LearnScrew Apple Mail and iCal, I'm moving to Outlook 2007


writes on March 22, 2007

I switched to a Mac last year and I couldn’t be happier … except for one thing. Apple Mail and iCal just aren’t powerful enough for me.

As the Director of Carson Systems, most of my day comprises of emailing, coordinating things and checking to-dos. Ever since I’ve moved to a Mac, I’ve been frustated with the disconnected nature of Mail, Address Book and iCal.

Here’s what frustrates me about Mail/Address Book/iCal:

  1. There’s only one flag in Mail. Life is complex and email doesn’t often fit into one category. I hate having to move mail into seperate folders as it’s a waste of time. I’d rather keep everything in my Inbox and categorize and flag it as necessary.
  2. To-dos in iCal are a complete joke. The lack of categorization and easy reminders makes life hellish.
  3. Address Book is pretty good, in general. But it doesn’t need to be a separate program.
  4. Mail often freezes up on me as it’s not built for the huge amount of email I send and receive.

I’ve tried really hard to make Mail/iCal/Address Book work. But it’s just not good enough. I know that a lot of folks preach about how simple software is better. But you know what? If you’re a power-user, early adopter, it often isn’t.

Why I’m switching

Here are the features in Outlook 2007 that I’m switching for:

  1. Categorization of emails, todos and calendar items is simple yet powerful. Instead of moving emails into folders, just categorize them appropriately (You can create custom categories and assign them colours).
  2. You can choose from a set of flags (Today, Tomorrow, This Week, Next Week).
    The beauty of this is that as soon as you flag it, it automatically creates a to-do for you and sets a reminder. Bam!
  3. The calendar in Outlook 2007 now supports the ical format, so you can subscribe to Google Calendar. We do this at Carson Systems to share the company calendar (annoyingly, however, you can’t update from Outlook – you have to go to Google Calendar).
  4. You can assign to-dos to people. This is brilliant for delegating (which is how Directors spend most of their day!)

Latest version of Parallels makes it even easier

I just upgraded to the latest version of Parallels and it makes it even easier to use Outlook 2007. Here’s why:


The above image is a screengrab of my OSX Dock. Parallels actually seperates out each Windows program! Now I can go straight to Outlook, Excel, IE, etc with one click, like native OSX programs.

And running Parallels in ‘Coherence Mode’ means you don’t have to look at the rest of the (ugly) Windows XP/Vista OS.


Getting things done?

As probably most of you know, I’m a GTD freak and I love being efficient. I thought I had it nailed with my Omni Outliner to-do method, but I found it was starting to slow me down. The fact that Omni Outliner doesn’t support due-dates and reminders is a real problem. I found myself having to go into iCal and set reminders for the really important date sensetive stuff.

I’ll report back to you with how it’s working for me.

The annoying parts

Before you all go off and buy Parallels and Outlook 2007, let me tell you about what isn’t so great about it:

  1. Key-mapping is a bit of a pain. For instance, you have to hit fn-backspace to delete things (MacBooks don’t have a Delete key).
  2. You need to have a seperate backup solution for Outlook. We use Super Duper for OSX and it rocks. But now that all my super important data is in Outlook, I’ve got to figure out a seperate solution for it as well (any suggestions welcome!)
  3. It’s expensive (XP + Outlook 2007)
  4. You have to spend a day moving your data across, which is major pain-in-the-neck
  5. If you’re in an airport and you buy a wifi pass (while in OSX), it won’t let you use it in Parallels, as it thinks it’s another computer. Argh!

However, even given those negative points, I’m very excited about the productivity gains I (and the company) are going to reap for switching.

Tips for migrating

If you’re going to follow my lead (which I recommend you think long and hard about first, here are some useful tips for moving over to Outlook 2007.

  1. Use this tip for moving mail from Apple Mail to Outlook 2007. It’s a bit crazy, but it works. Some of the characters in email get screwed up, but overall it works fine.
  2. Use this vCard converter tool to import your contacts into Outlook 2007. It’s well worth the $25. Outlook supports vCards (hooray!) but has problems importing more than one at a time (boo!). This tool helps you get over this problem.
  3. Get your to-dos into CSV format and then import them into Outlook.

