Vanessa Ann Rich

1951 - 2015


2020 e-VRLE! 

Join us for the

"Virtual Vanessa Rich Summer Leadership Retreat" 




e-VRLE Dates
Tuesday, July 21,  2020 
Thursday, July 23, 2020 

e-VRLE Times: 

Tuesday from 1:30 - 3:30pm 

Wednesday rom 9:30 - 11:30am and 1:30 - 3:30pm 

Wednesday Evening: Virtual Happy Hour from 5:00-6:00pm 

Thursday from 9:30 - 11:30am



 Zoom links will be emailed to participants after registering.



$195.00 per person for IHSA members only

$345.00 per person non members

Registration Fee Includes:

three days of training, kindle download of e-book to go along with the phase you choose, electronic resources/handouts from the phase you choose & FUN & EXCITING virtual happy hour on Wednesday night! 



Michelle Iocca
Illinois Head Start Association


Meet Your Leadership Guides: 

Phase One: Yolanda Winfrey

Yolanda Winfrey, a past Head Start Child and a past Head Start Parent (her son Douglas is a Head Start Alumni as well) has worked in the early childhood field for over 20 years. She has held various positions including Head Start/Early Childhood Director and Chief Talent and Organizational Development Officer.  Yolanda has a Master’s Degree in Education (Early Childhood) from Concordia University Wisconsin, a Master’s Degree in Social Work from the University of Wisconsin-Madison, and an Advanced Practice Social Work Certification from the State of Wisconsin. In 2013, Yolanda received an award from the Milwaukee Community Journal for her Contributions Towards Making Our Community Stronger (in the area of Education). Yolanda combines her educational background, knowledge and skills with that of her experiences as a past Head Start Child and a past Head Start Parent to bring a unique perspective and approach to her work in this field. Yolanda is experienced in systems development; management systems, policies and implementation practices; providing training and technical assistance to administrators, board members, managers, staff, and programs in program design and service delivery; grant writing; and customized consulting services. The perspective Yolanda provides has led to numerous, positive and innovative approaches that has helped her program and others develop and ignite the passion in their work to improve outcomes for children, families, staff, and organizations.

Phase Two: Dr. Tim Nolan 

Dr. Nolan is about to complete his 50th year as a Head Start Executive Director serving National Centers for Learning Excellence, Inc. He has been a consultant to business organizations for over 46 years. He is author or coauthor of 47 books. He is known across the Head Start world for his work on Compassionate Partnering™. His Applied Strategic Planning™ model has been used by thousands of organizations across the English-speaking world, including the FBI, the U.S. Treasury, Allied Van Lines, the Los Angeles public library and over 470 Head Start agencies. A psychologist by training, Tim is CEO of Innovative Outcomes, Inc. and the Center for Leadership Excellence, Inc.  He has been a consultant for 46 years and has trained over 3,100 consultants so far in his career. One of his consulting specialties is individual and organizational innovation, having done his doctoral work in creativity and thinking skills. Tim has enthusiastically provided leadership for numerous special projects on behalf of NHSA over the last several years. He is President of the Wisconsin Head Start Association and is highly involved with the Region V Head Start Association and its Parent Gauge™ project. His professional mission is to shape the future, one child and one family at a time! Tim absolutely loves Head Start!

Event Contact

Michelle Iocca
Illinois Head Start Association

Leading and Thriving in the New Head Start.


As we approach the 5th Annual Vanessa Rich Leadership Experience, we must stop and think how differently things are today compared to five years ago. We are living in especially troublesome times - sandwiched between the current public health threat of COVID-19 and the longtime reality of police brutality and racism. IHSA created this leadership opportunity to continue the legacy and passion of Vanessa Rich. To honor Vanessa's legacy in 2020, we know that she was a brilliant and formidable leader, a fearless advocate and a kind, devoted friend and mother. We know Vanessa was extremely passionate around equality and inclusion. She not only worried about the risks to her own children but advocated and fought for all Black and Brown children. We know Vanessa was vocal and that there wasn’t a shy bone in her body about expressing and fighting for the things she believed in. We know, right now, she wouldn’t be watching the current world from afar. She would be "all the way in"...advocating, marching, protesting, and giving voice to the grief and anger that generations of black Americans have suffered. She wouldn’t stop until every Black person has the social, economic, and political power to thrive. We know, in more ways than many, that Vanessa’s legacy was being a true leader. Being true to Vanessa’s spirit and continuing a legacy that would make her proud means incorporating and addressing these relevant and hard issues into the Vanessa Rich Leadership Experience. Let’s come together to discuss the current environment and how leading and thriving in the new Head Start starts with YOU! Redesigned with the current lens, join us for the three day virtual Vanessa Rich Leadership Experience that will allow you the opportunity to reconnect with yourself, gain a greater knowledge of who you are and where your strengths and challenges lie during this changing and challenging time, finding a voice that can carry your agency through uncertaintly and lead in ambiguity and enhance and refine your skills and competancies to create greater inclusion for all children, families, and staff. 



