Generation gaps are influenced by many factors: Some are moral, religious, and sociopolitical, while others are little more than quibbles over style. (Though at 18, fashion can take on fairly grandiose connotations.) While some gaps can be measured in hair or skirt lengths, others are almost unquantifiable in scope: shaped by political transformation, war, economic collapse.

I believe that—while our world faces many factors shaping us all—the generation that is in college and entering the workforce today grew up on the other side of a gap that will not be readily traversed. While many of my peers didn’t use computers—much less the internet—until college, and my superiors may not have used them until well into their careers, Digital Natives grew up in a web-connected world. There have certainly been generationally transformational technology shifts in the past: the industrial age; the rise of radio, then television. I know that books have been written on the impact of the telegraph, and there’s probably a tale of woe pictured on some cave wall about how kids just don’t get what life was like before the wheel.

Yet the gap between the Digital Native and the generations who need to teach, manage, and market to them may be one of the widest yet. I peer over the edge of this cultural chasm every day. I see it in the helplessness of new hires when internet access goes down; in young lives lived publically—from 15-seconds-of-fame video sexcapades to chronicled crime sprees; in the extension of one’s circle to span the globe with relationships quantified through clicks, subscribers, and friend requests. This generation won’t trade loyalty for a paycheck and doesn’t respect a supervisor who can’t grasp the power of the social web. They don’t learn (just) to earn, and they value the collective wisdom of strangers more than that of a solitary authority figure or static information in magazines or art history textbooks. They exist as part of a savvy, fickle hive that buzzes onto the next thing at the speed of a 13-year-old girl’s fingers on the keypad of her cell.

I sometimes wonder if Moore’s Law now applies to generational shifts, in which case the gap between Boomers and Digital Natives isn’t a question of a few decades (and hiring a Gen X middle manager to bridge it). Instead it is an exponential leap in the way humans relate to community, consumption, creation, and so much more. In a mashed up, re-Tweeted, groupthink world, who owns what? And how can we sell anything to anyone? How can we inspire a mosaic-minded employee in a cubicle-centric workplace? How do we rethink learning to leverage global-think in a standardized test educational system?

As each generation is reared and educated, as it enters the workforce and becomes the dominant consumer force, it overlaps and interacts with, is managed and educated by (and eventually manages and educates), and buys from or sells to members of other generations. As each generation thinks it invents sin, so the cycle repeats, in which we are baffled by the actions and opinions of those outside our peer group.

Invariably, there are those who can turn these differences into opportunities. The ones who “get it,” who become the gap gurus and can not only talk to “kids today” but find the way to effectively incorporate their distinctive qualities into the project at hand or to profit from their particular pattern of consumption.

We need insight into this generation of Digital Natives, which is transforming the way successful business is done today. I also see that certain organizations are able to beat the odds and find a way to play nice with Digital Natives. Sometimes they are creations of the Natives themselves (Facebook). In other cases, they are organizations led by what I call “naturalized citizens,” who are tuned into the way Digital Natives think: They don’t restrict social media access; they harness it. They reward employees with cachet, not just cash. They recognize that the isolated office cubicle or library carrel has been supplanted by infinite connectivity; they are mastering the new math of monetizing what appears to be free.

Margaret Weigel, who has worked at Harvard and MIT researching digital media engagement, measures generations not by age or year but by media use. Blogger Penelope Trunk and Weigel teamed up to offer a wonderful test to figure out where you fall in the generational spectrum on Trunk’s Brazen Careerist blog. I scored an 11 without owning a cell phone (which isn’t generational, just weird). Neither Weigel nor Trunk falls into the age bracket of the Digital Native, but I’ll wager they scored in the Gen Y range. Both write eloquently on the subject of Digital Natives. More importantly, they are  making a good living through their understanding of how Digital Natives tick. Are you?

While you may not profit so directly (by writing about  them or giving them career advice), your organization cannot afford to turn a blind eye to how the Digital Native is transforming the way business is done today … or it may not be in business tomorrow.