One Question for Maira Kalman by Anne Kreamer

Maira Kalman has worked as a designer, author, illustrator and artist for more than thirty years without formal training. Her work is a narrative journal of her life and all its absurdities. She has written and illustrated thirteen children's books, is a frequent contributor to The New Yorker Magazine and the creator of an illustrated column for The New Yorker that morphed out of her travels to museums and libraries.

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

Maira: i never think of any project as being risky. i have an idea and then decide to go ahead. later on i realize that i am incredibly anxious that it be something wonderful. knowing that it could be a mess, or a bore. collaborating is also risky i suppose. it is very very hard to be completely honest. brutally honest with another person. of course there has to be love and mutual admiration, (though they are not always apparent), otherwise it won't work so well. if you find a smart person that you can be absolutely honest with and who is absolutely honest with you, hold on to him or her for dear life.

Maira and Max

Maira and Max

Trust Your Gut When Founding A Company by Anne Kreamer

This piece first appeared on Quartz. In 1996, Carley Roney and her husband David Liu, launched a wedding site called The Knot. Creating a wedding information business was not an obvious next step for the couple, who met while attending New York University film school.

Today, it is the premiere wedding site. The metrics are frankly astonishing. Each year, roughly two million marriage licenses are issued in the US—and each year about 1.8 million “wedding events” are registered on The Knot’s database. According to ComScore, The Knot receives five million unique visits a month, more than the next four wedding sites combined. That means 80% of American couples (predominantly brides) planning a wedding visit the site.

But serving this kind of massive female audience wasn’t an obvious internet play at the time Roney and Liu conceived of the business. “The internet was brand new,” says Roney, “and it was all men in those days—sports stats, computer message boards, etc.—so launching anything women-oriented was a stretch.”

Roney and Liu told Quartz about the biggest professional risks they’ve taken. For Roney, it was committing to The Knot as a brand, for Liu, an acquisition the company made shortly after its IPO.

The following has been edited for clarity:

Roney: In hindsight, it seems like a brilliant brand decision, but in 1996, naming our “new way to plan a wedding,” The Knot, was just a risky move made by an amateur. I literally pulled this idea out of thin air. Cool name for the service that will solve all your wedding problems and be different, modern, and fun? The Knot, like “tying the knot.” Simple. It became the first of hundreds on a whiteboard. I had absolutely no experience in branding, but it was the only name I believed in. Not everyone agreed. I had no budget for a focus group, but the informal research I did attempt garnered mixed responses, at best.

“The what? Not? Not what? Oh, with a K. Knot. Oh, OK. Yeah.” Not exactly a homerun. The silent k. The awkward idiomatic reference. Our founding investors at AOL were so against the choice that they held our wire transfer hostage in the hopes we’d change our mind. (They preferred the more literal “Weddings Online”—better for search, they begged.) But I held my breath, dug in my heels, and promised my partners it was perfect. We were headed beyond the internet, and it was the only name that would both differentiate us from all the tired bridal clutter and work when we wanted to brand books, magazines, TV, etc.

This quirky name, with all its faults, could have been the death of us in a search and data-driven world, but it is considered by many to be one of the secrets to our success. It worked. Once people heard it (plus the explanation of course, “…As in Tying the Knot…”) they didn’t forget it, and wanted to tell someone else about it. Eight of 10 couples in America now use our service, and this marketshare was won almost exclusively by word of mouth.

Liu: One of the biggest risks I’ve taken was an acquisition we made right after our IPO. We went public in December 1999 and we were one of the last consumer internet businesses to get out. It was the first internet bubble so we were not profitable with very little revenue, but we managed to get a $150 million valuation and raised $35 million. Most dotcoms back then used their IPO proceeds to feed the beast by either buying traffic or spending breathtaking amounts on advertising. Super Bowl ads were very much in vogue with the newly IPOed dotcom set.

Instead, we used a big chunk of our cash to buy a 12-year-old, money-losing, local magazine business [Weddingpages] in Omaha, Nebraska. I think what made it so risky was that it was universally frowned upon. The equity analysts who covered our stock could not believe we would jeopardize our pure-play digital media multiple by introducing into the mix, a low-margin traditional publishing business—that was losing money to boot.

I remember shareholders would post on the Yahoo Finance message-boards under our stock quote and accuse me of smoking crack. Internally, the difficulty in integrating the business was absurd. I remember the first big meeting post-closing was assembling the 60 local sales people and giving them laptops and our co-founder walking everyone through the steps on how to turn the machines on. Later, when I gave my speech to the group about my belief that one day, the internet advertising they would sell would exceed the print sales, I remember you could hear a pin drop in the room. Most of the salespeople thought I’d lost my mind because back then they gave the internet away for free as value add to sell the print. It was a hard three years, but we were able to generate enough cashflow in three years to pay back the purchase price. Today, our local business accounts for over 70% of the total revenue of our company.

Not Taking Risks Is The Riskiest Career Move Of All by Anne Kreamer

This piece first appeared in Harvard Business Review.

