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, 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 a nonprofit wasn’t just a career pivot — it was an act of obedience. I discovered that 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 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.
For Organizations and Companies
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 starting an edtech company that gained global recognition in the venture capital space, to navigating philanthropy and nonprofit leadership, to pivoting between careers while living with chronic illness. 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. Instead of filtering out candidates with “gaps” or unconventional experiences, I show how those very pathways — caregiving, freelance work, side hustles, community leadership, or nontraditional degrees — can be assets that strengthen your team and culture.
TEDx: First-Generation Graduates Drive Business Success
With over 160,000 views, this talk centers on the experiences and power of first-generation college students to drive business success and innovation and tangible ways we can support first-generation college students in their professional careers.
Work With Me
Speaking
I bring powerful storytelling, lived experience, and actionable wisdom to every stage — from corporate retreats to college campuses. My talks invite women, first-gen professionals, and emerging leaders to rise with faith, purpose, and freedom.
Courses
These practical, heart-centered classes walk you through the inner and outer work of growth — whether you’re rebuilding confidence, navigating a career pivot, or ready to live with more peace, clarity, and purpose.
Coaching
This is for the woman who’s accomplished on paper but quietly wondering, what now? Through private, high-touch coaching, I help you clarify what’s next — not just in your career, but in your life, leadership, and walk with God.
Workshops
Whether you’re leading a team or launching your future, these transformative workshops create space for reflection, resilience, and reinvention. With a focus on confidence, identity, and redefining success, each session helps participants grow with clarity, courage, and purpose.
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.
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Build confidence through faith-rooted declarations. Download Here
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Learn the basics of mentorship to help you strengthen your personal and professional journey. Download Here.
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5-page guided journal designed for the strong ones who are tired of carrying it all alone. Download Here.
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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.
Engaging Keynotes for a Variety of Audiences
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Resilience & Grit: Thriving Through Challenges
Fueled by my life experiences, challenges, and triumphs, I share personal anecdotes and practical tools to develop a resilient mindset that fuels success in academics and beyond; strategies to overcome imposter syndrome, financial stress, and career uncertainty; and methods to reframe failure as the path to longterm grit and success.
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Social Entrepreneurship: Turning Passion Into Impact
I have launched two successful social enterprises—one in education tech and another in higher education access— without coming from a wealthy background or having startup funding. In this talk I share the real behind-the-scenes of what it takes to build a business that makes an impact and pays the bills.
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Charting Your Own Path: Creating a Career That Fits You
I did everything “right.” I attended Princeton and graduated from Harvard Law—only to realize that the traditional career path wasn’t for me. I reinvented myself, shifting from law to educational entrepreneurship, proving that success doesn’t have to be linear. This talk is for students who feel lost or unsure about their next steps.
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Leadership, Networking, and Mentorship Strategies for Young Adults
I am passionate about helping. young adults feel confident in their leadership skills, redefine leadership and success for themselves, and realize that the key to success involves growing their support circle through networking and mentorship. As a first-generation student, my success came in large part because of the village that supported me and I’m thrilled to demystify networking for the next generation.
Supporting First-Generation Students Through Barrier Breakers®
As a woman of color who navigated both Princeton and Harvard, I intimately understand the obstacles faced by first-generation and marginalized students in achieving educational and career success. This inspired me to found Barrier Breakers, an initiative dedicated to dismantling those very obstacles. Through mentorship, access to vital resources, and strong advocacy, we empower students and professionals to overcome systemic barriers and achieve their full potential. Join us as we build pathways to success that are inclusive and equitable.
“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 G.
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