Winning Ways is a 501(c)3 non-profit organization that provides access to vital resources to empower our community

Building Stronger Communities Through Connection and Growth:

At Winning Ways, we transform lives through The Winning Circle Series™ — a trauma-informed initiative offering financial literacy, digital skills, employment training, and expressive arts. Our core programs include Spit and Paint™, Money Talk™, Empower Your Employment™, and Basic Needs Support — all designed to foster healing, build confidence, and support long-term success.

Whether you're rebuilding after hardship or looking to grow, we provide the tools to take your next step — with dignity, creativity, and community.

More About Us

Empowering change in Connecticut

Transform lives with Winning Ways Inc, supporting successful reentry and recovery journeys in Connecticut communities.

Winning Ways Inc. empowers underserved communities across Connecticut through trauma-informed, community-driven programs that promote healing, resilience, and growth. We connect individuals and families to vital resources and peer support, creating lasting pathways to personal and professional success

Data-Driven Change

Impact in Connecticut: See the Stats

Empowering lives in Connecticut: Explore how our programs foster recovery and reduce recidivism through comprehensive support.

Healing & Empowerment Programs

Our Healing & Empowerment Programs support individuals impacted by incarceration, trauma, and recovery through creative and therapeutic approaches. Services include Spit and Paint™, peer-led support groups, and family healing resources that promote emotional wellness, self-expression, and long-term healing.

Financial Empowerment & Stability

The Financial Empowerment & Stability initiative equips participants with tools to take control of their financial futures. Through Money Talk™, one-on-one counseling, and recovery-focused financial education, individuals gain critical knowledge in budgeting, banking access, and long-term wealth-building strategies.

Employment & Educational Access

Our Employment & Educational Access programming prepares individuals for success through Empower Your Employment™, digital literacy, and career development workshops. These services help participants build confidence, learn marketable skills, and access meaningful employment opportunities.

Community Connection & Navigation

The Community Connection & Navigation program provides essential support with basic needs, housing referrals, reentry resources, and family stabilization. Participants receive guidance navigating systems and services to help them reintegrate, restore relationships, and thrive within their communities.

Bridging Recovery

The Winning Circle Series™ Curriculum

Empowering Futures Through Financial Confidence, Career Readiness, and Healing-Centered Growth.

SPIT AND PAINT™

Harnessing creative expression as a tool for healing and personal growth. Fostering emotional wellness and resilience through trauma-informed expressive arts workshops.

EMPOWER YOUR EMPLOYMENT™

Career development and job readiness rooted in lived experience.
Offering coaching, resume building, and vocational training to help individuals reenter the workforce with confidence.

MONEY TALK™ & FINANCIAL COUNSELING

Partnered with the Yale PRCH Recovery Finance Project.
Offering group-based financial discussions and one-on-one counseling to build financial confidence and stability for individuals in recovery and reentry.

BASIC NEEDS PROGRAM

Meeting immediate needs to support long-term success.
Distributing essential items such as food, hygiene supplies, and clothing to promote dignity and stability.

Federal Work Study FWS program documents and pen.

FEDERAL WORK STUDY SUPPORT

Supporting students in recovery and reentry with educational employment opportunities.
Partnering with local colleges to connect students with federally funded work-study positions