Divided Loyalties

Sara is the executive director of a national nonprofit that represents the concerns of America’s independent workforce, including freelancers, consultants, part-timers, and the self-employed. Sara’s grandfather was vice president of the International Ladies’ Garment Workers’ Union, and although she never met her grandfather, she has been very much influenced by his work as a union organizer. Soon after being recognized as one of a group of outstanding social entrepreneurs, Sara was invited to the World Economic Forum (WEF), a meeting of leaders of governments and corporations from around the world. Because the WEF gathers so many powerful individuals together, there are often protests of one form or another, and Sara was forced to cross a picket line in order to attend the WEF. In this case, she felt torn between a loyalty to her roots in the labor movement and a responsibility to her role as a successful social entrepreneur.


Sara is the executive director of a national nonprofit organization that represents the concerns of America’s independent workforce, including freelancers, consultants, independent contractors, temps, part-timers and the self-employed. The mission of the organization is to make it possible for independent workers to gain access to financial services, benefits (health insurance, life insurance) and products previously available only to “traditional”—full-time, long-term—employees. The organization educates policymakers about the needs of the independent workforce, and advocates for policy changes that will benefit this new workforce. For her work, Sara received a MacArthur Prize Fellowship in 1999. 

In May 2003, they introduced the Freelancers Union, which provides health benefits and other services for independent workers. Initially, the Freelancers Union planned to offer membership and services to part-time and temporary workers in New York. Sara wants to create a new labor organization that has staying power and offers a safety net for how people work. Her goal is for her organization to outlast her tenure. 

Current political thinking is, in Sara’s mind, “ahistoric.” She describes herself as a “New Deal leftist,” and very much admires Eleanor Roosevelt. In fact, when asked about philosophies that guide her work, she quotes Roosevelt, saying, “‘The future belongs to those who believe in the beauty of their dreams.’' Sara wants to talk about these issues in a real way and may well become politically active at some point in the future. 

Sara was born into the labor movement. Her grandfather was vice president of the International Ladies’ Garment Workers’ Union. Her father was a labor lawyer, as is her husband. Sara’s mother was a teacher and educator. As a child, she visited her mother’s classroom and remembers thinking her mother looked “like a movie star” standing up at the front of the room. She describes her father as someone who did not fit into the world that he was raised in, and who would have been better off growing up in the 1960s: he was “all about” social change. She recalls a time in elementary school when she made her father particularly proud. A new Burger King was being built in her Brooklyn Heights neighborhood and all of the liberals in her neighborhood protested because they did not want a fast-food chain in their part of town. Sara’s father thought that the protests were actually a front for racism; it was not the Burger King that they objected to, but rather the black urban families that the chain would bring in. In response, Sara wrote a paper explaining how nonviolent means of protest can be as destructive as violent demonstrations.

The beliefs that influence Sara’s work come from a variety of sources. Sara’s parents were older when they decided to have children (her mother was thirty-nine; her father was forty-five). She and her sister were treated like “little adults.” As a result of what Sara describes as a “laissez-faire” (or “hands off”) parenting style, she has little respect for authority and believes that with proper determination, anything is possible. Quaker school had an enormous impact on the formation of Sara’s beliefs. From second grade on, she felt a commitment to “something higher.” As a result of this education, she has come to believe that “dreams really matter,” they “have legs” and are at the “root” of many accomplishments.

Sara started doing political work at a young age. In the eighth grade, in accordance with the women’s liberation movement, she called her own strike at the Quaker morning assembly. To her surprise, many of her fellow classmates took her seriously, and decided to strike instead of going to class. Growing up, she thought everyone was union-oriented. Although she never met her grandfather, his work as a union organizer was also influential. During her freshman year in college, she was interested in labor, wrote to the union her grandfather had worked for, and became involved. Sara’s own organization is not always recognized as part of the labor movement, and this is particularly painful to her because of her family’s history.

When Sara was twelve, her father was diagnosed with lung cancer. This incident changed the family. The loss of both parents several years ago was the most transformative time of her life and she describes their deaths as “epiphanies“. Building her organization has also been transformative in that everything she has traditionally believed in has had to be taken apart and refocused. In essence, she had to get rid of all of her “extraneous, ideologically loaded” concepts. She views the creation of her organization as a “clarity of mind.”

Clarity of mind may well be what she calls upon when making difficult choices. Soon after being recognized as one of a group of outstanding social entrepreneurs, Sara was invited to the World Economic Forum (WEF), a meeting of leaders of governments and corporations from around the world. In 2002, the WEF was held in New York City, as a sign of support after the tragic events of September 11, 2001. Because the WEF gathers so many powerful individuals together, there are often protests of one form or another. This year was no exception: there were many organized demonstrations, in particular from opponents of globalization. Sara faced a tough decision:

“Because of this whole social entrepreneurship thing, I had been invited to go to the World Economic Forum. And it was like the classic example of pitting two parts of yourself against the other. Because I identify with the labor movement and felt very much—not that I actually agreed because I think … it goes back to that earlier conversation: people have this thing about globalization, and I don’t even know what they are talking about. I think that there are legitimate issues around what’s happening in world economics. But there’s nothing that’s shown me that there is [a] plan or an agenda or anything that I can wrap my hands around. 

And so … I was having this thought about how am I going to go to this World Economic Forum and cross the picket line?—because, you know, in my family you don’t cross the picket line … And so that really killed me. I’ve spent so many years trying to be careful, as you have to be in terms of building the organization. I’m very strategic and I really want this thing to happen. But there’s also a point where you really have to stand up to say, “This is what I am and this is what I’m not.” And it was a moment that just recently I marked a change for myself. And the point is not that I didn’t stick up for things before. It was that in the set of decisions I was making over the last three or four years I’ve started to say, “You know what? I’ve built it enough that now I have a responsibility to come forward [when] I’m not agreeing with the people on the ‘do-gooder’ left.” 

Sara is called a “social entrepreneur:” someone who approaches a social problem with a businesslike solution. In the situation she describes above, she felt torn between a loyalty to her roots in labor and a responsibility to her role as a successful social entrepreneur.

How would you advise Sara to consider her conflicting responsibilities? What do you believe is most important in this situation? Have you ever felt torn between conflicting responsibilities and if so, how did you resolve the issue?