There’s an early episode of The Simpsons where Homer learns he has a long-lost half-brother named Herb who’s a major automobile mogul. Out of love for his newfound family, Herb lets Homer design and build his ultimate car. The result is a piece of pure American id, in which Homer’s most extravagant obsessions combine to create an unmanufacturable $82,000 boondoggle—complete with bubble windows and a place to put a really, really big fountain drink.

In that pioneering national spirit of favoring geegaws and fantastic chimeras over practicality, here are a few completely random ideas about a notional productivity application I’d like to see someday (as well as few bitches about the lame state of the ones we have now).

See, the thing of it is, there must be something in the air right now, because I’ve talked to no fewer than six (6) people in the last three months who want to build some kind of a new productivity app. I must say, the ideas so far are varied and novel in their approaches to tackling a basic set of problems. There’s a good deal of overlap to be sure, but there’s enough divergence to make me tell one particularly talented friend:

I think it’s heartening to see so much enthusiasm for app development but it reminds me a little of that scene in Jaws where everyone’s crowding into separate boats, firing off pistols, and nearly running into each other right in the harbor.

So here you go. A bunch of nutty bullets about a non-existent program:

• Cocoa - Whatever piece of app-based functionality resides on my Mac, I want it to be developed with Cocoa. There are some arguments about this issue (with people who are much smarter than me) that I’ll never win, but I still feel strongly that Cocoa represents more than an arbitrary preference about programming. Cocoa apps work together with other Cocoa apps, most all Cocoa widgets (iSearch, anyone?), plus, as I understand it, they capitalize on numerous salutary functions of the OS X architecture itself. C’mon guys. We stopped making “Bed and <BR>eakfast” sites when that seemed like a daunting curve; we owe it to ourselves to encourage good developers to move on as well and start taking full advantage of what a Mac can do today.
• Hooks and more hooks - As I’ve repeated until I’m hoarse, apps like Quicksilver change the way you use your Mac. Drastically. Ditto for any app that’s open to interaction via (the vastly underutilized) OS X Services. There are smart ways to provide some kind of access to most any program without switching from the foreground app and the task at hand. I want ways to append information, create new items, and do any “capturing” from wherever I am. At the very least, I want a universal “drop box” to which I can periodically return to process, file, and enrich any kind of productivity app data (reminders, phone numbers, notes, etc.).
• Tags - People have strong feelings about metadata and the smart money is usually against letting The User™ apply his or her own tags and titles for important shared data (“They do it wrong or not at all,” the burghers moan). But things are changing for personal users. Two examples? iTunes and del.icio.us. Nobody cares what “metadata” means, but they for damn sure know they want their mp3s tagged correctly. Ditto for del.icio.us, where Master Joshua has shown the world that people will tag stuff that’s important in their world. Don’t like someone else’s homebrewed taxonomy? Doesn’t matter, because you don't need to like it. If I have a repeatable system for tagging the information on just my Mac and it’s working for me, that’s really all that matters. I would definitley love that tagging ability for the most atomic piece of any work and personal information I touch.
• IMAP-like syncing - For me, the Hegelian truth between the “OS <whatever>” vs. “Web OS” rhubarb is that’s it’s both and neither. Personally, I want my important information stored on a secure server, but I want the data and its structure seamlessly sync-able to applications on the web, via wireless devices, and yeah, in my most important desktop apps. Why is there not “IMAP” for my address book and task outlines? Why the heck isn’t there a standard calendar format that lets me collaborate with colleagues and use whatever program I want? Why do I have to learn CVS to have smart versioning on plain text? I don’t know either. (insert image of Merlin angrily kicking his slippers at the television)
• Syndicated everything via secure http - Flickr does a fantastic job of letting you pluck out just the stream of information that you’re looking for (threads I've commented on and the Dr. Phil graffiti group are two favorites). I want the same from a productivity app. For example, I want to flag an email with a special tag and then have it generate an expirable Atom/RSS feed to follow the thread and alert me of updates (oooo...maybe via Growl, too?). And I want it secure. That means no passwords in the URL, and no way for Bloglines searchers to accidentally run across my stuff. (Oh, man, is that ever a bomb waiting to explode).
• Smart groups and ad hoc collections - The upcoming Tiger release of Mail.app brings iTunes-like smart folders to your mail, and that’s so great. But I also want a Gmail-like tagging system that lets me create multiple non-destructive groupings without multiple copies or resorting to complex hacks. I want all my “stuff” to reside in a big pile, and then I want smart help to script it, organize it, and associate it however I like.
• Smart associations and intra-project linking - Related to the previous wish, I want a more mature version of Entourage 2004’s “Project Center” that lets me identify items (contacts, todos, calendar items, notes) to automatically be associated with a given project. The catch is, I want those projects themselves to be nestable, so that I can scoot them around, change their status, or even move them to a completely different client with dragging alone: no time consuming manual re-tagging, please (thanks for that boat anchor, Entourage!). Somehow, on this matter, I think there’s some good lessons to be recycled from the 3.0 Pro release of OmniOutliner. It gets so much right about how I want information like this to behave. Really terrific app.

There’s a million other specifics that I won’t go into just now (fast and savable searches, endless import/export options, robust support for structured text everywhere …), but I at least wanted to give a flavor for what’s important to me and the way that I like to work.

I suspect that most of us feel kind of stuck right now; there are a few servicable (but extremely dull and inflexible) productivity apps with which we’ve had to learn to satisfice. Our expectations have gotten depressingly low, and, unfortunately, they’ve been glumly met at most every turn. Bloated proprietary formats, locked up information, non-standard menus and key commands, and totally weak categorizing are just the beginning of the problems in a vertical that, to me, has been feeling moribund for five or more years now.

It’ll be interesting to see whether Apple pulls out this rumored iWork package at MacWorld next week, but that still leaves us with scant options for integrated calendaring, mail, and note-taking. Regardless of what Apple does, I would still love to see the nerds keep collaborating openly on novel solutions for collecting, mining, organizing, and streamlining the way we deal with the growing amount of “stuff” in our lives. I'm not necessarily asking for a silver bullet in a single app or one Great Idea™—these things take time, iteration, and patience. It's just that there are so many wonderful sites and web apps that are getting aspects of this exactly right. Shouldn’t we expect at least some fraction of that power and innovation from the software that runs our lives?

So: “blue sky.” What do you want from an unlimitedly awesome productivity app? What’s your biggest hangup with whatever your current apps are?