Getting to Know You: Sydney Montgomery

Sydney Montgomery ’18, is the CEO of S. Montgomery Admissions Consulting, where she specializes in working with first-generation and minority college and law school applicants. 

Tell us about your path to Harvard Law School. Why did you pick HLS?

I knew I wanted to be a lawyer since I was eight. I wanted my parents to adopt because I was tired of being an only child, and I really wanted an older sibling. I saw programs on television that showed children ready for adoption from the department and mentioned this to my parents. Even though they decided against adopting, this experience ignited a passion for foster care children and children with different educational opportunities. When we talk about the academic gap in this country, we mainly focus on teachers, funding, and resources. We don’t talk about the support gap, inequitable distribution of resources, or inequitable information dissemination. In high school, I decided that I wanted to address this educational inequality issue from a child custody lens and decided to pursue being a family lawyer. 

Despite this decision, I didn’t fully understand how to navigate the higher education landscape. Both of my parents were military, and my mom is a Jamaican immigrant. They both received their degrees non-traditionally after enlisting in the military. Through the grace of God, I became one of the first students from my high school to go to an Ivy League school. Princeton opened up so many doors for me. Fast forward to the law school application process, even though I had tremendous help from my pre-law advisor at Princeton, I almost didn’t apply to Harvard. I have never liked cities, and instead of focusing on clinics, journals, programs, and employment metrics, I mainly focused on geographical preferences until an HLS student at my paralegal summer internship set me straight right before applications opened. 

Even with this advice, I was careful not to choose Harvard for its prestige. I wanted to make sure I was choosing a school where the community would be supportive, and the finances made sense to me. The combination of grant money, the Low Income Protection Plan, and the wonderfully uplifting Black Law Students Association (BLSA) community made HLS the best choice for me, hands down. 

What made you pivot from practicing law to educational consulting? 

I started consulting accidentally in 2012 while I was still in college, giving back to my school, my church, and local dance studios in the area. When Princeton lost its pre-law advisor in 2015, I started helping out unofficially with Princeton students applying to law school as well. I did a lot of reflection my first two years at HLS, and really took stock of how blessed and fortunate I was to be at Harvard Law School through a series of divine interventions. I started thinking about the number of students who could have ended up in law school if they had only had someone to help guide them and steer them in the right direction. I knew I wanted to practice law, but I also knew that the field of admissions was important to me, so I started exploring what a career in admissions could look like. I actually worked up the courage to ask Dean Jessica Soban for a meeting. She was so generous with her time and gracious with her answers; she became a great role model for me. When I graduated from law school, I clerked for a judge on a family rotation in Montgomery County, Maryland, but I also simultaneously pursued my certificate in Independent Educational Consulting from UC Irvine and joined professional associations, such as the Independent Educational Consultants Association and the National Association for College Admission Counseling, because I believe that professional development is crucial to success. I also learned how to use my platform to speak out against systemic racism in education. Even though I joined a family law litigation firm after my clerkship, when I realized the impact I could potentially have on equity in law school admissions, I did a lot of praying and decided to pivot to educational consulting full-time. Only 2% of lawyers in this country are Black women, and I am one of few prominent Black law school admissions consultants. 91% of my students are first-generation or minority applicants, yet over 78% of my students have enrolled at a T30 law school and over 56% of my students have received at least a half-tuition scholarship to law school. This is important because I want to help students break generational cycles of poverty and debt. 

What are some of the challenges with the legal market and what kind of impact do you hope to make with your company? 

