Working the Big Picture: Project Management on the Mac

iCal handles basic time and task management fairly well with the addition of a few utilities (see Unleashing the Power of iCal and Managing Tasks with iCal's To-Do Feature). But what about working through larger projects and working with other members of a project team? Do Apple's applications serve as a suitable replacement for Entourage in this case? Can iCal step up?

I say yes, but not because of an elaborate project setup like Entourage.

Project Center - Thumbs Up or Down?

Entourage's "Project Center" is, admittedly, a pretty sweet tool. Those who require this kind of project management power will appreciate how Entourage handles them - the direct integration with the mail, calendar, and task-list functions of Entourage is an obvious strength. It also integrates well with Word, Excel, and PowerPoint via the Project Gallery and the Toolbox.

Project Center can help organize documents, emails, tasks, dates, contacts, and other files all into one conglomeration. There is a lot of power in Entourage's Project Center - I'll be the first to admit that.

I have a few complaints about it that shape my use - or lack thereof. To begin with, Project Center seems like a thin version of Microsoft Project, which is only available for the Win-d'ohs platform.

Think of it this way: Project Center is to MS Project what Outlook Express is to Outlook. While I don't particularly like MS Project or Outlook, I can at least appreciate the power and usefulness that each includes (ones their scaled-down counterparts often lack). If I'm going to the trouble of setting up a project in Project Center, why can't I at least have a Gantt chart to accompany it?

Also, there are a number of features that are prominent in Project Center, but there is no easy way to figure them out. What is a clipping, after all? Okay, so after some digging I find that it pulls things from the Microsoft Scrapbook. What's that? Do I have one? Yes, it turns out - think of it as a "permanent clipboard" of sorts, but it's apparently available only through other Microsoft apps.

Another one: Do I need both "Projects" and "Categories" for my items? There's a place for both, and while neither are required, there's a good bit of overlap. Microsoft doesn't want to give me much guidance with figuring out when I should use which - or both, for that matter.

My biggest complaint with Project Center - and Entourage as a whole - is that it is inflicted with the common Microsoft problem: being overly feature-rich. The default algorithm in Redmond appears to be this one: If faced with a choice of simplicity or feature-richness, always choose feature-richness.

This defeats the Mac's zen-like appeal every time.

There is just too much stuff to manage, set up, check off, or import with Project Center. Like I said, it is an admittedly sweet tool for those who need it. Though I would like to think of myself as someone important enough to need such a tool, I just don't need that much project management. (And, frankly, I'm probably happier that I don't.)

Project Management, Mac Style

When it comes to project management, I mostly rely on the built-in elegance and integration that exists in the Apple "suite" of applications. As I've covered in previous articles, there's already plenty of integration among Mail, Address Book, and iCal.

Let me take a moment to liberate some of you Entourage folk: Just because Microsoft designs it that way doesn't mean that it is the only way it can work. To unpack that a little - like many of you, I had gotten so used to programs working "the Microsoft way" that I had difficulty adapting to other ways.

It's okay to admit it if you feel this way too. So many of us believe that the only way the functions of an application can "integrate" is if they all appear in the same window - or at least there must be a button, tab, or menu to invoke them.

I, too, was skeptical that it was possible to break outside of this paradigm.

To those of you still locked inside it, I have two words for you: AppleScript. Spotlight. (Okay, one more: Macintosh.) Apple has been building a system that allows more and more integration, collaboration, and cooperation between applications, and dadgum if they haven't just about hit the nail on the head.

So when I set out to manage a project, it's sometimes as simple as creating a set of folders - or better yet, smart folders - in each application to organize the "stuff" for that project. Believe it or not, this might be all that's needed.

Make It a Little Simpler, Please

All right, if you must have a shortcut, try Working Pathways's ProjectMaker widget. When you install it, you'll be surprised (and probably a bit disappointed at first) at its simplicity: clean, bare, Mac-like. Choose which folders you want created, give it a name, and you've just made new folders or other units in (you pick): Address Book (creates a group), iCal (creates a calendar), Mail, and your Documents folder. Now you have ready-labeled repositories for everything related to that project.

