I’m probably dating myself with the reference to Oldsmobile’s disastrous marketing campaign (click here if you have no idea what I’m talking about), but it’s deliberate: one of the things that’s becoming more and more clear to me as I investigate Web 2.0 vendors, products, and services is that there are some very important social/cultural differences between the way that three or four generations of end-users are now interacting with the Internet and the Web. I’m not just referring to such obvious examples as the fact that college-age kids love MySpace while Baby Boomers find it an alien concept; I believe there are a number of subtle nuances about the way my generation organizes the details of its day-to-day life (based on what it considers critical, moderately important, and mundane) versus the way the twenty-something generation organizes its details, and young teenagers organize theirs. God only knows how elementary school kids are reacting to the Internet, but somebody better start paying attention, because they are on-line.

Most of the startup Web 2.0 companies I’ve visited recently understand all of this at a “gut” level, whether or not they can articulate it crisply. A few of the older computer companies “get it,” too, at least to some degree; Apple is obviously savvy enough about cultural/generational issues to take advantage of iPods and iTunes, but it’s not entirely clear to me how much of their energy is still devoted to selling traditional desktop/laptop computers to the same marketplace that they’ve been dealing with since their origin in the mid-1970s. Meanwhile, I think there are more and more indications that behemoths like Microsoft just don’t get it; and companies like IBM are still trying to sell their father’s Oldsmobile. I suspect the same is true for many of the Fortune 500 companies, too, and it means they run the risk of losing the next couple of generations of potential customers to savvy upstarts.

Some of these thoughts began to crystallize in my mind after a very interesting interview this morning with Narendra Rocherolle, of 30 Boxes. I can’t imagine a nicer locale for a discussion: Narendra arrived via ferry from his home in Marin, and we met at Peet’s Coffee Shop at the Embarcadero in downtown San Francisco. I had visited the 30 Boxes website, so I already had a basic understanding that his company is offering a Web-based, shareable calendar product, which has mashup capabilities for incorporating content from various other Web sources.

“Okay, fine,” I said to Narendra after we had gotten our lattes and settled down at a table, “so it’s a calendar on the Web. What’s the big deal? Where’s the competitive differentiation?” I already had a sense that the product was aimed at consumers rather than the corporate marketplace, but I hadn’t given much thought to the notion that these two markets think about calendars, and related office-suite productivity tools, from a very different perspective. 30 Boxes is aimed at the college-age and 20-something youngsters who are not using Microsoft Outlook, and whose first reaction is that Outlook is too heavy-handed, too complex, and too demanding in terms of the forms-based data entry user interface (UI) that one has to deal with in order to enter a simple calendar item.

This may seem like heresy to a typical 30-something corporate employee who’s been using Outlook for 10 years, and who has internalized all of its commands. And at first, I was inclined to shrug off Narendra’s comments, and blame it all on Microsoft’s heavy-handed UI. For a couple of years in the mid-90s, when I seriously worried that Apple might go bankrupt, I succumbed to the Dark Side, and transferred all of my computing activities to a Windows platform; and I still have a Windows laptop today for the occasions when a client insists that I work in that environment. But during the couple years that I did all of my work in Windows, I was constantly amazed by the practical consequences of the UI: things that would have taken one or two windows and two or three mouse-clicks on a Mac typically took three or four windows and five or six mouse clicks on Windows. All of this became irrelevant when I shifted back to the Mac in the late 90s, but I’ve never forgotten the comparison.

But Narendra was really focusing on something more subtle: he argues that the dominant focus of Outlook is its email functionality, and he asks the simple question: if you go to your email window, with its list of 200 unanswered messages, does it tell you what you’re doing today, and what your friends are doing?

My immediate response was: who cares what my friends are doing? My primary focus, when I start each business day, is: what am I supposed to be doing today, and when does it have to get done, and when will I have to do it again? That’s “task-oriented,” of course, and you might expect me to answer those questions by looking at my to-do list; but the reality is that a large percentage of my day-to-day tasks — especially the ones imposed by uncontrollable and unpredictable external forces like clients and business colleagues — show up as email messages. So for me (and I suspect for many others of my generation, in a typical corporate work-environment), I start with my email to see what new demands are being made of me, and from there I go to my calendar (to see when I can schedule the accomplishment of those tasks, and/or what conflicts are involved) and my to-do list.

But my email also functions as an implicit (and sometimes unmanaged) addendum to the to-do list: the primary reason that an email lingers in my inbox is that it represents an onerous task that I have to admit is unfinished, but which I haven’t had the time, energy, or mental discipline to acknowledge as such, and add to my “official” to-do list. For many corporate workers, I suggest, the email inbox is the bane of one’s existence; on the rare occasions that it gets erased because of some computer glitch, we cheer even though we feel guilty.

By the way, Narendra does not deny the importance of email, nor he suggest that it will disappear — it’s just that he has a different opinion about its importance and its role. He argues that email is the key to the identity of someone whose activities end up getting linked to your calendar; and he says that 30 Boxes is now working on developing an “identity platform,” which will involve a “truthiness” score (click here if you haven’t heard Stephen Colbert’s satirical term before). But he argues that MySpace was, among other things, one of the first public indicators of the failure of email: young people don’t want to live in an email-mediated world, they want to live in a world of social networks. During the early stages of email frustration, Narendra argues, youngsters switched to instant messaging (which they still use to an enormous degree), but IM is synchronous (if the recipient isn’t there to receive, and respond to, an IM it’s useless), and it’s not group-oriented.

