An artifact from The Ihnatko Archives. It’s my own artwork: this appeared on the back of a tee shirt. It also represents a pretty bold case study illustrating how great organizations can crumble.

Let’s say that your Mom’s next-door neighbor has a big riding mower, and truth be told, he really enjoys driving it around. So much so that when he’s done cutting his own half-acre, he’s still got a lot of counter-horticultural bloodlust left inside him and he goes ahead and cuts your Mom’s lawn, too.

How do you react to this? Do you:

(a) Thank him kindly for being so nice, and also surprise him with a $50 gift card to the Outback Steakhouse sometime during the summer as a tangible and tasty symbol of your sincere gratitude? Or do you

(b) Stand in his mower’s path just as he’s about to enter your Mom’s property, wave him to turn off the engine, and then make him sign a liability waiver? And then ask him for proof that he’s bonded and insured? And insist that he stop and phone you before entering the sunny side of the yard, so you can drive over and verify that he’s raised the blades to prevent burnouts? And ask him if he really thinks that a tee shirt and shorts conveys the sort of polished appearance that properly represents your Mom and her household?

The first attitude is the reason why the Boston Computer Society was the largest computer user group in the world for the first fifteen years of its existence. The second one is the reason why it died a deathly death just shy of its 20th anniversary.

I was an active volunteer with the BCS’ Macintosh special-interest group for many years and I can honestly say that it was one of the happiest chapters of my life. The BCS•Mac’s Somerville office was like a clubhouse, like Ralph Kramden and Ed Norton’s Raccoon Lodge. You’d drop by just about anytime you wanted, and you’d discover cool people to hang out with, cooler hardware to play with, and some jobs that needed doing.

Example: I came in one afternoon and discovered that Apple had donated a 300 dpi (!!!) scanner. Awesome. I unboxed it, hooked it up to the lab’s Mac II, and spent the whole afternoon playing with the scanning software. I got a whole mess of experience in digitizing photos, the BCS•Mac got their new hardware installed and a whole drawer full of graphics and images scanned…it was one of those mutually-beneficial relationships.

I mean, hell…they even let me be an artist. I have the lumpy physique and the Skinner box-influenced personality that instantly communicate “Of course I can figure out why your your office WiFi base station isn’t showing up anywhere.” But you don’t really look at me and think “Yes, that’s the guy to design our organization’s tee shirts.” And yet, that’s what I did, for nearly every Macworld Expo.

This thing was different from scanning photos or setting up a network. Actual money was involved. But still, it was a completely low-key operation. When an Expo was about a month away, I’d kick a couple of ideas around with the leader of the Mac group, draw up the winning design in MacDraw or Illustrator, take it to Harvard Square to be rendered on a then-exotic 1200 dpi phototypesetter, and then go to Chinatown and drop it off at the silkscreeners’ shop. Two weeks later, boxes of Hanes Beefy-T’s littered the office. Thoughout, there was the same supportive attitude that the BCS brought to every job that needed to be done. If a volunteer was eager to jump onto a handcar and start pumping, then the leadership’s job was to grease up the rails and get out of their way.

As usual, there was never even any need to get the central office involved. The central administrative offices of the Boston Computer Society were located downtown in offices at One Center Plaza but really, the dozens and dozens of BCS Special Interest Groups more or less ran themselves. Center Plaza’s chief duty was to divvy up the annual membership fees and other sources of income into the subgroups’ operational budgets. Occasionally, they could also be counted upon to bail SIG leaders out of jail when they were off representing the BCS at a trade show and they got confused as to what level of alcohol saturation constituted a DUI in that part of the country. Overall, though, it was a hands-off relationship.

But a funny thing happened to the group in the Nineties. If you wanted to be charitable about it, you could say that Center Plaza’s salaried directors saw an opportunity to evolve the BCS from a shoeless nonprofit into a true educational institution and a valuable consumer brand, which would in turn guarantee that the Boston Computer Society could continue its important mission into the year 2000 and beyond. And therefore, for the first time in the group’s history, they insisted on running the operation like a formal, hierarchical, accountable business.

The uncharitable — but probably more accurate — way to describe the overall change would be to note a universal truth: the only thing more annoying than an organization that requires your constant attention and input is one that runs just fine without your interference, thank you very much. Wreaking untold havoc via petty, random, and incessant meddling is much, much more satisfying. At least then you can see that you’re having an impact on the operation, you know?

The Mac Group was the Boston Computer Society’s superstar performer. But technically, the BCS•Mac’s money came from Center Plaza. So if the salaried employees at HQ wanted to give themselves the pleasant, nougaty, leadership-ish sensations of being an absolutely essential part of the BCS•Mac’s success, they found an easy way to go about it: they demanded that all Mac Group expenses greater than, say, nine dollars be submitted to Center Plaza and be subjected to a formal approval process.

Every Macworld Expo, the tee shirts sold out and made money for the group. No worries there. Regardless, our silkscreeners’ invoice had to be approved by Central Plaza before the shirts could be printed. Here, my sorrows began…and my career as a tee shirt designer ended.

I thought a Batman-themed tee shirt would be a damned cool thing for the 1995 summer Expo. The first “Batman” sequel was about to be released and the posters and ads were all over the place. I designed a two-sided tee, with a parody of the Batman logo on the front. And on the back, I created one of my most satisfying pieces of artwork ever: Batman, perched confidently and menacingly over Boston’s landmark CITGO sign in Kenmore Square. Very dramatic up-angle shot, with his cape spilling and flapping over the front of the sign. I’d morphed the CITGO triangle into an approximation of the BCS•Mac’s sigil.

I had a few weeks to put the design together and I finished my Adobe Illustrator artwork well ahead of schedule. “Awesome,” the head of BCS•Mac pronounced. “We can get this to the silkscreeners just as soon as Center Plaza cuts us a check.”

Two weeks later, we still hadn’t heard back from the mothership.

