Wow, the internet is lousy with halfway-there GTD apps. It’s disappointing, because as much as you can do this whole thing with paper and pencil, it lends itself supremely to the digital world.

First things first: chop off the parts of GTD that won’t work better in the computer world. Ubiquitous capture just can’t happen online, in a desktop app, because you aren’t always there. (If you are close to always there, then you are close to ubiquitous capture, which isn’t ubiquitous at all.) So throw that out. Higher-level reviews are really about life planning and not losing what you considered life-focusing or important at any day or time, so I guess some sort of master list of that stuff could go in there, but you’d really want it journaled, wouldn’t you?

It leaves a to-do list. Really, really amazing to-do lists are trying to pass themselves off as “GTD solutions”, and I’m not buying it. The key to the GTD to-do list is that it has to be multi-dimensional.

Basically, all the tasks have to have a matrix of optional attributes, including:

• project
• context
• topic (high-level project)
• time estimated
• deadline
• urgency
• importance

Some of these dimensions are actually multi-dimensional themselves, like a project tied to two life-goals or a task that can be completed in any of a few contexts. The kids today love organizing that by “tags”, because it’s a freeform way to describe your stuff, but the open-ended tagging systems I’ve used (in stikkit, rememberthemilk, and others) are simply too open-ended. It’s great to be able to describe your tasks in these ways, but you can’t stop there. I haven’t seen in any system a way to pull the tasks that are lacking a context, for example, or the ones that don’t have time estimates, or ones for which the deadline is in the next 7 days, or whatever.

If you think about it, this is the exact same kind of filtering that iTunes does. I think the optimal solution is something along those lines: enter a ton of tasks, projects and ideas (as simply as possible), and then slice and dice through those based on what attributes they need defined (to finish up the data entry) or already have. iTunes playlists can tell you what jazz tracks, four stars or higher, haven’t been listened to in the past four weeks. Address Book can tell you which contacts you have in Ohio with no home phone number defined. A GTD to-do list should offer just as simple filtering.

The best thing about this approach is that it’s not too difficult to set up (if the data entry is simple enough), maintain, or tweak. iTunes newcomers don’t have their custom playlists tweaked out into infinity, but those who do can share their playlist definitions with others. It’s simple and extensible.

The important part of this is getting out of the way of data entry, because “task definition, assign context, tie to project, set importance, enter deadline, estimate time” doesn’t work for everyone and/or every task.

Honestly, I think the problem is pretty simple, and is just being danced around / poorly understood by the people who are doing this work. I like ThinkingRock best so far, because it actually meets you halfway between “anything goes” data entry (because this kind of work really is creative) and a supportive structure. It doesn’t go tag-crazy (and it could, and it will, I’m sure), it doesn’t accommodate time estimates (which I find useful, just because I pick off 15 minute things more often than I plan half-day things), but it reflects what I understand about GTD better than any other solution (downloaded or home-brewed).

It was one of the few reasons I got interested in Macs in the first place: sure, iTunes is awesome on XP, but if I got a Mac, then I’d have a bunch of other like-minded applications that could work with iTunes.

And then it was one of the only reasons I was apprehensive about the MacBook Pro: I have about 50% MORE in iTunes gigabytes than the MacBook has hard drive space. And I’ll need some of that space for, y’know, the OS.

But I got the MacBook Pro, added a 160GB portable hard drive, and I was off and running. (Actually, I plugged it into a USB 1.1 hub, and wondered why the whole thing was so damn slow, but eventually figured out my problem.)

iTunes on Mac is nice because:

• It’s pretty zippy. My XP copy gets caught up on little laggy issues every once in a while, but I’m not sure if that’s memory or what.
• While it’s not quite what they promise you with “the lifestyle” on Macs, being able to pull actual iTunes playlists into random apps (like Apple’s presentation software, iDVD, Dashboard widgets, or even third party slide show software) is pretty close to magic.
• There are some killer AppleScripts that do really nice things. (I believe I’ve mentioned that one runs through your selection, cleaning up improper title case. That’s just one example.)
• pzizz talks directly to it, as does Handbrake, which meant DVD rips happen with about two clicks. Scary fast.

iTunes on Mac is pretty much exactly the same for:

• Working with iPods. I was really expecting to see some magic here, but it’s just as fast on XP, and just as easy.
• Large playlists. I was thinking that my thousands of songs might get sliced through a little more quickly, but no. Even Cover Flow is about as laggy on my Mac as on my PC.
• Purchasing / burning / etc. There are no additional barriers to buying, downloading, or burning anything on either platform. They’re basically identical.

iTunes on XP is better for:

• MusicBrainz. Jeez, there’s a Mac equivalent called iEatBrainz, and it’s really pushing the limits of “equivalent”. I had no end of problems with that software. MusicBrainz is a remarkably complete solution (and usually has correct title case, to boot)
• VolumeLogic. I paid for this plugin a long time ago: it adjusts the sound from iTunes and equalizes the volume. Easy enough, right? Well, the Intel Macs confound the developers of the app, so they haven’t released a version I can use on my MacBook. And it’s all a moot point now, because apparently 7.0 broke their implementation, and it doesn’t work for PCs now, either. (If you’re on 6, get Volume Logic. Seriously.)

