One Question for Sheryl Sandberg

In the 90s, as an executive at Nickelodeon, Gerry Laybourne, my boss, and I began a trial flex-time program.  I'd already made the commitment to leave  the office at 5:30 two days a week to squeeze in an essential work-out before going home to my family.   Sheryl Sandberg, the Chief Operating Officer at Facebook, agrees that leaving work at a reasonable time still remains provocative.  In her new book, Lean In:  Women, Work, And The Will To Lead, she examines the progress, or not, women have made in securing leadership positions during these past two decades.   As a former Google executive and Chief of Staff at the United States Treasury Department, she has been at the table (one of her commandments for women to be successful) watching what separates the career trajectories of women from men.  Taking risks is a big piece of her manifesto to "lean in."

Q: What’s the most significant risk you’ve taken professionally?

Sheryl: This felt extremely risky.  After I had my first child, I began to leave work at 5:30 so I could get home in time to nurse.  Once my son was asleep, I would jump back online and continue my workday.  Still, I went to great lengths to hide my schedule and worried that if anyone knew I was leaving the office at that time, they might assume I wasn't completely dedicated to my job.

Once I became COO, I wanted co-workers to know that Facebook cared more about results than face-time so I opened up at a company-wide meeting and stated that I left at 5:30.  Later, this "news" became public and spread throughout the internet.  Journalist Ken Auletta joked that I could not have gotten more headlines if I "had murdered someone with an ax."

While I was glad to jump-start the discussion, all the attention gave me this weird feeling that someone was going to object and fire me. I had to reassure myself that this was absurd. Still, the clamor made me realize how hard it would be for someone in a less-senior position to ask for or admit to this schedule. We have a long way to go before flextime is accepted in most workplaces. And it will only happen if we keep raising the issue.

One Question for Jamaica Kincaid

Jamaica Kincaid was born in St. John's, Antigua. Her books include At the Bottom of the River, Annie John, Lucy, The Autobiography of My Mother, and My Brother.  In See Now Then, her first novel in ten years—a marriage is revealed in all its joys and agonies. This piercing examination of the manifold ways in which the passing of time operates on the human consciousness unfolds gracefully, and Kincaid inhabits each of her characters—a mother, a father, and their two children, living in a small village in New England—as they move, in their own minds, between the present, the past, and the future: for, as she writes, “the present will be now then and the past is now then and the future will be a now then.” Her characters, constrained by the world, despair in their domestic situations. But their minds wander, trying to make linear sense of what is, in fact, nonlinear. See Now Then is Kincaid’s attempt to make clear what is unclear, and to make unclear what we assumed was clear: that is, the beginning, the middle, and the end. Since the publication of her first short-story collection, At the Bottom of the River, which was nominated for a PEN/Faulkner Award for Fiction, Kincaid has demonstrated a unique talent for seeing beyond and through the surface of things. In See Now Then, she envelops the reader in a world that is both familiar and startling—creating her most emotionally and thematically daring work yet.

Q: What’s the most significant risk you’ve taken professionally?

Jamaica:  You mean apart from being born? Of course, this means that I have to admit to having a profession and what would that be? Well, I am a writer. I never learned how to type properly. I failed that course. I also failed my shorthand courses. If I had known how to do those things, I would have most likely gotten jobs as somebody's secretary and when I was young that was a proper job for a young woman. Since I couldn't find anybody who would employ me to answer their correspondence efficiently, I continued in my attempt to be a writer. See how that worked out.

One Question for Jim Cramer

Jim Cramer is host of CNBC's "Mad Money," featuring lively guest interviews, viewer calls and, most importantly, the unmatched, fiery opinions of Cramer himself. He serves as the viewer's personal guide through the confusing jungle of Wall Street investing, navigating through both opportunities and pitfalls with one goal in mind — to help them make money. He's also co-anchor of the 9 a.m. ET hour of CNBC's "Squawk on the Street" (M-F: 9 a.m.-12 p.m. ET). Cramer is the founder of TheStreet, a multimedia provider of financial commentary.