In more general terms, if I were in high school or college, my day-to-day life well have a different focus: what classes am I supposed to attend today, and when do they take place? What movies, parties, or other social events are taking place, and which of my friends are participating in which of those events? So I’ll start with my calendar, and follow whatever leads are suggested — including such “social” leads as the Flickr pictures uploaded by my friends from some recent social event, or the Myspace links that tell me whether the individuals planning to attend tonight’s party are as cool as I am. And as part of that process — but not the dominant part of that process — I might take a look at my to-do list to see how many unfinished tasks I should feel guilty about.

This sounds fairly abstract and philosophical, but it has some interesting practical consequences: when I created a (free) account on the 30 Boxes site, it automatically tracked down, identified, and linked to the pictures in my Flickr account; I didn’t tell it to do so, and was a little startled to see what had happened. And while the “preferences” section of a typical calendar/Outlook program is typically preoccupied with formatting and filtering of the task-oriented items, 30 Box’s preferences are heavily oriented towards linking/sharing/syndicating/buddy issues, so that various aspects of your personal life can be linked to, exposed to, and/or shared with whatever subset of the human race you’re interested in.

Narendra’s reference to the “heavy,” forms-oriented data-entry UI of programs like Outlook (and many others, too, like the Mac Now-Up-to-Date program that I use personally, to reassure you that I’m not trying to pick on Microsoft here) is also “practical,” rather than just abstract and philosophical; and it involves a computing-industry shift that was echoed in a later meeting today at Google, which I hope to blog about later tonight or tomorow. People are beginning to expect that computers will be smart enough to interpret and parse semi-natural English language, without a heavy-handed forms-oriented approach. Thus, Google Maps is smart enough to realize that a 5-digit numeric string in the midst of a user input is probably a U.S. zipcode, and that text string of the form “blah blah TO blah blah” is probably a request for directions from point A to point B.

Similarly, 30 Boxes dispenses with the forms-oriented Outlook UI for creating a new appointment with a free-form single-line data entry, with examples such as “run 10 AM repeat daily” and “Birthday Party sunday 12pm +joe@gmail.com”, which will cause an invitation to be sent to Joe. Aside from the obvious nature of the free-form syntax here is the more subtle point that today’s end-users (and yesterday’s users, too, I suspect) don’t want to read a user manual, even if it’s on-line, in order to figure out how to do whatever it is they want to do; they’d prefer to see a couple of typical examples, and then try it out. Maybe it will work, maybe it won’t; but today’s users are adventurous enough that they’ll play around with an unfamiliar UI for a little while in order to determine how best to interact with it.

Another aspect of 30 Box’s UI, which is increasingly common in Web 2.0 applications, is the use of tags with calendar entries, to-do items, etc. Many traditional calendar/to-do programs allow the end-user to specify a single “category” for an item, e.g., “work,” or “personal.” But with 30 Boxes and many other Web 2.0 programs, one can assign an arbitrary number of tags to an item, and then use those tags as a filter/search mechanism. All of this becomes more interesting when multiple users in a shared environment begin using common tags; and while this may be technically possible in older technologies and programs, it typically wasn’t emphasized or simplified. Thus, for example, 30 Boxes allows the end-user to use his tags as the basis for sharing calendar events; rather than creating a “buddy list” of people who can see all of the events for members of that buddy list, I can create multiple tags (”work,” “personal,” “Yankees baseball,” “X-files trivia,” etc.) and associate those tags with arbitrary individuals to determine the nature of calendar-sharing.

This is all very interesting, but I could imagine a skeptic asking me, “Okay, Ed, you sound very impressed — but are you willing to put your money where your mouth is? Are you going to start using 30 Boxes as your calendar system from now on?” Well, no, though money isn’t the issue, since the 30 Boxes calendar system is free. There’s something else at stake here – inertia — that’s either a positive or a negative factor, depending on whether you’re 30 Boxes or Microsoft or some other vendor.

The reason I won’t switch to 30 Boxes right away is very simple: my wife and I have been using a networked version of Now Up To Date’s Mac-based calendar since 1993; to switch to anything else at this point would require persuading my wife that it’s worth the effort, and then taking on the task of converting 13 years of calendar data to some other format. But even more important, it would require convincing myself (and my wife, too, I guess) that a substantially different perspective than the email-based/task-oriented orientation of existing calendar programs would be a substantial improvement. It ain’t gonna happen: we’re not twenty-something youngsters any more.

Similarly, I doubt that a lot of large corporations would seriously consider switching their hordes of employees from an Outlook-style calendar system to 30 Boxes, no matter how technologically superior it might be; there’s too much inertia, and there’s too much invested in their email-centric/task-oriented view of the universe. But I don’t think 30 Boxes has any illustion that they’re going to capture General Motor’s business, or that of any other Fortune 500 company; they’re going after the young, individual users, and the equally young small businesses that not only look at the world through a different prism, but also have nothing invested in a current calendaring approach. As Janis Joplin told us back in 1971, in Me and Bobby McGee, “freedom’s just another word for nothin’ left to lose.” If you’ve got no legacy, you’re free to investigate new calendar programs, and the new UIs and perspectives they provide; but if you do have a legacy, as most older computer-users and most Fortune 500 companies do, then it’s extremely difficult to adapt to some of the possibilities that Web 2.0-related products like 30 Boxes provide.

Bill Gates, are you listening?