A long introduction about a postage stamp, a purple E and why you should read this:

This is a article story for MAC OS X users. It'll explain how and why i switched from Microsoft Office's Entourage to native MAC OS X applications about 12 months into using my Mac. As you can see above, it's not a straight switch - it's a migration from one program to three.

I booted into MAC OS X for the first time about 18 months ago. One of the first things i did in OS X was play around with the built-in applications. I remember opening them up one after the other, only to find myself largely disappointed with what i found.

I hadn't realised how Windows had ingrained a set of values in me through extended use. In the Windows model, applications had to have complex interfaces with multiple toolbars, panel sets and dozens of small icons - after all they were smart, so they had to be vast, right? Programs came with huge lists of features and considerable licensing fees. In contrast these Mac applications, bundled for free with OS X, looked incredibly simplistic and weak - just a few buttons and a couple of viewing panes in each. Moreover, Mail had this postage stamp icon with an Eagle that made me wince each time i came across it.

I didn't think long before installing the entire Microsoft Office suite onto my new Mac. After all, this machine was for my contract work, and everyone uses Microsoft file formats in the so-called 'Real World'. I wanted enterprise software for business use - none of this flimsy, gratis, bundled-with-my-machine Apple type stuff. I felt at home straight away in Entourage, which gathered all my emails, contacts, projects, tasks and notes. All these things needed to work together, so bundling them made sense to me. I hadn't realised it, but i was implicitly using Entourage as a fully-fledged project management tool as well.

And so i went along with this set-up for months. Along the way I started getting a feel for third-party OS X software; how most of it looked and worked the same, how well the applications talked to each other and how this was helping my productivity. By contrast, Entourage was a little clunky and difficult to work out at times, what with so many features hidden in so many nooks; and it refused to play nice with other applications. Still, it worked ok and did a million and one crucial things for me.

More time passed. My Mac was teaching me that applications that worked ok were not good enough for this platform. The word 'ok' is not in the Mac vocabulary. There was a bunch of software here that worked better than ok. It worked great.

Over time i had come to learn a single enduring lesson from my use of Max OS X,

• Do not fight the Apple. The Apple is always right.

And i had come to see how applications which played well with the Mac operating system ended up playing well with others, and how playing well with others is the single most important thing in the organisation of your digital world.

It was these observations, along with the realisation that i needed a long-term organisation solution, that finally caused me to switch to Apple's native OS X programs.

The difference with these Mac apps is each one carries out a clearly defined task without getting too ambitious. So where Entourage is a:

• Mail client


• Contacts manager


• Notes & tasks aggregator


• Shared project management tool


• Calendar

Each one of these important functions is picked up by a different OS X application. Each application is simpler to use than Entourage for the respective function. And they all talk to each other on OS X, so you get the integration too.

How You Do It

1. Mail

Importing your email accounts and archives to Mail is a cinch. Just open Mail (Applications > Mail in Finder) and select File > Import. Then select 'Entourage'. Mail will open Entourage for you and do the rest. You can get a cup of tea. In my case it took about 1 hour to import about 6000 mails from 3 accounts.

When the import is done, look under File > Preferences and click the Accounts icon to set up your account details as they were in Entourage. You can find your settings in Entourage under Tools > Accounts. You can also copy and paste your default signatures direct from Entourage and set the rest of your preferences while you're at it. Then close the Preferences tab and try to synchronize your accounts (Apple-Shift-N is the shortcut).

2. Address Book

Easy. Go to the Contacts section of Entourage. Highlight one of your contacts, then press Apple-A on the keyboard to select all your contacts. Then open Address Book (Applications > Address Book in Finder). Drag & drop all your contacts onto the Address Book window (you should see a '+' sign near the cursor when hovering over Address Book). You lose your GROUP information this way, but it's the quickest way to do it. I regrouped my contacts pretty quickly, and ordered their information/removed duplicate names in the process. Took me about 15 minutes, but i guess it depends how many contacts you've got :)

3. iCal

Again, open iCal (Applications > iCal), go to File > Import and choose 'Entourage'. You will lose the categorisations you have placed on existing events (bummer but no big deal for me - these have already occured, and all the information is intact minus the colour scheme). You'll need to re-declare categories in iCal. Tasks have been imported along with your events and are visible by clicking the pin icon in the bottom right. They're now called 'to-do's' - sounding altogether more friendly than the quite ominous TASKS. iCal has notifications built-in.

Your just rewards

Integration

Remember how i thought Entourage was smart for bundling everything i needed together? On a Mac you don't need to do this, since applications can talk to each other. For example,

• Drag a contact from Address Book onto an event in iCal and they'll be added as an attendee


• Click on an event in iCal and you can email all the attendees via Mail.


• Add photos received via email to your iPhoto archive with one click


• Contacts in your Address Book are automatically integrated with a bunch of applications, not just Mail/iCal.

Rules Rule

Look under File > Preferences in Mail and try the Rules icon. This is where the integration of the apps comes home. I use rules to colour my incoming emails based on which group in my Address Book the sender belongs to (friends/work/admin etc). Rules are easy to set up - you just complete natural language sentences by selecting from a list of options. Web designers take note - this is excellent design and makes setting the rules a breeze.

Smart Folders

Again in Mail - this allows you to catch emails that meet certain criteria, which you set up much like rules. Just like Smart Playlists in iTunes. I don't know if Entourage had this feature - if it did i never looked under the right stone. I use it to catch newsletters and press releases that drop into my gmail account.

Spam Filtering

Mail has an ace spam filter. It works. It learns. It uses cluster analysis and correctly junks about 98% of spam over time. More here.

iSync

You can use iSync to synchronise directly between Address Book/Mail/iCal and your mobile phone or palm device using bluetooth or USB. It's easy to do (for more info check here) and means the next time your mobile device gets lost/stolen (and let's face it - it's just a matter of time) you've got everything on the Mac, ready to import onto your next handset or PDA. No more tears shed over screwed mobiles.

Find mails/contacts/events quicker than you can say William Gates Esquire

Mac OS X 10.4 (aka Tiger - the latest version of OS X), introduces a small magnifying glass icon (Spotlight) in the top-right of the screen. It's a very powerful feature. If you click the icon you get a search box. You can use it to search any of your emails/contacts/events. Your entire database is accessible in seconds and the icon is always there, no matter what you're doing on your Mac. Spotlight + keyboard shortcut = stunning productivity boost.

Sharing

You can set iCal up for sharing calendars - a .mac account
is needed as with Entourage (alternatively you can share using WebDav). More on the Apple iCal page. You can also subscribe to public calendars, for shared timetables/schedules. Your address book is also easily shared. More on the Apple Address Book page.

Free Updates & No Extra Licenses

Apple will update these apps along with your MAC OS X updates, so you get the updates for free. The applications come with the Operating System, so no additional licenses for you.

Wrapping Up

Some Entourage functions haven't been addressed so far:

• Shared Projects
• Identities
• Notes

Shared projects worked really, really bad in Entourage and slowed it down to a halt during synchronisation. As you can see above, you can share calendars/address books no problem under the new setup. I would also recommend the web-based project management tool Basecamp.

Identities are now managed by your OS X username and password - each user on your system will have different Address Books etc.

As for notes - I use Stickies instead, a kind of Mac post-it note (Applications > Utilities > Stickies) or Omni's excellent OmniOutliner for when i'm in meetings.

It's a good idea to plant Mail/Address Book/iCal on your dock. I keep them open all the time - just click Apple-h to hide them and keep your desktop uncluttered.