Rep. Ayanna Pressley and Authentic Leadership

Cyndi Suarez: Hello. I’m Cyndi Suarez, editor in chief at Nonprofit Quarterly. Thanks for joining me for another episode in my podcast series, Women of Color in Power. I talk to women of color who are leaders in civil society to learn more about what drives them, what challenges they’ve overcome, and, in doing so, perhaps learn more about the different ways that women of color lead. Today, we look at what it takes to run for Congress.

Rep. Ayanna Pressley: I was very fortunate to have, both as a part of my core campaign team, and also sort of my broader kitchen cabinet, diverse representation, and that emboldened me. If I didn’t have that, who could have understood my having a conversation about, “Oh, people are saying you’re running for Congress, you have to get rid of your braids”? I mean, you have to have people around the table that understand what you’re navigating to even be able to have a conversation about that. You know? And when you are tempted to forget who you are, they remind you.

Suarez: Today, I am speaking with Congresswoman Ayanna Pressley. I am proud to say that she represents my district, Massachusetts’s 7th Congressional District, in the US House of Representatives, which she describes in her profile as, quote, “the most diverse and most unequal district in the state.” Welcome, Congresswoman Pressley.

Pressley: Thank you. Good to be with you.

Suarez: So, when you started your career in politics in the 1990s, you were an aide to Joe Kennedy, right?

Pressley: Right.

Suarez: And I was working in political organizing at the time in Boston, in the Northeast. And women of color back then were extremely underrepresented in politics. In the early aughts, I was part of an initiative to create a pipeline for women of color in politics in Massachusetts, which is now well established and called the Women’s Pipeline for Change. And you were the first person we approached to run.

You were working with Senator Kerry at the time. You won your first seat in 2009 when you became the first woman of color ever elected to the Boston City Council. There had never been a Black woman on the city council, let alone a Black woman elected to Congress. You broke through both those barriers. What enabled you to do that?

Pressley: Well, it’s a testament to my first teacher, my mother. I grew up in a household where my mother did not sing to me traditional nursery rhymes or read me traditional children’s stories at bedtime. She read me the speeches of Barbara Jordan and Shirley Chisholm. So, where I find myself now in the movement is really a testament to my first teacher, to our ancestors, and my fundamental belief in the power of the people. I would not have been elected to the Boston City Council, certainly not to Congress, were it not for the strength of this movement.

In my congressional race in particular, I remember being days out from Election Day, and I was never one to “ride the poller-coaster.” I knew that those polls, which were predicting our defeat—decisively so, to the tune of 13 points—that they were not capturing the electorate that we were expanding. We never made assumptions about who desired and deserved a seat at the table of democracy. I had 250 Black men behind the wall of MCI-Norfolk who were engaging and organizing their families on the outside to go to the polls. We had 14-year-olds who were canvassing and knocking on doors on days that it was as hot, it seemed, as if walking the surface of the sun, and they were out there pulling very long shifts. I had unhoused persons who had invested a dollar in this movement and were volunteering. I knew that the polls were not capturing what we could feel: a shift was occurring. You cannot poll transformation. So, I credit those electoral victories to the movement—and to my mom, may she rest in peace and power.

Suarez: It also seems that you had the political bug early on in your life. Your profile states that you were elected class president every year from seventh grade through senior year of high school, and that you were named “Most Likely to be Mayor of Chicago,” where you grew up. Did you imagine yourself being where you are now, back then?