Y’see…there had been Meetings.

“We can’t allow you to produce this shirt,” they finally proclaimed. “Batman is a registered trademark. Do you think you can get a signed clearance from DC Comics?”

I wasn’t entirely certain that I could, no. But I wasn’t the least bit worried that I’d actually need one, either. I knew enough about intellectual property laws to know that so long as you could provide a trademark/copyright holder’s attorney with enough reasons to advise against a lawsuit, you were bulletproof. A low print run, a one-off design, modifications of the source material, and a nod towards Fair Use was all it took. Any sane lawyer would look at this shirt and realize that there was no money in this prosecution…assuming that they could even win.

But this time, it wasn’t the sanity of someone else’s attorneys I needed to worry about.

“Look, it isn’t undeniably Batman,” I said, fairly. “It’s merely a Batman-ish superhero. You could just as easily make a case that it’s Moon Knight, or Spawn…or really, any other cape-and-cowl superhero.”

“We’re not really comfortable with your using the CITGO sign, either,” BCS Central replied.

As the clock ticked down and Macworld Expo loomed closer and closer, Center Plaza fired off micro-edict after micro-edict. From “Batman can’t be the dominant figure” — damn, out went the back-panel art I was so proud of — to “You have to round off the points of his ‘ears’ to make him more distinctly ‘not Batman’,” to “You need to add editorial content to the design, to give it extra legal protection” to…to…

Well, all the way to my vowing “If I live to be a THOUSAND, I will NEVER design another tee shirt for the Boston Computer Society!!!”

I think the thing that finally broke my spirit was their testy demand that the shirt also include the Boston Computer Society’s formal mission statement. My dear reader, if you’ve ever made use of the phrase “Are you f***ing SH***ING me?!?” then well, you have me to thank. I invented it right there on the phone, when no other response seemed suitable.

Over the next two or three years, One Center Plaza alienated so many of its most productive volunteers through endless bureaucracy and mindless micromanagement that all of the people who were actually keeping the subgroups running got fed up and left.

Yup, myself included. The tee shirt thing was just the first push down a long slide. I stopped doing artwork, stopped writing for the monthly magazine, stopped pitching in to help run the monthly meetings. Ultimately, I even stopped hanging around the Mac Group’s office. It wasn’t my clubhouse anymore. Spontaneity and excitement and a sense of purpose had been driven out, replaced by rules, forms, and a deadlined proposal process that provided ample time for lots and lots and lots of valuable discussion and feedback on every idea.

The functions of these active volunteers were usually taken over by people who needed to be paid, and who didn’t work half as hard. Thus, my vow to never design another shirt for the BCS was ultimately in vain. I had barely not designed the next two shirts (I was very pleased to note that they sucked, and went mostly unsold) before the Boston Computer Society died a deathly death.

The rise of the Web certainly contributed to the BCS’ collapse. All of a sudden, computer users could get advice from strangers without having to drive through the snow to a lecture hall at MIT on a specific day of the month. But I’m convinced that a scaled-back group would have endured to this very day. Because a user group doesn’t need to be run like a business. It needs to be run as though the organization sees volunteers as assets, and not liabilities.

Better, they should see them as people.

Postscript: and of course, the BCS does endure, in the form of BMAC. For all intents and purposes, this is the Boston Computer Society Macintosh User Group monthly meeting. Same place, same schedule, many of the same people, even. Except that these meetings are actually happening. Which is the best revenge of all, don’t you think?

Postscript to the Postscript: I was suddenly reminded of the true fetid cherry that topped this whole miserable experience: the silkscreening job was awful. I’d rendered those gradients to print at a specific dot-screen angle to make for smooth transitions without any loss of detail. The yellow logo on the front had been specially trapped with a holdout, to make for a nice, intense color.

I got the first shirt. The back was printed like mud. The front…well, the front was comical. To get a nice, intense yellow without the black fabric bleeding through, my artwork called for the logo to be printed in white with a thin layer of yellow on top of it. That’s a standard trick. Instead, the screener had thrown away the “white” layer and kept adding layer after layer after layer of yellow. This had two effects: (1) Indeed, the black didn’t bleed through a bit, but (2) the logo contained at least an eighth of an inch of built-up color and caused the whole front to pucker and sag.

This was way out of character for our usual silkscreener in Chinatown. If I handed them a design that they knew wasn’t going to print properly, they’d mentor me through the changes that needed to be made. If my design was “close enough,” they’d find a way to make it work. And the shirts were always perfect.

Ah. But the BCS•BAT shirt wasn’t printed by our usual guys. No, see, BCS Central had insisted that the job go out for competitive bids. You know…to make sure it was a fair and open process.

The winner of this Fair and Open Process? Some friend of a BCS boardmember.

So you’ll understand why I wasn’t exactly teary-eyed when the Boston Computer Society finally went out of business. I’d tell the story of how this new regime fired me from the monthly newsletter, but (a) it’s a long tale, and (b) it’s not possible to make the BCS central management look more like a bunch of paltroons than I already have.

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Occasionally, Apple throws a special media event to announce Cool New Things. Unfortunately, they generally don’t hold them in the Boston area and in general, I can’t spend the $500-$1000 to head out to Cupertino for them unless I can manufacture another excuse or two to be in the area.

So I’ll be liveblogging the event just like the rest of my brothers and sisters in the press corps. Only I’ll be doing it from here in my living room, with a freshly-made lunch on a TV tray (turkey and swiss on wheat, with a handful of Doritos and a soda) and last night’s TV shows on the PVR. I’ll be following Macworld’s reliably-excellent liveblog, posted by my Close Personal Friend Jason Snell.

I stress that this is the reason why you bought a copy of the Web. Where would you have been twenty years ago, unable to read about how I was reacting to reading the news online via someone else’s liveblog?

Actually, twenty years ago there wouldn’t have been a liveblog for me to post from.

Nor an iPhone for this event to have been about.

