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10 Dares to Take in Your 20s

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When you look at my CV -- a founding writer of New York magazine, bestselling New York Times author, political writer for Vanity Fair -- you might think to yourself: Oh, she's glided right through. But my career almost ended before it began.

Married at 23, a mother at 24, and blindsided by divorce at 28, I found myself struggling, like many young women I meet today, to strike a balance between my personal life and my career.

I had to scramble to pay the rent by working full-time. But to be present for my toddler, I had to give up my dream job. Could I really afford, as a woman in the Sixties, to pursue a career as a freelance writer? Would anyone take me seriously? I could easily have given up -- gotten a job selling Tupperware. But I didn't.

We really only have two choices. Play it safe, or take a chance. For me, pulling back because of fear has always made me feel worse. When I tried overcoming my fears by taking a leap -- even if I didn't land on my feet the first time -- it made me stronger. I developed an impulse to turn anxiety into action.

When I fear, I dare.

And I want to inspire other women to dare, too. As an extension of my forthcoming memoir, Daring (Sept. 2), I've started The Daring Project -- a digital initiative showcasing the stories of women accomplished and aspiring, from feminist icon Gloria Steinem to professional protestor Shannon Service, and more. (You can submit your own story here).

To encourage you -- the female pacesetters of today and tomorrow -- to take risks, conquer fears and act with confidence, I've compiled the dares that have defined my life and the lives of women I've met throughout my career.

1. Dare to Dream Dangerously

In my early twenties, I dreamed of joining that distinguished cadre of male writers like Tom Wolfe and Gay Talese who were creating New Journalism in the Sixties. I wasn't going to allow being a "girl" stop me -- and you shouldn't either. Just because women aren't allowed to become Navy SEALs doesn't mean you shouldn't dare to train as a fighter pilot. Just because the Catholic Church forbids women from becoming priests doesn't mean you can't aspire to become a spiritual leader -- like Pema Chodron. Dreaming dangerously changed my life, and it can change yours too.

2. Dare to Act Confidently

You don't have to feel confident to act confident. In fact, it's the most important acting job you can learn. When my editor (and future-husband) Clay Felker asked me to follow Senator Robert Kennedy on his Presidential campaign in California, I'd never written about politics before. I was a nervous mess. But I did it anyway--and I got to interview Bobby Kennedy the day before he was assassinated. Recent studies of the brain and gender differences in the workplace agree that acting confidently is the surest key to success. If you fake it, you will make it.

3. Dare to Discard What You Don't Want to Do

You come out of school with everybody's expectations riding on your back. A summer's internship on Wall Street may cure you of any Wolf fantasies, or you find out after a year at Pratt, you really hate to draw! This is good. Discarding what you don't want to do makes room to discover what you DO want to do. Just ask my friend Caroline Dowd-Higgins, author of the popular book, This Isn't the Career I Ordered, and a blog of the same name.

One of the ways we women often handicap ourselves is thinking that once we've made a decision or a commitment, we can't change. Dowd-Higgins devoted years to training as an opera singer, believing that to be her own true course in life. Once married, but constantly on the road and away from her husband for weeks at a time, she dared to re-imagine another life. Once she found her calling as an executive coach, she trained herself to become a best-selling author. She has been deliriously happy ever since -- and still sings.

4. Dare to Fail Your Way to Success

Walter Isaacson, author of two mega-bestselling books about solitary visionaries -- Steve Jobs and Einstein: His Life and Universe -- comes back this fall with a book that shows the breakthroughs of the computer age were made by dogged inventors who dared to try again and again. The Innovators, coming in October, highlights a daring digital prophet from the 19th century, Ada Lovelace (whose name sounds more like a porn star). He finds daring female computer programmers from WWII. His riveting biographical sketches reveal that success as a techie comes from having a stomach to fail early and often.

5. Dare to Pursue the Career You Love -- Meaning Over Money

Coming of age in a tanking economy with college debt weighing down their dreams, Millennials are naturally more worried about money than previous generations. But the meaning of life is not fully satisfied by fame and wealth. Personal happiness is crucial. According to a recent report from the Brookings Institute, more than 60 percent of Millennials would rather earn less than 50k at a job they love than six figures at a job they find boring. Rejecting the false security of a corporate job and taking the risk to pursue your own venture offers a better chance for the big payoff.

For many, the greatest satisfaction of all is found in making meaningful connections with others. And that kind of meaning is mostly offered in low-paying fields, such as the fine arts, social work and teaching.