Pressley: It’s interesting, because I’m an only child, and I’m also an Aquarius, and Aquarians are humanitarians, but we are also sometimes more personable than we are sociable. So, I offer that to say that I’m more shy and introverted than a lot of people realize. In school, I recall often having the answer, but not being the first to raise my hand. I sort of sat in the back and felt I had the right answer but wasn’t always so brave and assertive in offering it. So, in some ways I think I was more of a reluctant leader. But because of the organizing household I grew up in, because of the super-voter household that I grew up in, and because of the unapologetically Black household I grew up in, my mother made sure I knew that to be Black was a beautiful thing and something I should be proud of, but that I was being born into a struggle, and she had an expectation that I would do my part in that struggle; again, my first memories of my coloring books were of coloring the Black Liberation flag. That’s the kind of soil from which I was rooted. So, even if my shyness, and even insecurities, had me reluctant to step forward, my sense of responsibility to the work of Black liberation, my love of organizing and movement building as an only child, sort of this chosen family that you find and create along the way, working with people aligned with one common purpose…I loved that. And of course, I wanted to effectuate real change. And I did believe that the only way to do that was through organizing and through movement building.

I remember my mother taking me with her to vote in every election. She would pull the curtain, and she would turn to me—and I’ll say my whole name, because she would—and she would say, “Ayanna Soyini, never forget that on Election Day, we are powerful.” Now, I know she felt that we were powerful always, but especially so on Election Day, and I would stand a little bit taller. I believed her, then, in the power of the ballot and the power of the people. And I still do.

So, although I had some of those more traditional, conventional things on my resume, as it were—I was a competitive debater, and class president, and student government president—I guess that doesn’t seem consistent with my characterizations of my being more shy and introverted and reluctant. But the fact that I was an aide for 16 years, that’s probably more consistent with where I thought I would remain. I really loved being the “person behind the person.” There is great meaning, reward, and purpose in being the one at the elbow of the person whose name is on the ballot. And I had seen that when I whispered in Senator Kerry’s ear about an issue, or brought to his attention a certain community leader, or things like that, that it had an impact. And I found a great meaning, reward, and purpose in being the person behind the person.

So, in 2008, or ’09, I’m not sure, when Avi Green first approached me, he was at MassVOTE at the time, and he called me and he said, “This is the year that a Black woman will be elected to the Boston City Council, and that Black woman will be you.” And I said, “No, thank you.” [laughter] He persisted, and I repeatedly declined. And then, after a lot of meditation and contemplation and prayer, decided that it was really a furthering of what had been a lifetime of service. And as much as I had had the opportunity to be in rarefied spaces, working with people like Congressman Kennedy and Senator Kerry, who we were aligned in many ways, that this was an opportunity for me to amplify my own unique and authentic voice. Because when you’re an aide, no one really knows how you feel about anything, if you’re a good one. You’re only representing and advancing that agenda. And again, if you’re fortunate, it’s an agenda that you’re equally committed to. But ultimately, I said yes. I had no idea what I was getting into, especially in that Boston is an adopted home for me. I’m from Chicago; I came here to attend Boston University. This is a very parochial, tribal place, and I really had no idea what I was getting into. But, certainly, I have no regrets, and it was an incredible experience and education serving on a municipal level, the form of government closest to the people. It’s really shaped my leadership in organizing practices and principles. I really practice something I would characterize as “cooperative governing.” I believe the people closest to the pain should be closest to the power, driving and informing the policymaking. And that practice was shaped, the contours of that defined, from my eight years on the Boston City Council.

Suarez: Wow.

Pressley: I know I’ve said a lot. This is a—

Suarez: No, I love that, I love that, because, you know…

Pressley: Notice I didn’t say I was a quiet child.

Suarez: I mean, I can imagine.

Pressley: Shy, but not quiet. A voracious reader and lots of opinions, so…

Suarez: Yeah, as you were talking, I think about how I see you out and about in Roxbury, which is where I’m from, and I, like, jokingly call you “the queen of Roxbury,” because the way that the people have embraced you in such a parochial town is actually amazing.