So, in a fair fight, I think iTunes on Macs is a better app / experience than iTunes on PCs. But there’s one thing to consider: how light and portable the MacBook Pro is.

I don’t think twice about bringing my Mac anywhere: even if I’m pretty sure I’m not going to use it, it packs up so small that I don’t mind carrying it around. However, with the external hard drive connected, you have to remember to eject that before you go. Even if the Mac is sleeping, you have to wake it up, eject the disk (closing iTunes first, of course, unless you want all those hateful little exclamation points to tell you your music is missing), and then disconnect it. Then, when you’re on the road, you can’t use iTunes (all or most of your music is back on the detached HD, and even if you partition your music, you get those evil exclamation points). You have to come back and reconnect the drive before iTunes is an option again.

So I started noticing all this psychic inertia to not move the Mac, because I like iTunes to be running, or feeling like I was constantly connecting and reconnecting USB cables. That’s something I thought I was leaving behind. For all the advantages iTunes offers in a Mac environment, the problems of the laptop-two-disks scenario can’t overcome the ease-of-use offered by a desktop machine - PC or Mac - and the 24-7 docking / charging you’re probably pretty used to.

But: there no reason for this. Seriously. I spent a chunk of yesterday moving my iTunes installation back to my XP desktop. I mean, I really like using iTunes on the Mac, but I have too much music to really use iTunes on a MacBook. (Of course, now they come with enough room to store my whole library, and the next ones will probably have twice again as much room, but that’s the “buying from Apple” experience for you - as soon as you get it home, they’ve innovated yours into shame and ridicule.)

It’s freeing. There’s only one cable connected to my MacBook now: the power. When I want to take it somewhere, I’ll only have to shut it and go, not dismount the external drive (which I can use for backups now, I guess). When I want to dock an iPod, I won’t have to worry about if my Mac is where it’s supposed to be.

And the killer feature is that, thanks to what iTunes does over the network (playlist sharing), I can enjoy what’s on the PC’s iTunes with the Mac. (There are limitations: I can’t rate songs, my listens don’t bump the listen count, and I can’t edit song titles to correct their improper title case, but those are all my neuroses, and you shouldn’t have to worry about them.)

I thought I might detail “moving an iTunes library from one PC to another”, but I’ve already gone on at Scorcese-length about this one dumb thing, so I guess I’ll spare you for now.

A couple people have told me that they can’t believe I bought a Mac. (I’m still a little surprised by it myself some days.) I am not a raving evangelist, but people still ask me if I’m happy with OS X and how it works and stuff.

First: I am very happy with the Mac. If I think about why I’m happy, there is probably some tendency in me to say “I spent all this money and so I have to be happy - it would be a financial disaster for me not to be happy, therefore I am”. But I know my motivations pretty well, and I don’t think I’m justifying the risk I took by writing about it. (I have my suspicions about the people who are grilling me about it: most seem honestly curious about Macs, but a few seem more interested in how much it cost, why I felt okay spending that kind of money, etc.)

A couple people have said “so tell me one thing you really like about it - what’s so great about it?” Assuming they are asking that question for legitimate reasons, it’s hard to answer. If it were a debate, asking me to limit my lines of argument to one really good one would be a clever ploy, but I don’t want to argue with anyone about this: I like it, and you might not.

But here are three of the things I have said when people ask me to elaborate on Just One Thing.

Installing applications. This one is really big, and it’s kind of silly how great it is. When you download Mac applications, they (usually) come compressed. You open up the compressed disk image, and inside is a little documentation (maybe) and an Application file. You drag the app to Applications (some packages include a shortcut to your Applications folder, so you don’t have to pull that up), and you’re done. You can run it from there. Everything for the app is (usually) in the “bundle”, so installation doesn’t involve copying a ton of files all over everywhere, or setting registry stuff (the installer, not you)… it’s just all-in-one.

Huge apps don’t install like this. I’m not sure why. And you don’t have to put apps in your Applications directory (they’ll run, largely, from anywhere you put them), so some of that organization is just gentle recommendations, and you can clearly overcome it if you’re messy enough. Uninstalling an app should be as easy wiping the bundle from wherever you’ve put it, but running an app for the first time puts preference files in certain places, so if you want something really gone, I guess there are more steps than that, but I’m telling you: it’s something to overcome the new-app inertia that you get as a long time Windows user. I catch myself thinking “that looks like an interesting app, but I don’t want to try it only to have to wait forever for it to install itself, maybe reboot, definitely leave junk where I don’t want it, maybe install an icon on Christie’s desktop, and maybe never come completely clean” - and I remember, I can just give it a shot.