He graduated from Harvard College where he was President and Editor-in-Chief of the prestigious daily, The Harvard Crimson. After graduation he became a reporter for the Tallahassee Democrat and later for the Los Angeles Herald Examiner where he covered stories ranging from homicides to sporting events.

Cramer is a former hedge fund manager and founder/owner and Senior Partner of Cramer Berkowitz. His compounded rate of return was 24 percent after all fees for 15 years at Cramer Berkowitz. He retired from his hedge fund in 2001, where he finished with one of the best records in the business, including having a plus 36 percent year in 2000.

Jim Cramer of Mad Money

Q: What’s the most significant risk you’ve taken professionally?

Jim:  

You want risk? Walk away from a job that you worked years to get, walk away from a job that paid you more your first month than you had made your whole life. Walk away from Goldman Sachs.

Yet, that’s what I did in February of 1987 because I always wanted

to work for myself and even though I loved the place, I knew that if I didn’t make a move I might never do so.

I first tried to get a job at Goldman in 1981, the year I enrolled in Harvard Law School. I loved the stock market and while I wanted to be a prosecutor, I knew that the summer between your first and your second year at law school tended not to impact where you ultimately worked.

I figured if you want to go to work in stocks, you might as well go for Goldman Sachs, the best there was and the best there still is.

There was a huge problem, though. They didn’t want law school kids. They wanted business school students. So began what amounted to a two year odyssey to prove that I deserved a slot, one of the coveted 25 or so positions that they granted to those who graduated business school every year.

In the next two years I interviewed with Goldman Sachs ten times, got turned down three times and simply didn’t take no for an answer.

And when I got hired for Securities Sales, advising high net worth individuals and smaller institutions on what to do with their money, I couldn’t believe my good fortune.

The payoff was immediate; the commissions bountiful, the people terrific, the excitement non-stop.

Yet, somehow, it wasn’t enough. Somehow I wanted to work for myself. So I made the most stupid and the most brilliant move of my life, I quit. Four years into it I walked away to start my own hedge fund.

Stupid? Yes, because two months after I started I was already down ten percent for the year. I had lost almost everything I had made in the time I worked at Goldman. Then, after clawing back to plus 3%, I ran smack into the 1987 crash. Fortunately, I had been able to cash out ahead of it, one of those moves that in hindsight looks like genius but at the time was just total self-preservation because the market before the crash had been horrendous.

And that’s where the brilliant came in. Because I had cashed out ahead of the crash, I managed to have a positive return, something that almost no hedge fund manager was able to claim.

In fact, almost everyone else I knew who struck out on his own to run a hedge fund during that period ended up blown to bits.

That meant tens of millions of dollars came my way to manage. Fortunately, I got back in close to the bottom, and the rest was pretty much history as I managed to rack up a return of 24% after all fees over a 14 year period and then retired to move on to full time writing and television.

When I look back at what I did, I still can’t believe that I took that risk. I would have been happy if I stayed at Goldman Sachs, I know that for certain. By my goal had always been to work for myself and when I had enough capital to make a go for it, I jumped at the chance. Even as it was catastrophic at first, I would do it over again in a heartbeat.

But, and this is the big but, I was single at the time, I had no kids, I wasn’t fearful. I didn’t have responsibilities beyond my own rental apartment and share in a place in the Hamptons. So while it was the riskiest move I ever made in my professional life, I knew I did have the rest of life to make it back if I failed.

Looking back 25 years later, that’s certainly not the case anymore.

