Journey to Esquire

Kayla Britt

Amanda Freeman

Kristin Hommel

The path to law school is challenging, and for many women, it presents distinctive obstacles. But with the right mindset, strategies, and a strong support network, it can also be a transformative and empowering experience. Women often face unique challenges and barriers to entering the legal field, which are both baked into the system itself, and perpetuated by those who operate within that space. Yet, there are many examples of women who overcame these hurdles to carve their own paths and achieve success in their own right.

The women interviewed for this article all come from nontraditional backgrounds, some coming to law school after already having entered into the workforce (like Amanda Freeman, who worked for nearly ten years for American Airlines prior to starting law school), while others pursued other graduate programs before pivoting to a legal education (like Kayla Britt, who obtained her Masters of Public Administration). Kristin Hommel, a graduating 3L at Penn State Dickinson law (and author of this article) was adrift prior to law school, living in France for a year as a teacher following her college graduation before working as a paralegal for three years. Rather than the exception, more and more these types of nontraditional paths are becoming the norm. These women have navigated both coming into law school with families, and starting families while in law school; they have dealt with disappointments, taken unanticipated paths, and fought against the voices who told them they could not “have it all” or did not have what it takes.

Now, they want the next generation of female law students to know what they went through, and to know how to get through it themselves.

Looking back on their law school journeys, both Kayla and Amanda wish they had been better prepared for some of the unexpected challenges. For Kayla, a key lesson was that no amount of preparation for class can replace understanding the importance of applying the material through practice questions in preparation for the all-important final exam. In law school, often the final grade in class is determined not through homework throughout the semester, but rather one, massive final exam that determines the entire grade; moreover, most law schools employ a “curve” that allows only a small proportion of the class to get an “A”, with the puzzling result that not everyone who writes an “A” exam will actually receive that A. This oversight led to Kayla’s academic dismissal, but it ultimately became a lesson in resilience. “Everyone told me everything I needed to hear, but I had to learn the hard way,” Kayla reflects.

In contrast, Amanda, a first-generation college graduate, emphasizes the importance of networking. Unfortunately, first-generation law students are at a distinct disadvantage from their classmates who have lawyers in the family, as an established network can often make or break your career. “Find a mentor. Having someone outside of law school (someone who practices law) can provide a perspective you won’t get from professors or fellow students,” she advises. Early connections are vital, especially for those without a pre-established network in the legal world. Kristin echoes this advice; as a first-generation law student herself, Kristin cannot say enough about the importance of networking. “I owe my 2L summer internship to a contact that I made while networking at the annual AILA [American Immigration Lawyers Association] Conference during my 1L year,” she reflects. “His good word resulted in more than 6 interview requests and 5 job offers.”

Although this may sound like bad news to those future lawyers who are introverts or who dislike small talk, networking is a skill that can be learned through continual practice. Kristin notes that she developed her own network only after forcing herself into uncomfortable settings time and time again. “It’s all about making relationships,” she says, “and honestly it becomes very easy when you realize that networking boils down to asking one simple question: ‘how did you get to where you are today?’” By asking this question (and analogous follow-ups), you key in to one simple fact; lawyers love talking about themselves. Practice asking this question, she recommends, and “you’ll be surprised by how much the other person has to say.”

For women considering law school, the balance between academics, personal life, and future career goals is critical. Kayla advises prospective students to be honest with themselves about the demands of law school. It’s a rigorous journey that requires sacrifice, and it’s essential to understand the mental and emotional toll it can take. “Law school is the mental Olympics,” she says. "Understand the rigor, know what to expect, and find your balance early on.”

Amanda’s advice centers on finding flexibility within the structure of law school. As a mother, Amanda quickly realized that she needed to carve out time for herself, even when the law school workload felt overwhelming. “If you don’t make time for yourself, it can really hurt,” she explains. Learning to strike a healthy work-life balance is possible, but it requires conscious effort and self-care.

