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Jamie Szal of Brann & Isaacson: “More sobering ”

More sobering — Think long and hard about taking on law school debt before you do. Talk to people to have a realistic understanding of what the salary expectations in different employment situations truly are. I did not do that, and it is one of my biggest regrets. You have to pay back those student loans. You […]

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More sobering — Think long and hard about taking on law school debt before you do. Talk to people to have a realistic understanding of what the salary expectations in different employment situations truly are. I did not do that, and it is one of my biggest regrets. You have to pay back those student loans. You may be stuck in a higher paying job that you do not like in order to pay back your loans. You may be eligible for the Public Service Loan Forgiveness Program, assuming it still exists long-term, but even with that program, you should strongly consider living a very frugal life while you are in repayment. PB&J for breakfast, lunch, and dinner, anyone?


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 Jamie Szal.

Jamie Szal is an attorney at Brann & Isaacson, where her practice focuses on assisting businesses in all aspects of state and local tax controversy, from audits and administrative proceedings through civil litigation. Jamie’s practice has taken her to state trial and appellate courts, to state administrative tribunals, and to state agencies throughout the country. She advises internet retailers and tech companies on state and local tax compliance and privacy. Prior to joining B&I, Jamie worked for the Massachusetts Department of Revenue. Jamie earned her J.D. from Northeastern University, and her LL.M. in Taxation and SALT Certificate from Georgetown University Law Center in its inaugural Executive LL.M. in Taxation. Jamie also is a passionate volunteer with her alma mater (Vice President of the Trinity College Alumni Association), Community Dental (a dental service organization whose mission is to serve Maine’s most vulnerable residents), and for MothersEsquire (an organization whose mission is to serve and advocate for lawyers who are mothers). Outside of work, Jamie enjoys raising her fiercely independent, impish daughter; singing; and exploring the hiking trails of Down East Maine with her family.


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 was interning at NASDAQ when the 2008 equivalent of Black Tuesday occurred. The market tanked within minutes of opening. I remember sitting around the trading screens with my colleagues, watching the market dive, waiting for a call from NYSE on the red emergency phone to shut down the market. It came very close. The days and weeks that followed as markets issued emergency orders to address what became the Great Recession were fascinating. I realized then that financial services enforcement was it for me. But at the time I still held out hope for a career in Constitutional Law. Low and behold, in my next internship, I found the very combination in state and local tax.

The very foundation of state and local tax is Constitutional Law — implicating the Commerce Clause, the Due Process Clause, the Supremacy Clause, the First, Fifth, and Fourteenth Amendments. We make these arguments in the context of financial services enforcement. I loved the combination of creative, industry and company-specific arguments combined with the hard-analytical results of tax. After all, at the end of the day, there is a right number to calculate.

My career journey highlights how important internships can be. My final internship in law school was with the Massachusetts Department of Revenue, which ultimately became my first job after law school. 2009 was an awful year to graduate. Because of that internship, however, I already built a relationship with the attorney in the DOR, knew I loved the practice area, and knew I could do the work. When the DOR called me and asked if I wanted to return, I jumped at the opportunity. I spent eight years working in different divisions within the DOR before being approached by a recruiter with an opportunity to join B&I. My family had been looking for a chance to move to Maine for a long time (my husband was born and raised here), but my practice area is niche. B&I has one of the top state and local tax practices in the country. For such a small team, here in Lewiston, Maine, we provide really, really good work for our clients in tax matters across the country, from audit straight through to the U.S. Supreme Court. It was an opportunity I could not let slip by.

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

In a former life, I was a Broadway junkie and actor wannabe. I went into law as my “stage” to perform, little thinking that I would be hooked back into my musical days on the job. One year a former employer decided to roll out a mediation program and wanted to drum up excitement internally. A music video! they thought. One colleague, who was gifted with words, wrote out a parody to the tune of “Celebrate” and roped me into providing the lead vocals and dance moves. We did a mean grapevine, let me tell you! The music video aired internally only for a few short months, but several colleagues saved recordings and every few months as I walked down the halls I would hear the faint strains of “Mediate, good times! Come on!” coming out of someone’s office.