One Question for Rosanne Cash

Rosanne Cash has recorded eleven No. 1 singles, blurring the genres of country, rock, roots, and pop. She has received one grammy and twelve grammy nominations, among other awards and accolades, including an honorary doctorate from Memphis College of Art. A prolific writer, Cash has written Bodies of Water (Hyperion, 1996),Penelope Jane: A Fairy’s Tale (Harper-Collins, 2006), edited the book Songs Without Rhyme (Hyperion, 2001), and recently penned her memoir Composed (Viking, 2010). Rosanne’s prose and essays have appeared in the New York Times, The Oxford-American, New York Magazine, Newsweek, Rolling Stone, Martha Stewart Living and various other publications. Her last record album, The List, won the Americana Music award for Best Album of the year and was a critical and commercial success.

Q: What’s the most significant risk you’ve taken professionally?

Rosanne:  

There are series of small risks in my work every day-- going for a different note, improvising, trying out a new song in concert for the first time or working with a new musician. Just walking on stage sometimes feels like a risk. I performed at the Rolling Stones tribute earlier this year at Carnegie Hall and when they asked what song I wanted to do, I immediately said

'Gimme Shelter', because I've always thought it was one of the top five greatest rock and roll songs of all time. There couldn't have been a riskier choice for me. It was thrilling.

Those are the fun risks.

I've taken two really big career risks. In 1989, I had a hugely successful album that had four number one singles on it, and I had some leverage with my label, Sony, so I asked if I could produce a record myself. I made a small, dark, acoustic record called "Interiors". It was something of a mission statement for me. It was authentic and personal and kind of rough around the edges. I thought I had done the best work of my life. My record label heard it and said 'We can't do anything with this.' They put out a single, but didn't do any promotion for it, and clearly wanted to let the record disappear. I was devastated. About three months after the release I was on a plane, staring out the window, and it came to me that I had to ask to be released from the label or at least transferred to the New York division from Nashville.  I called my dad and asked his advice (something I rarely did). He said 'screw 'em. You belong in New York.' I called a meeting with the head of the label and went in alone-- no manager or lawyer. I asked them to let me go. I had been there 12 years. Basically, they said 'we'll miss you', and the meeting was over in 20 minutes. I walked out and had to lean against the wall, I was so dizzy. I was scared I had made the biggest mistake of my life.

It was the best thing I've ever done for myself. I moved to New York in 1991, I got divorced, I met the love of my life, and that dark little record was nominated for a Grammy in the Contemporary Folk category. It gave me a new set of bona fides in the industry. Things didn't go easier after that-- in fact, they became much more difficult for quite some time. The divorce was excruciating, I was broke, I was the subject of a lot of vicious rumors, and I had no more chart hits after that. But my life opened up and I started relying more on my own instincts. Four years later, I took another risk when I asked to be released from the label entirely, even though my contract wasn't up, because it just wasn't working. Again, I went in alone, even though my manager thought it was a bad idea. They let me go, and I started from scratch again. Those career risks are like chess, in a way. There is an element of instinct, but it's mostly logic and planning and creating a new vision for the future. The other risks-- the artistic risks-- are the ones that infuse my soul with inspiration and propel me forward and refine my skills and intuition. Those are the risks that connect me with my own authenticity. The career risks are a First World Problem, and anecdotal in retrospect. The artistic risks make me who I am.

One Question for Lawrence O'Donnell

Lawrence O'Donnell, Jr. is a political analyst, journalist, actor, producer, writer and host of The Last Word with Lawrence O'Donnell, a weeknight MSNBC opinion and news program.  He was an Emmy Award-winning producer and writer for the NBC series The West Wingand creator and executive producer of the NBC series, Mister Sterling.  He's also an occasional actor, appearing as a recurring supporting character of the HBO series Big Love, portraying a lawyer.  He began his career as an aide to U.S. Senator Daniel Patrick Moynihan and was Staff Director for the Senate Finance Committee.

Q: What’s the most significant risk you’ve taken professionally?

Lawrence:  Not going to law school.