My head hurts.

Liveblog starts. Hit command-R on the Macworld page. Jason Snell identifies the file-in song as “27 Jennifers.” Cool song. Go to iTunes store.

Try to buy “27 Jennifers” but this is a loaner MacBook Air and I’ve already authorized my 5 computers for iTunes purchases.

Oh, right, the event. Refresh page. Apparently this “Steve Jobs” (of the Cupertino Steve Jobses) is heading this thing.

Whoops, no he isn’t: he hands it off to Phil Schiller. Who always makes me think of the guy who made those awesome short films for the original seasons of “Saturday Night Live.”

He leads off by talking enterprise. Check off the first item on the expected announcements.

Tab over to Google Reader. 5 new articles in ModBlog. Do I dare? Hell yeah. Fingers crossed…

…the score: one “holy CATS is that an extreme mod (extensive facial tattoos + piercings + horn implants” one “okay, kind of an interesting tat” (cute cartoon of a giraffe and an elephant on someone’s chesticological ladyparts), one flat-out “Ewwwww…” (gross, in-your-face pornographic cartoon on someone’s calf), one fairly interesting tribal backpiece (though as always, those tribal designs make me wonder if in the future, people will point to that and say “2004, right?”).

Back to the event…

Cool, Apple’s giving the enterprise IT managers nearly everything they’ve asked for. Microsoft Exchange compatability…they’re licensing MS ActiveSync, push services for calendar, contacts, etc., support for more VPNs, tools that allow remote admin of phones….meaning, the ability to set up hundreds of phones at once, and wipe phones remotely if they get lost or stolen.

Let’s see how my man in the office Iditarod pool is doing…

Awesome! Martin Buser has passed Ed Iten and Hugh Neff and is now at the Cripple checkpoint in 4th place. Still with 15 dogs, nearly his full original team. This means he can start choosing his team for the “real” race to come. Wouldn’t be surprised if he dropped two dogs before taking off for Ruby.

From Ophir we swing our Camera of Truth back to Cupertino, where the local residents would bravely throw their bodies in front of those 15 dogs to prevent them from being exploited thusly. (And then the dogs would immediately pounce and eat them).

Demo of Exchange contact syncing (if Bob adds a new contact to his iPhone at the trade show hospitality suite, it immediately appears in Alan’s iPhone at the strip club champagne room five blocks away from the convention center). Demo of push email (you don’t have to “check” email…there’s just a wide-open pipe from the company mailserver to your iPhone).

What’s going on at Twitter? Tab.

….nothing much. Hokay.

Second of two cans of Diet Pepsi With Cherry is poured into an insulated travel mug. Hmm, ice has melted. Back into kitchen.

Did I mention how awesome it is to own an icepick? I used to have to toss the bag of ice in the air and let it smash to the floor to break it into cubes. Having the right bar tool for the job makes me feel, y’know, sophisticated and junk. I bet Hef owned an ice pick back in the golden days.

I unmute “Dirty Jobs” on the PVR. It’s the one where he’s working at a tannery. Good god, I think there are visible, cartoon-like stink lines radiating off of the screen.

Back to Cupertino. The thrilling — seriously, the aisles at Town Hall are littered with convulsing bodies of industry analysts, like at a revival meeting with a good cover charge — demo of enterprise push email and contacts is over with and now Scott Forstall is talking SDK.

…After showing off web apps.

No, that’s good. I’ve said before that Apple has made a huge hit with their custom web hooks in iPhone Safari. There’s now actually three versions of the Web: the “real” web, the stripped-down no-fun version that exists for mobile browsers…and a version that only appears to people visiting with an iPhone. What an achievement.

On to the actual SDK (Mike Rowe is now shoveling huge, wobbly wads of deer flesh, fat, and hair from a rotating tanning drum). Sounds like a really cool talk; they’re finally saying “Here’s what we meant in January 2007 when we said ‘the iPhone runs OS X, with additions and deletions that make it relevant for a touch-based handheld phone instead of a keyboard-and-mouse computer.”

There’s a real sense of “pulling the tarp off of something you’ve been using for months” aspect to this. Truly, it is OS X, with all the familiar frameworks.

I’m seeing a lot of familiar terms and tech here. As a geek with some basic Cocoa programming skills — not “mad” by any means, but perhaps I could claim to have “irked skilz” — this is actually getting me keen to write iPhone software.

(Which of course is the whole point of this presentation.)

Now explaining “Cocoa Touch.”

The skins have been cleaned and tanned. Now Mike has taken them to the second floor, where they must be scraped and made supple once again.

Is there a name for those three or four sad little broken Dorito corners that are left over on the napkin, from the original handful you plated from the bag? Part of me says “they’re still tasty” and eats them. Part of me wonders if this isn’t like an alcoholic sucking on the ice cubes left over from a glass of scotch.

Onward to a demo of XCode. Oh, awesome: developing iPhone apps uses Interface Builder just like any other apps. I wonder if it works with AppleScript Studio?

(I am drooling at the thought of being able to simply port all of my script-based XCode apps onto the iPhone. Hell, man, I could have six useful things on my iPhone a day after I get the SDK.)

Sounds like a very slick development system. You get an iPhone simulator for “live fire” exercises. When it’s done, you build the app as usual, select an option, and bango, it lands on the iPhone you’ve got tethered to the build machine.

Cool demos of sample apps, demonstrating full access to the touchscreen and the onboard accelerometers (demo app that “distorts” a photo by letting you mush things around with your finger, like mashing up a Polaroid; shake the iPhone like an Etch-A-Sketch and it restores the original photo.

Equally neat is the fact that this is just OpenGL. So no need to learn anything new…just as in the Mac, games and graphic apps written to use that library are a (relatively) straightforward port.

Oh, good Lord: Mike is using a scraping machine that looks like it’s designed to grab your wrist, skin all the skin and muscle from your arm, and then rip the skeletonized limb from your shoulder. Wisely, Mike is having little success with operating it.

