Something happened to me a few years ago. I’m not exactly sure where I got started on it or what caused it but I became very interested in the topics of productivity and organization. I think it had something to do with having a zillion and six things to do at work and a paralyzing fear of forgetting to do one them.

Since then I’ve been in a constant battle to find the best system by which to keep organized and productive. I’ve talked about this stuff a number of times here before. I even considered writing an application of my own to help me keep it together.

Now a huge influence in all of this has been Merlin Mann. For those that haven’t seen it his Inbox Zero presentation was spot on to an email method that I already swore by, empty out that inbox. Get a drink, watch the video and then starting deleting like its going out of style:

But it was when I first heard him mention OmniFocus on one of the Macbreak Weekly podcasts that I knew that I had found what I was looking for. My requirements, they’re so modest:

0. It had to subscribe to the GTD system or something darn close to it
1. It had to be a native Mac application, bonus points for Cocoa
2. It had to be ridiculously stupidly easy to use

You’d be amazed at how hard it was find something to fit those criteria. Well, ok, maybe you wouldn’t. Chances are you never even thought about it before just this moment. Chances are even better you’ve already moved on mentally.

Anyhow, OmniFocus is from the same guys that do the awesome OmniGraffle so I signed up for the “Pre-release Alpha ‘This isn’t a beta’ it may just eat you computer and your family release.” That was a few weeks ago and I haven’t looked back. Everything that I was doing with BBEdit and some simple text files has been moved to OmniFocus. I have it running constantly and whenever I feel the attention starting to wander (like say, when I want to know how a water tower works) I immediately jump over there and choose the next action for anything.

I mean, seriously, doing any next action you have listed is better than wondering about water towers.

For you Mac folks out there go sign up for the sneak peak. Seriously. Do it now. Why haven’t you left yet? Then buy it when the folks at the Omni Group ship it, it’s worth it.

About once a year I get terrifically bored and decide that I want to mix things up. Unfortunately I never mix things up in a way that’s somehow a betterment of society. No, I just go and dork with my electronic system of working until I get fed up and go back to the old system.

This year, I decided I was going to ditch Mail.app and iCal in favor of Entourage.

My reasons were simple (digital wanderlust not withstanding):

1. We use Exchange for email and scheduling. iCal’s integration with Exchange is, hmm, “If you can’t say something nice don’t say anything at all”, all what the heck, it’s terrible.

2. Mail.app sometimes shows my read email as unread even after I tell it that yes in fact I did read it and no I didn’t just stare at it blankly.

I knew that Entourage wasn’t really an Exchange client like Outlook and it wasn’t a Universal Binary yet but I could add some rationalizations to my list of reasons:

A. The MacBU said that the Universal Binary version was coming out this fall so no more emulation was in sight. I even had a guy who had a source who knew some stuff that let it slip that this might actually be true.

B. Entourage has this tempting “Project Center” feature where I could setup these elaborate projects that would keep all the files, contacts, emails and everything together. In short, I would be The Organized.

As you can guess by now, this was all a dismal failure.

Before we get to the gritty details, here’s a little background on the two possible ways of dealing with email/calendaring data. The first way, which I will call “The Big Heaping Pile Stack” way works where you really only have two email folders, an inbox and an archive. When a mail comes in you read it, do something about it or reply to it, and then off it goes into the archive. There’s no hierarchy, no structure, just a big folder filled with all the emails mixed together which then relies on the power of search to find what you need later.

The other way, which I shall dub, “The Dewey Decimal without the Decimals” has a whole bunch of folders in which you can move emails. There can even be folders inside folders, massive towers of structure where everything has a place. The workflow here is that you read your email, do something with it or reply to it, decide where in the folder pyramid it is supposed to live, and then finally move it there. The theory is that because of the organizational structure and because you’ve preprocessed where the email is supposed to go that you should be able to find it when you need it.

Given my penchant for stacks, which one of these do you think is my more natural way of living?

Come on. Seriously. Look at the names for Pete’s sake.

“The Dewey Decimal without the Decimals”

“The Big Heaping Pile Stack”

Looking back at my rationales we can see being The Organized just doesn’t fit the way my mind is set up. I am certainly organized, but I have a hard time wrapping my head around any kind of taxonomy where I have to decide what I’ll need in the future now. “Do I put this email about how to apply field dressing for a burn into the ‘Safety Tips’ folder or the ‘One thousand reasons why owning a flamethrower would be the coolest’ folder?” See, there’s no right answer there for me and god knows I don’t want to go looking in the wrong place when I have a massive burn on one hand and a flamethrower in the other.

