Massachusetts State House.
Boston Bar Journal

What I’ve Learned So Far

October 31, 2024
| Fall 2024 Vol. 68 #4

by Rebecca M. O’Brien

Stepping into the practice of law can be both exciting and daunting. In this recurring column, the BBJ is pleased to offer seasoned advice and practical tips for new lawyers and law students to help them thrive in their careers.

I did not decide I wanted to be a lawyer until I was 23. Up to that point, my aspirations had ranged from (I kid you not) a Doctor of Nutrition Science to an English teacher in Germany to a WNBA basketball player. For as long as I can remember, I endeavored to find a career that would bring me joy and purpose. Still undecided as a college senior, I got a job as a litigation paralegal at a large New York City law firm, thinking it would provide good insight into a career in the law. And it did; I found myself incredibly intrigued by the substance of the cases to which I was assigned and eager to better understand them. Unfortunately, several associates at the firm staunchly told me not to go to law school because they were unhappy in their careers and feared the same for me. This was disheartening advice, but it did not deter me nor diminish my resolve to prove that I could and would find fulfillment as an attorney.

Now, nearly nine years into my legal career, I will readily admit that this is not an easy profession. On the contrary, the law is challenging every single day, and some days, it is also maddening. But it never stops being fascinating, humbling, and rewarding.

Even as a law student, I experienced the breadth of positions available to attorneys. During my 1L summer, I interned for the Criminal Division of the U.S. Attorney’s Office for the District of Massachusetts. By stroke of luck, I was assigned to the unit prosecuting one of the most infamous crime bosses in Boston’s history. Then, the first semester of my 3L year, I interned for the Office of General Counsel for Northeastern University and was introduced to the captivating world of higher education law, experiencing firsthand the many different hats these attorneys wear, all on behalf of a mission-oriented organization. I emerged from law school with an expanded worldview and intense excitement for my fledging career, but with some uncertainty as to the trajectory it would actually take.

Since my admission to the Massachusetts bar in 2015, I have worked as: an associate in the corporate restructuring group of a big law firm, a law clerk for a Magistrate Judge for the U.S. District Court for the District of Massachusetts, a commercial litigation associate at a midsize law firm, and lastly, as an associate at a new and growing boutique litigation firm.

My professional experience has clearly been quite varied, from the nature of the business to the area of law practiced, and I have learned valuable lessons in every role I have held, some of which include:

  • Take every opportunity to work on your writing. One of the most powerful tools that we have as attorneys (and certainly as litigators) is our written work product. With strong writing skills, lawyers have the freedom and flexibility within the page count to frame the facts, make all the best arguments, cite the most persuasive cases, and perhaps anticipate and address counterarguments. In my experience, junior lawyers do not get many opportunities to draft or otherwise substantively contribute to court documents or advocacy pieces. Therefore, I encourage you to seize any such opportunities that come your way. Ask if you can draft a section or subsection of a pleading or demand letter – the introduction, facts, a tertiary argument – anything. Or ask if you can conduct the legal research that will be incorporated into the document, and possibly, draft a memorandum summarizing that research and applying it to the facts of the case. Then, make sure to request feedback on your work and incorporate that feedback into subsequent drafts. Honing your writing, and demonstrating initiative in connection with doing so, will make you a vital member of any case team. The earlier the better!
  • Pursue your interests with persistence, and along the way, take note of the things that do not fill your cup. Early on in your career, you may find that you do not have a lot of choice in the kinds of cases to which you are assigned. But every assignment can (and should) provide you with useful information about your skills, areas of improvement needed, interests, and disinterests. If you are at a law firm with some flexibility, try out different practice areas. If you are at an organization that supports pro bono work, and you have the capacity to take some on, go for it. In one of my first jobs, I was able to assist several elderly individuals with navigating the Chapter 7 bankruptcy process. I also had the special opportunity to assist a 14-year-old Guatemalan child gain legal permanent resident status in this country. To date, these are some of my proudest accomplishments as an attorney. Additionally, in my clerkship, I was exposed to virtually every kind of case that can make its way into federal court, from highly technical intellectual property matters to those involving colleges and universities as litigants. The former felt like a different language, whereas the latter was wonderfully familiar and reinvigorated my interest in higher education law, a field in which I currently practice. I can honestly say that it is only through my own diverse professional experiences – including those that taught me what areas of the law I do not enjoy – that led me to find my niche.
  • Set reasonable boundaries early and often. I think every lawyer would say there are times when there are simply not enough hours in the day to accomplish all the work that needs to be done. In all my professional positions, I have tried to carve out time for my life outside work, realizing that doing so is essential to my mental health. Even so, sometimes work demands have severely minimized this sacred time, if not altogether eliminated it. When I became a mother in 2022, I experienced a cosmic shift in priorities. I could no longer be unavailable to my family for periods of time because of my job; on the contrary, my job was the commitment that needed to bend. We all have important obligations and/or activities in our lives outside of work that occupy our time and headspace. If those things are important to you, I highly suggest you make them known to colleagues, managers, and supervisors, and (reasonably) demand they have space, whether by requesting time to accommodate them or expressing your unavailability. You may receive pushback but, in my view, it is always worthwhile to be candid about your needs.
  • Seek out friends and mentors, then foster and cherish those relationships. Our job is fundamentally human and, therefore, also fundamentally built on relationships. Befriend your colleagues, seek out confidantes and mentors, and always be cordial and considerate to everyone involved in a case, including opposing counsel. You never know when you may need the advice or support of a colleague, or grace from someone on the other side. This lesson in particular has led me to where I am today, in an extremely fulfilling role working alongside my mentors and colleagues that I trust, admire, and respect.

By following these lessons, I have found my passion. I encourage you to navigate your own path so that you can do the same.


Rebecca (Becky) M. O’Brien is an associate at Cloherty & Steinberg LLP. Her practice focuses on complex civil litigation matters, including those involving education, business, and employment-related disputes.