I have been working in several locations today, a rare treat. I needed a change of scenery from Mobile Tech Manor, but still wanted to beat the insane heat wave in Houston. That meant heading out to coffee shops and the like and that’s where I’ve […]

DangerI have been working in several locations today, a rare treat. I needed a change of scenery from Mobile Tech Manor, but still wanted to beat the insane heat wave in Houston. That meant heading out to coffee shops and the like and that’s where I’ve been working all day. I even completely drained the MacBook battery, triggering a battery swap, something I rarely do unless on a trip. No matter where I’ve been working today and what I’ve been doing, I’ve run up against the same tech news item.

It seems like everywhere I turn on the web I see the news that Microsoft is bringing Outlook to the Mac next year. The next version of Office for the Mac will dump the terrible Entourage and replace it with the real deal — Outlook. This is no doubt good news to some enterprise workers and to those who have been putting up with Entourage’s shortcomings, but I’m afraid it’s too late for me.

I was a die-hard Outlook user for more years than I can count. I was in Outlook all day, every day, and I used features that few ever touch. I was the very definition of an Outlook power user. Outlook was an ingrained part of both my life and my work. I paid for a hosted Exchange Server for years, primarily because of how well it worked with Outlook. Yes, I was an Outlook fanboy.

Then a couple of years ago I started using Macs in addition to Windows systems. I brought the Windows / Outlook mindset with me to the Mac and quickly grew frustrated. I bought Office for Mac and I toiled and toiled with Entourage to make it work as well as Outlook. No dice.

Entourage didn’t play consistently with the Exchange Server; it didn’t like the fact that I used more than one system; it just didn’t work very well for me. I duly updated and upgraded Entourage every time I had the chance, each time hoping that Microsoft would make it work like it should, like my precious Outlook. They produced both programs, right?

As time progressed my frustration grew to the point I couldn’t stand the thought of continuing with Entourage. I would actually approach the Mac with trepidation each morning, wondering what pain Entourage would inflict on me, yet again. I withstood this abuse for far too long before I stuck my head out the window and did my “I’m not gonna take this anymore!” routine.

Dumping Entourage was the smartest, no, the most brilliant thing I have ever done. My days became nice, even fun once again. I began to enjoy my work. I explored other alternatives for working with my email, and eventually I realized that a big, bloated local application, even Outlook, is just not efficient for me. I use multiple devices across platforms, and I realized that a cloud solution was more logical.

I implemented a Gmail method, dumped my Exchange Server, and never looked back. I can honestly say that I can’t remember the last time I had an email-related issue. There is nothing I used to do with a complicated Outlook implementation that I cannot do today, and all with a web browser.

The massive failure (IMO) of Entourage to deliver an effective desktop solution for me is directly responsible for my discovering that I am better off without such a method, and that includes Outlook too. So it’s great that Microsoft is bringing Outlook to the Mac desktop, just not to mine. Too little, too late.

  1. Here’s something you can’t do with Gmail – be certain that your email isn’t being read by Google. Gmail isn’t even an option for anyone who’s concerned about their privacy and Google can’t be trusted with your data.

    1. But if it’s not being read my Google (and I am sure they have better things to do than read my mail), if your communications are really that interesting, they will only get read by somebody else (your ISP for example)

      At some point, your mail has to cross networks or servers that are not controlled by you.

  2. I had that brain fart a while ago to (windows user myself). Then I realized what a stupid idea it was when my schedule, tasks, and emails were not being handled.

  3. GoodThings2Life Thursday, August 13, 2009

    Never say never, James!

    I’m gonna bookmark this post and remind you of it in a year when you’re toying with it to “try it out” and “see what you’re missing” so that I can remind you how set in your mind you were today. :)

    1. You’re on. :) Of course, it would be a shame if this post tragically disappeared.

  4. It will be interesting to hear from you as a past power user of Outlook, what features Gmail is supplementing in Outlook needs??

    1. Off the top of my head:

      1. No maintenance. I don’t have to worry how many GB my PST file is growing. No need to archive it, and then make sure all past archive PST files are present on every system I use.

      2. Speed. Gmail is so much faster than Outlook.

      3. Untethered. I can access my Gmail from any system and have everything instantly available, including brand new systems.

    2. James, all those points were addressed long ago if you’d combined Exhange with Outlook 2007.

    3. I did combine the two, Jake. I stand by my experience.

    4. When setup properly (using HTTP over RPC) you would have an OST file rather than a PST file. AFAIK you will only have a PST file when connecting to your exchange server via POP3 or IMAP. The bloat issues you refer to are really a thing of the past.

