“It’s Irresponsible To Not Think About The Way Your Business Impacts Others”

Sydney Montgomery, founder of Barrier Breakers and Outline It J’nae Antoinette / IG @naerock4real 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 […]

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