CERTIFIED LIFE COACH
SPECIALIZING IN CONFIDENCE, RELATIONSHIPS & CAREER ADVANCEMENT
Now Accepting
New Clients!
Biography
Hi there - I'm Chrislin 'Chrissy' Flanagan, Born and raised on the southside of Chicago, I'm a dedicated mother, wife, and career professional. As an Executive Director and a firm believer in Christ, I have navigated my journey with resilience and determination. Educated through the Chicago Public School system, I became a teenage mother shortly after high school, giving birth to my oldest son. Committed to providing a better life for him, I prioritized education, earning an Associate's Degree from Kennedy King Community College. My passion for advocacy led me to further my collegiate education earning a Bachelor's Degree in Criminal Justice from Chicago State University and a Master's Degree in HR Management from Roosevelt University, where I graduated Summa Cum Laude.
I'm currently pursuing a doctorate in Organizational Leadership and Adult Learning. My research explores the intersection of imposter syndrome and HEART Leadership principles to foster sustainable, human-centered organizations.
WHO IS
CHRISSY?
I have accumulated valuable career experience in customer service and management across various companies. With over a decade of experience in the FinTech industry, I've excelled in supporting global training functions both onshore and offshore. My expertise spans across classroom facilitation, remote learning, new hire and ongoing training, coaching and development, organizational strategy, and internal/external marketing. Currently, I serve as the Executive Director for Urban Alliance (UA) Chicago, a non-profit headquartered in Washington, D.C. UA is dedicated to building a diverse next-generation workforce by providing job skills training, mentoring, pre-apprenticeships, and paid internships to high school youth and young adults from underserved communities, empowering them to achieve economic independence and upward mobility.
CAREER
I am an unapologetic truth teller, published author and a Certified Life Coach specializing in Confidence, Relationships, and Career Advancement. My survival of open-heart surgery inspired the evolution of 'HEART Leadership.' I currently reside in Chicago with my husband, children, and adorable puppy. I enjoy spending my downtime with family, reading, or hunting for great deals—especially hats and home décor. I am a true fashionista who loves capturing selfies, attending plays and concerts, and exploring the city. An avid traveler, I have visited over 35 states and 15 countries.
My favorite scripture is Jeremiah 29:11, which reassures me that it is God's plan for everyone to prosper. Grace and pace!
THE
REAL
CHRISSY
CONFERENCE AND PRESENTATIONS
Flanagan, C. (2025, August). Chicago Bears 2025 Career Expo: Building Your Professional Toolkit. Lake Forest, Illinois.
Flanagan, C., O’Brien, M. (2025, June). CASASThe Workforce Development Ecosystem. Garden Grove, California.
Flanagan, C. (2025, April). Generation Wealth Conference. Chicago, Illinois.
Durojaye, A., Flanagan, C., James, L. (2023, March). Maximizing Impact Through Workforce Partnerships Panel. Presentation at the Forum on Workplace Inclusion. Minneapolis, Minnesota.
Flanagan, C. (2022, January). Working Women Matter. Presentation at Associated Bank’s Women in The Workplace Seminar. Chicago, Illinois.
HONORS & AWARDS
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2025 Black Women in Excellence (BWIE) Honoree. May 2025
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Lavizzo Elementary School: Partner of the Year, May 2023
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Roseland Community Hospital: Employee of the Year, March 2023
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Chicago 300 Black Women: Woman of The Year, February 2023
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Victory Foundation: Leadership Award, November 2022
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Avant, Trainer of the Year, December 2017
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Roosevelt University (Suma Cume Laude), May 2017