Sydney Montgomery

Speaker | Mentor | Entrepreneur

Redefining Success.

Expanding Upward Mobility. 

Helping students, organizations, and leaders recognize the power of nontraditional pathways 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, 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 what success means beyond titles or checklists.

That’s why I speak now: to help individuals without a roadmap navigate nontraditional pathways to success — and to guide organizations in recognizing and supporting the overlooked talent already in their midst.

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 Organizations

Corporations

Too often, organizations overlook extraordinary talent because it doesn’t fit a traditional mold. I help leaders rethink recruitment, retention, and leadership — unlocking innovation and growth by valuing the strengths of nontraditional pathways.

Colleges

Today’s students are under more pressure than ever. My campus keynotes equip them to redefine success, embrace resilience, and thrive on nontraditional pathways — giving schools the tools to support retention and student belonging..

For Colleges and Universities

Signature Keynotes

  • Resilience & Grit: Thriving Through Challenges
    Strategies for overcoming imposter syndrome, financial stress, and career uncertainty.

  • Charting Your Own Path: Creating a Career That Fits You
    Why it’s okay to pivot, change paths, and redefine success in ways that honor your story.

  • Social Entrepreneurship: Turning Passion into Impact
    Behind-the-scenes lessons from launching social enterprises without traditional funding.

  • Leadership, Networking & Mentorship Strategies
    How to build meaningful connections and find mentors who change your trajectory.

Today’s students are navigating more uncertainty than ever — rising financial stress, imposter syndrome, and the pressure to follow traditional paths that don’t always fit. My keynotes create a space for students to breathe, reframe success on their own terms, and leave with practical strategies they can apply immediately. From resilience and leadership to social entrepreneurship, I meet students where they are and show them how to thrive without a roadmap.

  • 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

For Organizations and Corporations

Keynote Topics

  • Unlocking Upward Mobility: Rethinking Nontraditional Pathways to Success
    How to see talent beyond traditional resumes and linear career paths.

  • Hiring Without a Roadmap
    Why overlooked and underestimated talent is your organization’s best asset.

  • The Hidden Strengths of Nontraditional Talent
    How resilience and adaptability fuel innovation and performance.

  • Redefining Success for Organizations
    Building cultures where underestimated talent can thrive and stay.

Rethinking Talent. Rethinking Success.

Too often, businesses and institutions overlook incredible talent because they’re working with an outdated roadmap. The assumption that success only comes from a linear career path, elite schools, or traditional resumes is costing organizations the very resilience and innovation they need most.

I know this not only from my work with Barrier Breakers®, where I’ve supported more than 7,000 students from first-generation, low-income, and nontraditional backgrounds, but also from my own journey. My path has been anything but traditional — from pivoting between careers while living with chronic illness, to starting an edtech company that gained global recognition in the venture capital space, to navigating philanthropy and nonprofit leadership. On paper, my experiences don’t form a straight line. In reality, they’ve equipped me with adaptability, creativity, and vision that a conventional career path could never have produced. That’s the perspective I bring to organizations and leaders: how to recognize, recruit, and retain underestimated talent by reframing how you evaluate potential.

  • Recruitment

    Learn how to stop filtering out candidates with “gaps” or unconventional experiences, and spot strengths in nontraditional resumes. Caregiving, freelance work, side hustles, community leadership, or nontraditional degrees can be assets that strengthen your team and culture.

  • Retention & Culture

    Discover how to build systems where underestimated talent not only stays but thrives. From mentorship pipelines to equitable promotion practices, I help organizations create cultures that recognize contribution, reduce attrition, and unlock the full potential of employees from nontraditional pathways.

  • Leadership & Investment

    Explore why backing nontraditional founders, leaders, and career paths creates stronger, more sustainable returns. By reframing risk and valuing resilience, organizations and investors can tap into innovative solutions and long-term vision that traditional markers often overlook.

Book Now

Press

With over 170,000 views, First-Generation Graduates Drive Business Success centers on the experiences and power of first-generation college students to drive business success and innovation, and tangible ways to support them in their professional careers.

  • Forbes

  • The MoCo Show

  • Headspring Financial Times

  • Forbes

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.