Sydney Montgomery

Speaker | Mentor | Entrepreneur

Redefining Success.

Expanding Upward Mobility. 

Helping students and leaders access the support they need to achieve their pathway to success.

I’m Sydney Montgomery

I grew up the daughter of military parents and a Jamaican immigrant, believing that success meant survival: do everything right, endure, and you’ll get ahead. That mindset carried me to Princeton and Harvard Law, where, on paper, I looked like the perfect story of upward mobility. But what those accolades didn’t reveal were the hidden costs — financial strain, chronic illness (fibromyalgia and Ehlers-Danlos Syndrome), mental health struggles, and the constant dissonance of straddling worlds I wasn’t born into.

When my body and spirit broke under the weight of that path, I felt God calling me to step into something new. Walking away from law to start Barrier Breakers® wasn’t just a career pivot — it was an act of obedience. Through this nonprofit, I’ve helped thousands of students access higher education and pursue their goals, while also seeing firsthand how nontraditional pathways can produce extraordinary talent.

At the same time, my seminary training and ongoing PhD research in Christian leadership and spiritual formation have deepened my conviction: real mobility isn’t a straight line, and it isn’t something we achieve alone. It takes asking for help, embracing limitations, and redefining success beyond titles and checklists.

That’s why I speak now: to help students and leaders understand that their path to success requires asking for help, creating meaningful mentors, and networking purposefully. These tools will help even those without a traditional roadmap navigate pathways to success.

Book to Speak

For Individuals

Courses

These practical, heart-centered classes guide you through the inner and outer work of growth — whether you’re redefining success, navigating a nontraditional path, or ready to live with more faith, clarity, and purpose.

Coaching

Personalized guidance for those at a crossroads. In coaching, I walk alongside you to uncover resilience, embrace faith, and chart a path forward when the roadmap isn’t clear.

For Schools and Organizations

Keynotes

Today’s students are under more pressure than ever. My campus keynotes empower them to ask for help, embrace community, and redefine success — giving schools the tools to foster belonging, resilience, and student retention.

Workshops

Mentorship and networking are more than buzzwords — they’re essential skills that students often struggle to put into practice. My workshops break these concepts down into real-world tools and actionable steps, helping students learn how to ask for help, build networks, and find mentors. Perfect for student leadership conferences, affinity groups, orientation week, and student disability programming.

Book Sydney on Your College Campus!

I am a nationally and internationally recognized speaker who champions access to education, first-generation student success, and the power of mentorship and community. Through storytelling and practical takeaways, I help students and educators build cultures of belonging grounded in resilience and authentic connection.

As the founder of Barrier Breakers®, I have impacted more than 7,000 students nationwide, equipping them to thrive on their paths to higher education and beyond. My viral TEDx Talk — viewed over 200,000 times — showcases my signature blend of vulnerability, inspiration, and actionable tools that leave audiences both moved and empowered.

Book Sydney for Your Campus!

Signature Speaking Topics

Topics That Resonate

  • Asking for Help & Building Support Systems

  • Networking & Mentorship (Finding and Keeping Mentors)

  • Confidence and Self-Leadership

  • Overcoming Failure

  • Managing Burnout & Prioritizing Wellness

  • Navigating Imposter Syndrome

  • Redefining Success on Your Own Terms

  • Balancing Ambition and Rest

  • Thriving with Chronic Illness or Invisible Disabilities

  • Turning Pressure into Purpose

  • The Power of Community for First-Gen and Underrepresented Students

Every keynote and workshop is crafted to meet students where they are — equipping them with the confidence, clarity, and community they need to succeed.

Perfect For:
Orientation • First-Gen Week/Month • Wellness Week • Student Leadership Retreats • Women’s History Month • Black History Month • Disability Awareness Programming • Career Readiness Week • Resilience or Retention Series • Commencement & Senior Week • DEI or Belonging Initiatives

  • Sydney, words can’t describe the depth of gratitude I have for the knowledge, kindness, and authenticity you shared with us. I can wholeheartedly say that you have made this experience such a blessing. Thank you for standing in your empowerment and being such a wonderful example of who we’re trying to be. You are the goodness of the world.”

    Juliana, student at Ohio Wesleyan

  • “Thank you so much for joining us and sharing your story! Your work supporting and uplifting students from all backgrounds is inspiring, and we’re so grateful for the insights and advice you shared. We’re excited to take your messages forward and make an impact in our own ways.”

    Emily, student at Princeton University

  • “Sydney, you have blessed our lives with your wisdom, experience, and vulnerability. So many things you have told us have been infinitely insightful and will change how I live my life forever.”