Please comment and let us know how you get on with this, if you decide to migrate.


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52 Responses to “Screw Apple Mail and iCal, I'm moving to Outlook 2007”

  1. All you had to do was to get MS Office for Mac. It comes with Entourage (Outlook version for the Mac). No more Parallels, no more XP.

  2. Maybe this stuff will improve when Leopard ships with a new Mail.app or Mac:Office goes Universal binary…

  3. me too on May 16, 2008 at 3:55 am said:

    I’ve tied to like Mail at work (Tiger) and at home (Leopard) but I keep going back to using Outlook 2007 on my Windows system. One of my biggest complaints with Mail is its piss poor junk mail filtering. I’ve had mail that is CLEARLY junk e-mail, with its misspelled words in the subject line and odd characters in place of letters, while mail from people in Address Book wind up being tagged as junk mail. Outlook 2007 handles junk mail flawlessly. I don’t mind the separate apps but I do like having all the functionality in one app. I always wondered why Apple didn’t add buttons or other functionality that would make Mail, Address Book and iCal work a little more seamlessly together. It doesn’t need to be one app but at the very least, ways of opening one app from within another would be helpful.

  4. Whats wrong with Thunderbird!? Its way less memory intensive than Outlook and lets face it any MS product is so bloated you need a super powerful PC just to run it….. and being a PC tard I cant live without those lovely little animated characters (wizards or a dog to search your PC with) to do things!

  5. Ricardo on March 11, 2008 at 11:30 am said:

    Does mail supports microsoft exchange?

    When setting up the email account, it gives the option but so far have been unable to complete set up

  6. oops, this is under leopard i am not sure about tiger.

  7. Did you know you can just open the color palette and click on a color and get your color labels? I just found this out today.
    Select your mail.
    open the color palette cmd+shft+c
    Select a color.

    To get rid of a color set it to white.
    Also, you can create a set of label colors.
    Very easy.


  8. Address book should always be a separate program, and not part of any other. You lost me when you said otherwise.

    Perhaps you should go back to windows?

  9. Thanks for the post and replies! I stumbled upon GhostAction here. BTW, the performance of Entourage was fine on PPC, but it was unbearable on Intels since it’s not yet optimized. Microsoft promises the next release this fall, over a year since Core Duos shipped on Macs.

  10. Guys, never have had Your problems with mac and it´s apps neither Apple Mail – working with it ( Mac ) since 1986 without shutdown – o.k. close-to.

    Why should I try to import 8ooo mails a day not being able to read more than 80 ! And what for is outlook good than to import viruses not to talk about the normal running problems or how to get started on xp … Man I hope to get 50 yrs old the next few weeks. I wouldn´t have got that old with a gatesmachine ( it takes 5 min get my heart disrythmed and the pc to bag for shutdown ) and will neverever pay a dime for what they call software ( even I neverever would try to get that stuff without paying for it ).
    But – keep on with plug & pray. I´m too old for that stuff::: Best wishes from where the wind blows

  11. Omar Ferrer on May 24, 2007 at 6:27 pm said:

    Does anyone knows about an application like NEO but for Mac’s Mail App?

    I read a lot about NEO and apparently is quite good.


  12. Hi Ryan,

    Thank God I found your blog here, you save me a lot of trouble. But I can’t figure out how to get the icons from the window environment to my OS, so I don’t have to see the windowXP desktop anymore!


  13. James Smith on May 1, 2007 at 11:50 pm said:

    I am researching email and GTD solutions today and what made me stumble onto this excellent discussion is that I discovered “Midnight Inbox” which before much testing seems to touch on some of the gripes people have with mail.

    Reading about the other tools mentioned here, I decided to try and switch over to mail from Thunderbird to test different solutions out, accomplishing as well better quicksilver compability, which has been an itch for me for a while.

    I am feeling the Mail.app slowness pretty hard on importing some 8000 messages, but I aint very high volume on a normal day and so we will see if it won’t be workable.

    Have anyone experience or comments on “Inbox”? Perhaps beside the choice of name for the app …


  14. Hi Ryan,

    I wanted to ask you how the whole switch to Outlook is working out for you?

