Anyone who’s spent time in Madison’s activist circles will likely have encountered Jenny Pressman. Her commitment to and hard work on behalf of any number of causes—from LGBTQ rights to racial justice—make it almost a sure thing that most residents have at least seen her dark, curly hair and smiling (or serious) face.  

Pressman does not seek the limelight. She’s made a conscious decision to expend her time and energies in support of people and causes in which she believes, rather than running for elected office or other leadership positions. She’s a longtime supporter of and fundraiser for GSAFE, board member at The Progressive magazine and at the Arts + Literature Lab, and a frequent participant at Black Lives Matter and other racial justice-oriented protests and events. 

In her day job with the UW-affiliated Odyssey Project, Pressman has found a way to put her knowledge of development toward helping people who are facing economic barriers gain access to a college education.

She’s also opened her near east side home to a series of intergenerational and intersectional community meetings and fundraisers, largely focused on communities and leaders of color in Madison. It’s in this house that we meet for a lengthy conversation over tea about her life and work. She emphasizes that most everything she does, especially the hard work of being in community to make radical change, comes from a place of love: “Love of myself, my family, friends, and the community.”

Both / and

A self-described Jewish, first-generation, New York City-born, middle-aged lesbian, Pressman embraces the term “radical” to describe her approach to issues. She says, contrary to tired assumptions about becoming more conservative as you grow older, time has only made her more impatient with the need for major societal change.

“I do call myself radical, although now ‘radical feminism’ has a sort of unsavory connotation,” she says frankly. “I want to reclaim radicalism. To me, that’s based on my understanding that there are systems and structures in place—and I’m going to talk about this country in particular because that’s where I live—that are founded on and perpetuate racism and sexism, homophobia and transphobia, and a lot of them are based on the economic system, on capitalism.”

Throughout our long conversation, Pressman frequently touched on her belief that there are no binaries in either identities or issues. Painting anything in hard black and white, she says, is where humans run into trouble and limit our ability to grow and progress.

“The first thing for me is just understanding the connections,” she explains. “All of it is fraught and very complicated, and I’m always perplexed by why everyone wants to reduce these things to very simple terms—either/or. It’s not a binary that works for me! Most binaries don’t work for me! Both/and is a great starting place.”

A powerful legacy

Pressman credits her commitment to activism and justice to her upbringing. Both of her parents were Holocaust survivors who shared what they experienced with their daughter.

“From an early age I have been an activist,” she says. “Part of it goes back to my parents’ experience and understanding that there is great injustice in the world…and there are ways in which I perpetuate injustice through my own experiences and there are ways that I try to disrupt that. I work on that all the time. When I say work I don’t mean in a burdensome way, I welcome that opportunity. Especially now at this point in my life when I recognize that I have more time behind me than I do in front of me, it feels more urgent to me. It’s an imperative, and one that I embrace.”

The story of how her parents met, courted, married, and then survived the Holocaust is an incredible one. Pressman grew up knowing many other children of survivors, though, until moving to Madison—and she chuckles ruefully while relating—that she just assumed everyone’s parents went through a similar ordeal.

The elder Pressmans met while living in Warsaw, Poland, and both courted and married while living under Nazi occupation in the inhumane conditions of the Warsaw Ghetto. They bonded, among other things, over having lost their fathers to factors related to Nazi persecution (one to the typhus then rampant in the ghetto, the other from a vicious beating for daring to own a profitable business). After the uprising, in which both participated, they were separated while escaping certain death. Most of their family members died in concentration camps. After the war, a chance meeting brought them back together in Vienna, followed by narrowly escaping imprisonment by the Russians, fleeing across the Alps into Italy, and eventually settling in the U.S.

Pressman sees chilling truths and parallels to the modern day in their story. “There were people who risked their lives to save Jews,” she says. “And then there were so many who just turned away. Those are the circumstances that we find ourselves in, particularly it feels like that right now, but generally in the course of history you’ll see that there are opportunities for people to stand up for one another…and then times when, for whatever reason, people don’t.”

It wasn’t until moving to Madison in the early 1980s that Pressman encountered much serious anti-Semitism, or simple ignorance about being Jewish. It was—and remains—present in her life here.

“‘Where are your horns?’ someone asked me, and I was like, ‘what?’” she laughs. “I didn’t realize this was something you might have read and assumed was true.”