    Ruby, student at University of Idaho

  • “Dear Sydney, I didn’t think it would be possible for me to come to this 3-day conference and learn so much, and you are a huge reason for this. You have so much incredible experience and wisdom, along with genuine encouragement and the true definition of empowering leadership. Thank you for changing my life (quite literally)”

    Manya, student at Chapman University

  • “It was so wonderful to hear your testimony! It was super affirming, especially as a first-generation low-income Jamaican student. It’s amazing to see a fellow Black woman succeeding as an entrepreneur, child of God, and overall professional!”

    Gabby, student at Princeton University

Interactive Workshops That Build Real Skills

Popular Workshops

  • The Ask: How to Reach Out for Help (Without Feeling Awkward)
    Practical scripts, mindset shifts, and live examples that make asking for help approachable — not intimidating.

  • Mentorship Mapping: Finding and Nurturing Your Network
    Students leave with a personal mentorship map and strategies for connecting authentically with professors, professionals, and peers.

  • Confidence to Lead: Stepping Into Your Voice
    Tools for overcoming imposter syndrome and showing up as a grounded, courageous leader.

  • Resilience and Rest: Managing Burnout and Boundaries
    Techniques for identifying early signs of burnout, setting sustainable rhythms, and honoring your capacity.

  • Turning Failure into Growth
    Activities that help students reframe mistakes as stepping stones — and share those lessons to uplift others.

My workshops move students from inspiration to implementation. Through guided reflection, role-play, and practical exercises, students gain tangible tools to seek mentorship, ask for help confidently, and build networks that last.

Ideal for:

Student Leadership Conferences • Affinity Groups • Disability Services Programming • Retention & Belonging Initiatives • Career Readiness Week

Book a Workshop

Keynotes that Inspire the Why

Popular Keynotes

  • You Don’t Have to Do It Alone: Redefining Resilience
    A transformative message about shifting from self-reliance to community strength — reminding students that success doesn’t have to come at the cost of their well-being.

  • The Lie of Going It Alone
    An honest look at how perfectionism, pressure, and performance culture keep us from asking for help — and how to find freedom through vulnerability.

  • Thriving Without a Roadmap
    Perfect for first-generation and nontraditional students, this keynote equips attendees to navigate uncertainty and chart career paths that honor their values.

  • Strong Enough to Rest
    For students and staff battling burnout or chronic stress, this talk offers permission to slow down, listen to your limits, and find strength in stillness.

My keynotes weave storytelling, vulnerability, and humor into powerful messages that remind students they’re not alone in their journey. I challenge traditional ideas of success and resilience, helping audiences embrace community, ask for help, and thrive authentically.

Ideal for:

Orientation • First-Gen Week • Wellness Week • Student Success Programs • Women’s History Month • Senior Week • Commencement • Career Services

Book a Kenote

Press

My work has been featured by leading organizations and platforms committed to education, leadership, and impact.

  • Forbes

  • The MoCo Show

  • Headspring Financial Times

  • Forbes

Past Speaking Events

  • Gaithersburg High School Commencement

  • Clarksburg High School Commencement

  • Clarksburg High School Advanced Placement Power Scholars

  • Princeton University, Career Services

  • Princeton University, Entrepreneurship Club

  • Princeton Prize in Race Relations

  • Stanford Neurodiversity Summit

  • American University

  • George Washington University

  • St. John’s University

  • Yale Law School

  • MIT Generative AI Summit

  • Miami-Dade College

  • Princeton University Female Founded Conference

  • Indiana University

  • University of California, Irvine, Division of Continuing Education

  • Marion P. Thomas Charter High School

  • Tennessee State University

  • Harvard Alumni for Black
    Advancement

  • Rowan College at Burlington
    County

  • Marymount Manhattan
    College

  • The Independent Educational Consultants Association

  • National Association for Law Placement

  • The Equity Summit

  • Greater Houston Women’s Chamber of Commerce

  • Northeast Association of Pre-Law Advisors

  • National Black Pre-Law
    Conference

  • Break into Law Conference

  • Students of Color for College
    Conference

  • Kappa Alpha Theta Emerging
    Leaders Institute

  • Halcyon Opportunity
    Fellowship

  • TEDx Asbury Park

  • Mt. Calvary Baptist Church
    HBCU College Fair

  • Montgomery County
    Women’s Bar Association

  • Innovative Educators Summit

  • Association for the Promotion of Campus Activities (APCA) Regional South Conference

DIG DEEPER

Free Tools to Grow in Purpose — Personally, Professionally, and Spiritually

Whether you’re focused on your career, your confidence, or your calling, these resources are here to help you grow from the inside out. Dive deeper into the themes that fuel lasting change and help you move forward with clarity and courage.

  • Build confidence through faith-rooted declarations. Download Here

  • Learn the basics of mentorship to help you strengthen your personal and professional journey. Download Here.

  • 5-page guided journal designed for the strong ones who are tired of carrying it all alone. Download Here.

  • This guide will help you understand that the power to define yourself lies within you. Exlore identity work and mindset reset around hustle, shame, and false success. Download Here.