    Is there any speed issues or stability issues running Outlook via Parallels. I know that initially you said it ran at near native speed, just wanted to check with you a few weeks down the track. I use Entourage, but have considered the same route as you (mainly to make syncing to my PDA/phone a little easier).

    Anyway, just thought I would check to see how you are getting along with the switch.

  15. Craig, thanks for the tip on ‘Nelson Email Organizer’. I’ll check it out!

  16. I switched to Gmail for your Domain a while back, and haven’t looked back. Nonetheless, it’s convenient to have offline email access as well.

    I’d look at switching back to Outlook the moment that I can update my Google calendar from within Outlook Calendar.

    On a different note, where did you get that sexy hat, Ryan?

  17. No delete key on the Macbook, eh? I noticed that today on a friend’s computer. Insane.

    Next thing you’re going to tell me there’s no right-click button either. :p

  18. Jeff Ward on March 29, 2007 at 6:20 pm said:

    Using the “touch it once” philosophy of GTD. You should get everything relevant out of your e-mails and into your “trusted system”. For me, Apple Mail is so simple that it forces me to maintain my “trusted system”. Apple Mail has severly “underdone” the likes of Outlook and I like that.

    43Folders has some good tips for archiving your messages and relying on spotlight to retrieve what you need. Also MailTags have been useful – a plug-in for Mail.

    I moved to the Mac 6 months ago for a simpler life. From desktop to laptop. My life has been simplified and I cringe everytime I load up Parallels to test on PC.

    I wonder if the next version of Entourage would suit your needs.

    Thanks for the post.


  19. Ryan, keep this thread going – it is really useful for us all.
    I’d love to hear your summation of next actions.
    I think there are a lot of us who work ‘just like you’ and you can do the leg work for us as a service to humanity 😉

    Quality mate!

  20. Hi Ryan,

    Google Apps for your Domain is one of the best solutions and one that’s the fastest in performance, plus, available any pc that you’d want to use, anywhere you might be.

    I used Outlook from 2000-2004 and one of the main issues with Outlook is it’s speed once you have a lot of information stored on your .pst file (the file that stores everything), plus, it’s bloated when it comes to working with it.

    Searching your mail is quite slow, hang-ups are frequent (or untimely) and you have a huge problem with viruses (on the pc, not sure about the Mac, never used one!). I really don’t have the time to work with Outlook anymore – it ruins your time, over time.

    Instead of flags, you can tag your mail in Google’s Gmail and that way it makes recalling emails more relevant, at least a bit more web2.0ish. Each mail can also be linked to an event which helps integration with Google Calendar to set reminders.

    All this for no fee at the moment, unless you upgrade to their paid version and require around 10GB of storage per mail account. The standard you’d get is 25 mailboxes at 2GB each – not bad for office work at all.

    My entire company uses Google Apps for your Domain and we’ve been on Google Mail first and now Google Apps for your Domain, for the past three years!


  21. How about Google mail and calendar? You might miss the flags though!


  22. Craig Heimark on March 23, 2007 at 3:20 pm said:

    I run excatly the smae set up you do, meaning I know use Apple Apps for everything except email. For me the mailtags apps plus the functionalisy of the yet to be released Leopard has the potential to bridge most fo the functionality gap, but the real problem is the syncronization protocol.

    I use my mail as my storage file. Plus I travel a quite a bit and so the myriad of hosted email apps (gmail etc) without syncronization to a local store do not cut it for me. Further, without the security of everything being on both my exchange server and my local machine I would have to go to some other potentially complicated backup soulution. So my I cannot use an online version and the size of my email is huge. I have successsfully moved everything to the mac side, but the problems comes when I try to syncronize. It appears the Mac client does not have knowledge of which emails have changed so it checks is one of them individually. So even when I just have a handful of new messages it takes an hour or two just to connect and syncronize. This is a nonstarter. I have tried entorage with my excchange server baskend. I have tried moving the backend to Firtst Class. I ha vetried innumerable Mac clients, with a IMAP connection. None work for squat. I have been told the problem is a lack of a decent MAPI client (which is why I tried Frist Clas, but the local app was so bad, I couldn’t make the migration

    So my email remains in a windows prison, despite the fact that I like almost all of the other Mac apps better

    BTW, if you use outlook, consider a small app that sits on top of Outlook called NEO (Nelson Email Organizer) It essentially automatically tags and allows very efficient search on all of your email. It works for me and I love it


  23. Ryan -for backups I would suggest using something like handybackup to copy your outlook file to a shared parallels folder. This shared folder will then get backed up when you use superduper.

