Meet Joe. He’s an expert but frustrated carpenter that juggles all sorts o’ projects at a time. He also uses a Mac when he’s not making things with his hands. He would love to use OmniFocus to manage his carpentry projects. But he hasn’t so far because he just can not figure out how to sync OmniFocus with his tool belt.

Joe: a swell guy, but pretty stupid.

Windows as a context, not an OS

Substitute Windows for tool belt and knowledge worker for carpenter, and that’s where lots of you are today. I’m sure you’re sharper than Joe, but you want essentially the same thing he does. You love OmniFocus; you use OmniFocus; and you want OmniFocus to sync with all of your (non-Apple) tools.

Well, guess what. That grass you see over there? Not nearly as green as it looks.

As an actuary, I can’t get paid without working in Windows. Until someone writes software for OS X that lets me model massive insurance asset and liability portfolios under thousands of future scenarios, I won’t be in an all-Mac shop anytime soon.

And in all honesty and practicality, that’s okay with me. I have a choice. I can join my other not-all-Mac peers and get all pissy that I have to spend part of my day in Windows, or I can be happily realistic: I love my career (I’m not alone), and Windows is simply a tool I need to do my job. A single tool in my belt. Nothing more.

More accurately, Windows is just a context. It’s a place to to get certain things done.

To the future, briefly

Before you know it, you’re going to be absolutely enveloped in operating systems. Android—I’m certain—is going to be in every thing with an electronic pulse. It’ll be in your car’s dashboard, your home security system, your sprinkler, your [other un-obvious things you haven’t thought of yet].

And Windows. Oh, Windows. Like vaccination needles, fax machines, and other lingering unpleasantries in modern life, Windows isn’t going away any time soon either, but it will become much more niche than it is today. Much.

Even though most of the corporate world doesn’t yet know we’re in the “post-PC” era, it will soon enough.

I’m seeing more and more iPhones in the C-suite; iPads in boardrooms; MacBook Airs on podiums. Lightweight, stable, long battery life, and instant-on is kinda practical, for business even. Who’d a thought?

People, like me, that run proprietary software systems on Windows will increasingly do so through windows—to the cloud that is. I’m convinced that Windows will ultimately retreat from local desktops to data centers where it will be fed and watered by full-time staff.

People who work in Windows will use the window glass of their choosing—most likely tablets and other lightweight devices.

Back to practicality: When does the need to sync end and the work begin?

The fact that I’m already hopping from cloud to cloud as I work in Windows makes me wonder what value installing OmniFocus in Windows would have anyway. On a given day, I might be looking at virtual Windows Server desktops in Chicago, Toronto, LA, Alabama, South Carolina, and other cyber parts unknown.

If there was a Windows version of OmniFocus, where would I install it? Everywhere?

I hope not. Otherwise, I’d be a professional OmniFocus installer—minus the “professional” because that probably doesn’t pay a lot.

Windows isn’t the only non-Apple proprietary computer system I work with either. From decades-old homegrown admin systems to Linux, I touch lots of OSes over the course of a year.

I’m not that unique either. (Well, not in this context.) Ask anyone in the movie industry about the systems in their digital workflow—or ask anyone that creates anything from proprietary electronic tools.

Should your productivity system be inextricably embedded and synced with every tool you use in your life? No. Of course not. It’s impractical and completely unnecessary.

The ultimate PC peripheral

This year, I started using OmniFocus on my iPad to conquer the final frontier in my productive life: The fantastically complicated actuarial PC-based projects I balance. Between you and me, I didn’t think it would work.

Before the iPad arrived in my workflow, I was managing projects using a combination of spreadsheets and mind maps—some of which looked like billion-year-old phylogenic trees.

I’m happy to say that the iPad is working. As usual, not in the way I initially envisioned. But in a value-adding fashion nonetheless.

I really believe that the more of your projects you can manage in a central system, the easier it is to manage and review the priority you place on everything. It never felt quite right having PC-based projects managed separately.

The iPad adds another screen, not another computer

The iPad is the ultimate un-computer. It doesn’t create the perception of having another machine to maintain and fiddle with. When I use OmniFocus on the iPad in a PC setting, it exists solely to guide my productivity.

The iPad isn’t location-dependent either. It can go to a meeting just as easily as it can sit next to a desktop PC. The physical portability of the iPad combined with the very reliable Omni Sync Server make OmniFocus for iPad the most agile electronic productivity tool I’ve ever used.

Before the iPad arrived, I dedicated one of my two PC screens to Freemind, a mind mapping application. Now, I’m able to free up more PC screen real estate for work. Instead of having a mind map on one monitor and “work” on the other, I can have two spreadsheets open side by side—or maybe a spreadsheet on one screen with Remote Desktop on the other.