That's Not Enough

You're a madman! Okay - and this is it, I promise! - now go get Indev's MailTags and install it. Be sure to get the latest version, v.1.2.x.

I've talked about MailTags before, but the new version offers the missing link for doing even fairly complex projects with Mail. The new features include the ability to make a Mail message into a task-list item - yes, you read correctly - and it coordinates with the message and tags.

Further, you can have it added to a specific calendar if you wish. Add some meta-tags and other data via MailTags, and your stuff will show up in Spotlight more efficiently. (For the double-whammy - now this is not for you lightweights - install Indev's Mail Act-On and set up rules that will drop it into your project with whatever metadata you want.)

Beyond the Apple Trifecta

Mail, Address Book, and iCal end up being a solid bet for project management. But what do I do when I need more project management capability than the Apple apps can provide?

This is where Entourage really goes awry. Everyone is looking for the "magic bullet" productivity application, and Microsoft puts Entourage up as their "magic bullet" - or at least, they figure if there is no magic bullet, then at least they can give you a big, heavy, complicated-looking gun loaded with regular bullets.

The truth is that there is no magic bullet.

The truth is that there is no magic bullet. The beauty of working productively on the Mac is that there doesn't have to be. Instead, you can collect the small, clean, elegant apps that you like - and that do what you need them to do - and very often watch them integrate in a way that makes Entourage users and others drool. (In a sense, then, you could call OS X the "magic bullet" killer app, since it enables all of this to happen.)

So here's where it gets fun: When the projects I'm managing gets bigger than what I've already described, I turn to Ethan Schoonover's Kinkless GTD. Kinkless GTD (or kGTD) is an OmniOutliner Pro template and a set of AppleScripts. That's it. But for the hardworking, productivity-needing efficiency guy what it does is just short of amazing.

Well, okay, it is amazing.

kGTD lets you plan out projects in detail, following (as loosely or rigidly as you'd like) David Allen's Getting Things Done system. While this is a thorough and well-developed productivity system, the gist of it is this: You'll get a lot more done if you can just get all of those things that you think you need to remember into a trusted and accessible system - something you know you can count on - so that you can finally forget them. Then just focus on the next thing; your trusted system will remind you of what's next after that.

kGTD provides that trustable system. Get it all out - whatever you need to do - into the system, and then let it do its job. Here's what you'll find: a way to look at your comprehensive project (or projects) by action item, project, context, start date, end date, or priority. You can view them as complete projects or as a list of "next actions". And the best part is this: You sync it with iCal, and all of these become task items in your iCal world.

Like MailTags, kGTD has just seen a new release that brings some major additions and new tools. Besides simplifying the interface considerably (since kGTD uses AppleScript buttons in OmniOutliner Pro), one of the really big ones is the ability to sync both ways: Not only can kGTD inform iCal about new tasks and projects, iCal can also create new tasks and projects in kGTD.

And you can also use MailTags to create a new task in kGTD: You'll need to set your "MailTags" iCal calendar as a context for kGTD, and when you use the "shorthand" for kGTD in MailTags, you leave out the context. But once you've got it in kGTD (and in the right project), you can edit the context and use kGTD for what it is best at, organizing project tasks.

Here are a few things you need to know: First, kGTD requires Omnigroup's OmniOutliner Pro, which costs money (US$70). But, as software goes, it's pretty affordable, and there's student pricing available if you're eligible. Second, it's very helpful to be familiar with, if not actively practicing, Allen's Getting Things Done (GTD) method of task management. Finally, there's a whole lot more information available about GTD, Kinkless GTD, and using both. A few mandatory starting points are Schoonover's Kinkless site and Merlin Mann's 43 Folders (be sure to check out his series on using kGTD).

In large measure, these tools cover my project management needs. When it comes to working with others on projects, that's a different story - and a different article. Check back on Thursday for some ideas about tools for working on projects with others. 

• Link: ProjectMaker
• Link: MailTags
• Link: Mail Act-On
• Link: Kinkless GTD
• Link: OmniOutliner Pro
• Link: 43 Folders