And even if the process of installing apps is 50% nicer instead of 500% nicer, think about disk images: there’s a standard disk image format that all Macs understand and (again, most) developers / publishers use. That is getting fairly geeky, but for the times when you want to send someone a folder, stash a collection of files somewhere, password protect a set of documents… it’s handy.

Quicksilver. Yeah, that’s usually the second thing I tell people. But it’s what sold me on Macs two years ago - reading Merlin Mann write about having everything about the computer at your fingertips, paying for AppRocket, and then reading for months about the feature gap between the two programs.

There is nothing, in truth, wrong with the Start menu. Good on Microsoft for keeping it around in their next thing. After about two months of adding programs in any version of Windows, though, I desperately needed to weed out a ton of stuff I didn’t need right there. After three months, I needed to look into alternatives: quick launch works for a while, that list of frequently launched programs is okay, I guess… and Vista even has some sort of something that lets you progressively search through programs or documents or something. That will be a big step.

But Quicksilver is ahead of everyone else in the user experience area. It’s not close. It lets you progressively search everything. Programs, documents, the insides of documents, online stuff. It lets you plug everything (text scraps, clipboard junk, images) into everything else (the ends of documents, your calendar, Flickr, etc.). It gets out of the way every time.

The gorgeousness. And this is where the argument gets all weird and subjective and I start to admit that of course you shouldn’t talk to me about it because I’m not thinking clearly because you’re obviously not thinking clearly because the whole thing is gorgeous and why don’t you just open your eyes?

It boots fast. It puts stuff where you can find it. It lays out security options in a way that you can actually make informed decisions (and feel like your wishes will actually be honored). It’s for grownups. It doesn’t fight you all day long, and when you’re not fighting all day long, you can get some other stuff done.

There’s a small pile of stuff it doesn’t do. You could take a principled stand and stick with Microsoft through all this, and I wouldn’t ever tell you you were wrong about it. But if you’re like-minded, and curious about this stuff, it’s really worked out well for me so far.

Hi everyone. I’m ready to spend some time out of my shell again. Get ready for a very large post.

First off, there hasn’t been a whole lot going on. I haven’t had a whole lot to say here for a lot of reasons, but let’s just get the what’s-going-on trivia out of the way.

I turned 30

That happened. It was fine. Almost six months in, that term is actually starting to fit. At 28, I really thought I’d want to just lose a weekend in Mexico or something. At 30, I can’t exactly remember what I did that weekend. That’s okay.

I took up knitting

Yes! Christie and I hadn’t shared any of our mutual interests, so I just had her sit me down and walk me through the basics of knitting. I made a hat. I plan to walk her through the basics of taking apart a $5 PokerStars sit-n-go, but the opportunity hasn’t exactly presented itself.

I bleached and then cropped my hair

I must have been completely blond for less than a month… I’m not sure. It was kind of fun. My kids didn’t mind. I am not exactly sure what I was going for, and I’m not sure what anyone else would tell you I accomplished. (I may just have bothered some people who didn’t want to think about my hair.)

I went on vacation

I read a poker book and won a poker tournament. Other than that, it was a lot of sitting, and that’s really okay with me.

I started watching Lost

And I’m only up to the very start of the second season. I was reading some stuff about the alternate reality (not stuff that’s happening in the show, but websites and games and “clues” about the universe the show takes place in) and decided it was probably worth checking out. After 26 episodes, we’re just at the point where the alternate reality stuff starts happening. We’ll see.

Bought a Mac

Yep, a MacBook Pro. I have a lot reasons for doing that. Mostly, I just don’t like the vibe that XP/Vista is giving off. And I’m fully aware that Apple’s marketing campaign is “we give off a different vibe” - 100% empty, in other words. But I am really enjoying the experience so far (there I go again).

Booked a trip to Las Vegas

I’m going in two weeks.

Mourned internet poker

They tried to stop people from gambling online. They could have regulated it, taxed it, even analyzed it, but Congress instead opted for a prohibition. They are trying to cut off funding (so people like me that only make withdrawals appear to be okay, for now), but it was certainly the first blow against the game. I still play, making about $30 a day, but the game as we knew it has certainly come to an end.
Joined the Y

Yeah, we did that. We like it. We belonged to a Y in Uptown, but this one is bigger and has cooler toys. We’re still in the first month of that, so we go all the time and talk about how toned we are.

Bought some bookshelves

These items are getting more boring.

Halloween was cute

Ask me if you haven’t observed Adam and Becky as Mario and Luigi. It was pretty great. (Would have been better if they’d consented to mustaches, but that was a game-time decision and they said no.)

I no longer really expect comments on this site, but if you have something to say, go ahead and say it.