One Question for Sarah Jones

Sarah Jones is a Tony Award winning playwright and performer. Her multi-character solo show Bridge & Tunnel was originally produced Off-Broadway by Oscar-winner Meryl Streep, and went on to become a critically acclaimed, long running hit on Broadway. Educated at Bryn Mawr College and the United Nations International School, Sarah recently returned to her UN School roots by becoming a UNICEF Goodwill Ambassador, traveling as a spokesperson on violence against children, and performing for audiences from Indonesia to Ethiopia, the Middle East and Japan. Winner of the 2007 Brendan Gill Prize, Sarah has also received grants and commissions from The Ford Foundation, NYSCA, the W. K. Kellogg Foundation, and others, and theater honors including an Obie Award, a Helen Hayes Award, two Drama Desk nominations, and HBO’s US Comedy Arts Festival’s Best One Person Show Award, as well as an NYCLU Calloway Award in recognition of Sarah as the first artist in history to sue the Federal Communications Commission for censorship. The lawsuit resulted in reversal of the censorship ruling, which had targeted her hip-hop poem recording, “Your Revolution.”

Q: What’s the most significant risk you’ve taken professionally?

Sarah:   I always thought the most significant professional risk I'd ever taken was dropping out of Bryn Mawr College as an aspiring lawyer to instead place my destiny in the hands (and voices) of an unruly bunch of fictional characters who lived in my head. But over the years my 'people'  have had more of a steadying influence on my life, both on and off stage, than I'd ever expected--or have ever given them credit for.  So I thought I'd ask a few of them what they think my most significant professional risk has been so far.

Rashid, an African American ("Why can't I just be black, son?") hip-hop head, sometime rapper, and full time Brooklynite still recovering from the gentrification of Bed Stuy, had this to say: "Sarah Jones' biggest risk? I'ma have to say turning down a couple of different TV shows cuz of her principles and whatnot. I'm like, yeah, you gotta have your morals and all that, but if them dudes in Hollywood ain't worried about it, why you gotta be all Holy Dalai Lama and whatnot--just get that check, you feel me? If you still feel bad at the end, at least you got some loot, you could pay for a therapist!"

Lorraine Levine, an octogenarian Jewish bubbie with Eastern European roots who has been in nearly every performance I've given, shared the following: "You want risky? I always say Sarah is a very nice young Black performer, but I remember one time she was pale as a ghost--the poor thing, such agita she had--because she agreed to perform in Israel at an Arab theater as part of a multicultural event, trying to be all things to all people, and instead she ended up stuck in the middle. I had told her, with some situations, no matter how much your heart is in the right place, you can't win.  But did she listen?"

Nereida, an ambitious young DominiRican (half Dominican, half Puerto Rican, all proud) who grew up in what she calls "the capitol of the Dominican Republic, otherwise known as Washington Heights" opined: "Sarah Jones' riskiest decision has to be when she sued the FCC for censoring her feminist poem/song from radio airplay. I mean, I agree the FCC was clueless, but suing the US government? And on top of that, her lawyers eventually won the battle by forcing them to reverse their decision--I think she really got on their bad side. I mean, not that they would ever retaliate.  I'm sure the IRS audit a few years later was a total coincidencia!

Ms. Lady, an older black woman and self-described PhD (Poor, homeless, and disabled) wanted the last word: "I think the riskiest thing Sarah Jones ever did is what she doing right now--trying to write a commission for the Lincoln Center Theater, and they ain't gave her no deadline, no subject she gotta stick to, no rules at all. Not like most recent things she been writing. So she got to go someplace she scared to be at--the place where she started from--total freedom, to try, to risk failing, to tell the whole truth like she see it, to let go of fancy expectations if she brave enough. Ain't nothing and nobody in her way. So naturally, all this freedom got her acting more like she got a prison sentence than a commission. But I tell her everyday, keep on feeling that scared feeling, and when it gets to be too much, lean on into it a little bit more. Then wake up the next day and do it again. The risk gon' be worth it.

