Sydney Montgomery, JD

Today’s students are under constant pressure to figure everything out early, get it right the first time, and carry success on their own. For first-generation and nontraditional students, that pressure often comes with silence, self-doubt, and the fear of asking for help.

In this message, Sydney Montgomery helps students challenge the lie that success requires doing everything alone. Drawing from her journey as the first student from her high school to attend Princeton University and later Harvard Law School, and from her work supporting more than 7,000 students nationwide, Sydney shows students how real success is built through relationships, mentors, and community.

This session gives students permission to ask for help, language to advocate for themselves, and practical tools to build support around them. Students leave with clarity, confidence, and a renewed belief that their path does not have to look like anyone else’s to be valid or successful.

Learning Outcomes:

• Reframe asking for help as a strength, not a weakness
• Identify who to turn to for support in academic, personal, and career settings
• Understand how mentors and networks actually work, and how to begin building them
• Navigate imposter syndrome and self-doubt with greater confidence
• Define success on their own terms, even when the path forward feels uncertain
• Take practical next steps toward their goals without needing a perfect plan

Sydney has presented this work for students at:
Princeton University, Stanford University, Yale Law School, MIT, American University, George Washington University, Indiana University, University of California Irvine, Tennessee State University, Miami-Dade College, Rowan College at Burlington County, Marymount Manhattan College, Marion P. Thomas Charter High School, Gaithersburg High School Commencement, Clarksburg High School Commencement, TEDx Asbury Park, the National Black Pre-Law Conference, Students of Color for College Conference, and APCA Regional South.

Schools have made real progress in expanding access. The harder work is ensuring students actually persist, belong, and succeed once they arrive.

In this message, Sydney Montgomery helps educators and leaders move beyond good intentions and toward practical, human-centered approaches that help students follow through. Drawing on her work as a first-generation Princeton and Harvard Law graduate and the founder of a nonprofit that has supported more than 7,000 students nationwide, Sydney clarifies what students need most from the adults who serve them.

This session equips staff with realistic strategies for building trust, normalizing help-seeking, and creating pathways to mentorship and support that students actually use. The focus is not on adding more to already full plates, but on doing a few critical things better, together.

Learning Outcomes:

• Recognize why access alone does not guarantee persistence, belonging, or achievement
• Identify common points where students disengage, hesitate to ask for help, or quietly fall through the cracks
• Apply practical approaches that make support visible, relational, and easy to access
• Strengthen mentoring and referral practices without overloading individual staff members
• Respond more effectively to student burnout, imposter syndrome, and disengagement
• Create clearer pathways that help students move from opportunity to follow-through
• Leave with tools that can be applied immediately across classrooms, advising, student services, and leadership teams
• This keynote aligns directly with institutional goals around retention, belonging, wellness, and student success, and gives schools a shared language for the work that happens after access is granted.

Sydney has presented this work for educators and leaders at:
Princeton University Career Services, Princeton Prize in Race Relations, Stanford Neurodiversity Summit, Yale Law School, Harvard Alumni for Black Advancement, The Independent Educational Consultants Association, National Association for Law Placement, Northeast Association of Pre-Law Advisors, Innovative Educators Summit, The Equity Summit, Greater Houston Women’s Chamber of Commerce, Montgomery County Women’s Bar Association, and professional gatherings nationwide.