Sydney Montgomery, founder of Barrier Breakers and Outline It
Sydney Montgomery, the 29-year-old founder of education non-profit Barrier Breakers and ed tech company Outline It, has dedicated her career to helping students from diverse backgrounds pursue new opportunities. She’s been an entrepreneur from an early age, having taught piano to her neighbors at the age of 10 years old and later becoming a tutor.
Both of Montgomery’s parents received their degrees only after joining the military. She herself was the first person in her own high school to go to Princeton, where she studied English. Later she attended Harvard Law School. In 2018, she launched S. Montgomery Admissions Consulting (now part of Barrier Breakers) with a mission to increase access to, and success in, higher education, for marginalized students.
In this Q&A, Montgomery discusses purpose, social impact, and the most important leadership lessons she’s ever learned.
Sally Percy: What stops underrepresented groups from applying to law school in the US?
Sydney Montgomery: I would say the biggest blockers are finances, lack of information, and imposter syndrome. Applying to law school can require a tremendous investment of time and money. Some of the financial barriers to applying to law school include the cost of undergraduate education, the cost of taking the Law School Admission Test, the cost of applying to multiple law schools and, of course, the cost of test prep and any admissions consulting services.
The other barriers include not knowing how to navigate the application process, not being aware of available resources and financial aid, and not having access to mentorship or guidance from individuals who have successfully navigated the process. This knowledge gap shows up in pretty drastic ways. For example, a 2017 study found that although the majority of non-Black applicants applied to law school in November, the majority of Black applicants did not apply to law school until March. Since law schools are on a rolling admissions cycle, that four-to-five month delay could be the difference between a student getting admitted with a scholarship and a student being denied.
Percy: Why is purpose important to you, as a leader?
Montgomery: It's important to have purpose when you’re a leader because intentionality is what breeds greatness. We all have greatness inside of us, but if we aren’t clear about our goal, then we will continue to move incrementally in 50 directions without moving significantly in any particular direction. My overall mission and calling is to reduce the educational equity gap in this country.
Percy: Do you have a mentor?
Montgomery: It’s hard to just name one person. I strive to form connections with people and maintain those connections throughout my entrepreneurship journey, which has led me to have a large number of mentors in various areas of my life. But when I think about the last couple of years in my entrepreneurship journey, I would be remiss to not mention my business coach, mentor and friend, XayLi Barclay. XayLi has not only pushed me in business, but as I’m almost 10 years younger than her, it’s so inspiring for me to see a very successful Black woman entrepreneur doing business on her terms, staying close to her values, and leading with a heart of service, while also still being profitable and creating the life that she wants.
Percy: Why do you think it’s important for leaders today to have a social impact?
Montgomery: In today’s world, it's irresponsible to not think about the way your business impacts others. Social impact isn’t just a feel-good afterthought. As a Black woman founder, I don’t have the space to not be thinking about these issues. Most people who don’t think about having a social impact are the people who aren’t impacted by lack of equity and unjust systems. Experiencing the weight of these systemic barriers first-hand has led me to creating businesses that directly address these problems. Furthermore, caring about people and social impact does not have to run counter to maximizing profitability. Some of the smartest and strongest businesses today focus on their double bottom line – marrying their financial profitability to social responsibility.
Percy: What are the most important lessons you’ve learned as a young, female Black leader?
Montgomery: Two lessons stand out. The first lesson would be to always look for opportunities to make genuine connections. In other words, always be networking. There are so many articles about how your network is your net worth and that sounds so clichéd. But coming from an underrepresented and disenfranchised group, I have been able to network my way into rooms and situations that otherwise would have been completely barred to me, no matter how hard I would have worked.
The second lesson I had to learn was to stay true to what I knew to be my vision and north star. There are so many people who will try to tell you what your business should be, or how you could be better if you changed a core part of what you are trying to accomplish. Some of the advice could be helpful, but as a CEO, it is your job to learn how to filter advice and learn which parts to act on and which parts to file away, or even completely discard. If I had listened to how other people told me to run my business, even when it went against what I knew was right in my gut, we would have failed.
