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Celebrity Attorney Stacy Phillips: “There’s a Very Fine Line Between Caring and Going Overboard”

April 20, 2018 | Filed in: Woman of the Week

One of the country’s most well-known family law practitioners, Stacy Phillips is famous for handling high-profile divorce cases (she’s represented Britney Spears and Bobby Brown, among other celebrities) as well as sticky custody battles. In other words, she works with people at some of the worst moments of their lives, and she’s very good at it—which takes a thick skin and an open mind. She’s also heavily involved with mentoring other female lawyers at her firm, Blank Rome, and spearheaded the organization’s first women’s summit last year. We spoke with her about the fine line between caring enough and caring too much about work, what to wear in court, and why phone calls are better than alarm clocks.

I THINK THIS WORK IS PART OF MY GENETIC MAKEUP; both my grandfather and my father were lawyers. Of course, rather than just doing what came naturally, I had to fight it. I worked in government for a few years before recognizing that I was interested in law. I had a job on Capitol Hill, worked for Donna Shalala when she ran HUD, and then worked for a research company in Washington, D.C. Then I went to law school at Columbia.

THERE WEREN’T THAT MANY CAREER OPTIONS for women when I was growing up. You could be a nurse, a teacher, a travel agent, a social worker, and that was it, basically. But my dad’s firm had several female partners, so I had them as role models. I’m ambitious by nature, and ambition was also expected of me by my parents, my father in particular.

Stacy wears the Sarah dress in deep indigo.

I’M FROM NEW YORK, BUT DURING LAW SCHOOL, I came to L.A. to be a summer associate and felt pretty strongly that I would end up here. It seemed easier to be a professional, be involved in the community, and have a family in L.A. than in New York. I raised my two kids here, and I still think that’s the case.

I LIKE FAMILY LAW BECAUSE your clients have a heartbeat. But there’s a lot of responsibility. If you screw up a custody case, you can screw up a child’s life. I think I’m good at it because I care, but there’s a very fine line between caring and going overboard. You can get enmeshed in your cases and then you’re not objective and that doesn’t do your client any good. I’ve had to work on that throughout my career. I’ve gotten better at finding the appropriate distance as I get older, but it’s always hard. I’m very protective toward my clients. I want to take care of things and make things right, and sometimes I can’t. I’ve learned that the hard way. Some people can’t get out of their own way, and that’s difficult for me to deal with because I know what’s going to happen if they don’t listen, and I know it’s going to be horrible. But what keeps me going is that I know I make a difference. Not every lawyer can say that with the same degree of certainty. We work with people during a really bad time in their lives and we try to make things better.

Stacy wears the Cindy dress in black.

ONE WAY THAT I MAINTAIN SOME DISTANCE FROM MY WORK is that I try to check it at the door when I’m home. I’m not sure I’m always successful. What I do for a living is hard, and very painful, and sometimes it takes its toll. There have been a few times when I thought a judge made a bad decision, and it felt awful. One time, a custody evaluator made a very bad decision, and it took me several years to prove to the court that the position my client was taking was right. These things keep you up at night.

PEOPLE DON’T HIRE ME TO BE COOKIE CUTTER. One thing that makes me stand apart is that I often use experts in court who aren’t what’s customary. Even if one case looks just like another, I think you have to treat each one as unique. That’s what makes it exciting, and I think that’s what makes me good. Still, a lot of other lawyers are not used to people like me. I tend to come up with ideas that are unusual and outside the box, whether it’s about a case or developing business. Thankfully, my colleagues know this and put up with me because of it.

IN MY TIME OFF, CATCHING UP ON SLEEP IS A BIG PRIORITY. I didn’t sleep for many, many, many years, but I’m getting better about it. I used to sleep through alarms, so years ago I enlisted two friends to call me in the morning to make sure I got up. Now I don’t sleep through alarms anymore, but I still like having those two friends call me, so they do, every morning during the week. It’s selfish, maybe, but it’s a nice way to start the day.

Stacy wears the Etsuko dress in deep plum.