As I mentioned, only 2% of lawyers in this country at Black women, and statistics show that Black and Hispanic applicants and women applicants of all races matriculate to law schools with lower bar passage rates than their counterparts. Black applicants borrow 97% more for law school than their white counterparts. I believe we need a cosmopolitan legal world that reflects the citizens and the changing demographics in this country. I work with students of all backgrounds on the law school application process: college students, non-traditional students, single mothers, recovering addicts, military veterans, trauma survivors, and everything in between. I work with students in private consulting, in small group boot camps, and through asynchronous courses. I also try to increase information dissemination through my Barrier Breakers® Facebook group, YouTube channel, and Break Into Law School™ podcast. One of the things I would love to do is change the stigma surrounding educational consulting. I don’t believe that educational consulting has to be viewed as helping wealthy students and privileged students gain even more privilege. Educational consulting can disseminate information and increase access to higher education for minoritized populations. I’m now the chair of the Graduate School Committee of the Independent Educational Consultants Association and I have used my power and position to push the profession to be more culturally competent and anti-racist in its efforts.

Circling back to your law school experience, what were some of the greatest moments from your time at HLS?

One of the greatest things that I did at HLS was taking advantage of clinical opportunities. I had a mentor who emphasized that even though I knew I wanted to practice family law and do direct services work, it wouldn’t be a bad idea to get some policy experience under my belt. This was probably one of the best pieces of advice I received during my law school career. I looked at the open clinics and decided that I would sign up for the Food Law and Policy Clinic for my 2L fall. The Food Law and Policy Clinic at Harvard Law School is hands-down one of the best clinics offered at school. Emily Broad Leib is one of the most fantastic Clinical Directors the school has. Not only did I do the Food Law and Policy Clinic that fall semester, but I continued through my spring semester because I enjoyed the work so much. I became a policy “expert” on urban agriculture and school food waste and had the opportunity to travel to Iowa to Drake Law School to meet farmers and discuss the Farm Bill.  I also traveled to my home state in Maryland and presented in front of legislators in Annapolis on food law policy. The Food Law and Policy Clinic was such a transformative experience that I ended up doing another policy clinic at the Attorney General’s Office in Massachusetts with the Child and Youth Protection Unit my 3L fall. I worked on DACA legislation and reports for the child welfare system in Massachusetts. I did get direct services experience my 3L spring with the Domestic Violence and Family Law Clinic. There, I not only helped women with their family law litigation issues, but I also made friends who I’m still very close with today. 

I could not talk about my time at Harvard Law School also without mentioning the HLS Parody. My greatest regret is that I didn’t do Parody my 1L year, but in Parody I found more than just a community of people I could interact with; I truly found my home. I went through so much during the three years that I was in Cambridge and in many ways Parody saved me. When I first moved to Cambridge, I was recovering from a dance injury and dealing with medical issues. I ended up having an undiagnosed autoimmune and connective tissue disease the entire time I was at school. Getting to reintegrate into dance and eventually become Co-Head Choreographer my 3L year meant everything to me. 

What is one piece of advice you would give to prospective law school applicants? 

I don’t believe this process has to be stressful. I try to encourage students to incorporate mindfulness throughout this process, whether by listening to Headspace or Calm, enrolling in a mindfulness course, or through my Mindful Prayers for Students podcast. The pressure I see applicants putting on themselves is so detrimental. I tell my students just to be themselves, be authentically them. They don’t need a gimmick; they only need to present themselves genuinely through their essay and application materials. There are many paths to a successful legal career — no one school or tier of school is going to get you there. It is also impossible to predict the future. When I started HLS, I could never have imagined that this is where my life would have led. You end up where you’re supposed to be in life, and as long as you keep following your passion and your calling it will all work out exactly as it is meant to. 

Sydney Montgomery is the CEO of S. Montgomery Admissions Consulting. Sydney graduated from Princeton University in 2015, where she majored in English and received a certificate in French Language and Culture. At HLS, she was the Co-Symposium Chair for the Harvard Negotiation Law Review and Co-Social Chair for the Black Law Students Association. In 2020, Sydney was awarded the Making a Difference Award (Independent Educational Consultants Association) and was named a 2021 Counselor of the Year (PCACAC). Sydney received Kappa Alpha Theta’s 35 Under 35 Award in 2021 and was named one of the 21 Leaders of the 21st Century (Women’s eNews). Sydney is currently pursuing a Graduate Certificate in Anti-Racism in Urban Education through the University of North Carolina, Charlotte.