A few months back, an executive in the software industry received an unexpected E-mail — a message from a former classmate whom he hadn’t heard from in years. It was easy for the ex-classmate to track him down: a Google search on almost any senior executive (or anyone residing in the troposphere, for that matter) tends to produce a match. In fact, the ex-classmate located not only the businessman’s E-mail address but also a recent photograph. “She dropped a note to say hello,” says the bemused executive. “She also commented that I’d put on some weight since college.”

That’s hardly the most egregious example of the Law of Unintended Consequences. Still, it will ring true for anyone who has ever been Googled, paged, beeped, spammed, or otherwise confronted by the dark side of the Information Age. Microchips, global networks, and other technologies have made life vastly more convenient, productive, and safe. But at the same time, technology has created new risks, unforeseen costs, additional responsibilities, and at times, just plain annoyance. We’ve all sat next to a cell phone user who apparently doesn’t know that his handset contains a microphone, spent the Monday after a vacation deleting huge numbers of unwanted E-mail messages, and prowled the aisles of the local electronics superstore in search of antivirus software, memory add-ons, and other paraphernalia that will help us squeeze a little more life from our flagging home computers.

Sometimes it seems that Newton’s Third Law should be tweaked for the Digital Age: “For every convenience there is an equal and opposite inconvenience.”

Move from the consumer side to the corporate side, and it gets worse — at least as a consumer you don’t have to sit through 12 meetings before you decide on a course of action. And a dozen more to reverse that course.

Indeed, it’s not surprising that a look back at the technology coverage in CFO during the past 20 years reveals stories about not only scientific breakthroughs, visionary leaders, and dot-com fortunes, but also technological headaches, missteps, and outright failures. How misleading the sense of steady progress.

The Old Acoustic-Coupler Trick

The very first article on IT ever to grace these pages, in fact, perfectly encapsulates the ensuing two decades. It reviewed several “personal productivity software” packages, priced from $50 to $200, which could potentially replace a CFO’s Filofax organizer (at less cost!) by allowing the user to load contact information, meeting schedules, and the like onto a “microcomputer.” Epson offered a package (proprietary, of course) that allowed certain functions to be executed with the single stroke of a dedicated key. To make that possible, however, the manufacturer had to supply a new, extended keyboard, further impinging upon whatever desk space wasn’t occupied by the gigantic monitor. That meant you pretty much had to computerize your Filofax and Rolodex, because there was no longer any place to put them.

Even back then, ROI analysis loomed large. We pointed out that, at an average cost of $125, these software programs cost less than a deluxe Filofax (then $150) and could do things a Filofax could not (autodial your telephone, for example, or provide stationery templates). Of course, by the time we finished explaining how the programs worked (“think of three transparency masters laid one on top of the other on an overhead projector”), the Filofax was sounding better and better. Then as now, the computer scored points for its ability to integrate a number of disparate capabilities, but in retrospect we should have acknowledged that the Filofax had a distinct edge in the portability department.

And yet as early as 1985, computer makers were keenly interested in satisfying the needs of mobile workers. Our inaugural issue also treated readers to an exhaustive comparison of the new “lap portable” computers, priced as high as $4,995 (or $8,500 in today’s dollars) and weighing as much as 10 pounds. With as little as 5K of RAM and tiny displays measured in lines of text rather than inches, these machines were more like typewriters than desktop computers. Their lack of processing power did offer one big advantage, though: a battery charge could last as long as 20 hours. Today the Websites of computer and chip makers, not to mention technology magazines, are full of tips for extending the battery life of notebook computers (anything that lasts more than 4 hours is considered outstanding). And every finance manager has an anecdote about the machine that ran out of juice at exactly the wrong moment.

Already the issue of compatibility demanded attention, and we pointed out that “[i]n transferring data from a lap computer to either a desktop or another computer it’s essential that the machines use the same operating system and, ideally, the same applications software.” We went on to point out that MS-DOS had the market lead in apps that ran on a single platform (the “MS” in MS-DOS was as close as we’d come to mentioning Microsoft in that issue; later in 1985 Microsoft would get plenty of coverage when it began shipping the first version of Microsoft Windows).

Still, we may have been a bit too blasé in saying that “[i]f compatibility poses no problems, proprietary software may be perfectly satisfactory.” For most of the next 20 years, corporate buyers of IT would grapple mightily with the issue of proprietary versus interoperable systems. In fact, the saying “Nobody ever got fired for buying IBM” (with its implication that getting hardware and software from one vendor was the easiest way to make sure everything worked together) would become synonymous with playing it safe.

While we helpfully explained how to use an acoustic coupler from a phone booth to send data from your lap portable back to HQ, we neglected to mention any of the risks that greater mobility entailed. Today hundreds of thousands of laptops are stolen in the United States each year, and the cost of replacing them is of much less concern than what will become of the data they contain.

Sites Unseen

We did, however, point out that you could use lap portables to “log on to an information utility such as The Source or Dow Jones News/Retrieval, call up information from on-line databases such as ABI/Inform or Dialog, [and] send electronic mail and telexes with Western Union’s EasyLink.” By 1995 those “information utilities” had given rise to the Internet, Netscape went public and saw its share price double, Amazon.com began accepting orders, and our 10th anniversary issue featured an article that explained how to navigate something called the World Wide Web.

At the time, one big corporate concern was how to get potential customers to actually find the company home page. “We haven’t gotten even one [online] inquiry,” complained a bank executive we spoke to. “One of our guys, who is almost a computer genius, had a hard time even finding our site.”

No surprise there, we said, given that there were a stunning 22,000 commercial domains in existence. A decade later, there would be 34 million active domains (and millions more registered but inactive), with 25,000 new sites added each day.

Things have come full circle: corporate managers no longer worry about not being found, but lose plenty of sleep at the prospect of being found by the wrong sorts of people. Hackers pose a very real external threat, and the astounding usability of the Web (not to mention those millions of Websites) presents a potentially limitless distraction for employees — as, for example, when a Web search leads to a corporate Website and then to an unsolicited E-mail that provides a perhaps unwelcome reminder that waistlines, like technology, advance.

Scott Leibs is editor of CFO IT.