      Also, Outlook 2007 takes advantage of the built in search in Vista/7 or Windows Desktop Search in XP and doesn’t suffer from any performance problems even when searching through large inboxes. I’ve never experienced any performance problems with any other aspect of Outlook but would be interested to hear how it has performed slowly for you.

    5. 1. Same when using Outlook. Also no need to archive.
      2. Outlook is virtually instant on modern hardware while Gmail adds internet latency, and requires more than one click to get to.
      3. Same with exchange. Exchange is supported better by more systems including phones. Ability to connect by Outlook is a feature which is useful (increases performance among other things) if you use the machine regularly.
      Of course a disadvantage of exchange is cost.

    6. Of course if you really love Outlook that much (and for my work email, I really do), you still have the option of using outlook with a Google account so if there is a feature you are really missing then you don’t have to say goodbye to it.

      Having said all of that, I have just made the jump to Google Apps myself and was intending to do just this with Outlook on the desktop and Google in the background but it has only taken me a couple of days to realise this is pointless and that running the Google web UI on the desktop (especially using the frameless option rather than my main browser) is just as efficient.

      Could I do this in the office? No but only because the whole company runs on Exchange so I NEED Outlook to access room bookings, shared calendars and so on.

      If however the company moved to Google (or something else for that matter) then it would not matter as much.

      Remember that a mail system is made up of TWO components. The desktop interface and the mail server in the background.


      Have you noticed that Microsoft seem determined to move Outlook into the browser as well?

  5. Our university just made the switch to an edu version of gmail. We get to use our domain name, we have no ads, and it’s free!

    This is way better than the hosted exchange, not just for the thousands of dollars we save, but also because not every student has outlook or IE (running 2003 exchange, webmail looks like crap without IE).

    Now students can create and share their calendars, collaborate with google docs, put up their own website, not to mention check their email on every device they own.

    And for the privacy issue? In my opinion, if you have something that you don’t the possibility of being read, then you don’t email it. Period.

    1. Good Lord, the same thing happened in my college. i can finally have a familiar interface for my tasks, calendar and most importantly, Email!

  6. I don’t understand the outright paranoia, bordering on hostility that I frequently read about Google handling mail. Sure it’s technically possible for them to index, search, aggregate and even read your e-mail. But so what? Doesn’t everyone assume that e-mail is inherently insecure?

    If you are using a corporate Exchange server and only send mail to other employees using the same server there are probably dozens of IT people, consultants, HR staff, lawyers, etc. that could read your mail (plus your company owns all of your mail anyway and can do what they want with it).

    If you are a small company using any kind of hosted Exchange, or any other hosted mail servers, those are subject to the same security problems Google might pose. But I would definitely trust Google’s physical and procedural security over any of the dozens of smaller data centers I have visited.

    Even if you are hosting your own hardened Linux Postfix servers in a bunker under your bedroom and PGP encrypt every message, what happens to your precious mail when the recipients get it? Their mail could be hosted at Go Daddy, Google, or Mails-R-Us. They’ll probably unencrypt your messages and, for convenience, let Google Desktop index them. They might have their system and e-mail passwords taped to the top of their monitor. They could print a copy and forget it on the table at Starbucks.

    Sorry I veered off topic there, but I find it odd that the Outlook/Exchange/Microsoft crowd has convinced themselves that their “solution” is not only technically superior, but somehow more secure and reliable. It just ain’t so.

    1. Well said. When I worked in IT for Fortune 100 companies, I routinely heard the Exchange admins sharing deets of inappropriate emails and such. Should they have done it? No. Do all Exchange admins do this? Of course not. But the fact remains that they can, just as Google can. In my mind, the whole “…but Google has access to my email” defense is a poor one at best.

  7. Is Google bound by law not to read the mails?
    I mean to ask naively, if this is an agreement with the users or a US/European laws that would prevent them from doing it.
    Sure they can do it anyway – but for me that is the main question. Anybody?


    1. I haven’t scoured through the entire privacy policy, so I don’t know the legal limitations / implications. But according to Google: “Google does NOT read your mail.” (Emphasis theirs)

      Here’s my starting point, which leads to their full privacy policy. I haven’t read it through yet. http://mail.google.com/support/bin/answer.py?hl=en&answer=6599

    2. Here’s a link to Google’s Terms of Service which should govern your contractual relationship with Google. (Rules might be different outside the US.)


      The only sentence that bothers me a little is this one:

      “Google reserves the right to syndicate Content submitted, posted or displayed by you on or through Google services and use that Content in connection with any service offered by Google.”

