The rubicon (for the historically challenged), is a small river that flows into the Adriatic Sea, and in Roman times it marked the boundary between Cisalpine Gaul and ancient Italy. In 49 B.C., after some hesitation, Julius Caesar crossed the Rubicon to march against General Pompey in defiance of the senate\u2019s orders. In doing so, he committed himself to conquer Rome or to perish trying. Hence the phrase "to cross the Rubicon" has come to mean risking all, taking an irrevocable step. In 1959, when I was a very young kid living in Southern California, my parents took me to the then recently opened Disneyland. My two most vivid memories are of walking with my father to shake hands with Walt Disney himself, and of gazing at the fabulous improbabilities of Tomorrowland, the 1950s equivalent of Comdex. Tomorrowland as it was in 1959 stands as just another reminder of the axiom that we tend to overestimate technological improvements in the short term, underestimate those improvements in the long term, and occasionally pursue the wrong improvements altogether. Bell Telephone sponsored an exhibit that proudly demonstrated the "picture phone," a technology, universally accepted as a future given (think of any movie about a nonapocalyptic future made in the past 50 years that doesn\u2019t feature one). And yet, it has been universally rejected as unnecessary, ineffective and distracting by those who have used it, and intrusive and unwelcome by those who occasionally like to hang around the house in their underwear. Hope springs eternal in some quarters though. The Asian Wall Street Journal recently reported that Kyocera Corp. will soon market the Personal Handyphone System, a mobile videophone that transmits and receives two video frames per second (standard full-motion video is 30 frames per second). Good idea, guys! Microscopic screens featuring the fluid motion of Japanamation. What happened to the picture phone back then, and what is happening (or not happening) with video conferencing today, serves as an object lesson in the hazards every organization faces trying to identify and deliver technologies and projects that have competitive value for their companies. This, as we all know, can be a tricky and, at times, very frustrating exercise. It demands that we continually reexamine our priorities to make sure we are delivering what the company actually needs to make a real difference instead of what the company, or factions within it, want. Sometimes you sweat for months, even years, over a mission-critical, complicated, time-sensitive project, executed and delivered flawlessly in spite of budget cuts and personnel shortages, only to earn little more than a yawn from your effort\u2019s beneficiaries. Then the next week you do something painfully, embarrassingly simple, almost as an afterthought, like adding a field to some report, and the users are so amazed and delighted they practically carry you around the office on their shoulders. The fundamental unfairness of it all screams for a villain. Fortunately, you often don\u2019t have to look very far. We tend to ignore the influences that history, economics and even anthropology have on real and perceived value. In the face of the gee whiz effect, we seem unable, sometimes, to look for deeper insights like how or why a particular technology or process might be used, misused or ignored when introduced in a broad continuum of circumstances. Forgotten in the excitement is the hard certainty that all gee whiz is relative, that the value and importance of an idea or project is not measured in its cost, complexity or breathtaking novelty, but in its situational impact on customers, users and the bottom line.This simple notion speaks volumes about the difficulty of selecting the winners of this year\u2019s Enterprise Value Award. The judges and CIO\u2019s staff have gone to extraordinary lengths to fairly and accurately assess value (impact) in selecting the winners, all of whom deserve the recognition they receive. However, it goes without saying that there are thousands of projects out there just as deserving, many of which are comparatively low- or no-profile, low-budget affairs that nonetheless have a profound and profitable impact on the companies they are built for. God forbid I should get too mushy here, but allow me to congratulate the award-worthy organizations and projects we will never hear about. Here\u2019s to their ingenuity, their technical prowess, their dogged belief in an idea and their salesmanship to an often less-than-receptive clientele. Most of all, here\u2019s to their confidence and fundamental bravery, their willingness to cross the Rubicon while so many of their feckless brethren freeze midstream, willing to squander their opportunities for the false promises of outsourcing and packaged solutions.While the need for this kind of risk taking has never been greater, it\u2019s getting harder to convince most companies to actually make these high-risk commitments. In most businesses, there\u2019s never been much patience for mistakes, and as things get more demanding, running faster and faster, that impatience is turning inexorably to contempt. Among the more unfortunate byproducts of our accelerating times is that as the gap between thinking and acting shrinks, the confidence, self-awareness, control, expertise and humility that come with laboriously developing unique solutions is vanishing, with unpredictable results. The way to deliver competitive advantage (value) is to summarily reject canned solutions. Embark on a process of discovery during which you move in a given direction, find yourself at a dead end, back out shaking your head with frustration or disgust, puzzle out why that particular path was wrong and start again. With every wrong turn you figure out more, so every process is an education. The benefit of false starts and ideas that don\u2019t pay off is that going through the process of discovery often alerts organizations to unexpected new directions and applications. Like the rigors of evolution, this approach has the happy effect of eliminating solutions that might not be fit enough to survive in the long run and refining solutions that will, one day, propel a company to the top of the food chain. All of the IT organizations considered for this year\u2019s award understand this. They, and the companies that they support, have come to grips with the notion that risk taking is inherently failure prone (otherwise it would be called "sure-thing taking"). If we always knew what we were doing, always knew how long it would take and what it would cost, it wouldn\u2019t be IT, it would be...um...accounting!I have a long and somewhat checkered past when it comes to projects, including my share of rather expensive failures?my picture phones. Some of my failures were a result of betting on the wrong technology, but most were because of the higher risks associated with opting to write custom applications instead of buying software that our competition would also be able to go out and buy. Some of my mistakes cost me bonuses, some promotions and once (very early in my career) my job. I do not have a single regret about any of my decisions. It\u2019s hard to imagine a work life of no risks. It\u2019s hard for this year\u2019s Enterprise Value Award winners to imagine it too.