    This is exactly what I do for my Quickbooks company file which I run in Parallels. Handybackup is useful as you can get it to zip up the file, do incrementals etc.


  24. Ben Williams on March 23, 2007 at 9:56 am said:

    You may qualify for the Microsoft Action Pack subscription which at £200/year gets you tons of software that you can use to run your business on- basically all the non development software microsoft produces.

    10 XP licenses, 10 office 2007 licences all the servers etc etc. Stop subscribing and your licences exprire but I can think of no better way of kitting out your entire office with XP and Outlook2007 (+Excel etc) so that everyone is on the same page and you can really maximise Outlook’s benefits.

    You get quarterly updates sent through the post with all latest software updates and releases (it include Expression set of tools as well as for some reason these are not classed as development tools). A total bargain for your business.


  25. Why do you need all of this? Looking at the screenshots, it looks like you just need to go over and talk to Gillian more often 🙂

  26. Yikes, Outlook… you must have been desperate.

    I can highly recommend Daylite, it’s a Mac app which blows Outlook (and iCal/Address Book) out of the water. It syncs every which way, does loads of neat stuff for managing projects, leads and more…

    You really need to check this out before you get too committed to Outlook and it’s infamous disappearing data.


  27. “Why I’m switching # 3”: Have you looked at http://www.spanningsync.com ? It’s bidirectional syncing for ical and Google Calendar. It’s a bit pricey but if it solves a real problem it might be worth it.

  28. Leopard is just around the corner, it addresses tasks, todo’s notes and the underlying architecture of Mail. I get the feeling you’ll want to switch back when it’s released – but believe me, getting your super important data back out of Outlook is one hell of a task.

  29. Luciano on March 22, 2007 at 3:16 pm said:

    Great post because i was looking for a better to-do application for mac and here i found it
    What do you use for invoiceing and accounting in MAC Saludos

  30. Ryan,
    I’ve been using Google Apps for my firm since it was in beta and really like the ability to tag emails as opposed to putting them in folders. You can multiple tag things and star them for really pressing matters.
    Also, Google Calendar is integrated with the Apps Gmail, and you get the ability to set up company calendars, a company start page, etc.
    It’s a nice solution. And I’m still using the free version, which is nice. Even premium is pretty cheap…

  31. Hey Ryan, thought I’d pass on an Outlook keyboard shortcuts post I wrote. Helps you to quickly file away stuff that has already been dealt with (or that needs to be dealt with!).

  32. Leopard’s Mail app will be superior and I look forward to it. It has Notes and ToDos which you can prioritize etc.


  33. Are you using Parallels from a Boot Camp partition?

    If you use it as a virtual machine file I think it could still be backed up with Super Duper.

  34. Ryan, what do you mean it doesn’t solve the problem of iCal and Mail not talking to each other? That’s exactly what it does.


    It integrates scheduling and todo’s directly in to mail with mail messages.

    You should also check out MailActOn by the same company:


    It lets you attach key strokes to action so you can organize or take some other action by simply pressing a couple of keys.

  35. Try this to connect your vm through osx without using another IP address.


    is there any reason why Entourage doesn’t do it for you?

    Entourage is like Excel for Mac. Its a sad, sad shadow of it’s Windows counterpart. Poorly designed and executed.

  36. Have you checked out MailTags?

    Yes, and it’s great. However, it doesn’t solve the problem of iCal and Mail not talking to each other (which is ridiculous, IMHO).

  37. I never use Mail either, just Gmail, but is there any reason why Entourage doesn’t do it for you? Same MS product.

    Maybe this stuff will improve when Leopard ships with a new Mail.app or Mac:Office goes Universal binary…

  38. I have to say I am more than a little surprised that that you never mentioned Thunderbird from Mozilla at all, not even in the comments thus far? Thunderbird is much more superior than Mail!

  39. For annoyance 5, try switching to “host only” networking. That way Parallels doesn’t have to have its own IP address – it uses your regular Mac as a router.