Mark was a survivor. Until he was fired in 2012, six months shy of his 50th birthday, he’d done everything right — rising through the ranks of the book publishing industry, from editorial assistant to associate editor to senior editor, then into management as an editor-in-chief. But as e-books and Amazon destabilized the industry, and waves of consolidation contracted available jobs, Mark (not his real name) admits today that he hadn’t “paid attention to the writing on the wall.” He confessed that he’d spent the 18 months prior to being fired living in denial as his team was reorganized. “Despite that,” he says, “I clung to my job rather than start thinking about how to leave. At that point, I couldn’t conceive of a life outside of the confines of corporate publishing, of not being at the center of the club I’d been a part of — and a star in — since the age of 21.”

Mark’s story is a cautionary tale for us all. In my experience, Mark’s kind of wishful thinking — that things will sort themselves out on their own — rarely works out. Not taking action has costs that can be as consequential as taking risks; it’s simply less natural to calculate and pay attention to the “what-ifs” of inaction. In today’s marketplace, where jobs and job categories are being destroyed and invented at an accelerating rate, I’d argue that the riskiest move one can make is to assume that your industry or job is secure. Just ask former employees of Countrywide, British Petroleum, or Newsweek if you doubt me. Former Chief Talent Officer of Netflix, Patty McCord, says that companies should stop lying to people about their job security, because there’s simply no such thing.

Research I conducted in 2012, 2013, and 2014 with the global advertising agency J. Walter Thompson for Risk/Reward, my forthcoming book, suggests that anxiety about our job futures weighs heavily these days. More than half of the respondents to our surveys — all over the U.S., with people ranging from janitors to CEOs, old as well as young — were thinking of changing not just their jobs, but their careers. Think about that. Half of all Americans long to do something dramatically different with their working lives.

But it’s hard to jettison a career decades in the making in the pursuit of something new. There’s an enormous gap between dreaming about doing something different, particularly if one has spent years building skills and rising through the ranks, and actually doing anything about it. It’s terrifying to think about just letting go of one’s hard-earned law degree and years invested on the law-firm partner track in order to write for television, as an acquaintance of mine has done. Most people dream, but fail to act.

What stops us? There are all sorts of complicated financial and behavioral barriers to risk-taking — loss and risk aversion, the sunk-cost fallacy, poor planning — but basically it boils down to the fact that as human beings, we are wired to resist giving up the known for the unknown. None of us tolerates ambiguity well — particularly when the losses and gains underpin our livelihoods or the projected long-term happiness of our families. Psychologically, particularly during tough economic times, people feel driven to hold onto an unsatisfactory job rather than gamble on something with uncertain odds that might be better in the long run. And we all have different levels of innate risk tolerance that inform our calculus for evaluating probable gains and losses. So how can we turn self-defeating inaction into sensible action?

Start by building vibrant networks. In Working Identity: Unconventional Strategies for Reinventing Your Career, Herminia Ibarra, an organizational behavior professor at INSEAD, writes that people’s existing “contacts [don’t] help them reinvent themselves…the networks we rely on in a stable job are rarely the ones that lead us to something new and different.” There’s a reason, when we’re interested in making a 45- or 90-degree career shift, why most jobs suggested by headhunters rarely feel right. The majority of people we know in one line of work can only imagine us continuing to do the same thing.  So as we meet more people employed in a wide range of professions, our ability to imagine ourselves doing something different grows stronger.

Stanford sociologist Mark Granovetter discovered that the contacts most helpful to people looking for new jobs were neither their closest friends, nor new acquaintances, but rather people with whom they had relatively weak ties that had been forged and maintained over several years. In addition, the more different their contacts’ occupations were from their own jobs, the more likely people were to successfully make a major career change.

Perhaps the biggest impediment to change in our working lives is the sense that any significant change has to be all or nothing. I either quit my miserable job or just suck it up and grind along.I’ve got to make a comprehensive business plan before I test whether my English muffin/croissant hybrid and baked-goods truck can generate enough income for me to live. I’m good at structuring logical arguments so I should quit sales and become a lawyer. Instead, we need to break problems into small actions. The more logically-oriented person might, for instance, test-drive the legal profession as a paralegal before assuming the expensive three-year commitment of getting a law degree. The amateur cook with a killer recipe could approach a local bakery with his novel product to see if they’d be willing to sell it, getting market feedback before spending time crafting a business plan for a new venture. The person in the miserable job could volunteer weekends in an organization they think might make them happier — learning what the work is really like from the inside before chucking it all on a dream that may be a fantasy. Then, armed with real-world data, each of those hypothetical career-changers would have more clarity and about the correct next steps. The trick is to start with the immediately, manageably doable and do.

We need to continue to find new challenges, and to acquire the skills to meet those challenges. Moreover, according to Sonja Lyubomirsky, a psychologist at the University of California, Riverside, the act of committing to goals also provides structure and meaning to our lives that leads to more overall happiness. She quotes G.K. Chesterton in this regard: “There is one thing which gives radiance to everything. It is the idea of something around the corner.”

