Classroom Teacher, Grades 6.7.8
St. Michael’s Country Day School
Past affiliations include associate, Palmer & Dodge
JD Catholic University Columbus School of Law
BA Boston College
From dealmaking to the classroom
On the background needed for teaching
On the failure of Myers-Briggs to assist in escaping the law
On working as a teacher and working as a lawyer
Listen to interview:
EXJ: With us today is Carolyn Anquilla who teaches sixth, seventh and eighth grade at Saint Michael’s Country Day School in Newport, Rhode Island. Thanks for being here.
Our core mission at ex judicata goes to redefining what it means to be a JD. More specifically, providing lawyers with viable alternatives to the practice of law and making these job opportunities accessible to many for the first time ever. In some cases, we’re helping young law firm associates move to entry level executive positions in everything from HR to marketing/sales to investigative services. And in other cases, we’re working with more seasoned attorneys, mostly partners, and introducing them to companies that want to hire people with their expertise and as well as potential board of director roles..
Teaching is a natural for a lot of people that have a JD degree so many of the same skills–the study, the preparation, the analysis, the ability to juggle many things at once. So far, we’ve interviewed 40 different JDS who transitioned and you’re the first teacher. So, welcome.
Carol Anguilla: Thank you.
EXJ: Do you teach specific subjects within those grades, or do you have a sixth-grade class. A seventh-grade class? An eighth-grade class?
Carol Anguilla: No, I teach history. I teach world history for the younger students and American history for the seventh and eighth graders.
EXJ: How long have you been at this school, Carol?
Carol Anguilla: This is my 13th year.
EXJ: Wow. Looking at your background, you gave the practice of law a good run. A number of years. Starting with being a legal assistant at Milbank before you became a lawyer. Did you take that job to see if you’d like law and then decided to go to law school?
Carol Anguilla: I’d like to say that I planned that far ahead. But no, I graduated college an English and Philosophy major, which doesn’t directly prepare you for a whole lot. And at BC, we had these on campus interview sessions where you just went from room to room. So, I had offers at Toys R Us and other places, but this was position was in New York City, a place that I really wanted to live. It was a great two-year paralegal program at Milbank. You had only children of employees and students right out of college. They’d come for two years and then move on to something else. It was really wonderful transition from college to the real world.
EXJ: Oh, yeah, it sounds terrific.
Carol Anguilla: Yeah, it was. It was great. And you got to live in New York. And so, from there, I applied to law school. My older brother is a lawyer. He’s a litigator.
EXJ: So now back then, I’m going to guess that Mel Immergut was the Chairman of the law firm. Does that ring a bell?
Carol Anguilla: That does ring a bell. Yes. I’m trying to remember. I was in the corporate finance division, and I remember the name.
EXJ: It is someone Kim and I did a lot of work with many years ago when we had our first startup, Fulcrum Information Services. He was wonderful to work with. So, after law school you were a corporate associate for a number of years. Was the goal to become a partner in the firm?
Carol Anguilla: Yeah. At the time I thought this was what I would do. I was at Bryan in in their securities division in Washington, DC. I did some international law and as well.. It was exciting because it was a lot of travel, a nice career for a young attorney. And yes, I think back then partnership was the plan. But as you know, life changes.
EXJ: Yes, absolutely. When did teaching enter your mind? Was this something that you may have had at the back of your mind all along?
Carol Anguilla: No, definitely not. I became a teacher via a very meandering road. After Bryan Cave, I moved up to Boston in late 1999 and worked at Palmer & Dodge doing a lot of biotech work and M&A there. Palmer Dodge was not my ideal place to be. One day I saw a listing for an in-house position, an Assistant General Counsel at Liberty Financial, which was a public company, but was 79% owned by Liberty Mutual Insurance Company. I got that position. It was excellent and, honestly, had that job continued to exist, I might still be there now.
It was a perfect pairing of my legal background with what I thought I really wanted to move into which was more of a business role. Because I could farm out any of the legal matters that I didn’t want to handle and then work the business side which was really interesting to me. But the job was short term. The company was sold. I sat at the holding company level. We sold all our subsidiaries off to insurance companies and annuity companies, and we dissolved the, the holding company. So, with that, I got a very attractive severance package. I was pregnant with my twins, so I took that opportunity to take some time off with the kids.