Pressley: Something I do want to just offer is that growing up in Chicago, the very first campaign I worked on, I was 10 years old, and it was to help elect the first Black mayor of the city of Chicago, Harold Washington, who inspired me by his example. Not just his representation, but he was the original Rainbow Coalition, in terms of the electorate that he was able to unify. I also grew up under a female mayor. So, it was very interesting to come to Boston and to see that lack of leadership parity when it came to gender and racial representation, because in Chicago, that was all around me. And I had gravitated towards coming to school in Boston because I thought there were many similarities. Both cities usually had lifetime mayors. They’re both, at their heart, they’re cities of working-class, immigrant neighborhoods, and also both very racially segregated. So, I felt this immediate affinity and sort of kinship, coming here from Chicago, but that was one of the things that I was struck by. And so, I came to Boston not knowing a single, solitary soul and found a purpose, and created a life, and threw down roots, and met the love of my life, and grew a family. Coming to Boston changed my life.

So, I was a student at Boston University and president of my college, and I was doing this unpaid internship for Congressman Joseph P. Kennedy II in his Roxbury satellite office, and I was working three paid jobs to do that unpaid internship, and that was when this was the Eighth Congressional District. And, ultimately, Congressman Kennedy hired me as a Social Security liaison, so I was working with our most vulnerable—our seniors, our veterans—helping them get benefits they had been denied. And I really found it a heady and enlightening experience that here I was, 19 years old, and with the weight of a congressional office behind me in making these phone calls, that I could stop someone’s home from being foreclosed on, or get their lights turned back on if they had been shut off, connect them to a food pantry.

The other lesson that I received working in that office was the power of policy. I had not up until that moment really had an understanding that the inequities and disparities and racial injustices that made every community of color, marginalized community, every Black community, ostensibly look the same no matter where you traveled, that this was not naturally occurring. This was the result of manmade, shortsighted, draconian, discriminatory policies and unjust budgets. And I saw that working in Congressman Kennedy’s office, people were coming in on the regular, and I was understanding the impacts of redlining and how that was impacting generational wealth. So, that internship is where the dots really began to connect for me in terms of the power of policy; the power of good, thoughtful, empathetic government; and the fact that now here I am, 25-plus years later, as the congresswoman for that very office, a seat that was once held by John F. Kennedy, and the first person of color, the first Black woman ever, to represent the commonwealth in the House of Representatives—and to think that that took 230 years. Dr. Carol Hardy-Fanta, who used to be a professor at UMass Boston, had written a book she called What Women of Color Do in Electoral Politics: Breaking, Not Glass Ceilings, But Concrete Ones. So, I did not anticipate, foresee, calculate, plan, for any of this. Probably the only person in the world who saw this all playing out exactly as it has, is my mother.

Suarez: She knew?

Pressley: She declared it early on. And—

Suarez: Really?

Pressley: Yes. In fact, when my husband, my then-boyfriend and I were dating, she said to him, “Ayanna’s going to run for Congress one day,” and so, you know, “do whatever you want, but just don’t get in the way of that.” And I had not even said that out loud. There was a lot of speculation. There were, you know, whispered conversations and ruminations and projections, which pundits and the most politically and civically engaged are always going to do, but it was certainly not a part of my own personal agenda. I’ve really just been following the work, and people find that hard to believe. But the only thing that I’ve been certain about is that I wanted to bring about transformative, systemic change. I knew that would require lawmaking. I had seen the impact of our legislating hurt and harm; I believed that we could legislate healing, that we could legislate equity, that we could legislate justice, in the same way that we had legislated hurt and harm. I wanted to replace systems of oppression with systems of liberation, systems of trauma with systems of healing. That was the clarity that I had. And so, my mother used to talk about the difference between your job and your work, and she would say, you know, your job is what pays the bills, and your work with a capital “W” is the work of the upliftment and the advancement of community.

So, I’ve just been following the work. I was never fixated on a position or a title to be in pursuit of. I just said, “I’m going to keep following the work wherever it takes me. I know what kind of impact I seek to make, and I’m just going to work backwards,” and that’s what I’ve done.