Put th PVr back on pause, back to the liveblog.

Oh, man: Apple is getting serious about the iPhone as a gaming platform. This takes me a bit by surprise as (frankly) so long as Macs and iPods can run both Solitaire and a Tetris clone, they seem to think that this side of the software business is more than covered.

Nice point they’re making: they invited a bunch of developers (under double-secret-probation NDA) to come to Cupertino and see what they could build in two weeks. First to demo: Electronic Arts, demoing some work on porting Spore to the iPhone.

(Sounds like a good demo, but…Spore? IMHO this is the most “You can’t have your dessert until you’ve eaten all of your vegetables” game that’s selling well enough to be well-known. Give me stuff to blow up, fer crissakes, and don’t make me think about Darwin!)

I feel sorry for the next guy to demo: showing off a vertical-market app for (I gather) organizing sales leads. This is like that day in school when the kids’ parents come to talk about their careers, and the nice Mom with a consultancy firm specializing in process control in light-industrial manufacturing has to follow the firefighter.

AOL is up next, showing off AIM for the iPhone. Good. And I’m absolutely confident that now, all of the bloggers and messageboard posters who bitchily insisted that Apple would never support chat on the iPhone because they didn’t want to give users a free alternative to AT&T’s text messaging are dislocating their wrists in their rush to post their apologies.

“I have besmirched not just Apple, but my own reputation as a technology observer” they will post. “If I do not retract these wild and unfounded claims, I cannot live with honor.”

I am so totally sure that this is what will happen. I imagine that you won’t be able to get your email for at least another twenty minutes, because of everyone posting at the same time.

Next is Epocrates. My folks have been having a batch of medical experiences of late, and so I’ve been spending a certain amount of time explaining to doctors and nurses the situation on iPhone software development. “If it doesn’t run Epocrates, I can’t use it,” they moan. Many just carry two phones and use their Treo almost exclusively for the doctor stuff.

Note how carefully this event is being orchestrated. Apple has carefully lined up a series of white porcelain plates at the far and of a shooting gallery. Each one is labeled with a known percentage of the marketplace that “can’t” buy an iPhone for specific technical reasons. Annnd…plink! plink! plink!…they’re knocking them all down.

Final demo goes to Sega, bringing monkey-based gaming to the iPhone.

Monkeys are like bacon. They improve just about anything.

Interesting that all the game companies are keen on using the iPhone’s acceleromoter. Call this the “Wii Effect.” I wonder if this will translate to truly effective game interfaces or if this will be a flavor-of-the-month sort of feature that soon gives way to a more practical static virtual gamepad.

(I predict that the first “iPhone as pedometer” app will arrive about 48 minutes after the SDK goes live).

Mr. Steve Jobs (of the Cupertino Steve Jobses) returns to the stage to talk deployment. Looks like the iPhone firmware will now include a built-in app browser and loader, like the iTunes Store widget. Slick and simple (but I wonder how folks will get a “try before you buy” sort of experience?)

Sounds like a fairly neat deal for small developers. Developer sets the price and there’s a simple 70-30 split between the developer and Apple. No service charges, it costs nothing other than that 30%.

Naturally, if you want to give things away for free, Apple will take 30% of $0. IE, it costs nothing to distribute freeware or open source apps.

But I’ll be interested to know how developers feel about this. This is the only way to deploy iPhone software. You cannot sell an iPhone app without paying a 30% tribute to Caesar. I suppose their happiness will be tied to how good this Apple store is at steering people to their products and converting casual interest into an actual buy.

Mention that some apps won’t be accepted into the Store. Porno, malware, apps that slam bandwidth…sounds reasonable, but this is the overture to a whole new discussion: “What right does Apple have to dictate what apps I can and cannot use on my iPhone?”

I don’t think it’ll be a big argument when it comes to porn. But what happens when an online poker site wants to create an iPhone app? Apple’s already kiboshed one department of the Vice Store…is gambling also an affront to God (meaning: Jobs)?

Hmm.

Surprise, the SDK beta is available today for free (but only to developers) (like me, hee hee hee).

Interesting note: joining the dev program costs $99. I wonder if this means “the iPhone developer program” or “the Apple developer program”?

Either way, a $99 buy-in to become a fully-supported developer isn’t a lot of money. Folks who bought the first Palm Pilot and found that the box contained a developer CD, a small assortment of quality chocolates, and a nice handwritten note reading “Please please oh pretty please write apps that make our hardware more awesome” might arch a Spock-like eyebrow, but again…$99 isn’t an exclusionary buy-in by any means.

(Remember: becoming a Newton developer cost about $800. This meant that you didn’t write apps for the Newton unless you had a business plan of some sort. Or if your company needed the SDK and you were able to cook your own apps with it on the side.)

Final announcement: the iFund. I have no clue what’s this about but I see “fund” and “$100,000,000″ and I think “How can I get my hand in the till?”

Event is over and ends with a good, strong comment: the iPhone and iTouch are now real, red-blooded platforms, not just a phone and an iPhone. Remote shared computers > desktops > portable computers > palmtops > touch computers?

Steve dismisses everyone but the press. Red Five, standing by…

…Time for Q&A.

Voice over IP? Yes for WiFi, no for cellular net.

Security? Obviously a big concern, but that’s part of the reason for the $99 fee. They collect lots of information about the developer so that people can be held responsible for Bad Apps.

“SIM unlock software”? Thank you, we’ve all enjoyed a good laugh.

Mmmm…okay, I’m ready to push the button, Frank.

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I’m a man who drinks lustily from the heady draught of adventure. So obviously, I’ve bookmarked ModBlog. This is a nearly-daily dose of photos of stories about people’s tattoos. And piercings. And brandings. And…well, apparently there’s this new thing where you actually have a design cut into your skin, and then the artwork turns into a raised scar.

