Analysis

How 2 Years In BigLaw Changed Judge Jackson's Career Path

(March 14, 2022, 10:05 AM EDT) -- After clerking for Justice Stephen Breyer, a young Ketanji Brown Jackson went to Boston to work as an associate for the firm Goodwin Procter LLP. Two years and countless billable hours later, she knew BigLaw's partnership ladder wasn't for her and set out on a different legal path that could now lead to a seat on the U.S. Supreme Court.

Judge Ketanji Brown Jackson, shown here on Feb. 25, has been nominated to take Justice Stephen Breyer's place on the U.S. Supreme Court. (AP Photo/Carolyn Kaster)

The 51-year-old D.C. Circuit judge, who could now replace Justice Breyer, is being touted by President Joe Biden and Democrats as bringing what would be a unique professional background to the Supreme Court. Never before has a former public defender joined the nation's top bench. And only one other justice, her former boss Justice Breyer, has had experience as a member of the U.S. Sentencing Commission.

Judge Jackson's career path reflects the trade-offs many women make, especially if they want a family too. For women of color, the frustrations that often accompany those compromises are compounded by the extra dose of scrutiny that comes with success, as her confirmation process is making all too clear.

In the early 2000s, the judge was just starting out her legal career after spending a year in Justice Breyer's chambers. With her husband, Patrick, completing his residency in surgery in Boston, Judge Jackson — then three months pregnant — moved her fledgling family to Massachusetts and, like so many other young lawyers from top law schools, took a job as a BigLaw associate.

So began what she would later describe as an "extremely challenging" two years in the Boston litigation department of Goodwin, a regional powerhouse that was expanding its presence across the country and had a seemingly endless pile of work for its associates. By the end of her time at the firm, the judge was eager to practice law in a more stable environment.

"Talia was born a few months after I started working at Goodwin, and the firm was very supportive, but I don't think it is possible to overstate the degree of difficulty that many young women and especially new mothers face in the law firm context," she said during a speech at the University of Georgia School of Law in March 2017, titled "Reflections on My Journey as a Mother and a Judge."

"The hours are long," she said. "The workflow is unpredictable. You have little control over your time and your schedule and you start to feel as though the demands of the billable hour are constantly in conflict with the needs of your children and your family responsibilities."

Judge Jackson was part of a large class of junior associates in the litigation department at Goodwin, which took up several floors of the firm's then-headquarters in downtown Boston. While there, she handled a variety of trial-stage litigation duties on behalf of the firm's corporate and nonprofit clients, from drafting pleadings to handling discovery. Cases ran the gamut from securities fraud to personal injury claims.

Despite feeling the weight of those pressures herself, 20 years after Judge Jackson's relatively short spell there, partners at the firm still remember her as a standout.

In an interview with Law360, Goodwin partner Tom Hefferon said there are many brilliant lawyers who pass through the firm's doors, but not all leave such a lasting impression. "There are a lot of people whose names somebody mentions and I don't even remember that person … That's not Ketanji and yeah, that speaks volumes."

During her time at the firm, Judge Jackson helped Hefferon, who was then a partner in Goodwin's growing D.C. office, advise a client on a complicated matter of class action law and accurately forecasted the direction in which the law would develop over time.

"To me, the thing that really sticks out is that she was a relatively junior lawyer who took a really complicated question of class action law, broke it down and delivered a really sophisticated analysis," Hefferon said. Judge Jackson "picked up immediately on the subtleties that were beyond her years in terms of her experience."

Rich Oetheimer, a Boston-based partner at the firm, had a similar impression of the judge after she helped him in a matter of real estate litigation concerning a lease on behalf of an institutional firm client.

"I had a chance to work with her, and it was clear that Ketanji was and is a superior talent and had the full package of analytical abilities, writing and oral skills and all the personal skills to be a star performer, and we would have been very happy if she remained at the firm," Oetheimer said.

Indeed, Judge Jackson has unequivocally praised her colleagues at Goodwin, which in 2017 she called a "great law firm."

Nevertheless, she would later say at UGA, "It just seems that the nature of big firm law practice is difficult to manage, no matter how nice the firm's partners might be."

"There are many women who can make it work," she said. "Some are quite well-suited to the pressures of big law firms. I discovered early on that I was not."

Jordan Singer, a former Goodwin associate during Judge Jackson's time at the firm, agreed that it was a "very high-stress environment."

In the early 2000s, Goodwin was still primarily a Boston-based BigLaw firm, but one with national aspirations. That meant keeping up with the sudden spike in associate salaries for top legal talent, especially those with prestigious Supreme Court clerkships like Judge Jackson. BigLaw had yet to fully grapple with concerns over work-life balance in those days, and associates were expected to justify those competitive pay packages with increased billable hours, Singer said.

"To be a litigator meant that you had to expect the possibility that you'd be working very late or coming in very early, or you'd get a call on what was then your Blackberry at 3 o'clock in the morning that something needs to be resolved," he said in an interview with Law360. "And so there was always an unsettled sense that even when you weren't in the office, you were in the office."

"I say that as someone who during my time there was in my mid-to-late 20s and single," said Singer, who is now a professor at New England Law in Boston. "I didn't have a family at that point and I certainly felt that pressure, and I would imagine that someone who did have a family and all the family obligations that come with it probably felt that pressure all the more so."

