When Ayanna Pressley was an unpaid intern, she worked three other jobs to get by.

“That was the situation for most offices at the time,” the Massachusetts Democrat says of those days without a paycheck, interning for a member of a big political family, Rep. Joseph P. Kennedy II. “I certainly hold no ill will.”

The internship set her on a path that eventually came full circle. But now that she’s a congresswoman herself, she hopes no one will have to retrace her steps.

When Pressley looks back on her early congressional career — first as an intern in a district satellite office for Kennedy, and then as a scheduler and political director for Sen. John Kerry — she sees experiences that “changed the trajectory” of her life.

She also remembers being the only Black woman in the room a lot of the time.

“I know there were questions I raised that would not have been raised if I was not at the table,” she says. 

Pressley spoke to CQ Roll Call about her political beginnings and what has and hasn’t changed.

Her advice? “Personnel is policy,” she says. “You have to have people around the table with you to bring that diversity of lived experience, perspective, opinion and thought.” 

“Ultimately, we’re all better served by the policies advanced when we do that,” she says.

Q: How did you get connected with Kennedy?

A: When I was a student at Boston University, I was part of the planning committee for the annual Martin Luther King Day celebration. I intended to invite two members of Congress, Barney Frank and Joe Kennedy. I believe Congressman Frank had a conflict and declined. 

Congressman Kennedy came, and at the end of that event, I asked him if he had any internship opportunities in his office. 

I was familiar with his work because I grew up in a household where we read the newspaper together and watched Sunday shows, and my mother had told me about his work on addressing the issue of redlining.

Ultimately, I did earn that internship, and it changed the trajectory of my life, because, of course, now I am — full circle, 25-plus years later — the congresswoman for that very seat. 

There were two offices, one in Charleston and one in Roxbury, and I worked in the Roxbury satellite office. 

Q: And then in 1996, you went to Kerry’s campaign, as a volunteer coordinator. How did that come about?

A: At the time Sen. Kerry was in a tough reelection bid against sitting Gov. Bill Weld. When a colleague looks like they might have a tough election fight, you’ll lend out staff to support their effort. And so that’s what happened. 

A few months later, [Kerry] offered me a position in Washington.

Q: What stands out the most to you, thinking back to those years?

A: Just the lack of diversity, both on the internship side of things and also on staff. 

It was my observation that the interns were usually the children of donors, and it was a real barrier to access the political process to get that tutelage and that training and that mentorship, especially because the internships were unpaid. 

I worked three paid jobs to support that unpaid internship. 

I should add that I certainly hold no ill will. That was the situation for most offices at the time. But as time went on, it became clear it was a barrier to entry disproportionately for low-income as well as for young people of color. So now I’m grateful for the advocacy of organizations like Pay Our Interns that have really underscored why it’s so important.

One way we practice the values that we espouse — certainly as Democrats — is to pay our interns a living wage. 

Q: What was it like as a Senate staffer?

I was very much in the minority in the United States Senate. 

I remember one day being in the elevator and I was carrying my lunch on a tray. I saw that people in the elevator were sort of nervously looking to one another and deciding — I realized later — who was going to ask me this question. Finally one of them said, “Can you tell us which senator likes turkey sandwiches?”

And I said, “Well, damned if I know. This is my lunch.” But it was their assumption that I must be delivering that lunch to someone, or perhaps that I was there in a service capacity. But not that I was an aide. 

There were many circumstances like that on the Hill. 

Diverse representation is so important. Constituents and advocates would lobby to get time with the member — and I know that because I was a scheduler for almost seven of those 11-plus years I worked for Sen. Kerry — but the policy aides play such an important role. Often they are whispering in a member’s ear right before a vote. They influence what policies are prioritized. So there’s power in being the person behind the person. 

I know there were questions I raised that would not have been raised if I was not at the table bringing my perspective as a Black woman.