    Hey Simon – I’ve done this and I’m having trouble. Any special settings you’re supposed to have in XP?

  40. Try this to connect your vm through osx without using another IP address.


  41. Couldn’t agree more. I have a mac (my wife uses it) and I think the mac is fantastic. I run Vista and I think that is fantastic too. My wife absolutely hates iMail and has switched to just checking her email on the web.

    I actually thought iMail was pretty good – far better anyway than Outlook express that I was using pre-Vista. Anyway – now I’m using Outlook 2007 and it’s the most efficient, fastest email client I have ever used, I couldn’t imagine using iMail it would be a huge step down.

    Typically everything on the Mac is better, but Vista really has raised the PC bar and for Mail, it’s hard to beat Outlook 2007, certainly iMail doesn’t even come anywhere close.

  42. As Simon said you dont have to use the bridged ethernet setting in parrallels. I thought the shared networking feature was for what you want, but the host only networking might work. I havent managed to get parallels to see the internet when using host only, but I can see it form my mac no problem.

    It’s a ballsy move to go wholesale into outlook, it does beg the question, why not jsut use a PC? You staying with a Mac for cool factor or because you have other apps you need to run in OSX? You could always move parrallels into bootcamp and have the best of both worlds?

  43. Ryan, Julian Schrader is head-on with MailTags and Ghost Action! Have you tried to fasten up Mail.app? Check http://www.hawkwings.net/2007/03/01/a-faster-way-to-speed-up-mailapp/

    There really isn’t any reason to use Parallels (it’s some nice software, but slow as hell…)

  44. Or, you could just do what I did, and put Outlook 2007 on Windows Vista… Who needs a Mac anyway? 😉

    Seriously though – I’m really loving Outllok 2007 too. Huge improvement over 2003. The upgrade to Vista is not really worth the money, but the upgrade to Office 2007 is. The whole suite has substantial improvements over pervious versions IMHO.

    Ryan, I don’t know how this works for your set up, but on Windows you just need to make a copy of your PST file – all you mail, contacts, to-do’s etc are stored there. Just need to access that file in Parallels from your Mac somehow.

  45. For annoyance 5, try switching to “host only” networking. That way Parallels doesn’t have to have its own IP address – it uses your regular Mac as a router. It solves all sorts of problems relating to things like VPN; the downside is that it’s much harder to connect to a server running in Parallels from a machine other than your Mac.

    Did you look at Entourage at all? I haven’t tried it myself, but I’ve heard good things.

  46. I definitely second the MailTags tip. It just makes Apple Mail so much more powerful (categorization by flag, tag/keyword, project or due date, create and sync events and todos in iCal …) and if several people in the company use, you can even include MailTags data in emails you’re sending to each other (might help with delegating, although I’m not really using that feature).

  47. I found an excellent program for (at least my) GTD needs in Ghost Action (http://ghostparksoftware.com/). It’s good in that it links iCal and GTD in a way that you can still use the Mac ToDo system, for checking stuff off etc without having to fire up the app. Not so great for the using email as reminders thing though I’ll admit, but my needs seem to be simpler than yours.

    As for slow Mail… there’s a quick hack (that should be built in) that lets you recompress your mail folders for extra nippy-ness… see http://www.hawkwings.net/2007/03/01/a-faster-way-to-speed-up-mailapp/

    Just my few cents.

  48. The Mail/iCal/Address Book combo works perfectly for me.

    Additional flags/create to-dos right within Mail? MailTags.

    iCal to-dos? Ghost Action.

    Address Book as a single app? Combine everything via Quicksilver—you can access contacts, quickly look up e-mail addresses and phone numbers, create to-dos, etc.

    And everything syncs to my phone—perfect solution.

  49. Hey Ryan.

    Have you checked out MailTags?

    It’s a great plugin for Mail.app that adds a heap of features, including tags and really nice integration with iCal.

    Might work out nicer in the long run then running Outlook…

  50. Boe! I hate Outlook, it’s the most disasterous program i have ever used. Although i really like Paralels…

    What are you planning to do when the new Mail.app is released with GTD functionality? Switch again i hope. 🙂 I would hate to see sometbody like you switch to the wrong e-mailclient.. 🙂

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