WHEN I’M GETTING DRESSED FOR COURT, I pay attention to who the judge is and how I think he or she will react to how I dress. I don’t wear pants to court, even though plenty of female judges and lawyers do. I love pants, but to me, it’s just a matter of respect and formality. I don’t wear pants to a synagogue, either. It’s just how I roll. When someone comes to court in blue jeans, I have a hard time with it. I don’t think it shows the respect that the bench deserves. I dress my clients a certain way as well, or suggest how they should dress. For example, if I have a client who’s in a custody battle, the last thing I want her to wear is a navy suit. I don’t want her to look like a businessperson; I want her to look like a mom. Preferably, she’ll wear a skirt or dress that is more mom-like. Nothing flashy, nothing revealing; I want her to look respectful but not too buttoned-up.

FOR A LONG TIME, I HAD ONE SUIT THAT WAS MY WINNING SUIT. It was a red Valentino suit—two pieces, no shirt—and every time I wore it, I won. I was careful about wearing it because I didn’t want to overdo it. Eventually, I gave it away, but I wish I still had it. I love things that are stylish and colorful. I have a lot of pashminas in different colors that I wear all the time. I also love jewelry. I have a necklace that two of my female partners gave me that has a round pendant the size of a silver dollar, and inside are shards of glass. It’s supposed to represent shattering the glass ceiling, and my partners bought for me because they looked at me as a role model.

Stacy wears the Sarah dress in deep indigo.

IN COURT, IT’S IMPORTANT TO READ THE ROOM and listen to the cues. One of the toughest things is knowing when to be quiet. For me and a lot of people, it’s easier to talk than not to talk. Years ago, I remember I was in the middle of an evidentiary hearing and one of my colleagues, who was also a friend, came in to watch. During a break, he said, “Just keep quiet. You’re winning.” So when the judge asked, “Do you have anything further, counsel?” I just said, “No, your honor.” And it was the right call.

I’VE ABSOLUTELY QUESTIONED MYSELF IN MY CAREER, but more so when I was younger. Now, I question myself to make sure that I’m not getting stale or taking things for granted. That’s one reason why, a year and a half ago, I moved my firm into an international law firm, Blank Rome, so that I could get a boost and collaborate with smart people in various types of law. Blank Rome has over 650 lawyers in it, based all over the country, and I make a point to speak to as many of them as possible. I am also very involved in developing women within our firm. After I’d been at the firm for three months, I pitched the idea of having a women’s summit, with all the women partners and general counsel invited. We did the first one last September, and it was huge. It generated a lot of business and created a lot of camaraderie and collaboration among the female partners. We’re doing the second one this coming September. I also have a women’s holiday party every year and a bunch of my female partners flew in for it. I hosted a dinner for everyone the night beforehand at my house.

Stacy wears the Cindy dress in black.

BECAUSE I AM AN OUTSPOKEN PERSON, I am often asked to raise certain issues within the firm that others might be nervous to bring up. The first time that happened, I was asked by three of my partners, all of whom I had on a pedestal. I was the new kid on the block, and I looked at them and said, “Why are you asking me to bring this up? Well, okay. I’ll go for it.” In fact, this week, I have a few things that I have to talk to the chair of the firm about. That’s a big deal. It’s a little scary.

I’M ALWAYS WORKING ON TRYING TO BE A BETTER BOSS. I’m direct, and I try to be kind. I empathize, but I also give structure. I tell my team what I think, but ultimately, I think it’s important to let people make their own decisions. I absolutely want other people to speak up, and more often than not, they can convince me. But sometimes, there’s a voice inside me that tells me to put my foot down and say, “It just has to be this way.” Every time in the past where I have not listened to that voice, it’s been bad. 

I AM BIG ON SOLICITING FEEDBACK RIGHT UP FRONT. I’ll say, “Dish it out to me, please.” Just tell me nicely. I will tee up questions: “I was concerned about this; how did I do?” Or, “I’ve been thinking about how I handled this; how could I have done it differently?” That’s one of the reasons why I like working with a lot of partners. Otherwise, I’d be here all by myself, and God, I’d hate that.

Photographs by Clarke Tolton.


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Charlotte Cowles is a New York-based writer​ ​and editor.​ ​Her work has been published in New York Magazine,​ Harper's Bazaar,​ and Art in America. She'd always rather be at book club. Read more of Charlotte's posts.


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