The thing that pushed me over the edge though was Office 2008 for the Mac being delayed until January. The speed penalty for running Entourage in Rosetta was just getting to be too much. I mean, if I was running in native speed checking two folders to solve my burn problem probably wouldn’t be too bad. I’ve got the feeling though that that situation has a real time is of the essence thing about it so I probably best not dawdle.

All this means is that I’m now back to Mail.app which has fast search for my big archive folder even if it still shows some mails as new. I’m also back to iCal and the copy/paste sit-ups that are required for using it with Exchange but the path is now paved for fun with napalm. Now I don’t have to waste time organizing my email and I can instead focus on buying something that will put me on a number of government watch lists.

Toasty yours,

Smokey Grant Lammi

Before we get rolling with the new stuff let’s pause for a minute for a little more old stuff. Honestly we could do it the other way around and put the new stuff first and the old stuff second as a kind of addendum. But you know, that’s just delaying the inevitable, it’s best just to get the darn thing out of the way so we can focus going forward. It’s like when you’ve just eaten way too much Skyline and you’re ready to get going on your way but that Skyline wants to see the world again. So it really really really pays to deal with that first. Not that I’m implying that the old stuff is, well, poop, but you get the idea.

Right.

So, all this talk about stacks got me some responses from people that fell into one of two camps:

1. You must a be big freaking slob.
2. You’re insane to be writing a blog post about stacks of a paper.

Through the power of digital photography I’ll prove #1 completely false. The other one, well, the jury is still out but my lawyer doesn’t seem particularly hopeful about the outcome.

So right now my desk looks like this:

and this:

There it is, thirteen stacks of stuff officially at the moment. Everything is orderly though, right angles and whatnot. So slob, no, obsessive compulsive, err, maybe.

One of the more interesting things I’ve noticed about my new job is how much more “stuff” I seem to collect. For whatever reason there seems to be more (and varied) files and printouts and pictures and videos and stacks.

Oi the stacks.

When I was still writing code all day, or least pretending to, I had one stack. It was the “This junk needs to be taken to the recycling bin downstairs but that implies carrying it all downstairs which considering the fact that downstairs is downstairs from where I’m at makes it a royal PITA stack.” Eventually the stack would quite literally reach a tipping point and the stack would become a pile at which time something simply had to be done.

Now I stop and look around and I have a least eight and a half stacks and I’m highly suspicious that there are another couple that quickly hide whenever I look in their direction. The old recycling stack still exists, which is a testament to laziness in that I could, if a standing wall were not withstanding, easily hit the recycling bin from my current seat. Given a couple of tries I could probably even do it left handed.

But now I’ve also got a TestTrack Pro stack, a TestTrack TCM stack, a Surround SCM stack, a book publisher stack, an unread magazine stack, and several funny little note card stacks that I blame entirely on Merlin Mann and David Allen. Well, truthfully, it isn’t all their fault, JK Rowling should shoulder some of the blame for interrupting The Process as it were.

If we really geek out and consider folders on a harddrive stacks then I think I’m just going to cry. Or perhaps I’ll just starting drinking. Heck, maybe I’ll do both, that seems like a reasonable multitasking pair.

And just imagine when Leopard ships with actual stacks. “Yeah, I’ll have a vodka martini. No, Goose is fine. And do you have a box of Kleenex back there?”

Now I have high hopes that the stacks will get better after they get much worse as the new TestTrack and new Surround releases get out there. I’d just as soon spill the beans and tell you all the new features now, I mean we’re all friends here. That way the product specific stacks could be merged with the recycling stack and I’ll guarantee you when that happens the bin will be getting a visit or twelve. Unfortunately, I can’t do that yet. I know, it’s killing me too.

I can give you a hint though. Or can I? Hmm, the decisions. Let’s just say that the new TestTrack will help me deal with the stacks. Kind of. Sort of. Unfortunately his brother Surround will just be an enabler and allow more stacks. Metaphorically, hypothetically, dodgy grammatically speaking that is.

So, anyhow, that’s my random observation of the day. I’ll even sum up the whole post in case you skipped to the end. “Blah blah blah stacks blah blah vodka blah blah blah I really shouldn’t so I won’t sorry about that blah blah to the blah.”

Someday, if you’re really lucky, I’ll work up the courage to talk about my lists. That’ll make the stacks look like simple piles of paper. Even the stack that’s made up of lists.