have a point. However, I had an iPhone for many years and the contact unification in iOS at least up until iOS 4.x was pretty lackluster. The key feature it missed, maybe they added that by now, is to be able to manually link contacts if the automatic unification failed. I had many duplicate contacts for friends and colleagues who use different email addresses for different online services or used their middle initial in one service, but left it out in another service.

        Being able to unify my contacts in the cloud rather than on each device has the benefit that no matter what device I use to look at my contacts, they are always unified correctly.

        Maybe I am unique with all the many devices I use, but I doubt it. I have a job and need to do productive work, so I'm still using computers. I think Sean Foley is correct with his comment. I don't email much from my phone. It's a pretty bad experience trying to read longer emails on the small display and respond with more than a sentence or two, so the majority of my emails are read and written on a computer. When on the phone, I text, skype, whatsapp or call people.
        superswiss
    • Huh?

      I've had my Gmail from the Beta and there is no grand fathered active sync... Not anymore, they shut it off.
      slickjim
  • Rules on Outlook Web App

    I just want to point out an inaccuracy with your statement about rules in Outlook Web App that says "Outlook Web Access doesn't even let you set rules from the Web environment". This is not true. You said you were using office 365, so you can edit rules under the Settings Cog > Options > Organise My Email > Inbox Rules. To be honest, I use the desktop version of Outlook 2013 everyday and had a bit of snobbery about OWA due to previous versions, but we recently moved to Office 365 its surprisingly good. On top of that, they are doing some amazing work with Office web apps, OneDrive for Business, SharePoint Online & Yammer which is slowly starting to trickle through...
    AndyEmm
    • Rules on Outlook Web App

      You can't set rules at all using the light version of OWA. And the full version contains a limited set of rules, even if you enable the advanced set. I can't edit any of my 20 rules using either version of OWA.
      dmw2
  • Excellent responses

    I did chuckle at several of them.
    Boothy_p
  • The fact is

    He's contacts and people he works with, are Google, his phone is Android and he uses Mac. No real surprise here.
    Everybody chooses environment, that suits him best.
    Andrej.G.
  • What about Thunderbird Hiatus?

    Hi, I'm a longtime Thunderbird user (on both Windows and Linux -- I use it to access the same mailboxes from many locations) and I don't understand the "hiatus".

    I've heard about Mozilla Foundation stopping funding Thunderbird development, but updates -- including many new features -- continue coming. I'm very satisfied with it and its vibrant plug-in ecossystem.

    I also had concerns about other mail clients, because they either don't deal very well with encrypted messages (specaillu PGP/GPG) and sometines they store the content unencrypted. Thunderbird + Enigmail was the only combo that passed without issues in mine (my customers) tests. Maybe Outlook improved so far, but at the time it was a disapointment. besides Gmail / Outlook.com looks like no way regarding crypto.
    fernando@...
  • My Nexus + Gmail works great

    I drank the Google-aide many years ago (probably as a knee-jerk reaction to anything but M$). I have no problem doing everything I need to do on my phone as well as using a browser. I don't know of any scenario where what I have is insufficient to my needs.
    Roger Ramjet
  • What about digital signing and encryption?

    David,
    I've not see you address how you deal with email signing and encryption.
    These things are difficult to deal with when using a non local email client like like a web based gmail interface.
    How are you dealing with email signing and encryption?
    bperrybap@...
    • I, too...

      ... am curious to this.
      jparnell8839