For Kristin, striking the balance between her personal life and law school obligations has proven to be a constant battle. “You’ll find that there is always something in law school that is vying for your time and attention,” she advises. “Learning how and when to say ‘no’ is crucial for preventing burnout, and allows you to concentrate your efforts on the things that are truly important to you!”

A common misconception that many women face when entering law school is the idea that there will be no time for anything outside of classes. Amanda, a nontraditional student and mother, found this belief to be untrue. "I thought I wouldn’t have time for anything other than classes, but that mentality led to burnout," she says. Over time, she learned to prioritize self-care, and now, she advocates for finding moments for yourself amid the chaos of law school.

Another misconception is that there's a "one-size-fits-all" approach to studying. Amanda emphasizes that different study methods work for different people. For example, while outlines are helpful for some, she swears by mind maps as a more effective way to retain information. The key is to find what works best for you and to be flexible in adapting your strategies. The common adage of “run your own race,” while perhaps overused, is absolutely true. Find what works for you, and stick with it.

Something that surprised Kristin about law school is how the intense grading curves can impact relationships and personal interactions. “When you throw a bunch of type-A students into a room and tell them that only 15% of them can get an A, the vibe sometimes gets very weird, especially during 1L,” Kristin reflects. “Once you reach 2L and 3L, you start caring a bit less about the curve, but that intense pressure to distinguish yourself during 1L can really hurt your budding friendships, if you let it.” Her advice? Don’t talk about your grades with your friends, and do not hang around after exams to rehash your performance. “Talking about your grades with new friends really only does one of three things: it will make them pity you, envy you, or feel better than you. It’s better not to infuse your new friendships with jealousy or pity unnecessarily.”

Gender bias and discrimination remain issues for women in law school and the legal profession. Amanda suggests that women should ensure they attend law schools that are committed to diversity and inclusion. This can significantly impact the support they receive throughout their education and beyond. “Look for schools that make it clear they are creating an inclusive environment for women,” Amanda advises. Beyond the traditional Women’s Law Caucus organizations on campus, Amanda recommends that prospective law students look at whether they have a DEI office, if they have courses that teach about gender equality throughout our nation’s jurisprudence, and any other outspoken commitments they have made to put women on equal footing with male students.

"FIND YOUR PEOPLE—THOSE WHO LIFT YOU UP AND MAKE YOU FEEL LIKE YOU BELONG."

- Amanda Freeman

When it comes to career progression, both women agree that confidence plays a key role. For women who fear discrimination or gender bias, Kayla advises, “You need to advocate for yourself, even when it’s uncomfortable. Do it scared. If you’re afraid of something, it probably means it matters a lot to you.” This applies when asking for a raise, negotiating benefits, or requesting training on a practice area that interests you. “You have to advocate for yourself with the same amount of confidence that a white man has,” Kayla jokes. “There were so many times in law school that I didn’t do something because I was afraid somebody else was going to do it better. Sure, you might not have the qualifications to do a certain job, but let them tell you that, apply even though you’re scared.”

Unfortunately, it is not uncommon even today for men, even potential mentors, to engage in acts of discrimination or harassment. “It really sucks when you realize that you were just being given time and attention because of your looks,” Kristin reflects, recounting one instance where a budding mentor relationship turned sour. “After he made it clear he was attracted to me, I struggled a lot with feeling like I had anything to actually contribute to the practice of law.” Ultimately, however, Kristin asserts that you have to realize that you have to keep pushing forward, strongly denounce inappropriate conduct, and know that with your entry into the practice, you have the opportunity to continue changing the practice for the better. “Know that you will likely encounter discrimination, harassment, and bias in your practice, but know that you don’t have to accept it or put up with it!”