EXJ: Sure. it made perfect sense. Yeah, I was going to ask because it looked like you were there for just a little more than a year. How would you compare working as an in-house lawyer versus working in a law firm?
Carol Anguilla: Well, law firms are tough because you’re beholden to the billable hour. And, eventually, you’re expected to bring in clients of your own. Also, as a young attorney you’re beholden to whichever partner(s) you are working with and their particular quirks and their particular desires. When you’re in-house it’s different. No billable hour and you’re working for one client. The path to success is clear. You’re able to build relationships with the people around you which for me, as a people person, in house was a better fit. There was always something new happening. We had acquisitions happening all over the place. I was able to travel to different locations
where we were buying companies or merging with companies. And I felt I had a purpose and a responsibility and value outside of the billable hour.
EXJ: The concept of value to a company as opposed to a law firm is something we talk a lot about in these interviews. If you could speak a little bit to that.
Carol Anguilla:. As a younger associate, you can’t do that much, you’re always learning. At the same time there’s always that sense of whether you’re going to be there for the long term. You feel like you’re jockeying with the people around you for the best cases. When you’re in house, you’re part of a team. It’s just a different vibe. There’s common purpose and a feeling of security. There is a difference in how you feel valued as mentioned.
EXJ: Yes. In a business role you are valued by how you work as a team–with your bosses, those under you and there is a clear chain of command. In a law firm you have as many bosses as there are partners. And team is often not a concept. I mean how often were all the attorneys working on a given matter gathered in the same room to discuss a strategy with everyone given a role and feeling part of working towards a shared goal. From my own limited experience, and it’s a question I’ve asked a lot of my friends, my guess is almost never.
Carol Anguilla: I will also say that I’ve had experiences in my legal career where I’ve had some pretty appalling interactions with clients who feel that you’re a hired hand and they can speak to you in a certain way. A way I would normally never tolerate.
EXJ:—That’s sometimes lost in these discussions where the focus is the sometimes difficult interaction within a firm while interaction with clients can be very difficult.
Carol Anguilla: I’ve had some very peculiar interactions with clients that put me in uncomfortable positions verbally and/or physically.
EXJ: Okay, so after you’re at Liberty, you’re off for a while with your family and then back to a law firm.
Carol Anguilla: I went to back to a smaller firm. It wasn’t all that easy to find a position because the longer you are out the harder it is. I was doing primarily real estate and some banking. The work wasn’t interesting to me and it was kind of a toxic environment as well. To make matters worse, I was not a member of the Massachusetts Bar. It was no problem when I was in-house but now, I had to study for and take the state’s Bar exam. We then moved down to Rhode Island, and I did a remote and commuting thing for a little while and it just it wasn’t worth my effort.
EXJ: So, then, Carol, how do you make the turn? What goes through your mind in deciding to leave the law. And at that point, did you know it was going to be teaching that you would go into?
Carol Anguilla: I was convinced that I was not going back to law. And I’m taking all the tests, the Myers & Briggs etc. to see where I should be. And every time I take a test, it comes up that I should be a lawyer. So, it’s not helping me.
I met someone at a party who was a partner at another law firm, and he said they could use someone with my background. So, I was there for a short time. I was then convinced my future was not in law. In the meantime, my kids were a little older. I had become very active in their elementary school. I was the president of the PTA. My husband kept telling me I should get paid for all the hours I was putting in. I couldn’t help it. I can’t just sit around. A friend had kids at a school in East Providence and there was a teacher residency program. I spoke with the principal who was very inspiring. We had an amazing conversation. I thought I’m going to give this a go.
EXJ: Did you need to take courses first?
Carol Anguilla: You need to be certified for public school, but you don’t need to be certified for independent schools. I’m a bit of a type-A personality so I thought, how can I possibly go start teaching without having any educational background as a teacher? . So, I did this one year master’s program in the Art of Teaching, which is about the pedagogy of teaching. From there I found an opening that happened to be for a second-grade teacher. I did that for three years and it was great. But I tend to be sarcastic and humorous, and those second graders didn’t get it. I’m like, I’ve got to teach older kids. There was an opening in the middle school for history and I was able to move into that position.
I was very lucky. Because the pay is so minimal, you must be financially well situated before you can make a move into teaching. I would never recommend this to a young person because at least in an independent school it’s very difficult to make a salary that you can support a family on.