One Question For Daniel Coyle

Daniel Coyle is the New York Times bestselling author of The Little Book of Talent, The Talent Code, Lance Armstrong’s War, and Hardball: A Season in Projects.  A contributing editor for Outside Magazine, he is a two-time National Magazine Award finalist.  Coyle lives in Cleveland, Ohio during the school year and in Homer, Alaska, during the summer with his wife Jen, and their four children.

Q: What’s the most significant risk you’ve taken professionally?

Daniel: It was 1991. I was 26 and working as an associate editor at Outside Magazine, which, in the kind of juxtaposition that happens in Chicago, happened to be located less than a mile from Cabrini-Green, one of the city’s poorest, most notorious housing projects. One day, one of my fellow editors told me about a youth baseball league that was starting in Cabrini. He and I started coaching with a few other guys our age, and quickly grew to love it -- particularly the remarkable, resilient kids we met. At the end of the first year, I realized that there might be a book to be written about our team: one that would tell the story of their lives over the course of a single season.

At that point, the longest piece of journalism I’d written was a one-page article on waterproof-breathable jackets. But naivete is a powerful fuel. I took an unpaid leave of absence from Outside and began spending my days at Cabrini. On the advice of a local social worker, I wore a worn-out sport jacket in order that local gang members would take me for a social worker instead of a police officer. I spent much of the summer in Cabrini-Green, rode with police, spent endless afternoons on the ballfield, and got to know that neighborhood better than I knew my own. Our team, which was average at best, somehow made it all the way to the league championship game. By summer’s end, I had the material for Hardball: A Season in the Projects.

One Question for Erika Andersen

Erika Andersen, my sister-in-law, is the founding partner of Proteus, a consulting and training firm that focuses on leader readiness. She serves as coach and advisor to the senior executives of such companies as GE, Time Warner Cable, TJX, NBCUniversal and Union Square Hospitality Group. Andersen is the author of Leading So People Will Follow (Jossey-Bass, October 2012), Being Strategic: Plan for Success; Outthink Your Competitors; Stay Ahead of Change (St. Martin’s Press, May 2009), and Growing Great Employees: Turning Ordinary People into Extraordinary Performers (Portfolio, 2006), and the author and host of Being Strategic with Erika Andersen on Public Television.  You can keep up with Erika on her blog and at Forbes.

Q: What’s the most significant risk you’ve taken professionally?

Erika:   Without a doubt, starting my own business 22 years ago. At the time my kids were 6 and not quite 2, and I was the primary breadwinner in our family.  I had what seemed to my friends and colleagues like a very good position, managing the instructional design group for a management training company in upstate New York – job security, a reasonable salary, and interesting work.  In fact, one night on the phone when I told a long-distance friend I was planning on leaving my job (and moving half-way across the country) to start a consulting company with a partner, there was a long silence on the other end of the line, and then she burst out, “My god, Erika, are you sure? – What if it doesn’t work?”

The odd thing is, I was completely sure that it would work. Looking back, I don’t know if that was hubris, or far-sightedness, or some combination of the two – but I could see so clearly how my new company, Proteus, would be able to support clients in a unique way, offering a kind of clarifying support that other consulting companies didn’t provide.

Fortunately for me and my family, it turned out to be true, and it’s been a great ride for the past couple of decades (and I hope into the next couple of decades, as well).

The main thing I’ve learned from this whole experience of being an entrepreneur is the importance, if you’re going to take a big risk, of having a clear vision grounded in reality, and then being passionate and courageous in moving toward it.  A lot of people simply avoid taking professional risks, because it seems too…well, risky!  And some people take big risks, but they do it in a high-risk way: metaphorically jumping off a cliff without a parachute.

I believe there’s a middle path: you need to start with a clear and accurate sense of what you have going for you and against you, and to then create a really clear idea of what success would look like.  Then you can mentally build a path to get there (staying as objective as possible about whether you really have what it takes to do what you’re envisioning).

Once you’ve done that, you have to be kind of relentless: to be consistent and resilient in moving toward your dream.  Every day you need to make decisions, take responsibility for your mistakes, and keep going. That’s what I mean by passionate and courageous.