Imposter syndrome is something many women law students face. Both Kayla and Amanda share personal experiences of feeling like they didn’t belong, especially when transitioning from other careers. Kayla's favorite mantra is to do it scared: take risks, apply for opportunities even when you’re unsure, and push through self-doubt. "You have to learn to fight for yourself and believe in your abilities, even if you have to fake it till you make it,” she says. “Do it scared. Doing it without worrying about what people will think of you is the only way to move forward and get through imposter syndrome. You’re not an imposter, the practice of law is full of people who are learning new things and who are “imposters” in their own right, but no one is truly an imposter.”

"DO IT SCARED"

- Kayla Britt

Amanda adds that finding a support system is crucial. Surrounding yourself with people who appreciate and value your perspective helps mitigate feelings of inadequacy. “Find your people, those who lift you up and make you feel like you belong,” she advises. Kristin seconds this sentiment, but also adds the caveat that you should not try to be friends with everyone. “Some of the best advice I received in law school came from my career services advisor. ‘Keep your circle tight and small, and be absolutely sure you can trust them’,” she says. “I took that advice to heart and have about two friends in the law school who are my absolute ride-or-dies. I genuinely don’t think I would have made it to the finish line without those two girls beside me!” Build and invest time in friends who will encourage you to grow, cheer you on, and who will ultimately help you make decisions for your future. “You need people around you who truly know you and what you’re capable of; no true girlfriend will let you succumb to imposter syndrome!”

Kayla reiterates that you need to “believe in yourself like a white man believes in himself.” Emphasizing that you don’t need to actually be confident to appear confident, Kayla and Kristin agree that the business of law is full of professional actors who are all just figuring things out as they go. “You begin to understand that a lot of people’s success comes from their arrogance,” Kayla says as she reflects on her experiences post-law school. “I’m told all the time that I look so confident and that I’m doing so well, but that’s only because I do it scared every day, because nobody else is going to advocate for me the way that I’m going to do it for me.” Similarly, Kristin’s favorite mantra guides her every decision: “Don’t let your fear of a ‘no’ keep you from pursuing the ‘yes’.”

Kayla, Kristin, and Amanda stress the importance of networking. “Networking is the most important thing you can do in law school, especially as a first-generation law student,” Kristin advises.

For Kayla, networking goes beyond exchanging business cards. It’s about building genuine relationships. "When you network, always get the name of another person you can connect with. Think of it as building friendships," she says. For both Kayla and Kristin, networking has become something they genuinely enjoy. “Networking is my favorite thing,” Kayla says. “It literally means more than anything else you do in law school.”

Amanda also emphasizes the value of finding mentors, particularly for women navigating law school. Having someone to bounce ideas off of who is not a professor or fellow student can provide a crucial outside perspective. “Networking and finding mentors can make a huge difference,” she says.

Kayla’s number one tip for anyone at a networking event is to “get the name of another person with whom you can network with.” Talking to new people is stressful, so Kayla advises that you “look at the human component to that person: they were you at one point, they have passions and were once in your position. Starting conversations that don’t fixate on the law is one of the greatest ways to make an impact and become memorable.”

"DON'T LET YOUR FEAR OF A 'NO' KEEP YOU FROM PURSUING THE 'YES'."

- Kristin Hommel

Having attended more than four conferences, two symposia, and one leadership academy while in law school, Kristin’s advice is to find common ground with the person you’re speaking; “if there’s one thing I’ve learned about immigration lawyers, it’s that they are massive nerds about immigration. But they’re also people too, so while you should absolutely demonstrate your passion for your field of interest (especially if they work in that field), you should also connect on other topics too,” Kristin reflects.

The most important thing about networking is to approach the opportunity with the right mindset; it is not about what jobs the other person might have access to, but rather about making a connection. On this, Kristin and Kayla agree: “networking is about getting to know people and developing friendships and relationships; not every networking opportunity has to be about what that person can do for you,” Kayla warns. “No one wants to feel used.”

The challenge of balancing career aspirations with family life is particularly relevant for women in law. Amanda notes that while transactional law offers more flexibility, litigation can be demanding, especially for those with young children. She encourages women to be proactive in seeking support from their workplace and to choose a practice area that allows for a sustainable work-life balance. "Make sure you have a good support system (whether it’s family, friends, or colleagues) because that’s key to balancing everything," she says.

