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No Choice but to Succeed: An Inspirational Conversation with Regina Calcaterra, Esq.

Elizabeth DiNardo, Esq. | Associate Counsel

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In recent months, there has been no shortage of distressing news. An inspiring story on beating the odds from someone who was able to rise above an extraordinarily difficult start to life is a refreshing change. This edition of Women in the Law profiles an extraordinary female attorney who faced hardships that many of us cannot imagine and has come out the other side with an intense determination to succeed.

Regina Calcaterra, co-founding partner of Calcaterra Pollack LLP, is a woman who thrives in the face of adversity and has done so her entire life. There has been no straight line in the story of Regina Calcaterra. Many can say that they worked hard at school from a young age with a goal in mind—perhaps to go to college and then to law school—but Regina’s story differs drastically. The details of her harrowing childhood can be found in the pages of her New York Times Best Selling book, Etched in Sand. Regina’s childhood was not a secure, happy place; instead, it was a daily battle to survive. During the years where most children are daydreaming on the playground about what they want to be when they grow up, an eight-year old Regina—without a stable and constant parental presence—was worrying about how she was going to feed her younger siblings and keep her family together under the constant threat of being separated and placed into the foster care system. Regina was forced in many ways to act as an adult at a young age and lived in a dark world where she wasn’t told she could be anything she wanted to be.

To a child fighting to survive day-to-day, the thought of one day becoming a successful lawyer and government official, not to mention opening her own women-owned law firm, would seem like an unreachable and implausible dream. But that is exactly what Regina has accomplished. To have attained that level of success coming from such a horrifying childhood, demonstrates her insatiable internal drive to succeed. “When I was a child, there were very few people in my life that built me up and gave me confidence and self-esteem. At that time, less than 1% of foster children graduated from college—the odds were stacked against me from the start,” she recounted. Reflecting back, Regina says that her life has been a series of difficult setbacks that she has had to overcome. She never had the opportunity to go to Ivy League colleges or law schools and she never had the same resources most people enjoy while in school. But those obstacles forced her to adopt the mentality that there was no choice but to succeed.

Realizing early on that education was the only way out of the cycle of poverty she grew up in, Regina set her sights on college and finally found the right fit at SUNY New Paltz, where she says she was provided with opportunities that she never knew existed. Pursuing a degree in political science is sometimes viewed as the natural precursor to a career in law, but at that time Regina was simply trying to survive school and graduate, all while working three jobs. The idea of becoming a lawyer didn’t really enter her mind until she embarked on a career in public policy and was inspired to become an advocate for others.

Regina’s first job after college was with the Eastern Paralyzed Veterans Association (EPVA), advocating for the rights of veterans with disabilities. Her time spent with the EPVA predated the passage of the Americans with Disabilities Act (“ADA”). Her responsibilities included lobbying in Albany to enact laws that would make everyday services accessible for people with disabilities. One of her first victories as an advocate came at the age of just 23, long before her career as a lawyer began. Regina helped to pass a New York State law that enabled drivers with disabilities to obtain full-service gasoline at less expensive self-service pricing.

Regina’s victory as an advocate for the disabled arrived just as the ADA came into law and enabled her to further her career in public policy at New Jersey Transit (“NJ Transit”) where she worked toward making the NJ Transit system more accessible to commuters with disabilities. It was at NJ Transit that Regina realized she was spending a good deal of time explaining the new federal law to lawyers, which gave her the confidence to consider applying to law school. She credits her early career in public policy and her experience lobbying for equality on behalf of those with disabilities as having sparked a true love of effective advocacy.

Thus, Regina embarked on obtaining a law degree—yet another challenge she faced head-on. Most law students treat their law school experience as a full-time job, at least during their first year. In contrast, Regina worked full-time to support herself and attended school at night, commuting from New York City and her job as chief lobbyist for the New York City Comptroller to Seton Hall Law School in New Jersey. She admits that the four years of working full-time and completing law school were a dark time for her. However, Regina recognized that she had no safety net and had no other option but to succeed—a theme that would remain a constant presence in her life and career.

Working full-time throughout law school meant Regina was unable to take part in the usual hallmarks of law school that help pave the way for a career in the practice of law, like clerkships or summer associateships. The moment she received the letter that she had passed the New York State Bar Exam, she says she collapsed with relief. She finally realized that she had done it—she had beaten the odds and her life had truly become one of the success stories that are told to foster children and the disadvantaged to inspire them to become educated and break the cycle. “I remember when I passed the bar, I fell to the floor and started hyperventilating and crying. Here I was, 30 years old, and for the first time in my life I realized that from now on all I ever have to do is work one job,” she said.

Throughout her impressive legal career, Regina has continued to bring her passion for advocacy and empathy for those facing injustice to every case. Prior to branching out on her own and starting Calcaterra Pollack LLP, Regina was a partner at securities and consumer class action litigation firms for twelve years, but with her drive to succeed and her innate desire to help improve the lives of others, she also worked in public service and held several crucial roles in New York state and local government: Executive Director to two of New York State Governor Andrew Cuomo’s statewide investigative commissions; Chief Deputy to Suffolk County Executive Steven Bellone; Deputy General Counsel to the New York State Insurance Fund; and Deputy General Counsel to the New York City Employees’ Retirement System.

Regina and her partner, Janine Pollack, started their 100% female-owned law firm, Calcaterra Pollack LLP, just as the COVID-19 pandemic was spreading across the United States. For most, it wouldn’t seem an ideal time to start a business, but for a woman like Regina, the difficulties posed by the pandemic were just another set of obstacles that she would overcome on her way to success. Alongside Janine, Regina has been able to build a law firm that is a model to those in the legal field, where everyone’s voice is heard no matter their position in the firm. Regina says that she and Janine believe it’s imperative that each person knows how their work will fit into the larger picture as a whole, so they firmly grasp their contribution to the overall success of the firm. Calcaterra Pollack is a firm built on the tenets of diversity and inclusivity, and the wellness of its team members is a primary focus.

To close, Regina imparts this advice for lawyers and non-lawyers alike: “I’ve always, even in the hardest circumstances, tried to behave with dignity. I always tell people that when things get tough, when something goes wrong with your firm or with your job, you are going to be remembered by your behavior at that time. So, act with dignity.”

To read more about Regina’s path to starting her own firm, click here.


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