Stiletto Network

Written by Megan Smith
Artwork by Janet Hill

Purely out of curiosity and on her own dime, New York Times writer Pamela Ryckman flew to Silicon Valley in 2010 where fifty of the nation’s most recognized, influential businesswomen were uniting at the Alley to the Valley Summit.

For this financial services expert turned journalist, the trip would become a series of ah-ha moments and revelations that would not only re-define Pamela’s view of the modern businesswoman, but build a platform for her to share with the world how the culture for women in business has undoubtedly shifted. “What surprised me most was that the room was full of powerhouse women who looked like women! They were feminine and fashionable. They wore stiletto heels and talked about healthy hair. They defied the stereotype of strong women in business. They were unabashedly women.”

Spend five minutes with Pamela, and the way you perceive the word ‘networking’ will forever be transformed. When she speaks about the connecting power of women, each word packs channeled energy and focused passion. It’s utterly contagious. Which is a beautiful thing, because, without a doubt, this ‘love story’ of women doing what women have always done—bonding together, from Girl Scouts to carpool to the PTA—is finally re-designing the corporate ladder. In fact, that steep corporate ladder is looking a lot more like a swinging bridge ropes course these days: tightly netted cords and knots interweaving and intersecting to make navigating the business world adventurous and experiential.

With a listening ear and a journalistic thirst, Pamela discovered much more than topics of social change, corporate philanthropy, politics and gender issues were being discussed in Silicon Valley that week. It was the side conversations these women were having about their networking dinner groups that perked her ears. Nearly all, with career experience unheard of in their mothers’ era, were connecting deeply with other women on a regular basis through the most basic ritual known to humankind: a meal. Pamela was captivated. She probed further, needing to know more. What she found over the course of several months after the Summit, through dozens of consequent interviews, phone calls and travels, was that these networks are emerging everywhere. Women from coast to coast are coming alongside each other, propelling one another forward and finding likeminded camaraderie across industry lines. Women with smarts, style and, of course, a dazzling pair of stilettos.

In May 2013, her book, Stiletto Network: Inside the Women’s Power Circles That Are Changing the Face of Business, launched with a hefty stream of press and buzz leading the way. “While researching for the book, I innately felt I was onto something.” She likens the experience to a starburst effect with leads and connections rapidly turning her ideas and hunches into a 100-page manuscript. Having personally reaped the benefits of this ‘stiletto network,’ Pamela attributes its power to two things: evolution and revolution. “For the first time in history, women have self-made wealth and are opening up their rolodexes to help other women. They’re taking risks for each other, which never would have happened 20 or more years ago when there was just one seat in the boardroom for a lady, and each was vying for it.” In terms of revolution, Pamela sees firsthand how technology is transforming the unifying power of women in the workplace. “Women have always been relationship maintainers. We are the ones carrying the family ties. These skills that have been honed for generations are now infiltrating the online world and connecting women across a multitude of fields.”

There’s something in Pamela’s voice when she speaks about this subject that indicates she’s only caught a glimpse of the tip of the iceberg. “The book proves the power of its thesis. Women connect, get behind each other and propel one another forward. You don’t have to be isolated in your work. Pick up your head and let someone provide the spark to move you forward.”

Pamela’s career journey itself also proves the power of her thesis. After years in the finance world, consulting and working for companies like Goldman Sachs, she had her ‘come to Jesus’ moment while pregnant with her first son. For as long as she could remember, she wanted to be a writer. Taking the leap, she went back to grad school to study journalism and became “the oldest pregnant intern at the NY Sun.” Her own struggle moving through a maze of competitors in a teeming publishing industry testified to the results of women going to bat for one another. “I was in a new industry trying to navigate my way into a career, with kids. It ended up that every opportunity I got came through a woman. They were the ones who could think outside the box with me and see me as a viable candidate.”

Don’t for one second question Pamela’s ability to balance life as a wife, mom of three young boys, freelance writer and book author…she’ll quickly nip that in the bud. She resolutely chooses to follow passion, not balance, in all areas of her life. She’s equally as passionate about lunch dates with her young boys at the local diner as she is about discovering those idiosyncrasies that make women unite. “I love learning what holds these women’s groups together because at the end of the day, it’s all about friendships. It’s organic and fluid. That’s the glue.”