      And of course “Content” is “…all information, data, text, software, music, sound, photographs, graphics, video, messages or other materials…”

      The reason this doesn’t bother me a lot is that Google has to retain the trust of us customers/users. If anyone (and a lot of people watch this carefully) demonstrated, or even reasonably suggested, that Google was using the “Content” in Gmail or Google Apps accounts in any way for their own purposes, they would immediately lose 99% of their users and be out of the Apps business forever. They really don’t want that to happen.

  8. Am I the only person that sees the ironic timing in this? MS has never given us even the hope of Outlook for the Mac until Apple decided to take all of Outlook’s functionality and build it into Snow Leopard. So not only do we all get to upgrade for $29 while XP and Vista users have to pay $100+, but now those of us that are forced to use an Exchange client no longer have to pony up for MS Office for the Mac. So MS seems themselves losing money on two fronts and their response is to finally cave and give us Outlook for the Mac. If Apple hadn’t licensed the support into iCal, AddressBook, and Mail, I doubt MS would’ve ever even thought of giving us Outlook for the Mac. Like James, I won’t be using Outlook for the Mac, but not cause I switched to Gmail but because I’ll use the tools built-in to Snow Leopard to do it.

    And some more irony… I have literally hundreds of apps on my Mac. Not one of them ever crashes… except for one. Care to take a guess? Entourage. I moved from the PC to the Mac to get the stability of a UNIX core with a usable GUI. I’ve had that stability and its been awesome. Then I went to work for a company with an Exchange server and was forced to use Entourage. I’d say that Entourage crashes or refuses to shut down cleanly at least twice a week. This is the ONLY app on my MBP that has this issue. Leave it to the maker of the most unstable OS known to man to make the only app that crashes or hangs my Mac. Thank you Microsoft! Now where’s my Snow Leopard?

    1. I disagree on upgrade cost, because it assumes that you’re already running an Intel Mac with Leopard.

      Got an early Intel Mac with Tiger? Better add on the cost of Leopard before you can go to Snow Leopard! Not so much cheaper now in comparison to upgrading from XP/Vista to Win7, is it?

      Got a PowerPC Mac? Looks like you’ll have to just buy an entirely new Mac now, though at least they should come with Snow Leopard out of the box by now.

      Don’t even get me started on the cost of keeping up-to-date with OS X ever since its inception. Cheetah (10.0) to Puma (10.1) was the only free upgrade; Jaguar (10.2) was full price, so was Panther (10.3), Tiger (10.4) may have had a discount if you were on Panther already, Leopard was full price, and Snow Leopard is 30 US$…only if you have Leopard and an Intel Mac.

      And while you might say “Why run the latest version of OS X on your old Mac?”, I’d normally agree-except that roughly 90% of the OS X apps I see nowadays REQUIRE Tiger as a minimum, and 5% of what’s left require Leopard. You might still get by with Panther, but Jaguar and earlier? Forget it.

      On the other hand, Windows XP-introduced roughly around the same time as OS X-can still run all the latest Web browsers, e-mail clients, productivity software, and just about anything else you can think of, unless it’s Vista/Win7-specific, so long as it’s topped off with the latest Service Packs.

      OS X is a better experience for many, but it is definitely not cheap-especially when you want to stay current so that the Web browsers and e-mail clients don’t leave you behind as the years pass.

      Oh, and for the record, I wouldn’t use Entourage on OS X either, simply because it’s unnecessary for syncing Windows Mobile PIM data. That just goes straight to the Address Book and iCal.

  9. um, ever heard of running outlook in fusion/parallels/etc? I do agree that entourage sucks but we havent been REQUIRED to use entourage for years. oh and gmail is hideous compared to owa, even in reach mode imho.

    1. Been there, done that. I stand by my own opinion, based on my own experience, that Gmail is the better solution for me. YMMV.

  10. I own a small company employing 12 people and recently made the decision to switch our email from outlook to Google Apps, which was the best decision I ever made. I was uncomfortable, not having a local copy in case I lost my internet connection but I have moved on. The things I like are;
    It is fast.
    Huge storage capacity.
    Maximum message size is 32MB. I send and receive many large files daily
    Easy to maintain
    The absolute best spam filters.
    The are very active developing new features
    Shared calendars and synch to mobile phones are very good.
    It is cheap
    Chat is good for sending short messages to team members.

    However, the things I don’t like about Google Apps are
    How to instructions are written a geek who assumes you already know a great deal about the product. Google to to employ some well trained people of average intelligence to write their help advisories.
    Reply to messages are on the underneath the original message.
    Mailto features don’t work.
    Docs and spreadsheet are elementary and buggy compared to Word and Excell.
    Sites feature is very difficult to setup
    Google’s support is terrible.

    1. Actually, if you install the Google Apps application (download for the domain control panel and then distribute the link or exe to all your users) then the Mailto: feature does indeed work


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