Suarez: So, politics has changed significantly in Boston over the last 20 years. When I was growing up in Boston, a person of color running for office was news. Now, it is not uncommon for the community of activists and civic leaders in Boston to split over various colleagues running for the same seat. I myself led Felix D. Arroyo’s first campaign team when he ran for city council, and I’ve consulted with various friends and colleagues running for office over the years. And one of the things I find so fascinating about politicians is the process of becoming one. I see people change—in essence, become powerful. I have witnessed your evolution, I feel, and transformation to the iconic figure that you are today—which, by the way, for me happened when you revealed your bald head, which was so powerful. And I wrote an article a few years ago called What Does It Look Like to Support Women of Color to Lead?, based on an interview that I did with Wilnelia Rivera, who was the strategist for your first campaign for Congress. And in it, she describes you as someone who transcends your insecurities by transforming them into your “biggest assets,” quote. So, how did you become powerful? What were the turning points in your story?

Pressley: I’m just emotional for a moment about Wilnelia. That’s a very astute observation, very generous of her as well. I think I’m someone who has never had a hard time with challenging systems. I think, and in large part, this might be about my being a survivor, both of childhood sexual abuse and also campus sexual assault, that I have never been great about asserting personal boundaries. I don’t gravitate towards personal conflict. I can be, for lack of a better word, confrontational and challenging about systems and structures and issues. But, given my aversion to personal conflict, I am stunned that I would challenge a nearly-20-year, deeply entrenched, beloved by many, progressive by all conventional standards, incumbent. I still am surprised. But again, I was following the work. Pundits will talk about “Black girl magic” and waves of women being elected. And we’re not flukes, and we’re not anomalies, and I would never give short shrift to my magic. But this is as much about Black girl magic as it is about Black woman work. And I’ve been putting it in, and for a very long time.

And so, certainly representation does matter; in order to be it, you have to see it, and so I think we see that reflected in what is now more commonplace. I know that, particularly in a city as parochial as Boston, it can be hard, now, with multiple people for whom you have deep affection and respect to be running against one another. But in many ways, this is what we worked for. This is what we prayed for. You know, no community is a monolith, and deserves to have diverse representation and voices running. And so, we need to just buckle up, you know, and ready ourselves for what that means from an electoral politics organizing standpoint, what it means from a voting standpoint. I know there are many people who felt that, that DA’s race in 2018, that there is no way that a candidate of color could emerge from that, because “conventional wisdom” is conventional wisdom until it isn’t anymore, and we really were disruptive. You know, like, what does it mean to be disruptive? It’s not the single narrative and visual that people would have you believe, of us with fists in the air and bullhorns and carrying signs. To be disruptive is to innovate. It’s to challenge the status quo—not just in our ideas, but how we actualize and advance those ideas, how we organize, how I show up in the world.

You mentioned my alopecia reveal. That was not something that I did from a place of great strength, but to Wilnelia’s point, it was something that I did from a place of deep insecurity, and even trauma. It was not easy—it still isn’t—to be mourning, particularly as a Black woman, given our complicated relationship with our hair, and after I had spent years growing my hair natural, and having this now new relationship with it, it was traumatic. It’s more than hair. And so now, as a Black, bald woman, how I show up in the world, as if it wasn’t already disruptive, is that much more so. It disrupts and challenges societal and cultural norms about what is professional, what is appropriate, what is pretty, what is feminine.

Suarez: And how do you navigate that? That’s a lot.

Pressley: I just remind myself that just because I lost my hair doesn’t mean that I was robbed of my crown. And when I’m tempted to walk with my head bowed and my shoulders rounded, I have people around me who straighten my crown. And, again, getting back to the movement and broader community, there are 7 million people living with alopecia in the country. There are three forms of alopecia; I have alopecia totalis. This is an autoimmune disease where your immune system attacks your hair follicles, so I was robbed of all the hair on my head, my face, eyebrows, eyelashes, my body, in basically a five-week period. And the night that I went completely bald was on the eve of the first impeachment.

Archive Tape: Please be seated. The sergeant-at-arms will make the proclamation. “Hear ye, hear ye, hear ye. All persons are commanded to keep silent on pain of imprisonment. While the Senate of the United States is sitting for the trial of the articles of impeachment exhibited by the House of Representatives against Donald John Trump, president of the United States.”

