Before that, I had been using The Omni Group’s venerable OmniFocus as my task management tool-of-choice, mostly because, in mid-2010, I convinced myself I absolutely needed over-the-air sync between my Macs and iPhone (Omnifocus has it; Things does not).

Now, if you’re like me, you probably follow the work of some notable figures in the Mac community; people like Ben Brooks, David Sparks and Merlin Mann. It seems that those guys are OmniFocus ninjas. There’s nothing they can’t do with OmniFocus. I’m just not that good, and I don’t think I ever could be. To make the most of OmniFocus, I feel like I need to become both a GTD guru and commit hours and hours of my life to learning the software. Things, on the other hand, is so simple it requires almost no learning. For someone as old and inflexible as me, that’s a bonus!

Fiddly Bits

In trying (for six months!) to really get to grips with OmniFocus, I discovered that its greatest strength can also be its greatest weakness — everything is just so endlessly tweakable! Start dates, due dates, priorities, flags, perspectives, custom folders, nested folders, projects, location awareness, contexts, actions and who knows what else all add to the mountain of fiddly bits of detail that can be added, edited and generally mucked-about-with. In fact, there’s so much scope for fiddly details that Omnifocus offers its own Inspectors to make it more manageable. To be honest, when I have to open an Inspector, I don’t feel like I’m using a to-do manager any more.

Let me be fair; OmniFocus is a wonderful tool. But I always felt like I was neglecting some awesome functionality that could make me super-productive. I suffered a kind of productivity anxiety with OmniFocus: a nagging worry that I wasn’t making the most of this fantastic software the Merlin Manns of the world talk about with such enthusiasm. Finally, though, I’ve arrived at something of an epiphany; I wasn’t missing anything other than the discipline to stop tweaking my to-do lists and just get things done.

Choices, Choices

Mac users today are spoiled for choice when it comes to powerful, beautiful productivity software. Don’t like Microsoft Office? No problem; use iWork. Don’t like Pages? There’s always WriteRoom, Scrivener or TextMate. Every one of those apps is a great word processor without the Microsoft bloat.

This philosophy of “less is more” should be familiar to us all; it’s baked-in to Apple’s DNA, and it seems poised going to become even more of a Mac feature with OS X Lion. It’s also the reason Pages isn’t like Microsoft Word, and it’s why the iPad isn’t a Windows 7 Tablet PC.

So why, when it comes to personal productivity software as fundamental as a to-do manager, do we often think we need more complexity, more sophistication and ever more bells and whistles? Could it be that we all trick ourselves into thinking that time spent poring over our to-do’s is time spent getting things done?

One of the primary reasons for my switching to the Mac was the Apple philosophy of design; everything that’s there — be it in the hardware or the operating system — is there for a clear and obvious reason. It’s simple; it’s easy, and it all just gets out of the way so I can concentrate on doing my work. That’s why I stick with Mail.app instead of using more sophisticated apps like Mailplane or Postbox. It’s why I use TextMate instead of Word. And I suppose I could even use TextEdit to keep a list of tasks; but then, that wouldn’t be as much fun as putting a tick in a box, would it?

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As I tend to work at home during early mornings and evenings, the biggest challenge in this new strategy quickly became how to keep files and app data in sync across the two computers. Now, to be fair, I didn’t approach this in any strategic way, but over the ensuing few months, I have migrated much of my Mac life into the cloud (for those interested in cloud computing or data centers, check out our Structure 10 conference in June). Here are a few of the key ways I made this happen.

Mailplane + Gmail

I have several email accounts for various projects and my personal needs, and they are all either Gmail or Google Apps accounts. Previously, I set them all up as IMAP accounts and used Mail.app as a client. Even though I accessed most accounts on a daily basis, Mail.app — despite its superior UI — quickly became an untenable solution. True, I can sync accounts, rules and other data using MobileMe, but I noticed some inconsistencies in the way messages were displaying, and I was using precious disk space on duplicate mailbox files, caches, and temporary files.

Mailplane is the perfect solution for me. As a direct view of the Gmail web interface, Mailplane ensures that there aren’t any inconsistencies. And nothing gets stored locally unless I choose to download it. Like Mail, I can easily switch between accounts, and I also have direct, integrated access with Address Book.

MobileMe for Address Book and Bookmark Syncing

Speaking of Address Book, Google’s contact manager is pretty weak, and despite integration with Gmail, I am not ready to turn my contacts over to Google’s less than desirable product. So I keep Apple’s Address Book as my primary contact manager, and sync it across MobileMe among my Macs and the iPhone. Syncing only certain contacts with others — my wife, for example, for our shared social contacts — is the next step for me. I am also using MobileMe to synchronize Safari bookmarks. Having the same bookmarks across devices has proven to be a lifesaver from time-to-time.

