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Jeffrey A. Weissman of Gladstone & Weissman, PA: “Get comfortable being uncomfortable”

Get comfortable being uncomfortable — there is a vast amount of information to digest and learn. You will be unsure of yourself for at least the first 3 years of your practice; 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 […]

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Get comfortable being uncomfortable — there is a vast amount of information to digest and learn. You will be unsure of yourself for at least the first 3 years of your practice;


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 Jeffrey Weissman.

Jeffrey A. Weissman is a Principal/Shareholder of the law firm of Gladstone & Weissman, P.A.

Mr. Weissman limits his practice to complex matrimonial and family law cases. His clientele consists of many successful entrepreneurs, business owners and executives, doctors, lawyers, television personalities, and professional athletes. He is a Fellow in the International Academy of Matrimonial Lawyers. He is also a Supreme Court Certified Family Law Mediator, and is formally trained in Collaborative Law.


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?

In the summer of my second year at the University of Pennsylvania Law School, I accepted an internship with a top firm in Fort Lauderdale. Multiple assignments were delegated to me; however, I was ultimately presented with a permanent offer from the family law department. I accepted and the rest is history. My current law partner, Peter Gladstone, also worked in the family law department of that firm for a period of time, and several years later we reconnected and started our current firm, Gladstone & Weissman, P.A. We specialize in high and ultra-high net worth family law cases.

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

Ethically, I cannot divulge any specifics, but I can say that every day is a little more interesting than the last! My clients never cease to amaze me with what they believe is important to share.

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

I truly believe the timeless advice of doing what you love. Currently, I am working on complex business valuations and related buy-out structuring in several high-end cases.

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

Hard to say without sharing anything confidential. I pride myself on never disclosing anything that could potentially compromise the identity and privacy of my clientele, many of whom are well known. They entrust me to keep their matters outside of the public eye.

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

Set up informational interviews with attorneys in various fields and have them explain their experiences and career trajectories. College students should seek out summer internships, without pay if necessary and feasible, in order to see what it is like to work for a law firm. Make sure that you are passionate about the law before experimenting and incurring the time and expense of law school.

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

1. Greater availability of and access to dispute resolution alternatives for pro se litigants;

2. Greater resources for pro se litigants to help file and process cases correctly; and

3. Judges or divisions that solely handle pro se cases and process them more efficiently through the system. Believe it or not, the vast majority of litigants do not have the financial wherewithal to engage counsel and must proceed on a pro se basis. There is a vast disparity in the resources available from jurisdiction to jurisdiction.

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

I have accepted numerous pro bono cases throughout my career, in addition to my private charitable endeavors. Professionally speaking, I have served as a mentor to many young lawyers and taught them to practice with honor, integrity, and competence.

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

What drives me is being able to help very good people who are paralyzed by fear and uncertainty transition to a better, hopeful place.

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. Get comfortable being uncomfortable — there is a vast amount of information to digest and learn. You will be unsure of yourself for at least the first 3 years of your practice;

2. Learn your craft first and it will make networking and client development much easier;

3. Find an accessible, welcoming, and friendly mentor who can guide you through the complexities of case and practice management;

4. Learn how to read your judge and stop talking when victory seems apparent; and

5. Do not be afraid to fail. Success comes from failure.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this.

Generally speaking, I would like to have a private breakfast with someone who faced adversity and/or suffered a trauma growing up but did not allow that to immobilize their ambition. Instead, that person summoned the strength to become one of the most respected people in their field or industry. I am inspired by those who achieve, despite the odds being stacked against them. I think we can all learn a lot about inner fortitude and perseverance, and we can incorporate these teachings into our personal lives and impart them to others.

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