MEET
Sheila Maloney
Founder of Sheila Maloney Connections
Facilitator • Coach • Author • Advocate • Mediator
Sheila Maloney’s career has centered on one powerful belief: relationships are the new wealth.
Through her company, Sheila Maloney Connections, she helps individuals and organizations build, nurture, and repair the relationships that matter most—whether at work, across cultures, or in their personal lives.
WORKPLACE CONNECTIONS
As an expert in negotiation, mediation, conflict resolution and organizational decision-making, Sheila brings decades of experience to her trainings, facilitations, and retreats. She has served as an Administrative Law Judge, Chief Hearing Officer for the City of Chicago Board of Human Resources, and the Assistant Director for the Center on Dispute Resolution at Northwestern University School of Law. A certified mediator since 2004, Sheila has worked with law firms, nonprofits, and corporations across the country to deliver dynamic workshops on negotiation, mediation, creative problem-solving, and inclusive communication.
Her passion for justice extends to the next generation of leaders: Sheila is a founding board member of Legal Prep Charter Academy and the creator of Chicago LegalTrek, a pioneering diversity pipeline program that prepares students from underrepresented backgrounds to thrive in the legal field. Sheila is the author of “The American Bar Association Guide to Resolving Your Dispute Inside and Outside the Courtroom.”
PERSONAL CONNECTIONS
Finding the right partner isn’t easy — especially if you’re successful in many areas of life but still searching for a sustainable, healthy, long-term relationship. That’s where I come in.
Through boutique matchmaking, personalized coaching, and retreats, I help you cut through the noise of modern dating and connect with successful professionals who are truly aligned with their values. I’ve created Real Love Blueprint 42 to guide people toward relationships built on authenticity, respect, and shared goals.
Whether you’re ready to meet your match, improve your dating approach, or gain clarity about what kind of relationship will bring lasting happiness, I bring warmth, insight, and years of experience to help you get there.
CULTURAL CONNECTIONS
Sheila is the Director of The Brazilian Blueprint - Intercultural Learning Lab at Stories Change Power.
As U.S. Americans, we find ourselves in a deeply unsettling moment in our 249-year-old country. The threat of authoritarianism feels closer and more familiar than ever before. We have long imagined ourselves as a beacon of democracy, yet now face institutional breakdown, polarization, and public distrust from within.
Many look to historical comparisons, particularly the rise of fascism in 1930s Germany. But these analogies, while important, offer only partial relevance. Germany is smaller than Texas, and its historical, social, and political contexts differ widely from ours.
Brazil, by contrast, offers a more resonant, relevant, and underappreciated model. It is the second-largest multiracial democracy in the world. Like the U.S., Brazil is a federation of diverse, independent states. It bears the legacy of slavery and colonization. But unlike the U.S., Brazil has rebuilt its democracy within living memory—emerging from dictatorship in the 1980s with a new constitution designed to fortify democratic institutions.
The Brazilian Blueprint centers Brazil as a democratic peer, not a case study.
The Brazilian Blueprint is very personal for Sheila. She was born in São Paulo during Brazil's dictatorship, which her family fled. She is bicultural, bilingual and feels very much a part of both countries. In 2018–2019, Sheila and her family spent a transformative “Family Gap Year” living in Vitória, Brazil. Her bestselling memoir, Family Gap Year: How We Moved to Brazil, Dropped Our Overscheduled Lives, and Created a Sustainable, Happy Future for Our Family, chronicles this experience and has inspired many to rethink success, time, and connections.
