When I was but a wee lad, in my early 20s, my mind functioned like a well-oiled and dangerously sharp steel trap. If you mentioned to me that you wanted to schedule a conference call in six weeks, six weeks later I’d remind you of it. No notes, no tasks, no calendars. I just remembered. Everything. All the time.

Then I reported to a boss for whom this thing called memory was a dangerous trick, to be feared and avoided at all costs. She bought an expensive Franklin planner for me and “encouraged” me to use it religiously to record notes, contacts and appointments. Seeing that fighting would be a useless exercise, I complied. Six months later, my memory degraded to the point I could barely even remember my own name. Oh, and my note-taking skills? Subpar. I ended up the worst of both worlds — someone who didn’t have the discipline to use a day planner properly coupled with the recall of a brain-damaged squirrel.

Over the years, I’ve experimented with different approaches. Nothing ever really proved truly satisfactory, but I’ve learned a lot about what doesn’t necessarily work. Here’s why:

1. Huge, all-in-one day planners are great. Two problems, though — you have to lug them around EVERYWHERE, and you need to review old notes to keep abreast of what you need to focus on. If you’re not willing to do both, then the best-organized planner simply won’t solve your structure problem. Paper-based solutions provide the most versatility if it’s self-contained, but if you don’t have the discipline to use it, all you’re doing is lugging around extra weight.
2. Remember those old Palm Pilots and iPaqs? I had one. It, too, was great — but it was one more device to lug around. And to keep synchronized.
3. Smartphones are great for tracking contacts and email and calendar items, but the form factor doesn’t help much for task management (especially strategic goals) or substantial note-taking. Yes, you can deploy a third-party tool like Evernote or Remember the Milk, but then you need a strategy for keeping all these tools synchronized across several devices and possibly even different operating systems, and don’t get me started on app interoperability. You end up with a series of interfaces and links that don’t work exactly smoothly, forcing you to spend more time tweaking the system than in using it seamlessly. When one app wanted me to connect my tasks to Google so I could sync them with RTM and then import them into Outlook, I cried uncle.
4. Tablets are better, but they have their own limitations. Typing on a tablet for an extended period is a pain in the butt without a Bluetooth keyboard, and those are just one more expense and one more thing to carry around. And if you’re not an Apple or Google fanboy (I’m not), then … good luck with that.

So what’s a guy to do?

I’ve found that keeping all my devices on the same platform helps. I run Windows 8 (consumer preview) on my primary home desktop and Windows 7 on my netbook; I keep core files in sync using Live Mesh, so I never get stuck with a “missing file” problem as long as I don’t get lazy and leave stuff cluttering the desktop. (If only the “Mesh” part and “normal” part of SkyDrive didn’t have an utterly unnecessary wall of separation between them.)

I subscribe to Office365 and use it as the primary mail domain for Gillikin Consulting. Thus, I get full access to a juicy Exchange server and a nice SharePoint allotment, to which I can connect all my Microsoft-based OSes. 

OneNote keeps my reference knowledge and planning notes readily available. Mesh keeps them in sync across my desktop, netbook and Windows Phone 7. This is the one solution that does solve my problems, for many things.

The missing solution is a tablet, but I’m excited for Windows 8 when it releases presumably later this year. With luck, a quality device manufacturer like HP will release a tablet early. I do use a TouchPad — dual booted to Android 4 via CyanogenMod 9 — but the lack of apps that sync well with my Windows infrastructure cause more grief than joy. At least Android has a working copy of OneNote now.

The best solution for any person is the solution that provides the most benefit for the least amount of effort. I know some people who continue to use paper for everything. Or who put their lives on their iPad. Or who scribble things in a notebook here, a notebook there but still keep it all sorted mentally.

Don’t let a misplaced desire for elegance detract from effectiveness. If using App A for tasks, App B for calendars, App C for email, etc., makes sense for you — go for it. It may not be pretty, but if it works, who cares?

The biggest thing, though, is self-awareness. If you lack the discipline to use your organizational infrastructure, it doesn’t really matter what the infrastructure looks like: Your life will still be chaos.

And when in doubt, switch it out. Changing systems every now and then at the very least will help you better understand what doesn’t work.

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