Ramona S. Chaplin: “Stay prepared”

Stay prepared: An attorney comes to a court conference and more importantly a trial, fully prepared and has a thorough understanding of the facts and legal issues involved (both pros and cons). You should immediately sets the tone of the case and sends a message to the adversary that he/she is ready for anything that comes. […]

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Stay prepared: An attorney comes to a court conference and more importantly a trial, fully prepared and has a thorough understanding of the facts and legal issues involved (both pros and cons). You should immediately sets the tone of the case and sends a message to the adversary that he/she is ready for anything that comes.


As a part of my series about “5 things I wish someone told me when I first became an attorney” I had the pleasure of interviewing Ramona S. Chaplin.

Ramona is the founder of the Law Office of Ramona S. Chaplin, P.A. and licensed to practice law in the State of Florida. Ms. Chaplin was born and raised in Jacksonville, Florida. Ms. Chaplin attended and earned her Bachelor of Arts from the University of North Florida and received her Juris Doctorate (J.D.) from Florida Agricultural and Mechanical University College of Law in Orlando, Florida. In 2010, Ms. Chaplin returned to Jacksonville, Florida and began a solo practice.


Thank you so much for joining us! Our readers would love to get to know you a bit more. What is the backstory that brought you to this particular career path in Law?

I’ve always had a passion for helping others. In my career, I try to focus on being the voice for people and communities that don’t have one. Some times the difference in the outcome of a situation is having knowledgeable representation that can help you navigate, this has always been my goal for any of the clients I work with.

Can you share the funniest or most interesting story that occurred to you in the course of your law career?

I represented a client in automobile accident where she was involved in three separate accidents on the 13th day of October, November and December of 2016. The case ultimately settled combined for 133K.

What are some of the most interesting or exciting projects you are working on now?

Most recently, I have committed my time to the Amendment 4 Fines and Fees Campaign, which is a project of FRRC Education Fund. FRRC’s Fines and Fees Campaign helps returning citizens break down any barriers they may have to voting from financial obligations (e.g. fines, fees, or court costs) that arose from a felony conviction (excluding murder or felony sexual offenses). FRRC has raised over SEVEN MILLION dollars since its inception.

What are some of the most interesting cases you have been involved in? Without sharing anything confidential can you share any stories?

Unfortunately, the most interesting cases I have been involved in have been heavily litigated and I can’t share those details. I work with clients in varied situations with a focus on the best possible outcome. At times that outcome is positive and at times it’s the best possible option at the time. Either way, I work hard on behalf of my client and fight for the best route.

Which people in history inspire you the most? Why?

Shirley Chisholm is one of my biggest inspirations. Mrs. Chisholm truly practiced what she preached. During her seven terms in Congress, Chisholm hired an all-female staff, half of whom were Black women. While serving in Congress she supported civil rights, women’s rights, social welfare programs and spoke out against the Vietnam War. She worked hard to support women’s rights to choose during pregnancy and sought to uplift women, especially Black women, up from restrictive gendered roles.

Following in the steps of Mrs. Chisholm. I’ve hired an all female staff.

What advice would you give to a young person considering a career in law?

My advice for anyone considering a career in law is to find an attorney mentor that you can learn from and volunteer at a law firm. Build up your experience and knowledge base in law as early as you can start.

If you had the ability to make three reforms in our judicial/legal system, which three would you start with? Why?

1. Eliminate Personal Responsibility and Work Opportunity Reconciliation Act (PRWORA): PRWORA is a denial of federal benefits to people convicted in state or federal courts of felony drug offenses. The ban is imposed for no other offenses but drug crimes. Its provisions that subject individuals who are otherwise eligible for receipt of SNAP or TANF benefits to a lifetime of disqualification and it applies to all states unless they opt out of the ban. Currently 37 states either fully or partially enforce the TANF- ban, while 34 states either fully or partially enforce the SNAP ban. Florida partially enforces the SNAP and TANF ban which means an offender cannot receive FS or TANF/cash assistance for a felony conviction.

2. Eliminate cash bail system: Eliminating bail will aid in making the system fairer for poor people, who are far more likely to get stuck in jail while awaiting trial. Only in the cases of the most serious charges are judges allowed to decide whether to set bail or to order someone held behind bars until trial. The purpose of the original bail reform law was to reduce the number of people jailed while awaiting trial simply because they could not afford to pay bail.

3. Ban the Box- This calls for removing the question and check box, “Have you been convicted by a court?” from applications for employment, housing, public benefits, insurance, loans and other services. 1 in every 4 adults in the United States has a conviction in their past that can make it hard to find employment or a place to live. Discrimination towards returning citizens must stop, in order for them to move forward with more positive lives. (-https://floridarrc.com/)

How have you used your success to bring goodness to the world?

As a managing owner of my firm, I offer internship opportunities to law students and high school students who may otherwise may not have one. This gives them an opportunity to gain more experience. I also provide pro bono representation. I firmly believe in equal access to justice for all. The cost to hire a lawyer should not stand in the way of someone being able to defend his or her rights. I believe it is my duty and privilege as a legal professional to offer pro bono services to those in the Jacksonville, Florida community. My firm’s pro bono involvement offers financial support to legal aide in the Jacksonville area.

I know this is not an easy job. What drives you?

What drives me is creating opportunities or myself and others as well as the ability to help others. Lawyers are in a unique position to further the public good and have an impact on the way the world runs. As I stated before, many people in the legal field perform pro-bono work during their career. This helps undeserved parts of the population including low income clients, victims of abuse, and the elderly.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or an example for each.

  1. Stay prepared: An attorney comes to a court conference and more importantly a trial, fully prepared and has a thorough understanding of the facts and legal issues involved (both pros and cons). You should immediately sets the tone of the case and sends a message to the adversary that he/she is ready for anything that comes.
  2. Don’t be afraid to ask for help: Law school teaches students how to “think” like a lawyer, but the learning process does not, and cannot stop after graduation. Personally, I discovered very early in my career that I still had much to learn if I wanted to become an effective lawyer. I have found that many of my colleagues have had similar experiences.
  3. Prioritize selfcare: Be sure that you have developed positive coping mechanisms. Take intentional time for yourself every day — be it meditation, yoga or a walk outside the office. Be self-aware and recognize if stressors are flaring up and if you need to talk to someone! If you do not yet have a trusted office colleague, reach out to the state Lawyer Assistance Program (LAP) for confidential assistance.
  4. Learning is lifelong: You are not going to know everything once you pass the bar. But if you commit yourself fully every single day to learning, listening and putting in the time and effort to become the best you can be, you will set yourself up to become a successful attorney and a role model to even newer attorney.
  5. Own your mistakes: You are going to spend the rest of your life trying to convince people they should take your word for things. It is easier to convince people you’re right if they’ve learned you will admit it when you’re wrong.

Thank you for these great insights!

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