Gail Sheehy’s 10 Dares to Take in Your 20’s Part I
I had the great pleasure of interviewing the iconic author, speaker and journalist, Gail Sheehy for my podcast series Your Working Life recently and I am honored to call her a friend. Gail’s new book Daring: My Passages is a memoir of delicious and difficult experiences from a woman who knows how to live life. Gail very generously agreed to allow me to feature her Huffington Post blog about 10 Dares to Take in Your 20’s – which I will share in two parts here on my blog. Even though her daring wisdom in this piece is targeted towards Millennials, we can all learn a lot about playing it safe, or taking a chance. Thank you, Gail for sharing your insights on my blog!
by Gail Sheehy:
When you look at my CV—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 memoir, DARING, 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.
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 Is Not 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 ten 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.
Stay tuned for Part II of Gail’s daring wisdom!