Pressley: It was going to be a very high-profile visibility day the next day. I had to go to the floor, explain why I was voting in the affirmative to impeach Donald J. Trump. I had to give a floor statement. I had to do interviews. And at one o’clock the morning prior, I went completely bald. And I called a dear friend of mine, Angela Rye. She connected me with a stylist, Jamal, and he, in the wee hours of the morning, custom fit a wig for me, and I went to the House floor…

Archive Tape [Pressley]: Madam Speaker arrives today to protect our democracy. Today, we take a stand against corruption and abuses of power…

Pressley: …and I gave my floor statement.

Archive Tape [Pressley]: …in the pursuit of our truth. Congress has done its due diligence. Today, we send a clear message: We will not tolerate abuses of power from the president of the United States of America. The future of this nation rests in our hands. It is with a heavy heart, but a resolved one, and because I believe our democracy is worth fighting for, I will vote to impeach Donald J. Trump, and I urge my colleagues to do the same.

Pressley: And I gave my floor statement, and I went into a bathroom stall, and I wept. I felt in costume. I felt in character. I felt betrayed. I felt hideous. And I knew at that moment that I was eventually going to reveal my diagnosis, because I did not—as a Black woman, I already have to put on so much armor every day, as a Black woman in Congress, as a Black woman in Congress under the Trump administration. So, I was already having to put on so much armor just to navigate and negotiate spaces in this world with hostilities and microaggressions. And I just couldn’t fathom that I was now going to have to get up every day and, not by choice but by societal expectation to be more comfortable for you, to now put on a wig, and draw on eyebrows, and apply eyelashes just to be socially acceptable. It was a very heavy burden, and I was carrying great shame.

So, the reveal was necessary, both for my authenticity—I wanted to be transparent. I kept thinking about all these little girls that had T-shirts that said, “My congresswoman wears braids, rocks a black leather jacket and a bold red lip.” And I said, “I owe them an explanation for why I’m no longer rocking those braids.” I don’t know if that was true or not, but that was how I felt. So, I knew in order for me to authentically lead, I needed to be transparent. And again, when we liberate ourselves, we liberate others.

Archive Tape [Pressley]: I’m Congresswoman Ayanna Pressley, and this is a word about why my Black hair story is both personal and political.

Pressley: This was a moment of transformation not of my choosing. So, the reveal was something that I had agency of.

Archive Tape [Pressley]: This is my official public revealing. I’m ready now, because I want to be freed from the secret, and the shame that that secret carries with it. And I want to be free. I am making peace with having alopecia. I have not arrived there. I’m very early in my alopecia journey. But I’m making progress every day. And that’s why I’m doing this today. It’s about self-agency. It’s about power. It’s about acceptance. Right now, on this journey…

Pressley: In doing that, I found a broader community, and this representation for them has meant so much. I was so focused on the people that I thought I was disappointing, that they wouldn’t have that representation of me with my Senegalese twists anymore—which was a statement of its own, that I was wearing a protective hairstyle and wearing my hair natural, and navigating corridors of power and sitting at policy and decision-making tables. But this was something else. I was so focused on what I was mourning, and what I was losing, and who I thought I was disappointing, that I had not considered what I would gain.

Suarez: And what did you gain?

Pressley: Community. Acceptance. You know, I’m asked often because some people with alopecia totalis, the hair does come back. It can be in cycles. It can come back, and you can lose it again, or it could come back and you never go through this again. It’s very unpredictable in that way. And so, just recently, someone asked me, if your hair grows back, do you think you’ll go back to braids, or would you start shaving your head? You know, what would you do? I said, “I don’t know. I’ll cross that bridge when I get to it.” But I will say, although I have my hard days with online bullying, and sort of the vitriol and venom, and…we were in the airport the other day, and someone repeatedly kept referring to me as “sir,” and my husband was very upset about that. Those situations, those dynamics, are more the anomaly. By and large, it’s been a very transformative, positive experience. But as I said in that alopecia reveal, I think I’m not here, none of us, to just occupy space—I’m here to create it. And so, with my alopecia reveal, I think we have done that. I’m taking up space unapologetically, as a bald Black woman, and I’m creating space. There’s power in that. There’s responsibility in that. There’s agency. There’s community. There’s acceptance. My husband has been extraordinary, as has my team throughout this, and my husband never made me feel less beautiful, less loved, or less worthy.

