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Gossip Girl to Geek: Transitioning From Quarterlife Crisis to CEO

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I noticed her immediately.

The line I was in was moving at the speed of molasses, and I was looking for a distraction. I found one in a beautiful post-collegiate girl enjoying her Saturday in the hip Dupont Circle neighborhood of Washington, DC.

"Hi boys!" this darkly-tanned brunette exclaimed, upon encountering two young men she knew, also waiting in line. And to her friend on the other end of her iPhone, an immediate: "Let me call you back."

I have to admit, I couldn't help myself -- I eavesdropped on their small talk, holding my bag of French Roast beans and pretending to consider buying a croissant.

My temporary distraction used to live near this particular coffee shop, but had since moved to Chicago and in with her parents. This "boomerang" maneuver can be a terrific way for parents to ensure their children hit the ground running in the early stages of their careers, according to a recent Washington Post op-ed by Columbia professor Steven Mintz.

Hitting the ground running sometimes looks more like hitting the ground walking, though. When one of the fellas inevitably asked about what this young lady was doing in Chicago, she casually and immediately replied, "You know, unemployed, so I have nothing to do."

Exhibit A: Generation Y, subspecies gossip girl.

Obsessed with the latest smartphones, cameras, and apps, constantly plugged into networks of people and information through social media, perpetually wired with caffeinated products, and yet can't find anything productive to do with any urgency.

While thousands of young athletes descend on London to compete in the Olympics, cities across America are currently hosting a different cohort of young people in their early 20's. They discuss their unemployment on iPhones at Starbucks, send out countless resumes to anonymous HR people, and email unfocused requests like "I will honestly work anywhere" to folks above them on the food chain they encounter.

And -- for the fortunate who have landed coveted internships at Goldman Sachs or on Capitol Hill -- many complain about their bosses and colleagues while doing late-night shots and then exhaustingly chronicle these outings on websites like (what else?) LateNightShots.com.

Less than a mile from my eavesdropping, something else is happening. On the 5th floor of a nondescript office building, a startup accelerator is hosting a dozen fledgling consumer tech companies they've invested money and mentorship in. Many of the founders are a bit older than 25 -- some are as old as 40 -- and most have experience working traditional jobs in technology, public relations, government, and other fields.

Hang around this particular incubator long enough, however, and you may overhear a mention of "the kids" -- a group of seven young folks (six boys, one girl) tucked safely in the back of this huge open space, diligently working on their new project.

The project -- which I've promised them I won't disclose for another month or so -- is revolutionary. It's meaningful for society. And most importantly, it's really cool. You can't help but be taken in by the "CEO," a freckle-faced boy with shaggy red hair, or the "director of marketing," an Asian girl with matching pink blouse and laptop.

Exhibit B: Generation Y, subspecies geek.

These high school students -- yes, high school -- have a full-fledged tech startup company. According to one of their mentors, they frequently work from 8am to midnight. Instead of picking up girls, they are picking up computer languages. They have attracted angel investors. And most importantly for the future of creativity, innovation, and commerce in America: They are making something.

In her book The Geeks Shall Inherit the Earth, Alexandra Robbins discusses the "cafeteria fringe" of high school -- the outsiders who are not part of a school's inner circle, society crowd. These tend to be the leaders of the next generation. And by extension, these are also the people who are personally successful (i.e., they make money), and create jobs for other people.

What to do if you're a Serena van der Woodsen who doesn't know how to transition into something like a real-life Danica McKellar?

I once taught a college class about how social media was disrupting journalism. We only had the opportunity to scratch the surface, so I bought every student a book that could help them take things to the next level without me.

The book is called Crush It. Its author, Gary Vaynerchuk, is an immigrant turned retail store owner turned online wine expert turned social media marketing expert turned keynote speaker and author. His book delivers the "101" about how to launch something new and take advantage of exciting emerging technologies. Crush It should be on Serena van der Woodsen's summer reading list.

The great news is that "being a geek" isn't as hard as it was when Bill Gates and Steve Jobs were building Microsoft and Apple. The computers they built were 10000+ times less powerful than the smartphone or computer you're reading this on. And if you're more business-minded than geeky, that's okay -- it's easier than ever to find a "technical cofounder" to help you start building your vision.

Don't be intimidated. You don't have to build computers, robots, or genomic sequencers if you don't want to. But everyone needs to be a little geeky these days. It's increasingly hard to imagine new ventures that don't take advantage of new, disruptive technologies.

What might such a new venture started look like? Carly Zakin and Danielle Weisberg recently quit their producer jobs at NBC News in New York to launch The Skimm, a daily newsletter that essentially skims the news and events of the world for you, with a decidedly young-professional-women's tone. (It's even a little controversial, warranting a defense in Slate.) I subscribe to it, and so far it's fun to read every morning (it's only about a month old).

More established companies following basically the same playbook include Daily Candy and Gilt Groupe.

The Skimm has a ways to go to prove it's a successful business. But if you're a "gossip girl" hanging out in Starbucks, underemployed, wondering what to do with your life, the story of Carly Zakin and Danielle Weisberg might be an inspirational tale (full disclosure: I know Carly a bit from when she lived in DC, and based on my chats with her, I'm not surprised she's upped her game). They are "crushing it," as Gary Vaynerchuk would say.

So, do you consider yourself underemployed and helpless and in a quarter-life crisis, or self-starting, empowered, and ready to start something new?