I could continue, but there’s an orange DPW sign posted in the road just past the scar art and it reads “ENTERING ANDY IHNATKO’S PERSONAL CREEP-OUT ZONE” and I don’t really hazard to proceed any further. Up until this point, I am full of respect and admiration for some fantastic artwork and for the sort of person with such a firm handle on their personal identity that they can upgrade their personal hardware with complete confidence and with stunning effects. No need to screw that up.

(All I’m saying is that when THE MODBLOG decides that a photo is so “out there” that it needs to be concealed behind a link or a blurred thumbnail…well, that really has to influence your decision whether to click through or not.)

I was interested by this little collection of Spider-Man tattoos that they posted this week. Each of the tats are very well-executed and tastefully-chosen. But isn’t it amazing how quickly I blipped past the “this isn’t a rub-on; this is a permanent part of the landscaping” bit and immediately dropped into Comic Book Geek mode?

“Frenz, McLeod knockoff, original art based on stock Romita pose, classic Romita…oh, they took the Mike Zeck Spidey figure from the cover of ‘Handbook To The Marvel Universe’ and replaced the black costume with his red-and-blues, very nice work, there…”

There are plenty of sites devoted to mocking awful tattoos (and I wouldn’t be surprised if I discovered the blog through one of those “Oh, get a load of THIS guy!” links from Fark or somewhere). But man alive, ModBlog has really done a fab job of promoting tattooing as an artform. Every now and then they post a shot of a piece that’s truly stunning…in which the design, the execution, the placement, and the personality of the owner are in perfect harmony with one another.

No, a tattoo isn’t in my future. I certainly wouldn’t rule it out completely. But I’m not the sort of person who’d ever get a purely decorative tattoo and I’ve never had a single image that had such totemistic power for me that I’d want to wear it for life.

Which is too bad, because I had an awesome idea for a nerdy Mac tattoo a few years ago.

A Happy Mac. “Wow, Andy…yeah, that’s utterly original. You’d totally be the only one who’s ever gotten that image tattooed!” Crankiness is a bad color on you, sir or Madam. Stick with me: you get this icon tattooed somewhere high up on an arm or a leg. Your hip or your shoulder, say. Or you get it in a spot where there’s plenty of real estate.

Your goal in life, from birth to death, is to continue to expand your capabilities as you go. Right? Okay: so you celebrate this with an ever-expanding sequence of startup icons, mimicking the classic Mac OS’s startup screen in which every time a new driver was successfully loaded, it’d draw a representative icon next to the previously-drawn icon, filling the screen with a long line (or even a full mosaic) of little pictures.

Next to the Happy Mac, you design an icon representing your first breath. Then the ability to process food. First steps. First words, Learning to read. Entering school. First real friend. First kiss. First real job. You learned to play guitar. You wrote your first novel. Lost your virginity. Hopefully nearby to that, an icon representing the first time you made love properly.

On and on. Over the years, more and more icons appear. True, you’ll be busy for the first few months as you fill in all of the individual icons representing the first couple of decades of your life. But after that, it becomes a far more leisurely pace. You only add an icon when it becomes compellingly and irrefutably clear to you that you’ve experienced something that’s made you a bigger and better individual.

The tricky part — and here’s where you’ll need to choose the executor of your estate properly — is that you won’t be able to go into the shop and have the Death tattoo put on:

So you’ll have to have the artwork printed up and inserted into your will. Ideally, accompanied by a link to a Python script you’ve uploaded to your website that can convert a date and time of death into hexadecimal, so that the artist can ink it into the proper spot under the icon.

It isn’t the most brilliant idea for a tattoo ever. That honor goes to the convict on “Prison Break” who had the blueprints and technical data for the prison inked all over his body before he was incarerated, concealed as geometric designs. But give me credit: this idea is definitely up there.

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So did you know that there’s a way to add a…

An…

Well, maybe instead I should just show you:

So you see what I’m getting at: you type something in the chat window and it appears as a “chat status” sort of thing instead of a bit of text being spoken by your buddy icon. You can do this by just typing “/me” and then the text you want to broadcast. iChat will paste down your name followed by the text.

I just learned this today and I’ve been trying to figure out just what you’d really use it for. I suppose the most likely application is, you know…”stage directions.”

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I had no idea. I had no idea that there was so much free-floating love out there for the late 12″ PowerBook. But the appearance of the MacBook Air has clearly wafted that familiar perfume back in the air, causing Mac geeks all across the world to adopt thoughtful, misty-eyed expressions that their wives/husbands/girlfriends/boyfriends will never understand. It seems like each and every day I come across another love poem to the long-lost 12″ PowerBook, rendered in fussy tetrameter.

You are now expecting me to say something bitchy about these people.

I totally see that. Clearly, you’ve been paying attention to these writings of mine. But…no. I have Mad Love for many unique old beasties of the computerological persuasion and when we both happen to be checking into the No-Tell Motel with our vices at the same time, I think there’s a certain gentlemanly agreement not to bring it up at church when we’re with our wives. Or under any other circumstance.

Still, I don’t get the affection for the 12″ PowerBook. By a lucky coincidence, I happened to have 12″, 15″, and 17″ PowerBooks in the house at the same time that I was shopping for Lilith 7. I spent a whole week round-robining between the three and I came back to the 15″ every single time.

The 17″ was fab, but traveling with it wasn’t practical. As for the 12″…it gave nothing and took plenty.

It was a smaller screen, so I didn’t have that extra 3″ of width that I depend on for tool palettes and drag-and-drop areas. It was a cramped little keyboard and I had to slow down my typing. And the damned thing was just 12″ wide. I know that this fact was made plain in the packaging and advertising, but facts is facts: a niddley-narrow little notebook is fine if you’re working at a desk, but unless you’re about 11 years old, it’s impossible for actual lap use unless you’re willing to keep your knees clamped together tighter than a female PR rep forced to enter Gene Simmons’ hotel room to discuss the next day’s radio promotions.