Choose Your Experience: Phase One or Phase Two!

There are two phases of this leadership retreat. BOTH PHASES ARE COMPLETELY DIFFERENT THAN PAST YEARS! This is your experience and it is completely up to you if you would like to attend Phase One or Phase Two. Please select one choice when registering. 


Phase 1:

Purposeful Action, Passion and Spirit in Uncertain Times

Welcome. My name is Yolanda Winfrey and I have the distinct honor and privilege of being your Phase One Leadership Guide.  Purpose is something done with intention.  It is usually fueled by our passion which are two concepts synonymous with the late, great Ms. Vanessa Rich.  This year, as we work to define (or reshape) our purpose, we will also focus on leadership reflections that include leading with issues and concerns surrounding COVID-19, racism, Black Lives Matter, and social justice.  With all that is going on surrounding these issues, how we engage and move forward is more critical now than ever.

During Phase One of the retreat, we will engage in rich discussion and reflections regarding living our lives on purpose.  In doing so, we hope you gain further understanding in defining (or re-defining) who you are, your values, and your focus.    Our goal is for you to leave with insights that aid in clarifying your  purpose, pushing past your fears, and living your passion thus enabling you to be the best leader you can be while having a positive impact on the lives of others. 

For this year’s retreat, I have chosen the book, “Purposeful Hustle” by Deanna Singh.  This book is a mix of stories regarding the author’s purposeful journey and a “handbook” on how one can live in their purpose.  It includes very thoughtful reflection exercises and activities which are woven throughout the chapters. I am looking forward to our time together. 




Phase Two:

Finding the Oasis of Peace in the Swirl of a Hurricane


The world is in a state of fear and uncertainty right now, and it’s stressful and overwhelming for most of us. This unpredictably causes varied emotions and mind states, many of which are extremely challenging and difficult, even unbearable at times.  People are feeling fear, outrage, sadness, and confusion. How can we possibly be leaders in all the chaos and uncertainty? How?

Be the example. As a leader, you often forget that all eyes are on you. Remember this may be especially true when times get tough. Leading in difficult times requires courage, emotional intelligence and integrity. Be humble and prepared. Be resolute in pursuing the principles you believe are right, even in the face of opposition. View and treat conflicts and controversies positively. Work cooperatively, rather than coercively. Implement a culture of compassion. Reflect on your organization's mission and purpose. Your purpose, mission and values are more important than ever and should be the north star that guides your decision-making. Your actions and your organization's actions should reflect these. As leaders, we need to ask ourselves these questions. Am I defining reality and creating hope in this unprecedented environment of challenge and change? Am I helping my team become the change agents we need so we can be successful in difficult times? And do they truly know the score so they can actively engage in improving the situation? This is the kind of leadership that confirms and validates diversity and advances a culture of inclusion. This is the leadership we would see from Vanessa Rich. This leadership starts with YOU! If circumstances can't be changed then we must change our attitude toward them--we can't control the wind but we can adjust our sails. Like water in a lake, when our mind is calm and peaceful we can see the depths below, but when our mind is disturbed it's easy to get caught up in the turbulence. Beneath fear or grief there is steadiness, inner stillness, independent of the circumstances. Phase 2 of the e-VRLE to help find your oasis of peace in the swirl of a hurricane. Come find the energy, vision and tools to lead and thrive in the new Head Start. This phase will be designed around the book by author Maria Shriver, "I've Been Thinking ...: Reflections, Prayers, and Meditations for a Meaningful Life”. Phase 2 will lead your mind to awareness and action and open your heart to kindness and empathy.