Kayla agrees, stressing that women need to be empowered to pursue their professional goals without feeling limited by societal expectations. "You can do it all, but it’s important to have the right resources and support," she explains. Most importantly, however, Kayla asserts that “women need to value our own potential.” More so than men, Kayla says that women have the ability to be “teachable” because we do not go into new careers thinking we know everything; “if I’m a hiring manager,” Kayla says, “I’m going to hire the person whose background shows tenacity, persistence, and the ability to be taught, even if they’re 20% less qualified, because I know that I can teach that person the 20% deficit, as opposed to the person who cannot be taught, who thinks they know everything, and who doesn’t want to hear anything they don’t want to hear.”

Women in law need to advocate for themselves, whether it’s negotiating salaries, pursuing promotions, or seeking recognition. Both Kayla and Amanda share stories of how they took the initiative to seek opportunities and raise their voices. “You need to advocate for yourself, even when it’s scary,” Kayla advises. Amanda echoes this sentiment, suggesting that women be upfront about their intentions with their employers. “Be honest about what you want and make sure they know you’re interested in growing with the company,” she says.

"A LOT OF PEOPLE'S SUCCESS COMES FROM THEIR ARROGANCE. BELIEVE IN YOURSELF LIKE A WHITE MAN BELIEVES IN HIMSELF."

- Kayla Britt

Kayla adds that women sometimes hesitate to ask for what they deserve because of the discomfort that comes with negotiation, but it’s essential to practice and get comfortable with these difficult conversations. “It’s always an uncomfortable conversation,” Kayla says. “But you never know if a new administration or leader of the firm or organization might eventually say yes.” Plus, “you just know that when a man who asks for a raise or to negotiate their salary, they certainly are not afraid to do so.” If you never speak up to advocate for yourself, after all, who will?

For Kayla, the most important message is to never let setbacks define you. “I was never supposed to be a lawyer,” Kayla reflects. “In my dad’s barber shop, I remember him telling his customers that I didn’t have the common sense to be a lawyer. It has been battle after battle to be a lawyer.” Proving her father wrong, Kayla advises, “s***t’s going to be hard, but I want you to know that you can do it. A setback is not the end of the world,” she says. “I want people to look at me and know that they can do it.” Kayla’s own journey from academic dismissal to Assistant Attorney General is a testament to resilience and determination.

Amanda offers a similar perspective, urging women to remain persistent and embrace their journey. “It’s so worth it. Don’t let unexpected challenges derail you. Give yourself grace and know that you’re capable of doing this,” she says. Emphasizing that challenges and setbacks do not define one’s potential, Amanda admonishes future law students to set their own pace and rewrite their own personal definition of success. “The thing about law school,” Amanda notes, “is it forces you to engage in self-advocacy.” But remember that you are not in this alone; “find a school that will support you in your goals,” Amanda says, “and build a supportive community who will cheer you on every step of the way.”

“Law school has perhaps been one of the toughest experiences of my life,” Kristin reflects. “Becoming a lawyer is a grueling process, and you should only do it if you are absolutely certain that this is what you want to do.” More than anything else, Kristin advises the would-be K through JD students to pause and take some time to get real world legal experience before entering law school. “Law school will always be there,” Kristin says, “but by working for a year or more prior to law school, you not only acquire skills that make you far more attractive to future would-be employers, but also discover whether or not you actually enjoy law.” Herself a paralegal for three years before law school, Kristin says she would not trade that experience for anything. “Yes, I was an older law student. But because of those years of experience, I knew precisely what area of law I wanted to practice, and I was able to tailor my legal education to serve my personal goals.”

The journey through law school and the legal profession is far from easy, but with the right mindset, strategies, and support systems, women can not only survive but thrive. The key is to lean into discomfort, find your community, and always advocate for yourself. The path may be long, but the rewards are immeasurable.