Google Calendar (including Mobile Sync) + Fluid for Calendars

As I described earlier, I have several Gmail and Google Apps accounts. With Mailplane, you get to see a list of accounts in a sidebar, and easily switch among them without having to enter your username and password each time. I’ve even combined some accounts by using one to send and receive mail from another, and deleting the account in Mailplane. To my knowledge, there isn’t a similar solution for Google Calendar. So I’ve set all my calendars to be shared with my primary account, then used Fluid to create an app-specific browser for the consolidated Google Calendar. As a result, I have one calendar app that displays all my various calendars but allows me to keep them separate (different colors, turn on/off, etc.).

SugarSync for File Synchronization

I have longed for Mac OS X features that allow file and folder-level synchronization across computers, to no avail. Many in the Mac community swear by DropBox, but I chose SugarSync for a couple of reasons. First, with SugarSync, you can add any file or folder on a computer to your sync profile, regardless of where that file lives. At least when I looked at it previously, DropBox required you to set up a special sync folder and move your files there, forcing me to reorganize my files, not something I wanted to do. And there’s always price: SugarSync is $5/month less than DropBox at the 100GB storage level. I now often save a file on my office computer as I’m leaving the office, then open it at home with those changes reflected.

Google Docs for Collaboration

More and more, I find myself working with others on projects that require collaborative editing. Google Docs is a great solution, as it allows multiple people to access and share documents, spreadsheets and presentations. The user interface and available styles aren’t exactly aesthetically pleasing, but Google Docs works really well. Google recently added the ability to entire folders, not just documents, which made it even more valuable to me and my collaborators.

OmniFocus and Evernote

I’ve got a lot going on (probably too much), and I’ve started and stopped using various task management applications multiple times. I love Things, but I can’t live without hierarchical organization of my information and the Wi-fi based syncing with iPhone is tedious. I also really dig The Hit List, but after many months Potion Factory is still taking pre-orders and hasn’t released an iPhone app. I’m worried that it has stalled. I keep returning to OmniFocus from The Omni Group, which has some powerful organization and management capabilities, and also syncs perfectly among Macs and the iPhone. Lastly, I’ve recently rediscovered Evernote, whose web-based syncing has proven effortless and reliable (more on Evernote in a future post).

My Mac Life in the Cloud

I haven’t yet bothered syncing media, as I tend to simply use my iPhone for music, photos and more when I’m away from home. In the meantime, it seems like I can be anywhere and have access to all the files and data I need.

So, how are you keeping multiple devices in sync and using the cloud to make your life easier and more efficient?

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Sadly, Gmail’s recently introduced Tasks feature doesn’t offer offline or mobile sync, my iPhone’s default Notes app has no desktop or web equivalent and Apple Mail‘s To Do capability send my Gmail account’s IMAP sync into a tailspin.

I’ve experimented with OmniFocus (a little complex for my taste) and  Things – supremely elegant, but quite expensive with iPhone and desktop editions priced separately. Now, my business partner swears by Hog Bay Software’s TaskPaper – a product we covered earlier this year, and has just rolled out a 2.0 update of its software.

As Mike alluded to in his May review of TaskPaper – ‘sometimes simple is best’. TaskPaper makes no allusions to competing with its GTD-infused brethren, such as OmniFocus or Things, but reinforces the notion that a plain text document, marked up coherently can be very powerful indeed.

TaskPaper 2.0 adds a search engine, quick entry window, keyboard shortcuts, themes, a projects sidebar, AppleScript support and some UI tweaks. Despite all these additions, the product still feels elegantly simple, powerful and lightweight, retaining its orientation around a text document. Indeed, despite the lack of web or phone editions, the plain text core is actually the foundation for a powerful ecosystem of third-party solutions, one of which – Taskphone – is looking to bring Taskpaper support to the iPhone.

Personally, I’m not fully won over by any solution yet – holding out for a good Google+Apple linkup – like the interoperability of Gmail+Apple Mail or Google Calendar + iCal. However, right now its a toss up between the versatile, but plain girlfriend (TaskPaper) or the glamourous and expensive mistress (Things).

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I’m sure most of you have read, or at least heard of Getting Things Done by David Allen. He started a real productivity movement, and has millions of dedicated followers. He has excellent and practical advice for organizing your life and work, and there are a lot of tools available that you can use to take advantage of his recommendations… some specifically designed around his methodology. OmniFocus is one of them. At its core, OmniFocus IS “GTD” task management. Don’t worry if you don’t know what GTD is, fortunately you don’t have to know anything about it to become more productive using OmniFocus. For more information about Getting Things Done task management, check out David Allen’s website.