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

For confidentiality reasons, I cannot reveal my current work. But I am excited to be a part of a team that is working at the forefront of state and local tax issues facing eCommerce and IT companies.

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

I think it is safe to say every litigator dreams of the chance to work on an actual U.S. Supreme Court case. It was a privilege and a career-high to be involved in one: South Dakota v. Wayfair, Inc., 585 U.S. __ (June 21, 2018). Attending the arguments was incredible. Justice Sotomayor pounced on questioning straight out of the gate. Although we, unfortunately, did not succeed, we came very, very close. My colleague, George Isaacson, argued so well. I’ll admit, though, a very small part of me wonders, in jest, whether we would have been able to convince Justice Ginsburg to side our way if we had used scrunchies or jabots in our examples, to put the economic impact in terms of an item the Justice herself may purchase online.

In its 5–4 decision, the Court’s overturned 50 years of precedence and completely changed the landscape in state and local tax. The short story is that as a result of the Wayfair decision state tax authorities can require retailers, vendors, and service providers to collect and remit state and local sales taxes if the business has a high enough level of economic activity (i.e., sales) in the state. The two years since the decision have felt like the Wild West — all the rules went out the window, and the laws and policies shift on a weekly basis around the country. If that was not chaotic enough, the state and local tax response to COVID business interruptions has amplified the effect.

Which people in history inspire you the most? Why?

RBG — Ruth Bader Ginsburg. As a lawyer, as a woman, as a wife and mother, Justice Ginsburg overcame so much adversity in the pursuit of her goals. Did you know the first case she argued before the U.S. Supreme Court was a tax case? So clearly, I am the next RBG. A girl can dream, anyway.

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

Take the time to be curious and learn as much as you can about a career in law before you commit to going to law school. Learn the difference between transactional law and litigation, and consider which best suits your personality and work strengths. Litigation often is combative and confrontational. If a confrontation does not appeal to you, don’t become a trial attorney! Talk to people who are lawyers, and learn why they love what they do. Talk to people who left the practice of law, and find out why. Finally, get at the very least an internship in a legal work environment (law firm, law school, government agency) and see for yourself if the work environment appeals to you.

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

First and foremost, as an industry, we must tackle gender bias and racism within our own industry head-on. We must address the institutional barriers that stop women, and in particular women of color, from thriving. In the last two years, the ABA Commission on Women in the Profession has tackled this issue head-on, starting with its landmark 2019 report “Walking out the Door: The Facts, Figures, and Future of Experienced Women Lawyers in Private Practice,” and most recently through its 2020 report, “Left Out and Left Behind: The Hurdles, Hassles, and Heartaches of Achieving Long-Term Legal Careers for Women of Color.” The Commission’s work is critical but only a start.

Second, I would ensure that all courts (state, local, federal, and administrative) have the funding and resources needed to invest in critical technological infrastructure. Quarantimes has demonstrated how incapacitated many of the tax courts were simply because they did not have the technology available to stay open.

Third, I’d revamp legal education, with a much heavier emphasis on practical skills and the business of law than legal theory. As lawyers, we are trained on how to think and how to communicate (generally). We are not taught how to run law offices, how to negotiate, how to draft critical legal filings. It is instead left to law firms to teach these practical skills. But if the Great Recession and current quarantimes taught me anything, it is that new lawyers who have these practical skills have a major leg up in the job market compared to their peers lacking this knowledge.

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

I am a passionate advocate for lawyers who are mothers through my involvement with MothersEsquire, a non-profit organization whose mission is to advocate for and provide a support network to lawyer-moms. The legal profession has been slow to come around to recognizing that moms, particularly those who are caring for newborns and infants, have specific needs. For instance, right now I am part of the MothersEsquire “Pump up the Bar” task force. Did you know that the vast majority of Bar Exam test examiners have adopted policies prohibiting test takers from bringing menstrual sanitary products with them to the test, and the majority require nursing mothers to either forego pumping or to pump in public in the testing room? If a nursing mother does not have regular opportunities to express, she risks not only physical pain from engorgement but also serious infection and mastitis. The mission of the Pump up the Bar campaign is to ensure that 2020 (and future!) test takers have the minimum accommodations necessary to address those needs, such as allowing test takers to bring their own sanitary products and to pump in privacy.

