Cara O’brien

Sponsored by RebuttalPR

What inspired you to specialize in plaintiff personal injury law?

I did everything in law school. I interned at the Equal Employment Opportunity Commission (EEOC), the U.S. Securities and Exchange Commission, assisted with protective orders for victims of domestic violence and helped a housing association through a clinic. I basically went through different areas of law to figure out what wasn't a good fit for me.

After law school, when I finally had the opportunity to clerk in a trial court and sit in a courtroom, it was the first time I got to watch attorneys in action. We didn't get much of that in law school. That's when I knew I wanted to be in the courtroom, but I realized criminal law wasn't for me. So, I focused on civil law. It was a process of narrowing things down: I figured out I wanted be a litigator, but not criminal law, and then I realized I couldn't represent insurance companies or corporations. Helping people is in my blood.

There are days I wish I had seen the other side, maybe briefly, just to understand its inner workings, but my heart wouldn't have been in it. I'm glad I landed on this side. My kids know I’m a lawyer and they say "Mom helps people," and that's how I see it too. I'm so glad I ended up where I did.

Can you share your experience of starting your own firm and what the journey has been like?

After I finished law school, I clerked for a circuit court judge in Maryland, which is our trial court level. Before that, I had no idea what I wanted to do. But sitting in the courtroom every day, watching hearings and trials, I realized, "This is what I want to do."

So, I answered an ad in our daily legal newspaper, The Daily Record, and joined a boutique plaintiffs’ firm. I thought I would get a few years of experience and then move on, but I really loved it and stayed there for eight years. The week I came back from maternity leave with my second son, the owner called me and he told me he wanted to retire and sell me the law firm. I was so flattered and very excited by the opportunity.

It was a gradual transition. So, I didn't start my own firm; I purchased an existing one. In June of 2022, we finalized the purchase and rebranded. I feel grateful for the chance to have the best of both worlds.: I had the benefit of an established firm with clients and systems, but I also got to make it my own.

Did the whole team stay on during the transition? What did that look like?

Yes, by that time, we were smaller because of COVID, but everyone stayed on. We're all women, which is awesome. Not that we wouldn't hire a man if the right one came along, but for now, it's just women and we really enjoy working together.

Is there a particular case that had a significant impact on you and why?

I just had a client reach out to me – it was a lead paint poisoning case – and we secured her a significant settlement. She not only moved out of state to a nice plot of land with a beautiful house, but she also started a business in her new location. It's a really nice success story, and it's great to stay connected to clients and know they're doing well.

How do you approach building trust with clients, especially from that first conversation or when you're transitioning them to a new firm?

I'm handling sex abuse cases now with another law firm. What I usually tell clients at our first meeting is that I understand they just met me, and I'm here to help them in any way I can. I know that discussing certain things can be difficult. I view this as a long-term relationship, and this is just our first, second, or third conversation. We don’t have to cover everything right away; we can go at their pace.

It's really hard to sit down with someone for an initial interview and expect them to share all the terrible things that happened, whether it’s a car crash, sex abuse, or something else. It takes time to build that relationship. As a lawyer, you have to understand that you can’t expect to hear the whole story during the intake or initial interview. Most people won’t share the full scope of what happened or how it impacted them right away. I try to ensure they know I care and that we're on their timeline, not mine. I'm not going to rush anyone to do anything.

What challenges have you faced as a female attorney in this field, and how did you overcome them?

I just met with a client a week ago, and he was a wonderful guy. He asked me the same question: "Have you ever had any challenges as a woman attorney in your field?" I told him, we all have those stories, like being mistaken for the court reporter. But my biggest challenge was when I started - I was trying to be someone I wasn't. In depositions or emails, I was mean and trying to fit a certain mold. A couple of years into practicing, I realized that's not who I am. I get more by being authentic and kind. I fight when I need to, but it was hard for me to understand that I could be myself, be kind to the defense lawyer, even the defendant, and still do a good job for my client.

What do you think made you realize that? Was there a specific moment or circumstance that crystallized it for you, or did it happen gradually over time?