How OmniFocus is Different

OmniFocus categorizes your to-do items in two different ways, projects and contexts. At first this may seem to waste time, but once you get in the habit you’ll find that it’s amazing how simply you can manage your to-do’s this way.

Projects
Just as they sound, projects are anything with a desired outcome. You can probably think of many projects right now if you try. Everything from “file taxes” to “go to the beach” is a project. You’ll have projects related to work, and projects in your personal life.

Contexts
Contexts are where or how you get things done. To write an article, you might need to be at your computer. To file paperwork, maybe you’d have to be at your office. To call a client, you’d need to be around a phone. Contexts associate actions with the context in which you’d perform them, so you can group actions by where you will be or what you have access to.

OmniFocus for Mac

The desktop application is a fairly straightforward but there is a great video tutorial on the OmniFocus website and a quick reference card you can download. The home screen is comprised of a menubar at the top, projects or contexts in a sidebar on the left and tasks on the right. When OmniFocus opens it returns the context or project you were last viewing before you closed the program.

Inbox
The inbox is the “home screen” of OmniFocus. Here any uncategorized tasks without a context will be waiting on you to categorize them. This is similar tot he GTD inbox in that it’s just a temporary holding bin for tasks you need to record quickly. You should go through the inbox regularly and give each task a project (even if it’s miscellaneous) and a context.

Quick Entry Shortcut
One feature that I absolutely love about OmniFocus is the quick entry shortcut. The shortcut lets you quickly enter tasks, even when OmniFocus isn’t the frontmost application.

Email Entries
You can email yourself tasks when you’re on the road, and OmniFocus will grab them and add them to your inbox. I tested the feature and it works well, but since I use the OmniFocus iPhone application, I don’t really have a use for it. Blackberry or Treo owners will find it’s a lifesaver though.

Backups
OmniFocus might just be a little OCD when it comes to backing up your information (which is a good thing). It seems by default OmniFocus backs up your database twice daily and when you close OmniFocus. If you open OmniFocus several times a day, you can easily rack up half a dozen backups in a day. Of course, this is better than losing tasks you’ve entered due to a software or system crash.

OmniFocus for iPhone

I’m surprised that over a year after it’s initial launch, the iPhone still has no ability to sync iCal tasks. When OmniFocus released the iPhone application, I immediately purchased it even though I had never used the desktop version. I had already tried several free (and a couple paid) task management applications from the App Store and none of them worked well for me. After looking at the information on their website, and knowing it was built around GTD, I was comfortable spending $20 on a quality GTD task management system.

The iPhone application is simple, easy to use and has some great iPhone-centric features.

Adding New Tasks
Adding new tasks is the best feature of the iPhone application, and the one that will likely be the most used. When you’re in the car or eating dinner at a restaurant and suddenly think of something you need to do, what do you do? Take out a napkin or scrap of paper to write on? Then what? A week or two goes by and you lose the scrap of paper containing the note, forget completely about the task and only remember it when it’s almost (or already) late. Adding tasks in OmniFocus for iPhone is extremely simple, and the new task button is on the menubar in every screen. You can also attach a voice recording or photo to the task, which is a very handy feature. You can give the tasks a context and project or just let them sync to your computer and organize them later.

Location Aware
You can associate contexts with geographic locations. Office and home are two excellent examples, but you could do many more. Then just hit the location icon in the menubar to find all the tasks near your current location.

Syncing
To sync with OmniFocus on your Mac, you have to have the latest “Sneaky Peek” version, which you can download on this page. The full upgrade from 1.0 to 1.1 will be a free upgrade, so don’t let that keep you from purchasing OmniFocus. I’ve found the “Sneaky Peek” version to be very stable. It seems the only changes over the stable version of OmniFocus 1.0 is the iPhone syncing.

Conclusions

I have found few flaws in OmniFocus. I’ve managed to get it to crash a handful of times but that’s not really any different from any other application on my computer. I crash Firefox 2 or 3 times a day so I can’t fault OmniFocus too badly for crashing 2 or 3 times in the month I’ve been using it. I’ve used it day-in and day-out.

If you need better task management and want something that will work both on your Mac and iPhone, I highly recommend OmniFocus. My only caveat is the price. At $80 for OmniFocus, the $20 iPhone application hurts a little. I wish they’d give the iPhone application to registered users of OmniFocus. It would probably increase sales of the desktop client (and $80 is better than $20!)

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The “Omni” apps are well-crafted products and their programmers do their part to make code available to the developer community so folks can use components that work well without having to reinvent the wheel. As a company, they also seem to care about the users of their products given that they went out of their way to cite a review on their blog which contained both praise and pummeling.

(D&D fans will also appreciate this entry which explains how to use OmniFocus to manage your 4th edition character sheet).

If you use OmniFocus for “getting things done”, drop a note in the comments with what works and what needs improvement.

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