Actually, not even then. Even when I had it on a table, my hands seemed to overwhelm the thing. I kept looking for places to insert AA batteries into the machine.

For all that, the smaller size offered me no advantages of any kind. It’s nice to have a compact machine, but honestly, it wasn’t as though I was being forced to jam my Titanium PowerBook into my laptop bag via the narrow end just to make it fit. A narrow notebook is a bit lighter, sure, but isn’t necessarily more portable.

But when you make a machine thinner? That I can work with. It means that I can fit more stuff into my laptop bag; in some cases, it means I can get by with just one carry-on. It makes the machine easier to grip, easier to tote, harder to drop.

So: I don’t get it. The MacBook is prolly the best compromise between size and practical concerns. It certainly fits into more bags than Lilith 7. I’m pleased that I can finally take my beloved 10-year-old Tenba bag out of storage and press it back into daily service. The 15″ sort of fit inside it, but the bag accommodated it only under protest. But the MacBook’s narrower profile costs me nothing (in a practical sense) in screen or keyboard real-estate.

Give me a MacBook. Or give me a MacBook Air, with its fullsized keyboard and screen and cleaver-thin profile. Keep your 12″ Slab-O-Mac. I hope you two are very happy together.

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Warning: a “First Flight” is an ongoing log of my impressions and experiences during my first and VERY first launch of a new app. You are reading exactly what I’m thinking when I’m thinking it, during my first ten or twenty minutes of hands-on experience with the thing.

I do think it’s valuable to document these things. True, true: you can’t possibly reach any conclusions about the nature of an app in the first fifteen minutes. But the joys and frustrations you experience right off the bat can be illustrative.

So: DO NOT refer to this as a review; DO NOT lambaste me for judging an app based on a quick launch; DO NOT point out that if I’d bothered to check the Help menu I’d have discovered that I could have fixed everything with a Command-Option-Shift-G.

Because the proper response to such a complaint can only me my pinching your nose tightly between my index and ring fingers and then slapping my other fist down my forearm so hard that the sound effects guy dubs an old-timey car horn sound onto the soundtrack.

You Have Been Warned.

Time to play with OmniGroup’s new OmniFocus task-management app. I’ve seen this in beta and was v.impressed with its approach and its goals. And I use OmniOutliner to run a fairish percentage of my life, so my expectations are high.

Macworld Expo also gave me the chance to get a 45-minute personal runthrough from the app’s designer, who was nice enough to work through all of my questions. I was certainly left thinking that this is could be a terrific product. I’ve never used a personal organizer or a project manager; they all seem to want me to run my life the way that programmers run theirs.

To this I respond: have you seen the way most programmers run their lives? Case closed.

The other problem is that acolytes of the “Getting Things Done” model of organization have been becoming increasingly PeTA-ish in how obsessively and annoyingly they pursue their Missions. Dine out with a GTD’er and you’ll have to walk to his side of the table and get your own damned salt. Because if you ask him to pass it to you, he’ll be lost in thought as he tries to work out how to contextualize that into an actionable result.

So that was my main worry as I read the product page; “GTD” is indeed spotted here and there. But they don’t seem to be all “blow up a research lab in the interests of protecting living things”-ish about it, so it’s all good.

Onward.

Launches with some helpful action items already in there. “Getting Started With OmniFocus” and (uh-oh) “Learn More about Getting Things Done” are my existing projects, evidently.

Merlin Mann gets a free bookmark? Why isn’t OmniGroup sending free traffic my way? Sure, I have nothing to do with this product or its goals, but still.

A summons for jury duty arrived while I was away. I need to fill out the little card and mail it in.

Tap command-N to create a new action item…it creates a new window, not a new item or a new project. Bad call. Am I going to spend more time in this app creating windows, or creating to-dos and goals? Exactly.

Ugh, it isn’t even command-SHIFT-N…that’s for creating new projects. It’s command-CONTROL. This is going to be a hassle. I remember from the demo that there are many ways to add actions; hopefully there’s something better in there.

Okay: command-CONTROL-N. Wait…that creates a new item in “Learn About Getting Things Done.” Well, that makes sense; I had that item open.

Err…okay, how about I drag it into the Inbox? Yup, that worked.

Hmm. I wish this window had column headers. I can get by context that the first field is the description, the next are Project and Context and other icons. But glancing to the top of the window and seeing it explicitly spelled out is reassuring.

“Mail in card for jury duty.” Tab.

Er…is this really a project?

Here’s where I usually fail at these apps. I like OmniOutliner because I can just build lists and check them off, free-form. But I appreciate that an app like OmniFocus can help me handle things that are much more complex.

Still, I’d love to have one single “dashboard” for everything I’d like to do, large and small. Let’s make this project “Snail Mail.” Type. Enter. It disappears.

Type, hit tab? Disappears.

Okay, I know this is a bit of a ringer. As I type, a little cue drops down from the field: “New Project: Command-Return.” No mistaking that. Still, I wish I knew why the keys that seem to work in every other app aren’t the ones I can use here. The Omni guys build great stuff and there’s prolly a reason. One that makes sense to them, anyway.

Now there’s a field for “Context.” Deep breath. This is the heavy-voodoo bit of this. I admit that “context” just makes no readily-apparent sense. You really do need someone to explain a philosophy behind it.

Off the top of your head, what’s the “context” of mailing a jury-duty form? Is it a piece of mail? Is it something you do because you don’t want to get arrested?

Context? I suppose I’ll be sitting at my kitchen table while I do this. Should I write “Just after lunchtime, when I’m not quite ready to go back to work and am looking for an excuse to get out of the house?

Here’s why my Macworld demo was valuable. I asked for a real bonehead explanation of what I’d use this for and Captain OmniFocus said that his own personal definition is “the one thing, person, environment, whatever that I absolutely need in order to make this this happen.”