EXJ: Yes, I know you had a husband that worked. When you make this kind of shift, to teaching or pretty much almost every other entry level job, it is going to pay less than you were making, at least if you worked at a large firm. So it sounds like that wasn’t a problem for you.
EXJ: So how does advancement work? Do you start in lower grades, like 6th and move your way up, or is it wherever there is an opening?
Carol Anguilla: In independent schools it’s really wherever there is an opening. A friend had told me about a new opportunity. They needed someone who could hold their own with challenging parents. They were finding it difficult. So, I interviewed and got hired.
I teach history which is a perfect fit for someone who was a lawyer. I let the parents know I am a teacher for two reasons. First, I want them to know that they can’t walk all over me. And, to let them know that I’m bringing a lot more into this classroom by virtue of my background than someone else might. We talk a lot about current events, we talk about politics. we have debates about what’s happening in the world. I think it’s a plus
for the students and they can ask me what it’s like to be lawyer. They always want to know what trials I did. I’m like, I didn’t do trials but contracts. And they think what’s that?
EXJ: You mentioned that the parents can be challenging. I’d guess that was the case in Newport, Rhode Island. But the power of the JD degree. You didn’t fall off the turnip truck, you’re a professional and their kids are lucky to have you. Appreciation from the parents and, of course, from the children. That’s what it’s all about isn’t it?
Carol Anguilla: Yes, t’s not for everybody, but it’s a very rewarding career if you can afford it.
EXJ: In your long, successful and varied career from lawyer to teacher, is there anything that you wish you had done differently?
Carol Anguilla: I probably wish that I had maybe given the corporate route more of a shot. I feel like I really would have been successful in business. As I said earlier, if my company hadn’t been sold I’d most likely have gradually transitioned to a business position.
I have on an off submitted applications these past couple of years but after you’ve been out of it for a while it’s a tough road.
EXJ: And those would be jobs in a corporate legal department?
Carol Anguilla: Yes, those were all for law department positions. It’s very interesting what you and Kim have started with ex judicata. I never realized, or knew, how to market myself as a business professional rather than as a counsel.
EXJ: I was just going to mention what you said, Carol. That’s what we’re all about at ex judicata. Working with someone, whether they are a young associate in a law firm or a more seasoned attorney and helping to direct them to business opportunities that they never would have considered themselves for in the past.
We’ve been hard at it networking with CHROs and Talent Acquisition leaders at companies throughout America to get our JDs considered for a whole range of opportunities. We call attorneys the hidden talent pool in plain sight.
It’s a two sided marketplace showing attorneys that they can apply for a multitude of nonlegal jobs and at the same time getting the buy-in from Corporate America I was just talking about.
Carol Anguilla: Yes, our skills are so transferable in so many ways in so many places that we shouldn’t be pigeonholed as lawyers who must practice law.
EXJ: Absolutely. We interviewed someone here who was a law firm associate for a couple of year and then moved to an in-house attorney position at Proctor & Gamble. After a year, he asked about moving into a brand manager role. He hadn’t studied marketing or sales. Nothing in his background. He simply explained that as a JD he was extraordinarily prepared for a role based on his analytical abilities, presentation skills, issue spotting expertise, and being able to manage huge amounts of information juggling multiple assignments over long hours. They gave him a shot. And he became a star.
Carol Anguilla: Nobody works harder.
People see me putting in long hours and they’re like ‘why, you’re not a lawyer anymore?’ Because I learned that everything has to be just right and that requires a large amount of preparation to prepare for any contingency. It probably brings my actual hourly wage down to something negligible. It’s ingrained in my attorney DNA.
EXJ: One last question. The fact that it is obvious doesn’t make it any less important. What advice might you give someone thinking about leaving the law?
Carol Anguilla: Well, if its for teaching it is an incredibly rewarding career but you have to understand what you are buying into as far as income and in some respects prestige. For example, whenever my mother and I meet new people she always says this is my daughter, she’s a lawyer. She never says I’m a teacher.
Carol Anguilla: But I am a lawyer and always will be a lawyer even though I’m currently not practicing. I think its exciting and fabulous to make a complete career change. It’s good for the soul and personal growth. Explore new things.
EXJ: That’s wonderful advice for all the JDS thinking about transitioning to a new career and a perfect place to leave it. Carol, thank you so much.
Carol Anguilla:. And best of luck. I think this is a fabulous venture you and Kim have launched..