I had a female defense lawyer who reached out to me after we settled a case in my first or second year of practice. I was rather mean to her and to the experts during the case, but she called me afterward and said, "It was a pleasure working with you. I think you're going to have a great career." Her reaching out like that, despite the adversarial nature of the case, made me realize that's the kind of lawyer I wanted to be. It unlocked something in me, showing me that we don't have to hate each other. We represent our clients, but at the end of the day, we're all human. Being honest and supporting each other, especially as women attorneys, was really impactful for me.

Who have been your role models or mentors, and how have they influenced your career?

The Maryland Association for Justice (MAJ) has a Women's Caucus, and every single one of those women is amazing. I adore them all and feel so grateful that I get to work along side them. The way they practice and balance their lives is inspiring. Everyone's life is different—some are moms, some aren't, and we're all from different ages and backgrounds.

How did you become involved with the Society of Women Trial Lawyers?

A friend, a fellow member of the Women’s Caucus, told Nancy [Holston] about me, which is how it should be; we should all be putting each other's names out there for opportunities. I'm so glad she did. This group of women is amazing. Like Julia said at the last conference, this is the one conference a year where I block the calendar—nothing is coming between me and this conference. The content is amazing, but it's also about the feeling I get from being there and leaving. This work can be really draining, so it's definitely a time to re-energize.

How do you balance your demanding work with your personal life?

It depends on the day. Having good habits is important. I have to start the day working out, even if it's just 10 minutes (though I aim for 30-40 minutes, preferably outside.) Usually, before I leave the office for the day, I need to clean up certain things. Mentally, that helps me be a better lawyer and also be better at home. But other than that, sometimes life is out of balance, and sometimes it's balanced. We just do the best we can.

What aspect of your work are you most passionate about?

Getting to know people—I love getting to know my clients and my colleagues. It's so wonderful to meet people and talk to them every day. I know it sounds cliche, but I think that's what life is about. As a lawyer, I get the chance to meet all kinds of people from all walks of life, and that's nice.

What advice would you give to women attorneys just starting out in plaintiff personal injury law? 

I did a podcast interview with Luke Russell. He asked a similar question: "What would you go back to and whisper in your ear?" I had listened to a couple of his podcasts, so I knew he was going to ask that. I thought about it for a long time, and I realized my advice would be: most of the things you stress over are not that serious. What we do is important and there are many things that we do that are very serious, but most of the things that keep you up at night don't matter in a day, month, week, or year.

When you think about it that way, you really focus on what's important and what helps your client and moves the case forward. You stop arguing over minor details like where the deposition is going to take place. You start to realize what is truly serious, and a lot of it isn't. I wish I had known that earlier. It would have saved me a lot of stress.

I used to lie in bed wondering if I asked the right question at the deposition. Of course, I did—I prepared for it. So I would tell women attorneys just starting out in plaintiff personal injury law to focus on what matters, and shrug off the small stuff.

What was the highlight of April’s Society of Women Trial Lawyers conference for you?

The goat yoga really nailed it. It was awesome. I was explaining to someone that I loved how last month's content was less focused on specific skills or tips and more on how being a woman makes you a better lawyer, and holistic approaches to things. There was a great presentation about connecting to your breath and to people, and the life coach was fantastic.

Dana's presentation on running a business was also valuable. That's the kind of stuff no one teaches you in law school, and our trial lawyer associations usually don't cover it either. I loved that Dana came in and said, "This is what you need."

The panel about money was refreshing because it encouraged open and honest conversations about topics that people often avoid. Some think talking about these things might undermine their abilities, or that only men discuss them. The content was awesome, and I loved how she put it all together.

Why are organizations like the Society of Women Trial Lawyers important to you?

Because we all need to share information, lift each other up, and refer business to each other. None of us can do this alone. From both a professional and personal perspective, it's so important to have a group you can trust that supports you.

How has your involvement in such organizations impacted your work?

From learning different skills at the conferences I've attended, I've literally gone back to the office and used them the next week. Also, not spinning my wheels over a question or an issue is great; I can just put the question out to the group and get a quick response. Knowing there are other women going through what I am is so reassuring. I'm not alone in worrying about being a good mom, daughter, wife, or lawyer.