Real life, by necessity, is improvisational and interactive, crafted incrementally through our responses to the particular circumstances at this moment in time, and the next, and then the next. As author Tom Peters wrote, “I have said and mean with all my heart I’ve only learned one thing ‘for sure’ in 48 years: WTTMSW. Whoever tries the most stuff wins.”

How 'Finding Nemo' Changed One Woman's Life by Anne Kreamer

I'm a firm believer that you cannot change your life without getting out of the house.  And that inspiration can be found in the most unlikely places.   Kiki Kienstra told Studio 360 how a kid's animated movie was the catalyst she needed to jump start her settled career.

From the Studio 360 blog:

"Kiki Kienstra had a good job teaching kindergarten, a nice apartment, and a community of friends. “I didn’t have a big need for change,” she remembers. “You know, everything was fine, so why rock the boat?”

One day, on a whim, she saw Finding Nemo, a Pixar movie about a clownfish named Marlin on a quest to find his missing son. At one point, Marlin and his traveling companion, Dory, find themselves inside a whale. They must decide whether to continue to cling to the whale’s tongue or let go and face an unknown future.

“I realized when I saw that scene that I needed to make a decision about my life,” Kienstra says. “Just staying in my life — just hanging onto the tongue — I wasn’t doing anything. I needed to let go of the tongue and see what happened.” When she let go, Kienstra packed up all her things and followed her dream to teach in a foreign country."

Listen here.

One Question For Seth Godin by Anne Kreamer

SETH GODIN has written fourteen books that have been translated into more than thirty languages. Every one has been a bestseller. He writes about the post-industrial revolution, the way ideas spread, marketing, quitting, leadership and most of all, changing everything. American Way Magazine calls him, "America's Greatest Marketer," and his blog is perhaps the most popular in the world written by a single individual. His latest book, We Are All Weird, calls for end of mass and for the beginning of offering people more choices, more interests and giving them more authority to operate in ways that reflect their own unique values, and Seth once again breaks the traditional publishing model by releasing it through The Domino Project. His recent Kickstarter for his newest book (The Icarus Deception out in January 2013) broke records for its size and the speed that it reached its goal.

As an entrepreneur, he has founded dozens of companies, most of which failed. Yoyodyne, his first internet company, was funded by Flatiron and Softbank and acquired by Yahoo! in 1998. It pioneered the use of ethical direct mail online, something Seth calls Permission Marketing. He was VP of Direct Marketing at Yahoo! for a year.

His latest company, Squidoo.com, is ranked among the top 125 sites in the US (by traffic) by Quantcast. It allows anyone (even you) to build a page about any topic you're passionate about. The site raises money for charity and pays royalties to its million plus members.


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

It's easy for this to become a semantic exercise (what means significant, what means risk) but for me, it was choosing to fire my company's biggest client.

At the time, I had about six employees, we were a book packager creating and selling and building book ideas, and our biggest client accounted for more than half our revenue. It was early days, the first year that I felt we might not fold at any moment.

The problem was that they ceased acting like our partner the day I ended up selling a multi-title book project for them. They thought that the project had gotten too big to share, so they became difficult. It was an organization that was already good at being difficult, one that brought a sharp pencil and little humanity to every interaction. After many months, it was clear that if we kept working with them, we would become an organization that was good at dealing with difficult clients. If we could survive this, the thinking went, then we could survive anyone.

The thing is, I didn't want to become an organization good at dealing with difficult clients.

So we gave them the project, here, take it, and we walked away, taking a huge financial loss. It was crazy.

The good news is that we were energized by our freedom and the lack of finger pointing and nastiness, and made back the lost business in less than two months.


One Question for Anna Quindlen by Anne Kreamer


Lots of Candles, Plenty of Cake is Anna Quindlen's most recent book.  She is the author of five previous bestselling novels (Rise and ShineBlessingsObject LessonsOne True ThingBlack and Blue), and seven nonfiction books (A Short Guide to a Happy LifeGood Dog. Stay.Being Perfect, Loud & Clear, Living Out Loud, Thinking Out Loud, and How Reading Changed My Life). Her New York Times column “Public and Private” won the Pulitzer Prize in 1992. From 2000-2009, She wrote the “Last Word” column for Newsweek.

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

Anna:  Here's what I consider risky professionally: hanging on to a position because of fear or inertia and waking up one day and realizing you've missed forever the chance to try your change-up pitch.  What's risky is realizing you've never terrified yourself with a flying leap.  When you're feeling completely comfortable in a position, that's the time to move on.There are a hundred reasons not to do that, but they are all grounded in fear and convention.

I think taking a job that scares the hell out of you is the key to success.  It's how you grow.  We're all like sharks: keep moving or die.  Not a dead shark: that's my mantra.

One Question for Kare Anderson by Anne Kreamer

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.

Kare Anderson

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.