While the lack of work-life balance was definitely a "drawback," Singer said, it was also a great place to hone your skills as a young lawyer. "There was very little effort to protect us or say, 'You'll eventually figure it out.' It was sort of, 'Let's throw you in the deep end and see if you can swim.' And again, I mean that in the positive and the negative sense."

For all her struggles in BigLaw, Jackson said she learned some valuable lessons.

"If I was going to make my life work as a lawyer and also have a family, I needed to use my legal skills in a more predictable, more controllable environment," she said in her 2017 UGA speech. "That was a realization for me — the understanding that if I was going to leave my baby and go and work outside the home, I needed to find a law job that was not only fulfilling but was also compatible with the needs of my family. And armed with that realization I began what can only be characterized as a professional odyssey of epic proportions."

Speaking with Law360, Hefferon said that "across BigLaw there probably is more sensitivity to [work-life balance] as an issue. My personal experience at the firm, anyway, is that Goodwin has been pretty good about that."

Oetheimer added, "Work is demanding and clients can be demanding, but I always felt that the firm compared to its peers does a pretty good job of promoting work-life balance."

"She wasn't at the firm very long and maybe concluded that she wanted to try something other than BigLaw. She certainly would have been a big success had she chosen to stay," Oetheimer said.

The next two decades would bring a whirlwind of career moves from Judge Jackson that ultimately led to her nomination last month to the Supreme Court by Biden. She left Goodwin for a job in D.C. at another firm, The Feinberg Group, before joining the U.S. Sentencing Commission as a staff attorney. After that, she developed her appellate advocacy skills as a federal public defender in Washington, D.C., arguing around 10 appeals in the D.C. Circuit. And then for "financial reasons," as she later explained, she left the government and was of counsel at Morrison & Foerster LLP.

In 2010, she became vice chair of the U.S. Sentencing Commission and joined the federal bench as a U.S. district judge in Washington in 2013. She was confirmed to the D.C. Circuit last summer.

Judge Jackson would not be the first female member of the Supreme Court whose disenchantment with the world of BigLaw set her on a different career path.

Despite graduating third in her class at Stanford Law School, Justice Sandra Day O'Connor interviewed with several California law firms, but was rejected by all — a familiar experience for female law school graduates in that era. One of those firms, Los Angeles powerhouse Gibson Dunn & Crutcher LLP, offered her only a position as legal secretary, a slight she reminded the firm of while a guest of honor at its 100th anniversary in 1990.

Before her death, Justice Ruth Bader Ginsburg similarly said that rampant gender inequality in the legal profession in the 1950s and '60s steered her away from private practice.

"I certainly lucked out, and Justice O'Connor would tell the same story," Justice Ginsburg said in 2019.

In contrast, many men who have served on the Supreme Court enjoyed thriving careers as partners at big firms before joining the bench, including three of the six who currently serve.

The legal industry may no longer be as blatantly sexist as it was when Justice O'Connor and Justice Ginsburg were starting their careers, but there are still many factors that combine to make a career in BigLaw difficult for women, and that is borne out in the data. In Law360's latest Glass Ceiling report, women accounted for 48.5% of associates at more than 270 surveyed law firms, but only 23.3% of equity partners. For women of color, the numbers are significantly more bleak.

At U.S. law schools, women of color now make up 20% of first-year law students. Yet, at the firms surveyed by Law360, women of color represent only 9% of attorneys, 4% of all partners and about 3% of equity partners.

Judge Jackson spoke about the barriers women of color face in the law firm context during her 2017 speech at UGA, including the lack of mentorship that leaves minority female attorneys "excluded from centers of power and influence" at many law firms.

"All this might help to explain why large numbers of women move away from big firm practice each year," she said. "And at the very least, it suggests that women may be turning elsewhere for greater professional fulfillment. In my case it was the inflexibility of the work schedules and assignments that became the deal-breaker as I struggled with being a young mother in the context of a firm."

For a 2020 report called "Left Out and Left Behind," the American Bar Association's Commission on Women in the Profession surveyed more than 100 female attorneys of color about their experiences and found that not much has improved over the last 15 years, when a previous ABA report found that 85% of women of color leave their practice at large firms within seven years.

One of the authors of the study, Eileen Letts, a partner at Zuber Lawler & Del Duca LLP, told Law360 that Judge Jackson's description of her experience in BigLaw is not necessarily unique to women of color, but rather to working mothers more broadly. Still, she noted, "our research did find that women of color tend to have more familial obligations."

What's even more distressing, Letts said, is how certain members of the legal community and news media have questioned Judge Jackson's credentials despite her graduating from Harvard Law School with honors and earning a clerkship at the Supreme Court. The Fox News personality Tucker Carlson, for instance, demanded to see Judge Jackson's LSAT scores. Carlson has not made such a request of any previous nominee that Law360 could find.

"That is a prime example of how there are so many impediments to women of color getting into the positions that she's in," Letts said. "'Well, was it affirmative action? Well, was she really that smart?' There are always those extra questions that are asked about ability and quality."

Letts said that helps explain why getting in the "pipeline" is not always a guarantee of future success for many women of color in the legal industry. "Even if they get in the pipeline, they can get clogged.

"You can imagine, only imagine, for someone who doesn't have her credentials, what questions are asked and why we don't go very far when we're in the pipeline," she said.

--Additional reporting by Jackie Bell. Editing by Marygrace Anderson and Alyssa Miller.

For a reprint of this article, please contact reprints@law360.com.

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