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Sigrid Olsen: Paradise Found

Words by Janet Holloway
Photography by Andrea Hillebrand

How is it that nearly every woman I meet who’s over 50, or even 40, is worrying about what’s next? It’s as if women are hitting a halfway mark on the time continuum or perhaps they’re discovering that the boomer bottom is staring them in the face. All those dreams. All those aspirations. Given today’s economy, it’s no surprise that some may be facing the loss of a job, a career, a home or worse. Women also report that they’re simply worn out from the daily grind, from more of the same, with no hope for change in the near future. Asking “what’s next?” may be their first step in making a crucial life change. Maybe it’s time to revisit those dreams and aspirations and redesign or repurpose your life around them.

Massachusetts fashion designer Sigrid Olsen had no choice about the change in her life. For more than twenty years, Olsen had filled a market niche for baby-boomer women who wanted to look bold and funky at the same time. “People came out of the dressing room with a smile on their face, saying my clothes made them happy,” she says. Her clothing designs were bright and colorful, well-made and comfortable. A woman of any size would look good in them. Under her trade name, Segrets, the business grew to $30 million in sales—a far cry from where she started in the 1980s imprinting colorful pot holders with her unique designs from nature. The company’s growth caught the eye of fashion giant Liz Claiborne.

“I was so happy that someone like Liz Claiborne, Inc. recognized what I was doing and offered to buy the business,” Olsen says. “My love has always been design, not running a multimillion dollar business.” Liz Claiborne’s offer of 10% ownership to Olsen, along with the title of creative director, sounded good at the time. Life was fast and fascinating at Liz Claiborne. Olsen had apartments in New York City and Boston, travelled to Los Angeles and Paris for trade shows and arranged photo shoots around the world.

“By that time, my kids had graduated, my husband was working in the fashion business, and I could devote myself full-time to expanding the clothing line,” she says. She took only one month off after breast cancer surgery in 2005 and then moved back into the fast lane. In 2007, with fears of an economic downturn on the horizon, Liz Claiborne began to cut back and streamline their brands. Segrets had been one of the conglomerate’s top 40 brands, but corporate directors felt they had overextended themselves. In 2008 the economy imploded, and, almost overnight, Liz Claiborne closed all fifty-four Segrets boutiques. Olsen lost her business, her brand and even the rights to her name.

“I had two choices then,” she tells me. “Either sit down on the couch, stuff myself with Haagen-Dazs and wallow in my disappointment—which I did for a while–or get up and start over again.” Wisely, she chose not to be a victim but moved ahead by asking “what’s next?”

“I realized that even though my fashion line had been wiped out, no one owned my talent. I began to consider what I could do to make the next two decades have meaning and purpose.” Now in her 50s, Olsen began to develop a vision of bringing together all the projects and experiences she loved: her art, running a small business, working with women, health and wellness. She returned to her art studio in Gloucester, Massachusetts, sold the big house she shared with her husband, and moved into the small room in back of the studio. It was a space where she could recharge her batteries.

More than five years later, Olsen has opened a second art studio in Sarasota, Florida, where she lives and works in winter. She’s written a book of recipes that includes her art work and anecdotes about how she bounced back from the loss of her company. With her step-sister and daughter, she has created inspirational yoga retreats for women in such places as Mexico, the Caribbean and Provence. Inspiration Retreats, Olsen says, “help women become attuned to their ‘inner artist’.” She acknowledges that the retreats are part of her own transformation, her need to refocus and be inspired. “We’re all in the process of reinventing ourselves.”

There’s a lilt, even a bit of laughter, in her voice that wasn’t there when I first interviewed Olsen five years ago. Today, she describes herself as an artist entrepreneur. “Both create something out of nothing; they figure things out along the way, seeing themselves as somewhat outside the mainstream. Both display enormous confidence in themselves, a commitment to hard work and perseverance in order to make their dream a reality.”

“You go on,” she tells me. “No matter what obstacles you have, you keep at it. You create a vision for your life and you keep working and trying new things. You just keep going on.”

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