Pressman says she’s since come to have a better understanding of why and how folks, particularly in the Upper Midwest, might have those igorances. She still encounters people for whom she’s the first Jewish person they’ve met, for instance.

“I came to understand and appreciate it as a statement of fact, not as a judgment,” she says. It’s been a learning process for both Pressman and the people around her. Everyday language became a point of constant study. She’d never heard slurs like “jew’d me down” in New York, but she encounters it somewhat regularly in Madison. When she questions people for using a term like that, however, she says most folks stop and realize they’d never thought about where it came from or what it meant.

“Everything is a reference to something or someone,” Pressman says. “The way that we move through the world is a reflection of our experiences. The broader our experiences, usually the more helpful that is. I mean there are people who grow up in small towns and are very aware of the issues, and then there are people who grow up in NYC and—let’s just say for example the POTUS—who didn’t manage to find a way to expand his worldview.”

A heady time

Madison also brought Pressman into the then-newly emerging field of Women’s History (now Gender and Women’s History). It was an ad in the back of Ms. magazine that alerted her to the fact that the UW-Madison was just starting up its pioneering program under the guidance of Gerda Lerner. Between that and the allure of a particular woman (“Truth be told, I also followed a girl here. It’s a constant theme in my life.”), Pressman uprooted for a career, she thought, in academia.

She says that she and Lerner butted heads almost immediately. Where Pressman was more interested in viewing history through a radical and queer lens, Lerner was busy trying to legitimize the study of women’s history, but it came mostly at the exclusion of queer people.

“She thought the labels [“lesbian” and “gay”] politically problematic and possibly historically inaccurate,” Pressman explains. “That’s why we clashed so much. She labeled as ahistorical my calling certain women ‘lesbian’ or ‘queer’ if they didn’t use that label themselves—knowing full well that language and times had evolved. It’s somewhat like the quest you see these days over whether to label people in the past who were born women and lived or dressed as men identified as butch lesbian, transgender men, or just women who wanted the freedom to travel and work without hassle.”

Pressman concedes that her methods may have been somewhat ahistorical, and realized at the time that she had a more political agenda to her studies. It’s part of what drove her to eventually leave academia entirely.

There are a lot of fond memories from the era for Pressman, too. She credits “some really great professors” who were at the UW then, including Judy Leavitt, a professor in the history of medicine, and Evi Beck, who taught a first-of-its kind lesbian studies course.

“If you talk to a number of—and I’m gonna put this in a frame—white, middle class academics in that era, it was a really heady time,” Pressman explains. “What can I say? It was fabulous. We were finding each other and exploring our sexuality, our power; women’s music was an anchor.”

Looking at the work she does now particularly to lift up the voices and leadership of women of color, Pressman recognizes that the movement was often beset by racial fissures. Still, she stresses that women of color were very much present and a part of those earlier efforts.

“I try and make sure that I’m not remembering a revisionist history, but it was a fairly diverse community,” she notes. “There were women of color in all of those settings—Take Back the Night marches and rallies. No, they were not centered. That much I know in terms of numbers. But I sometimes am concerned that we’re erasing some people’s history and that we paint with too broad a brush in saying that it was just white and just middle class.”

There were people and several books that helped her better understand the struggles and work of women of color at the time. Pressman highlights the 1981 feminist essay collection, This Bridge Called My Back: Writings by Radical Women of Color, edited by Cherríe Moraga and Gloria E. Anzaldúa, as well as Yours In Struggle: Three Feminist Perspectives on Anti-Semitism and Racism, by Elly Bulkin, Minnie Bruce Pratt, and Barbara Smith, which centered the experiences of queer/women of color.

Courageous conversations

These days, Pressman finds herself wanting to bring more people together for “courageous conversations,” particularly across racial and generational lines. Those are the divides she sees having the most negative impact within the LGBTQ community in particular.

We talk about the differences in preferred terminology: younger folks seeming more comfortable with umbrella terms like “queer,” for instance, whereas some folks from previous generations still resist using the word to describe themselves.

“I’d love to have conversations with people who find that term [queer] really hard and dismissive of their identity, or that it’s traumatizing, and with those who don’t understand why that might be,” Pressman says. “Some of that’s generational, some of it’s situational. Some lesbians feel ripped out of both history and their present lives and that’s a disquieting, distressing feeling, especially for some lesbians who fought hard for visibility.”