I think about it for a few moments. “Post Office,” I guess. “Mailbox” seems stupid and pedantic, as does “stamps.” I’m trying to think of this as something that would be useful to me later. If “Post Office” is the context, then it can also be applied to things like buying stamps, picking up mail on hold, paying the annual rent on my PO box, that sort of stuff.

“Post Office”…done.

Hey, maybe Snail Mail is indeed a good Project. Just remembered that I need to mail off two copies of my new book to some contest winners.

Command-N…NO! Control-Shift-N. (I hope I get used to this)

Hmm…nothing happened. The title of “Inbox” highlighted but that’s it.

Wait…Control-Shift-N is now simply selecting Actions every time I hit it?

Ohhh…according to the File menu, it’s Control-Command-N. My fault. But dammit, these things happen when you make me learn a new command instead of allowing to use the old command that seems like the best, most obvious choice.

(Sigh.) Nope, still does nothing. Wait, now it does. Did I screw it up again, or is it context-sensitive? I bet I screwed it up. But (hate to keep harping on this, but I must) if it were Command-N as it should have been, I wouldn’t keep messing up.

Cool. Auto-complete on both Project and Context.

Still feels a little weird to refer to post-office stuff as a Project. Seems a bit like referring to American Pie 5 as Cinema.

Need to finish up a list of products I’ll be including in a Consumers Digest feature. That one has a deadline…and it’s a very natural project-ish sort of thing.

“Finish product universe,” project is “Consumer Digest,” context is…

Hmm.

I suppose I’ll need my Mac for this? “Mac.”

Open Inspector, add “today” as due date. Item immediately turns red. Crap, I’ve only been using this app for ten minutes and already deadlines are turning red on me.

Date and time appear as a popup calendar and time bar. I wonder if there are shortcuts for “Today” and “Tomorrow”? Seems like those would be handy. One ongoing annoyance of these kinds of apps is that something isn’t necessarily due at a certain time or even a certain day. I wish this app would let me say “Next week” and understand this as “Doesn’t really matter when, but if it isn’t finished by Friday morning, it’ll become urgent.”

I also feel weird tapping in “Midnight” when (again) the actual time doesn’t really matter.

Let’s try something with Attachments, which impressed me in last week’s briefing. I’m planning on a blog post about the ModBook and Paul Lee, a comic artist I met at the booth.

“ModBook blog post”; Project: okay, “CWOB”; Context? Umm…”Blog,” I guess. Can’t blog without the blog though I can’t help but think I’m making an error by choosing a Project and a Context that are damned near identical.

Again confusion about Contexts. “Where” is this action item? “What” do I need to do it? It could be almost anything, which in one sense gives me a lot of power to organize my world as I see fit, but in another sense gives me a slight blip of confusion every time I create something. Worst-case is that I simply leave this blank for most things.

Writing this blog post will involve pasting up a bunch of questions that Paul answered via email, and some digital art that he’ll be sending me when he has a chance.

Click on the “Attachments” icon, drag in a drawing he sent me over the weekend. Cool; shows up right under the action, indented slightly. Wish it were a thumbnail instead of a generic JPG icon. But good news: it supports QuickLook so I can check it out without opening it in Preview. Cool.

Drag in an email message. It appears as a link to the original message in Mail (good) but it appears on the same line as the JPEG icon (not good). Drag in the remaining two…same deal. If I want each one on a different line, I have to insert the line breaks myself. Seems like “put each attachment on a new line” (or some other thing that makes it easy to separate multiple attachments) would make sense.

Another situation where I wish I could deadline this as “This week, sometime.” Instead I lie and say that it has an actual deadline of midnight on Friday.

Recurring actions. I want to remind myself to spend at least half an hour cleaning my office every day. Action: “Clean office”; Project: “Maintenance”; Context: …

“Office”? Okay, nobody’s watching: “Office.”

Inspector: Repeat Every (1) Days. Bang.

Good. From my briefing last week I know that OmniFocus will create a brand-new Action with this information every single day. I should also create one for my Sun-Times deadline; he explained that every repeating action is in fact its own thing, which means that I can add individual details for each specific column.

Dangit, I need to select “Inbox.” I accidentally created it as an item in the project that was already open. I don’t know if I like that; instinctively I think “create a new action” should but a push-and-go thing; I shouldn’t have to think about where I am in the app, or navigate to a different place.

Select “Inbox.”

“Sun-Times Column”; Project: “Sun-Times”; Context…

“My genius”?

“Mac,” I guess. Sigh. It’ll take me a while to get used to this. I don’t know if I can rightly blame OmniFocus, though. I’ve never used this style of app before.

Add data for the recurring action. Simple. But I made the mistake of clicking on some of the other tabs in the Inspector:

Now I’m confused. Look at all those…things. I think I remember some of those from the demo.

I’m starting to wonder if I’m not being presented with way too many options here. Okay, so this “every week” thing isn’t limited to just actions; it can also be a whole project. So it might make sense to make “Write a Sun-Times column” a weekly project, with a batch of action items for each column (”Talk to Steve about where he got the idea for MacBook Air”, “Doctor up some phony pictures of the ‘Mac Air Nano’”…that sort of thing).

But would I really want that application sidebar to contain fifty-two Sun-Times projects every year?

No, what happens is that it disappears when completed. So only columns-in-progress would be there.

Okay…but when I add a new Action, would it be more complicated to figure out which week’s column it should apply to?

Overthinking things, Andy. Let’s just make a recurring Project.

(But will the new Projects be created on a weekly basis, or as I need them?)

Le Sigh.

I’ll return to this line of thought later. For now, I have plenty of actions and the window is now full of Projects in that sidebar. So now if I want to see all of the CWOB-related actions, I just click “CWOB” and…

Wait…where the hell are my actions? I only see one of them:

That’s the one that’s “due” by the end of the week. Where’s the other idea I had? The one with no deadline?

