S. Montgomery Admissions Consulting (MD)
NACAC member since 2021
Sydney Montgomery, Esq. has over a decade of experience working with and inspiring teenagers from all walks of life. Her experience has also included being a private performing arts teacher, academic tutor, and mentor. She has guided high school students through the college admission process since 2012, and has helped students navigate the law school admission process since 2015.
I found myself in this profession accidentally. My parents have always been staunch advocates of my education. Unfortunately, my college application process coincided with my parents’ separation and I found myself suddenly lost. Without access to adequate college counseling, I was left to my own devices on my college application list.
Despite my lack of guidance, I became one of the first students from my high school to matriculate at an Ivy League university; Princeton University (NJ) changed my life in more ways than I can count. When students at Clarksburg High School (MD) asked me to come back and speak to them about the college admission process, I jumped at the opportunity. I realized that there was so much misinformation about the college admission process and not enough resources to help students find their best-fit colleges.
I absolutely love what I do. I love my students and feel so privileged to share this special and sacred time in their lives with them. My desire to help children is what originally spurred my quest to go to Harvard Law School. While I enjoyed being a lawyer, there is something unique in experiencing the joy of watching a student have a breakthrough with her essay or an aha moment about his potential major. I feel privileged when students feel comfortable enough to disclose their personal struggles to me through their essay topics and I live for the moments when I can be their cheerleader, celebrating every small victory, every deadline met, scholarship won, and school acceptance letter.
My first experience with NACAC was actually the Financial Aid 101 course.
It is really hard to pick just one moment! I absolutely love all the ways I can interact with my students and my larger audience as a whole. Last year, I decided to launch law school application boot camps and create small cohorts where students could be guided on the application process together.
I would tell myself it’s okay to embrace the unexpected and it’s okay to chart my own path. Being a boxchecker is great, but sometimes the best things don’t come in boxes.
I pray about all tough decisions. My faith is everything.
If I am being honest, this is a continual discovery during this pandemic. I play the piano, listen to worship music, and have recently taken an interest in Shark Tank.
I am currently reading How to Be Antiracist by Ibram X. Kendi.
Caring. Transparent. Imaginative.
Washington University in St. Louis (MO) NACAC member since 2017
Washington University in St. Louis, a private institution founded in 1853, is a community where students can be individuals and achieve exceptional things. The school is committed to learning and exploration, to discovery and impact.
Like so many folks working in admission, I stumbled into this work after serving as a tour guide and student interviewer at my alma mater. I always enjoyed working with young people and after a few years, decided to teach high school in Saint Louis Public Schools. That experience helped me grapple even more with issues of educational equity, access, inclusion, and belonging. While I loved teaching math, I found myself being drawn back to working in college admission, armed with a better understanding of what life is like for high school students. I was fortunate that Washington University began to explicitly prioritize working with underrepresented populations, creating an opportunity for me to return to admission work in a landscape that was changing rapidly, both institutionally and nationally.
Believe it or not, although I’ve been doing this work for the better part of 10 years, I’ve never been to a NACAC conference in person! A few opportunities were derailed by unforeseen circumstances, most recently the COVID-19 pandemic. However, I was able to facilitate a Wisdom Circle session with a college counselor from a high school I work with in New York for the NACAC Virtual Conference in Fall 2020. It was a great experience.
The "Birthday Paradox" says it only takes a group of 23 individuals to reach a probability of 50 percent that two members of the group have the same birthday. Once, on my birthday, I met a student at a school visit who was also celebrating his birthday—it was a fun discovery and a really humanizing moment during what’s typically a stressful time of year! This discovery completely dissolved the tension!
My former students inspire me. Based on statedetermined evaluation systems, my school was metrically underperforming, and served almost universally students of color from limited-income backgrounds. The commitment many of my students displayed to their education inspires me to leverage my privilege to advance educational and economic equity in marginalized communities.
Growth comes from taking risks and often from failing when taking those risks. I was a very buttoned-up high school student, and while I excelled academically and in extracurriculars, I find myself wishing I had “gone for it” a little more.
It’s always important to build empathy with those who may be negatively affected by a decision. I try as much as possible to root my decision-making in logic, data, and evidence, which ultimately helps me communicate why a particular path was chosen. And if my time in the classroom taught me anything, it’s that you have to accept some responsibility and display humility when the decision wasn’t the best.
I love spending time outdoors hiking, biking, and backpacking. I also started throwing pottery a few years ago, and there’s something immensely therapeutic about sitting at the wheel and throwing a set of bowls or a new pot for one of my houseplants. Lastly, and perhaps most perplexingly, I find doing the dishes while listening to a good podcast really relaxing.
I’m reading Caste by Isabel Wilkerson, Blowout by Rachel Maddow, and There There by Tommy Orange. I’m watching Halt and Catch Fire, The Amazing Race, and anything produced by Higher Ground Productions.
Alert. Balanced. Curious.