I also take pride in giving back to my alma mater as a volunteer. Students are the next generation of leaders, entrepreneurs, lawyers, and advocates and I love being a part of their lives.

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

My daughter, trite as it may sound. I returned to working in the office recently, one day a week, after 4 months of working from home. My toddler protested. I’ll be honest, it was harder than returning to work from parental leave! But what I said to her is as true now as it was then: “I have to go back to work because I love my job and I am very good at what I do. I am going back to work to show you what a hard-working, determined, fierce, strong, independent woman who works in a job she loves looks like.”

On a more professional level, I really love knowing that I’ve been able to make a concrete, tangible difference in my clients’ businesses, and to be a part of the growth of their companies. One recent client turned her garage hobby into a thriving online shop and is busting sales goals left, right, and center. I love knowing that I’ve been a part of her success!

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. I started my legal career so young — 24. My career as a lawyer will span many decades. I still consider myself to be a young lawyer, but I have been in practice already for 11 years. Looking back, I realize I was very fortunate to discover, while in law school, an area of the law I genuinely love to practice. Especially when your career will be a long one, it is so important to find that practice area that makes you tick as early on as possible. Don’t pick a practice area because that is the one you are “supposed to” pick. You are far more likely not only to love practicing as a lawyer but will be more driven to continue growing as a professional.
  2. Practicing in an area you truly love makes the parent/professional balance easier to manage. I shared with my toddler daughter yesterday, when she protested my return to the actual office, that “I am going back to the office because I have to. I love being a tax lawyer, and I love my job. I work to show you [her] what being a strong, confident, proud, hard-working woman who works full-time in a job she loves looks like.” Being a mother is my greatest challenge — my daughter inspires me to be a better lawyer and to live up to my own expectations of myself for her. As for the balancing work and motherhood, I wish I learned earlier the importance of identifying my boundaries are early. It is important to figure out in your own style how to professionally and reasonably enforce those boundaries. For me, this means that there are certain hours of the day I have blocked off as my priority time with my daughter where, barring an actual emergency, I do not work and I focus on being a mom.
  3. It’s ok to change your plans. You may, and hopefully will, find the practice area you like early but that does not mean you are limited to the type of work environment. For instance, I practiced in the public sector for 8 years before switching to the private sector. Same practice area — state and local tax controversy — but I went from knowing one state to being responsible for fifty states, and I love the change of perspective! Other friends have loved IP law but realized that their ideal work environment was not in private practice, but rather in launching a business that revolves around providing legal IP services.
  4. Start networking now, and network often. Networking, particularly in these quarantimes, does not necessarily need to look like dressing in a suit and standing around in a large room full of strangers. Networking can also include one-on-one meetings, virtual coffee breaks. I strongly recommend starting with your alma mater (college or law school) community — you have a built-in point of commonality and it makes the initial outreach easier. Now that I have been in practice longer, I have found getting involved in local business groups such as the Maine Women’s Business Network, or being active on LinkedIn to be even better. Particularly now as we are all interacting virtually, LinkedIn is a great source of knowledge, networking, and comradery. I recently connected with a group of other women who are lawyers from a variety of practice areas and areas of the country — the deep comradery, knowledge base, and support network has been amazing!
  5. More sobering — Think long and hard about taking on law school debt before you do. Talk to people to have a realistic understanding of what the salary expectations in different employment situations truly are. I did not do that, and it is one of my biggest regrets. You have to pay back those student loans. You may be stuck in a higher paying job that you do not like in order to pay back your loans. You may be eligible for the Public Service Loan Forgiveness Program, assuming it still exists long-term, but even with that program, you should strongly consider living a very frugal life while you are in repayment. PB&J for breakfast, lunch, and dinner, anyone?

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. 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. 🙂

I’d love to sit down and pick the brain of Karen Cahn, of iFundWomen. I am inspired by her continual drive as an entrepreneur to launch businesses on her own (GiltGroup, GLAMSQUAD) and now her mission to support other women in their entrepreneurial dreams through iFundWomen. I would love to hear her story and learn from her. Women supporting women is my passion — Karen does through business and investing what I hope to do through tax law.

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