Chelsea Clinton Doesn't Know Exactly What to Do With Her Life, Just Like the Rest of Us

Clinton has switched careers frequently, is a pragmatic idealist, wants a meaningful life and married the guy who left his hedge fund job to become a ski bum, instead of the Rhodes Scholar whom her father adored. She also said, "I don't know" to a question about her five-year plan. So is she a quintessential millennial?
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Updated Sun., Oct. 6, 2013: 10:27 a.m.

During a recent press roundtable in Midtown Manhattan, Chelsea Clinton was expectedly erudite. But, there was also something unmistakably gal-pal-esque about her, too.

She spoke with us largely about social activism and young people reconciling prescribed measures of success (say, Wall Street) with wanting to make a real difference (say, global health startup) -- and their aptitude to do so.

"Role models really matter because it's hard to imagine yourself as something you don't see. I'm a big fan of Geena Davis," she offered the group of reporters and bloggers, as we sat in an intimate circle at the annual Clinton Global Initiative.

Though I wouldn't exactly peg the former First Daughter as being on the Thelma and Louise track, I didn't balk at the idea of hopping into a vintage Thunderbird convertible with her.

Clinton has switched careers a number of times, is a pragmatic idealist, wants a meaningful life and married the guy who left his hedge fund job to become a ski bum, instead of the Rhodes Scholar whom her father adored. And as recently as one year ago, she told Time magazine, "I don't know" when asked what her five-year plan was. Underneath it all, this Columbia professor and Oxford Ph.D. candidate really has the trappings of a millennial -- a fringe millennial -- the older, more realistic variety.

Chelsea Clinton is no dilettante, but her reticence to really nail down her future plans when asked by the media has led to a spate of suppositions about where her mixed-bag resume, which includes finance, journalism and philanthropy, will take her next.

But really, she's a lot like most people her age. She's figuring out how to live a meaningful life with purpose, exploring different professions and making few declarations about her life's plan along the way. Granted, the media did make out with some pretty good interview bounty just this week when Glamour revealed that Clinton and her husband, Marc Mezvinsky, said they are "going to make 2014 the Year of the Baby."

So she's doing what many of us do -- a few life dress rehearsals leading up to the final act, all peppered with some humor. And it's made her out to be really human.

Clinton's had to endure her foibles being public fodder -- being labeled, for instance, as "one of the most boring people of her era" by the Washington Post after her NBC journalism debut.

The late Michael Hastings wrote last year for BuzzFeed that "The days of Chelsea having it both ways are over," in regard to her desire to become a more public figure but still maintain privacy. But with Clinton declaring recently to CNN that “I had very much led a deliberately private life for a long time, and now I’m attempting to lead a purposely public life," it looks like she's slowly becoming OK with spotlight.

Now, with outlets such as the Atlantic declaring that "Chelsea Clinton has arrived," and others saying she's simply a vessel to young voters amid speculation that her mom will run for president, it's fair to say all eyes are on Chelsea Clinton.

But her palpable uncertainty surrounding it all makes her, in a word, relatable.

During the roundtable, Chelsea Clinton, the vice chairwoman of the Bill, Hillary & Chelsea Clinton Foundation, answered our questions casually, wearing a sheath dress in a bold print and heels. She pursed her lips and spoke in a way we've all come to know: rumination mixed with some apprehension.

One of the first questions Clinton posed to us was, "Maybe somebody here can tell me if I'm a millennial or not? I get a lot of different answers."

Technically, she makes the cut, born in 1980. And I know how she feels being on the outer edges. Having all the characteristics of Gen-Y -- a desire to be successful, give back and explore -- but knowing you have to be more practical than your earlier 20-something self.

Since I'm around the former First Daughter's age, I can't help but feel like I've grown up with Clinton to a degree. I commiserated with her during the braces years, felt like I could identify with her desire for privacy, and remember, during the Monica Lewinsky scandal, actually trying to empathize with what it would be like to possibly lose trust in your parents as your stronghold. (you know, normal teenager stuff). And even now, I could identify with her.

When Clinton spoke candidly to us about the different sectors in which she's been involved, it made it seem like it was OK for life to be a little nebulous.

In speaking with us, however, she did make one thing crystal clear: her passion to create real change. And she even threw in some tips for a more fulfilling life to boot.

Clinton emphasized the need to expand opportunities for service, particularly by increasing the Federal budget for AmeriCorps, which receives more than six applications for every open slot each year.

But for those who might be nearing a quarter-life crisis and applying for a position that pays approximately $14,000, even Clinton admits it's not the ultimate answer.

"AmeriCorps is not a panacea," she told us.

So, if a curated opportunity for civic engagement is not the answer, what is the path to a fulfilling life?

When asked why young people, saddled with college loans and an economic downturn, should feel optimistic about the future, Clinton said millennials can find that answer by asking themselves what triggers and inspires them -- and they'd better have an informed answer.

And then she delivered her peers somewhat of a roundhouse kick.

"It's not surprising I think voting is super important," she said, and went on to point out what she sees as a lack of civic involvement and knowledge demonstrated by many young people. And we're not talking about youth (or "youths," for New Girl fans). We're talking 20-and 30-somethings working in government, business and the social sectors -- people with every opportunity to be informed.

"Young people come up to me when I'm in Duane Reade and say, 'Hey, isn't it great about marriage equality?'"

Though she has long praised millennials for their passion, connectedness and eagerness to be advocates, she said what many people are thinking: Millennials aren't as informed as they could be.

She criticized the glib perspective some have, pointing out often they don't grasp the big picture involved with legislation or, in the case of marriage equality, the fact that it's not yet a federal law and the implications for that, she explained.

But for what could be perceived as scholarly superiority, Clinton seemed to carry this huge weight on her shoulders.

"I certainly feel responsibility here at the Clinton Foundation and around the world to feel our work has implications for women and girls," she said, describing how the Foundation has focused on gender equality.

Along with assuming more responsibility, she also told us that within her new role at the Foundation, she's owned her successes. "I've actually shut down things that didn't work. That's rare in nonprofits and government," she told us. "Inertia is a very powerful force."

To be sure, the Foundation underwent major changes and has been recently scrutinized by the press, namely the New York Times and The New Republic, which criticized its corporate ties, board of directors and spending.

Maybe it was knowing she really has unruly curly hair despite her perfectly coiffed style that day, but scholarly Chelsea Clinton made it feel like it was OK not to have all the answers, try new things and want to help save the world. Oh, and to know when to humble yourself. After all, she told Jon Stewart last month:

"Right now, I'm still trying to make my parents proud."

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