It was such an honor to chat with District Attorney Rachael Rollins last week. We covered her current role as Boston’s chief law enforcement official, her tireless work as a social justice advocate, and her triumph over breast cancer, all while juggling being mom and “auntie” to 3 girls. Trust me, you won’t want to miss this one.
Watch + Listen to the whole conversation:
Suffolk District Attorney Rachael Rollins has smashed through the proverbial glass ceiling more than once. As the first woman to serve as DA in Suffolk County, and the first woman of color to serve as DA in all of Massachusetts, she’s a role model to many and a vocal advocate for women’s empowerment and social justice. And yet, when we sat down to reflect on her career, she shared that the accomplishment she’s most proud of is being a mom. DA Rollins explains why being a mom makes women better executives, explains her role as both DA and a social justice champion, and the importance of raising “good, kind people.”
I know this is going to be a hard question because you’ve had such an impressive career, but can you share some highlights?
Not only because this show is about Work Like a Mother, but I have said many, many times- my most proud accomplishment is being a mom. In this role as District Attorney, I unfortunately see people on the worst day of their lives- either they’ve been accused of doing something or they’ve gotten really terrible news about a loved one being harmed or they’ve been harming themselves. It makes me realize it is so important for us to create and raise good, kind people and to love and to be supportive if we are capable of doing so.
And then regarding my career, I ran for office for the first time at forty-seven years old. I had never run for office before and was very fortunate to win my primary and general and now I’m an elected official. I’m the chief law enforcement officer in Suffolk County, which is Boston, Chelsea, Winthrop and Revere. We’ve implemented some amazing policies that are first in the nation and we are leading the way in social justice reform not only in Massachusetts, but in many ways across the country.
I love that you highlighted your role as Mom first- especially in that incredibly impressive list. Where were you working when you had your daughter?
My daughter is sixteen. I was working at a very large law firm in Boston, and I remember it was very different back then- almost seventeen years ago. I remember vividly there were not many female partners at the firm and when they were pregnant, they were hiding it. It was like those horrible sitcoms where everyone’s standing behind a big bureau to try to pretend they aren’t pregnant. What I love is now, I think motherhood is a strength. It always has been. However, with more women leaders we are showing that the ability to multitask and juggle are skills that make us even more exceptional at our job.
How did you decide to run for public office? Can you tell us a little bit about that process and how you were able to juggle family during that really intense time?
Back in 2017 I was at a crossroads in my life. I had just left my job as the Chief Legal Counsel of Massport in 2015 and I completed this amazing 7 month program at Harvard Business School for executives. I finished that program and felt like I was ready to change the world, but I didn’t know what I was going to do. And then I was diagnosed with breast cancer. It was relatively early stage, but it was a kick in the gut.
I was very scared and ultimately had a double mastectomy and several other surgeries. I did everything they said and I can happily say that I’m cancer-free now. But having to tell my daughter, who was twelve at the time, that I had cancer and answering all of her questions- one of which was, “Are you going to die?” was one of the hardest things I’ve ever done. But the night before my surgery, I remember writing her a letter just telling her how much I loved her and thinking what if this was the last time I got to speak to her?
So all of that happened and it took me 18 to 20 months to get well again. And what is so beautiful is that my daughter saw me from that day that I told her, through all of my surgeries, tubes and drains, medications, and doctors appointments. She saw me lying on a couch and wondering if I was going to live or die, to one day getting up and starting to work again. I looked at her and said, “I’m going to run for office and I’m going to be the first woman to ever be DA in Boston and the first woman of color to ever be DA in Massachusetts and we’re going to change the criminal legal system.” And then we did!
As an elected official you have a lot of responsibilities on your plate. How do you juggle your work with your family?
It is hard. I’ve been reading some articles showing that in marriages between women and men that women are bearing the brunt of the child care work and responsibilities at home during this crisis. I have three children- two nieces and one daughter that I am responsible for and I am homeschooling right now. I have a rising junior, a rising sixth grader and a rising second grader all in three different school systems. So with zooms, and all of this virtual teaching, it’s really hard to juggle it all!
I will say in the beginning, Covid-19 was terrifying, but there was a piece that I thought, ‘Oh this is great, I’ll be able to spend more time with my family.’ And then unfortunately the lines between work and home started getting blurred. The meetings that normally wouldn’t start until 9 or 9:30 because I wanted to bring my kids to school started at 7:00am. But what’s great is there are times where I can say to my staff, “No, I’m not doing that. I need to spend some time with my children and the answer is no.” What’s wonderful is, as the boss, I don’t have to ask permission.
How has being a woman impacted the way you see your role?
My gender definitely impacts the way that I look at things- as does my race. It has always been fascinating to me that court starts at 9:00 in the morning, but school sometimes starts at 8:30 or 9:00. So it is so clear to me that men make all of these decisions and are used to having a woman at home to handle all of the family business. We need more women in leadership to say, “No. Schools should open at 8:00 and work starts at 9:30.” I just remember all this angst I used to feel as a young lawyer because I would literally fling my child and nieces out of car to get them into school on time, Tokyo Drift into the parking lot at the federal courthouse, sprint upstairs to be in a chair at 8:57, sweating and getting ready for the jury to be called in and it’s exhausting.
Today, I would say, “Your honor can we start at 9:30? I myself have childcare responsibilities and I’m sure there are members of the jury that do as well.” We need bold leadership and people in positions where they can speak about that and demand it. And if the judge says no, at least he or she (usually he) will be aware that this is an issue if they weren’t aware of it in the past.
You’ve been such an advocate for social justice. How does that impact your role in public office?
Looking back at why I ran, we can talk about the moment we find ourselves in the United States right now with George Floyd, Ahmaud Arbery, Breonna Taylor, Tony McDade and Elijah McClain. I mean the list goes on and on and on. But many communities knew about this before the rest of the world caught up. I like to remind people- whether you agree with Colin Kaepernick or not- this is why Colin Kaepernick took a knee. He tried to do this peacefully. Now we see people responding to the protests and outrage. But there are communities that say, “When we asked you nicely or quietly you don’t listen. When we raise our voice, you don’t listen. When we start yelling, you don’t listen. The only time you listen is when we burn buildings or break things.” And yes, we hold people accountable for that. Buildings have insurance and glass can be fixed, but lives have been stolen. We have to be better at making sure we are having tough conversations and admitting that there are communities that are justifiably enraged right now as a result of what they’ve had to endure. So I ran because of George Floyd, Trayvon Martin, Tamir Rice and Sandra Bland. Sadly, this goes back centuries.
In this double global pandemic, both with Covid-19, and this racial reckoning, I need to be somebody who has character, is honest and is persevering. I need to find small moments of hope, but also hold people responsible that I’m responsible for and call out injustice when I see it.
What is your advice to your pre-mom self?
I’ll give you a funny one and a real one. Travel. Do everything you can and enjoy yourself because life changes significantly in wonderful ways, and then in other ways when you have a child. I would have been kinder to myself. I would have told myself, ‘It’s okay that you don’t have all the answers yet and it’s okay to just be responsible for yourself and to put yourself first.’ As an oldest child, I think I was always concerned about my younger siblings and other people and I think it’s the same thing I deal with now. There are times when it feels like The Giving Tree. At the end, I want to make sure I have something left for myself- and that’s not selfish.
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Bridget is mom to two little boys, Hudson and Brooks, and a champion of working moms everywhere. NeighborSchools itself was borne out of Bridget’s challenge to find high-quality yet affordable child care, and the realization that so many parents struggle with these same issues every day.