OmniFocus lets me utilize PCs for what they’re good for, not spread their use across work and task management. And OmniFocus lets me use mind maps for what they’re good for: brainstorming and organizing thoughts before and during projects.

Email marginalization

Rather than flagging action-oriented emails in Outlook, I prefer to archive them using a Gmail-like system that’s far beyond the scope of this post. If it’s an action-oriented email, I’ll tap over to OmniFocus to simultaneously make a simple task and jot something like “see 4/15 email” in the task notes. Sometimes I even make tasks to read longer emails.

Tip: If you record the sender and date of an email, you should be able to find it in seconds—even if you’re using Outlook1.

Honestly, I don’t see a huge need to electronically link email to tasks like you can when you’re in OS X. “Text to mind” links are pretty darn efficient and don’t require any snazzy plug-ins. More generally, if you get in the habit of leaving little text bread crumbs, you’ll shave innumerable hours off of the time it takes to complete large projects.

Your brain is the ultimate cross-platform synchronization tool if you’d just use it as such.

Notes are your friend

If you’re skimming this big bag of words desperately looking for something practical, then stop here for a minute. This is good.

The note field may be the best feature of OmniFocus for iPad. Now that the Omni Group added a full screen view to the notes field, it’s even better. Each action can become a full-blown task “document.”

Since there’s currently no way to paste a list of actions directly into OmniFocus on the iPad and have them become tasks, I often use the note field to create sub-tasks if I’m in a hurry. This is actually really powerful.

Say you already have a list of actions on your PC, or say you’d rather type them with a keyboard. Do it. Get it down.

Then, use an app like Simplenote or myPhoneDesktop to transfer the text to your iPad. myPhoneDesktop—an app that lets you instantly push text to your iPad—is my favorite method. I use it like crazy with OmniFocus to clip notes from email and other things.

myPhoneDesktop essentially “extends” a PC (or any computer) to your iPad making it dead easy to quickly hammer out mini projects on my PC that look like this:

    [x] Task 1
    [w] Task 2
        [] Task 2a
        [] Task 2b
    [] Task 3

Tip for Omni lovers: You can also build a bracketed list like this using OmniOutliner for iPad and then email the outline to yourself as text. Copy the outline into the notes field of OmniFocus for iPad.

An ‘x’ marks a “done” task, and ‘w’ denotes things I’ve started, or things I’m waiting on.

I know what you’re thinking. Just simmer down. I realize that this makes OmniFocus “actions” more like “projects.” Remember this though: You’re using OmniFocus to get things done. Whatever it takes to do that is fair game.2

Get faster

The more you use OmniFocus on the iPad, the more I recommend getting handy with shortcuts like these:

  • Touch and hold individual actions to bring up a cut/copy/paste menu.
  • Quickly duplicate individual actions by copying and pasting them on top of each other.
  • Touch and hold projects to focus them, add actions, or to paste copied actions.
  • Tap Edit then drag actions, projects, or contexts to re-order them.
  • If a project will pertain primarily to one context, assign that context to the project. This way, the context field for individual actions will be pre-filled
  • To quickly move actions under existing actions, tap Edit, then drag them under an action that already has some sub-items.
  • To quickly go from a context or perspective view to project view, tap an action to go to editor mode, then tap ‘Go to project’ next to the project field. Same approach for contexts.

IF(Feels Right, Do it, Don’t)

Not everything needs to go into OmniFocus. [Pausing until the murmurs die down and all swords are sheathed]

If a project can be managed better in a spreadsheet, mind map, wiki, or (God forbid) Microsoft Project, keep it there.

There are clearly situations where it makes sense to manage projects outside of OmniFocus. For example, collaborative projects where actions need to be kept in the open.

You can still use OmniFocus as a guide for these projects. What I do is create high-level “placeholder” tasks like “Working on X”, and I have an ‘IP’ context (in progress) that I use for “actions” that really aren’t single actions, but rather ongoing mini-projects. I like seeing the IPs separately in various perspectives.

The main goal is to keep all projects in view but minimize the need to rewrite projects in OmniFocus.

The right tool for the right goal

Until someone writes Mac software that lets me do 100 percent of my job on a Mac, I’ll be working on PCs at least part of the time. Until someone writes a better overall operating system, I’ll use a Mac for everything else. Until someone makes a better tablet, I’ll use an iPad. And until someone creates a better task management program, I’ll be using OmniFocus.

Whatever the context of your productivity, pick the right tools to meet your goals; don’t choose goals to fit your tools.

  1. I’ve been amazed at how much of my attention I’ve reclaimed by hiding email until I need it and “batching” email-oriented tasks with all my other tasks. There’s really no reason email should automatically get priority over anything else you’re actively working on.
  2. Another approach I’ve used is to paste a text list of actions in the notes field of the project, then cut/paste those into standalone actions as time (and importance) allows.