One example — and this isn’t policy related, but it’s still worth sharing — is there was a big controversy with Don Imus, the radio broadcaster. He’d made some disparaging, racially charged, really offensive comments about the women’s basketball team at Rutgers. Sen. Kerry had been a regular guest on Don Imus’ show, so there was an internal debate when he was invited to return. And I said, “Absolutely not,” because you cannot espouse a more inclusive — and I hate the word “tolerant,” because no one wants to be tolerated, but that was the verbiage at the time — racially just society, and then sit there with someone who has said such disparaging, racist things. 

[Kerry] never returned to the show. It just speaks to the power of having people around you who have had these experiences. Personnel is policy. 

Q: As a lawmaker, you’ve formed close alliances and found community in the “squad.” Did you have anything like that as a staffer?

A: Yes, there was an organization that still exists that did create a space for Black staffers to come together, depending on the day, to celebrate or commiserate.

We were all keenly aware of the fact that we were our ancestors’ wildest dreams, that we were navigating very rarified air. Sometimes because we were so busy sitting in the gratitude of that, I think there were indignities and we often endured microaggressions that in my 20s I felt perhaps less comfortable taking on. You were just so busy sitting in the gratitude and the responsibility you had. I know I certainly felt that early on. 

So yes, that group, [the Senate Black Legislative Staff Caucus], was very helpful.

Q: When you decided to run for public office, how did you define yourself outside of your former bosses? 

A: Because of the household I was raised in, which is a credit to my mother, may she rest in peace and power, I never was unsure about who I am, where I come from or who I fight for. I always had that clarity and that conviction. 

When I was an aide, I was a very good aide. And that means very few people knew what my actual, personal opinions were about most things, because when you’re an aide, by extension you represent someone else. 

And so it was very liberating to be able to express my point of view, to be able to express my worldview, to be able to express my voice. 

One of the challenges is that I had to learn not to be my own aide. [Laughs.] 

Once you’re an aide, you’re always an aide, and it’s very difficult to turn that part of your brain off. It took me some time to deprogram, if you will. 

But I’m grateful for the experience as an aide. It has certainly fueled my advocacy and my passion for the corridors of power, the halls of Congress, to be more diverse, both in our interns and also in our staff. 

It’s why I appreciate my staff everyday. As meaningful and rewarding as this work is, I know how depleting it can be, and the toll that it can take as well, the personal sacrifices that people are making. And I decided early on that I wanted to do everything I could to ensure that the morale was high, that they’re their most healthy and functioning selves, that marriages would remain intact, and the like.

Q: What advice would you give to a staffer wanting to become a candidate?

A: Think long and hard about the impact you seek to have in the world, and then work backwards. Rather than fixating at the outset on the position or the title, think about the impact you seek to have. 

That’s all I’ve ever done, is follow the work. Once it became clear to me that the inequities and disparities and the racial injustices that persist are not naturally occurring, but that they are legislated, I knew that these systemic hurts would require systemic response, and that meant that I needed to do the work of legislating.

But everyone’s walk is different. Perhaps you’re better suited for something at the executive level, or perhaps you’ll see the value of being the person behind the person. I think many people define the opportunities for civic engagement solely as running for office and voting, but certainly people can make meaningful contributions and lead a purpose-driven life and have a real impact being an aide. 

For those who might have their sights on running for political office, I would just encourage you to expose yourself to everything, get that experience on the campaign side, get the policy experience, get the operations experience. Get clear on your purpose, and then the position will follow. 

Q: Was there ever a time this term as a member when you had a flashback to being a staffer?

A: Anytime I’m contacting a staffer late at night, I immediately revisit what it was like for me, to feel tethered to your phone, to never set it down because you never knew when your member might need you. 

So I just try to always ask, “I’m sorry, is this a bad time?” or “Are you with your family right now?” 

Pre-COVID, when I would be making my way home and my legislative staff would still be in the office until 10 o’clock at night, working diligently, I would just think about all the times I did that very thing. 

This interview has been condensed and lightly edited.