I’ll share this final story. My daughter had a recital, and it was days after my alopecia reveal, and, you know, people were staring, and I turned to my daughter and I said, “Do I embarrass you because everyone is looking at me?” And she said, “They’re just looking at you because you’re so beautiful.” That’s the kind of support but I have, and it has made the difference.

Suarez: I agree. I think it looks so beautiful.

Pressley: So… thank you. Thank you.

Suarez: So, thank you for sharing so much of yourself. It’s so generous. I guess my last question is, what’s next for you? The way that you talk about your trajectory, it seems like transformation just kind of pulls you, right? So, maybe you don’t know. But I wonder if you have any ideas, just even for yourself or for just women of color in general in politics. What do you think is next?

Pressley: Wow. Projections, predictions, plans, are so challenging. You know, for a long time I felt that…yeah, I just think people have never believed that I’m not operating with this grand calculus, you know? I really am just following the work, and just caught up in whatever the moment and the people demand and require. You know—is it two weeks, now?—I was sleeping on the steps of the Capitol to organize and fight for an extension of the eviction moratorium. When I think of the future, I feel optimistic because there is a shift that is occurring, and I am looking forward to holding our party, to holding this country, accountable to this reckoning that they keep so casually referencing. As Reverend [William J.] Barber, who is a spiritual mentor by his example of the Poor People’s Campaign, he says, “I grew up in the church. A reckoning is something biblical, of epic proportions. So, if we are truly in the midst of a reckoning on injustice, on racial injustice, what’s our commiserate response?” To me, as much as I appreciate beautiful plazas that are painted with Black Lives Matter, that was not on my list in the work of Black liberation. I appreciate those things, but the only receipts that matter right now are policies and budgets.

Again, policy is my love language because policy has enacted great harm. I believe that another world is possible, one that centers the humanity and the dignity of people. I am emboldened by the strength of this multiracial, multigenerational, issues-based movement that made the Democratic majority possible. And I intend to make sure that the most marginalized, who mobilized, who met the moment and made it possible for democracy to breathe another day, that the needs of that movement are met. Not out of benevolence, not out of charity, but out of reciprocity. It is time. This is why I fight to cancel student debt.

Suarez: Oh, please do that.

Pressley: You can save your accolades about the role that Black women play on the ballot and at the ballot box. I appreciate it. Policy is my love language. Black women carry more student debt than anyone else. We are the most educated, and because of policies like redlining, which denied our families ability to build generational wealth, 85 percent of Black students feel they have no choice but to borrow to pursue higher education, and we are five times more likely to then default on those loans. So, the only receipts that matter in this moment, in this moment of reckoning, in this moment of recovery are policies and budgets.

So, I believe in the power of us. I believe in the strength of this movement. I believe in the transformative and systemic impact of policy. And I believe that another world is possible if we build it. And so, what does the future look like for me? I’m just going to keep being a community and a movement builder, and just keep practicing my love language: policy and cooperative governing. And God and the electorate will figure out the rest. I know it’s true, because that’s happened throughout my life. So, just stay tuned, you know?

Suarez: Yeah. Well, thank you so much. It’s so great to talk to you. Thank you for all the great work that you’re doing.

Pressley: Thank you. Thank you.

Suarez: That was Congresswoman Ayanna Pressley. Thanks to Joseph Fridman for his recording assistance. If you want to leave a comment about our podcast, please head over to nonprofitquarterly.org/podcast and subscribe to our podcast: Women of Color and Power on any platform where you listen to podcasts. Reach out to me on Twitter. I’m @CyndiSuarez. This is a podcast of the Nonprofit Quarterly.