She worries that those divides only benefit those who are already against LGBTQ people and “who don’t give an ish about all of us.” Pressman points to the divide between Jewish women and women of color at the Women’s March as another example of this.

“There were some fabulous Jewish women of color who stood up and said, “You can’t make this an either/or, this is my identity, all of this!”

We’re back to the idea of both/and, which underpins so much of Pressman’s approach to her life and activism. This very much applies to how she thinks about the ever-expanding conversations and ideas around gender identity.

When it comes down to it, she says, “I think the conversations we’re having now, far from erasing my identity [as lesbian and queer], it’s giving me the opportunity to expand it more and not to be so pigeonholed. Those are conversations that I welcome. I think it’s a great thing to feel more and more comfortable with who you are and the possibilities, and it doesn’t threaten me. I see that it threatens other people, and I’d like to sit down with people and see if there are ways that we can understand one another that don’t seem threatening to someone’s existence.”

Pressman brings up the now-defunct Michigan Women’s Music Festival as an example of something she says was a net positive for the community that was brought down by fear and misunderstanding.

“To jump into this fray, MichFest, and how that all went down, I never understood why,” she says. “I believe that trans women belonged there because it’s a women’s music festival! There’s something very deep there, and I’m not dismissing it. But the focus on body parts that you’re born with, or hormones that you have or don’t have, as opposed to the identity that one has within yourself, that’s where I really am struggling to understand. When people say trans women aren’t women, I don’t understand that. Trans women are women. I mean, period, full stop. So that whole controversy, which I think in large part brought down what was a very beautiful and diverse community of women and girls, not only did it end up being a loss for everybody…it’s a conversation that is fraught, but I think we need to jump in there and really let people hear one another. We don’t do that enough.”

Building the community you want  

The conversation turns to Pressman’s seemingly tireless work on behalf of intersectionality and racial justice. A recent fundraiser held in her home for local school board candidates Ali Muldrow and Ananda Mirilli also brought together local luminaries like Sabrina Madison (founder of the Progress Center for Black Women), Lisa Peyton-Caire (founder and president of the Foundation for Black Women’s Wellness in Madison), and Angela Russell (Vice President of Diversity, Equity and Inclusion at CUNA Mutual Group), among others.

“I looked around and [the gathering] was diverse in age, race, gender, gender identity, sexuality,” Pressman recalls. “That’s the community that I want to be part of.”

She’s quick to note that cultivating such community takes intentional and continuous work. Especially in Madison, which struggles with serious divides on lines of race in particular. Pressman stresses that it’s imperative for white folks to step outside of what might be their comfort zones to cultivate real friendships and connections outside of their usual spheres.

“It’s intentional, and it’s messy, and it’s very rewarding,” she adds. “This is not about self-sacrifice. This is about creating something to me that feels right.”

The rewards, Pressman emphasizes, are always worth the effort. She talks about engaging in small group discussions that bring together people from different racial and ethnic backgrounds to begin to tackle some of the thornier issues that often divide us as a community. Even there, she says, it’s crucial to be aware that those conversations are more difficult for folks from minority groups.

“Generally speaking, people of marginalized communities are going to bear more of the burden, whether they’re turned to as the ‘experts’ or whether they’re being asked to do more, explain more,” she says. “I’m grateful that I have friends in my life who are willing to engage in that work. They are always enriching, always challenging.”

Pressman is intensely introspective about her place in the world and what her own role is when it comes to challenging ideas and systems that oppress others. She’s the first to admit that her appearance alone can and does open doors for her that are not available to others.

“It is not always easy for me to face the areas in which I’ve been able to move through the world pretty easily, and without worrying about my personal safety for one, or my opportunities for work, for love, for whatever…because I’m white,” she notes.

As she does for herself, Pressman encourages others to make fewer excuses and to instead really listen to what different people are saying. Then, it’s especially important to center the leadership of those people who’ve been on the front lines of an issue all along.

“This country has not dealt with the history of slavery and racism, and it’s only making more pathological the divide,” says Pressman. “There are people who say, ‘Enough time has passed, can’t we get over this,’ without acknowledging what we did, what white people did as a country. For awhile I remember thinking to myself, ‘this is barely my country, my people weren’t here then’…but that’s just an excuse. If they had been lucky enough to come to this country several generations before the Holocaust, that’s who I would be.”