And I have to add that this biggest risk has had the biggest payoff – I have absolutely loved having and growing this business; it’s provided challenges and rewards on so many levels. I’ve come to believe that stepping outside of comfortable is one of key paths to having a life you love.

One Question for Kare Anderson

Kare Anderson is an Emmy-winning former NBC and Wall Street Journal reporter who now writes the Connected and Quotable column at Forbes, and speaks on communicating-to-connect. She’s the author of Moving From Me to We and co-founder of the Say it Better Center.

Q: What’s the most significant risk you’ve taken professionally?

Kare:   As a Wall Street Journal reporter, in my second week of work, based in London, and with no background in economics, I was told to interview one of the foremost economists in Europe.

He was so enraged by my “ineptitude” and “ignorance” that were “blindingly evident within minutes of my interview” that he stood up and started pointing and shouting at me in his office with the door open. Yes, I remember those exact words and phrases, and those are the ones that are “clean” enough for me to repeat here.

I kept asking for clarification of his terms and concepts and that irritated him more. A small crowd was forming just outside his door. I could hear tittering. The economy was bumpy then and he felt strongly about what the government should do. I simply did not understand him at first and it took quite awhile for me to decipher a couple of his views so (barely) adequately write my story.  My boss, the bureau chief was not happy with me when I returned and told him what had happened, including how he finally kicked me out of his office. Walking through that parade of chuckling staffers was not my best moment especially as he had spilled coffee on my skirt during one of his outbursts… I mean clarifications. He wrote a letter to the editor, quite articulately and vividly citing my flaws as a reporter. There were 30.

Yet several people wrote letters say they finally understood the underlying economic theory. That’s what most mattered to me, yet I know the writing was not my strongest because of the pressures I felt, being new to a news bureau and a country.

The unexpected upside for me (and I DO mean unexpected) was that his letter apparently boosted readership of my story… and many people, especially women, expressed outrage at him for his personal attacks. Even more women and men wrote letters to the editor in the coming weeks in support of me because the economist made the mistake of responding to some of the attacks by counter-attacking people by name, thus escalating it. I found it mortifying.

My boss was thankful that the battled was made personal, rather than about my “thin coverage” (his polite phrase) in my original story – and that the back and forth story had legs, getting picked up by other media outlets. My nimble French interpreter (I was moved around Europe and she spoke seven languages) and I bonded over the incident. She was wonderfully protective and reached out to her well-placed friends and family members to fan the flames of the story, I learned months later.

Ironically the visibility made people curious about me so it was easier to secure interviews. Above all it cemented my habit of doing more advance research before an interview and to grow credibility in one, specialized beat so it was less likely I had to cover stories outside my area of expertise.

One Question for Jim Morin

Jim Morin, whose work is distributed by Morintoons Syndicate, won the Pulitzer Prize for editorial cartooning in 1996 and shared the Pulitzer with other members of the Miami Herald editorial board in 1983. He was a Pulitzer finalist in 1977 and 1990.

Q:What's the most significant risk you've taken professionally?

Jim: The most significant risk I've taken was dedicating myself to the profession I chose in the first place. Editorial cartooning is a specialized field in many respects. Your drawing involves caricature, usually one that is negative or highly critical of its subject - not the kind of depiction that would make you popular at parties or county fairs. Your drawings ideally communicate strong, often controversial opinions as opposed to the safe illustration desired by newspaper and magazine editors. What other profession requires such skills? Putting "political cartoonist" on a resume hardly seems relevant for any other employable position. Those that do pursue this path walk on a high wire above a very small safety net. With the precarious state of the print journalism business I've worked to make that net a tad bigger by producing animated editorial cartoons for the Herald's online pages as a sort of insurance in the event journalism shifts its platform from paper to computer screen. Regardless, the employment security risks of drawing cartoons for a living are not a laughing matter.