Young people who go into teaching in New York City only stick it out for an average of 1.5 or two years. Jes Kruse has survived for 10 years and ultimately thrived. She took her first teaching job in a Brooklyn high school with so much gun violence there was a police officer on every floor. Her starting salary was $39,000, a decent wage for many Americans, but to rent in Manhattan in 2014 would devour all of that at an average monthly cost of $3,470, according to Bloomberg News. With no financial support from her family, Jes lived in a cheap rental in a sketchy neighborhood. She skipped the big social events and Broadway musicals and took four-day vacations.

But what gives her the most pleasure in life is what she continues give away every day. "I love seeing my immigrant kids come to class," she told me. "They don't have a lot of family support. I'm helping them develop a vision for their life, and a life that matters." She has sent all of her students to college. Her smile radiates a sense of well-being, a constant background tone of the life she has chosen.

Last year, Jes told her principal, "I'm going to work part-time (less than 80 hours a week) and date full-time." This summer, Jes became engaged.

6. Dare to Attach Yourself to a Mentor and Show Your Stuff

I would never have made it to prominence in my profession if I hadn't attached myself to a mentor in my twenties. As a graduate student, I appealed to renowned anthropologist Margaret Mead by letting her know I wrote for New York magazine. She literally let me ride with her to Columbia and made me her journalistic outlet, sending me to chase down stories about major cultural shifts. In turn, she gave me an insight that would became my m.o.: "Whenever you hear about a national tragedy or a racial clash or a controversial inauguration, drop everything to get there, look down into the abyss, and you will see the culture turned inside out."

Attaching yourself to a mentor is even more important for young people today. As my friend, the economist and acclaimed author Sylvia Hewlett has documented, "the route to success" for Millennials in the workplace is to identify a senior executive who will be your sponsor. Demonstrate that you will make her or him look good, and your sponsor will invest in your future and help you quick-climb through the ranks.

7. Dare to Postpone Marriage Until You Can Support Yourself Independently

"Every other generation before them said 'I'm waiting for Mr. Right.' Milllenials say 'I'm waiting until it's right for me.'" -- Celinda Lake, National President of Lake Research.

Being independent and self-actualized before marriage is crucially important to your career growth and personal happiness. Daring to delay marriage has elevated the socioeconomic status of women, especially college-educated women. They use their twenties to gain advanced education and build the competence and confidence that makes prospective employers salivate. By waiting to marry until they're 30-plus, research shows that women will make more money -- about $18,152 more per year -- and are also likely to be happier in family life and take more pleasure in their work.

The intrinsic benefit of delayed marriage may be even more important. Waiting allows women to reach for other life goals, like promoting diversity by joining Teach for America, or training to be a champion athlete, or following a passion for making music, or writing a novel, or launching a social movement. The longer you wait to attach yourself to a life partner, the less likely your marriage is to come apart.

8. Dare to Pursue a Career in STEM: Science, Technology, Engineering or Math

Women who work in STEM fields often face discrimination from their male peers, but perseverance can pay off big. As Lisa Lambert, a senior Vice President at Intel Capital, recently told me, daring to pursue a career in technology has allowed her to provide for her family in ways she couldn't have imagined. She isn't the only one. From mathematicians to dental hygienists to software engineers, women in STEM jobs earn significantly more -- a whopping 33 percent more -- than the average full-time working woman makes.

9. Don't Dare Let a More Senior Person Intimidate You or Steal Your Ideas

You are so enthused about your new theory of non-relativity, you spill it to your a tenured professor and he wants to own it. How to say no? That was one of my biggest dares.

When I interviewed a senior psychiatrist at University of Southern California about his study of adult development, he literally backed me into a corner and proposed that I collaborate with him on MY book. But I was the writer, and I was developing a new concept about the stages of adult development and the times of transition between each stage, which would become my book Passages. He threatened: "No one will take you seriously, you're just a journalist." He knew exactly where to needle my self-doubt. But I declined his offer. "You can write your own book," I said, "and I'll write mine." It paid off.

Passages
remained on the New York Times bestseller list for three years. His book never made the list.

10. Dare to Change Your Career When You Turn 30

So many of us grow up being warned not to quit. During your 30's, it is predictable to feel more or less restricted by the choices you made in your 20s -- even though those choices might have been perfectly appropriate at the time. Karen Fan, for example, chose to drive ahead as a supercharged seeker of success during her 20's, happily rising through the ranks of the banking world. But having a child completely transformed her priorities. In her early 30's, faced with the choice of succeeding as a high-powered executive and failing as an absent mother, she dared to quit her job and raise the money to start a business of her own. Now able to spend quality time with her daughter, Karen knows she's made the right choice for a different stage of life.