About Sydney Montgomery, Esq.

Sydney Montgomery, Forbes 30 Under 30, is the CEO and Founder of Outline It, and the Executive Director and Founder of Barrier Breakers®, a 501c3 faith-based education nonprofit with a mission to increase access to, and success in, higher education for BIPOC and other marginalized students. As the first lawyer in her family and a Princeton and Harvard Law School graduate, Sydney has used her platform since 2012 to help students break down generational barriers and step confidently into their future.

A woman of strong faith, Sydney is a dual-degree candidate for the Master of Arts in Christian Education and Formation and Masters of Divinity Program at Princeton Theological Seminary. She also holds her Certificate in Independent Educational Consulting from the University of California, Irvine.

Sydney cares deeply about making an impact and giving back to the community and sits on the boards of several non-profit organizations. Sydney is a Co-Founder of College Equity First, Inc., a Maryland 501(c)(3) non-profit with a mission to motivate colleges and universities to become places where women and BIPOC students are as safe, valued, supported, developed, and celebrated as other students. In 2021, through data collection, analysis, and substantive interviews, College Equity First, Inc. synthesized quantitative and qualitative data about each institution into the College Equity Index™ that ranks 105 top private colleges on the campus climate for Black students.

Sydney sits on the Board of the Institute for Anti-Racist Education, a New Jersey 501(c)(3) non-profit dedicated to creating decolonizing pedagogy and anti-racist curriculum, and she sits on the Board of Advisors to Girls with Impact, the only live, online entrepreneurship program made just for girls.

Sydney is a member of the National Association for College Admission Counseling, the Potomac and Chesapeake Association for College Admission Counseling, and currently serves as an Ethics Committee member of the Independent Educational Consultants Association (IECA).

Honors and Awards.

  • 2024 Forbes 30 Under 30 (Social Impact)

    Named one of 30 of the brightest young entrepreneurs, leaders, and stars in the country in the Social Impact Category.

    https://www.forbes.com/30-under-30/2024/social-impact?profile=sydney-montgomery

  • 2021 Kappa Alpha Theta 35 Under 35

    Recognizes young alumnae ages 35 and under for their outstanding accomplishments after college. The award has many categories to recognize all the areas where Thetas excel.

    https://www.kappaalphatheta.org/members/recognition/35-under-35

  • 2021 UCI Alumni Achievement Award

    Given to individuals who have demonstrated how the education and skills gained from the University of California, Irvine, DCE certificate program were applied in a distinctive and notable way.

  • 2021 PCACAC Counselor of the Year

    Recognizes Potomac and Chesapeake Association for College Admission Counseling members who go above and beyond in their work with students. Selection criteria include expertise, impact, advocacy, commitment to equity, and innovation in the industry.

    https://www.pcacac.org/counselor-of-the-year-award

  • 2020 IECA Making a Difference Award

    For positively contributing to the Independent Educational Consultants Association and profession, pushing for cultural competency training, and leading anti-racism efforts through presentations and articles.

    https://floridanewstimes.com/maryland-consultant-sydney-montgomery-wins-iecas-first-making-a-difference-award/91943/

  • 2018 Clarksburg High School Commencement Speaker

    Chosen by the Class of 2018 Class Officers to lead and inspire students at commencement to an audience of 4000+ individuals, including families, students, and educators.

  • 2010 American Baptist Churches of the South Oratorical Contest Winner

    ABCOTS is a non-profit corporation associated as a covenanting Regional organization with the American Baptist Churches, U.S.A

What People Are Saying

 

“You’ve given laughs and light to a very stressful and nerve-wracking time. I greatly appreciate your spirit and guidance.”

— Sofia F.

 

“Your feedback and input have been really valuable and the applications that I'm sending out are stronger because of your help.”

— Chad S.

“After hearing your experiences and advice, law school seems less like a pipe dream and more like a realistic goal.”

— Daniel H.

 

“Sydney believes in your abilities and is truly excited to cheer you on in the process which is invaluable.”

— Peyton T.