Click on “Snail Mail”…no actions.

Click on “Maintenance”…no actions.

What the hell?

Let’s do a search. Search for “universe” — I know that one of the actions was about a “project universe”…

No hits?!?

Click on “Inbox.” Okay, I have one item for “Finish Project Universe.” But why (the hell) didn’t it show up in a search? Why didn’t it show up when I clicked on the project title?

UGH. Okay, here’s what happened: it’s not a global search. It only searches the one thing you’ve selected. Which has a two-pronged bad effect: it doesn’t immediately understand a “find every action that matches this” request unless you think to somehow select your whole universe first, and secondly, if you forget that the search box has the word “universe” in it, when you click on other projects they’ll all appear to be empty.

Is that why I didn’t see any of my other actions?

Nope. All projects are still empty. Again I ask: what the hell?

Okay, I see most of these things when I click on the Inbox. And more clicking reveals that if I click on “no target in particular” in the sidebar, it seems to mean “show me everything”:

…But there are still empty projects which I know contain actions.

Do I have to manually drag actions out of the Inbox and into their related projects? I just assumed that defining a project when creating the Action would cause OmniFocus to do that sort of thing automatically.

Maybe I’ve made a poor assumption. I just assumed that the point of defining Projects and Contexts meant that I could do a one-click swivel search. “Show me everything in the ‘CWOB’ project” “Show me everything to do with the post office.”

Dangit. It looked so bloody simple in the live demo. It looks like I’m just going to have to sit down with the manual and read it. I did understand it when someone with lots of experience was showing the app off.

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Yes, fellow sensation-seekers, it’s time for another video from Macworld Expo. And this time…I actually talk about stuff regarding the actual show!

I’ve been home for five days and I already miss that huge bathtub. My own bathtub is that common sort of pathetic Bathtub-Shaped Object whose sole purpose is to just prevent the water from slopping onto the floor when you shower. I’d forgotten how nifty it is to just settle into a cubic yard of hot, fresh water and read comics until your fingers and feet get all pruny.

Just one more Macworld video is coming…then it’s on to new business.

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Wowwww. I’ve been using iTunes since it was called SoundJam and yet I’ve never seen an error message like this before:

I’m not saying that this error got me all upset or anything. But c’mon, Apple: is this a rational, reasonable, and most importantly a proportionate response? Let’s consider the actual problem here: when Joe Jackson’s “Happy Loving Couples” comes up on Shuffle Play, iTunes will be unable to show me a black and white photo of pointy shoes.

Honestly. You see this kind of stark, in-your-face error mode and you’re steeling your courage for the next sentence coming after it. Surely it’s something on the level of

“Mr. Jobs hates you and your work so much that he not only doesn’t want you to write about his products any more…he also doesn’t think you deserve to use them, either.

or

“iTunes will show you your album covers again after you finally admit that your interest in Star Trek/Dr. Quinn Medicine Woman slashfic goes beyond simple irony.”

or even

“…and now the zombified remains of the wicked shall rise from their unmarked graves, and feast upon the hearts of the righteous.”

If I were in charge of iTunes, I would have had the app simply drop a subtle red “X” over the Cover Flow area. I’m just not sure I understand why Apple would want to use an error display that clearly and definitively announces to all those present that This Piece Of Apple Software Has ****ed Something Up Mightily.

Do they think that this is, like totally the most awesome problem ever?

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Head on over to Macworld.com. I’ve posted a long piece in which I attach a dollar value to every major new feature of Leopard.

Macworld Feature: What’s Leopard really worth?

So how much is Leopard worth? If it were a collection of third-party utilities, I’ve got it at $409. And I’m sorry to have to tell you that you could have added a zero to that if your uncle hadn’t cleaned off that rich, 250-year-old  patina. Because collectors die for that sort of stuff.

I’m usually pretty critical of my own stuff, so I’m always pleased when I find myself laughing at something I wrote just 48 hours earlier:

And now we have the de-wussification of Mail. Mail was once a candy-apple red Mazda Miata. Now it’s a Ford pickup with a gun rack and a rear-window decal of a cartoon Calvin peeing all over the Microsoft Entourage icon.

Y’know, every now and then, the Plinko chip lands in the $10,000 slot.

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My iPhone woke me up at 7:30 AM on Sunday and about 9 AM today. The first time, it was an alarm that I’d set and it meant that it was time to pull on clothed, pull batteries out of chargers, and head off to the last MIT Flea Market of the year. Today, it was a phone call from a friend with a Mac problem. Yesterday’s wake-up was better.

When people call me in tech emergency, they’re hoping that the conversation will go something like this:

“I don’t know. It was working fine, but now when we push the power button it sputters for like two seconds and then goes dark again.”

“I can’t believe the magic Fix-O-Matic button didn’t work.”

“The…?”

“‘Magic Fix-O-Matic button’. There’s a big button inside the machine that automatically diagnoses your Mac and solves every conceivable problem, from a faulty prefs file to your hard drive being struck by a meteor. Have you pushed it?”

“I didn’t even know it existed.”

“Well, that’s why Apple hides it inside. Only paid Apple techs are supposed to know about it, so…schtumm.”

Sadly, it almost never goes like that. Instead, there’s an hour of me being very patient as the friend fails to understand what I’m trying to explain to him, and then my friend being very patient as I fail to understand his description of what happened after he did what I told him to do. If the friendship survives a session of phone diagnostics then we really ought to just go ahead and have sex, regardless of the friend’s gender. We’ve already determined that nothing can possibly screw this relationship up.
But today my friend’s dream came true because it was indeed a “Fix-O-Matic Button” situation. Unplug everything, pop the latch, find the power manager reset button just above the battery, give it an authoritative press, close ‘er up, plug everything back in, wait a few moments, and then power back up.

There was a bit of a hiccup when there proved to be too many air molecules between the video port and the end of the monitor cable, but otherwise, all was well.

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