One person’s radical…

A theme arises as Pressman comes back to the idea of radical politics all throughout our talk: who or what defines what constitutes a radical idea? She points out the Gillette ad that caused such a stir at the beginning of the year. The message was a simple one: as a society, we should raise our boys with emotional intelligence and depth, so that they become men who respect the humanity of each other and of the different genders.

“Some people saw that and felt that it was too radical because it asked men to be decent human beings,” she says. “If that is a radical concept, then we are truly in trouble.”

Pressman felt like another, just as important issue was missed entirely in the debate over the message of the ad, too: “What I had trouble with is the fact that you have a multimillion global corporation trying to make money essentially off saying we should be decent human beings.”

She feels similarly about the debate that surrounded marriage equality, and now concerning whether transgender people should be allowed to serve openly in the military. For Pressman, as always, the debate isn’t an either/or, though, but yet another instance of both/and:

“On the one hand, that’s clearly an injustice and it’s discrimination,” she says of Trump’s proposed ban. “Trans people serve with distinction and should not have their benefits or opportunities cut.” On the other hand, though, “We should really look at how much money goes into the military industrial complex and who ultimately benefits and who is harmed [by promoting economic opportunities in the military]. Again, that is not an either/or conversation.”

For marriage equality, she feels much the same. Pressman was there celebrating on the steps of the City County Building when same-sex marriage was legalized. She also wonders aloud what it says about our priorities and values as a community when we decide to throw so much weight behind an issue that may only really impact a select few, already more privileged people, and then struggle to find sustainable funding for programs that directly benefit the most marginalized among us.

“I’ve never been a fan of marriage. I studied the cultural and contractual history of marriage in grad and law school, and see it as a racist, patriarchal institution with deep economic roots in the whole notion of people as property in which one party benefits from the labor of others,” she muses.

Although her approach is far more focused on the hyper-local and in creating personal connections, Pressman never loses sight of the bigger picture, either. It’s the desire to redesign—rather than reform—systems overall that, she says, often earns her the “radical” label.

“The systems are operating the way they were designed and built to operate,” she says. “I think that, as the issues come more and more to flash points, there might be the possibility of addressing those systemic inequities. In my mind, that’s not so radical, but I understand that anything that shakes up particularly the economic status quo—capitalism, the school system, the prisons, and how they were designed to function—anything to change that will frighten people because we’re frightened of change, generally speaking.”

Expanding the possibilities

Pressman still has a lot of energy and drive to do her part to build a better, more equitable community, though she admits she doesn’t think the big, revolutionary changes she sees as needed will come in her lifetime. She encourages others to seek whatever ways they can to lend their support to people and causes that are doing the work, particularly when it comes to getting behind women of color, queer women of color, and trans women of color.

“Their own identities compelled them to say, ‘Is this not obvious that you can have all of these identities? We do have all of these identities in one body and person and this is who we are,’” she says. “That idea has always resonated for me. Maybe because I have always felt that sense of being other and so it’s made me think about identity and seeing how, even within what I can think of as a community, there are these distinctions that are used in some ways to divide us. I don’t want to overlook them. I don’t want people to say there’s no difference between us, and we’re all just people. We are people. But in my case I am a queer, Jewish, middle-aged woman with children. Those are various parts of my identity and some people share those identities and I don’t want to blur those distinctions. I really want to uplift the idea.”

The seemingly endless barrage of assaults on rights and on people outside what’s considered “normal” or “default” also lends itself to burnout and defeatism, she acknowledges. Pressman sees no option but to continue to fight the good fight, however—another bit of perspective instilled in her by her parents. The alternative is simply unconscionable.

“I live in this beautiful house, I participate in the economic system, but that doesn’t mean I can’t question it or wouldn’t embrace different ways of looking at things,” she says. “I think we’re capable of changing how we look at relationships, how we look at identity, and how we approach one another as human beings.”

It’s the continuous work to build the kind of community Pressman says she wants to be in that helps sustain her, too. “Whatever that looks like for anyone, I think showing up is really important for all of us,” she adds. “Showing up for others, showing up for communities. Going to different kinds of events than I would have in the past, really thinking about where I want to put my time and my resources. Getting more local. More grassroots. For me, that feels like the best place for me to put my time and my energy now.”

In the end, it comes down to embracing change, and allowing each generation to work with those who came before to push the needle further and further—on what’s acceptable socially, and what’s possible personally.

“I do think that when you expand the possibilities for being a human,” Pressman says, “that that will ultimately benefit everyone.”