DREAM BIG: Your Dreams Are Your Future

Brought to you annually by the Windward Parents Association and Windward Alumni Office, Dream Big: Your Dreams Are Your Future program began in 2011. Each year Dream Big features prominent, inspirational speakers who share their stories about overcoming obstacles and going on to achieve their dreams. The goal of the program is to engage Windward middle school students and our extended community in an encouraging, interactive event as a reminder that having a language-based learning disability need not hold anyone back from a lifetime of achievement.

Click Here to Register for the Event

Please note: The live webinar link will be sent to the email you used to register. 

NEW DATE: May 8, 2024
10:30 - 11:30 a.m.

Westchester Middle School
40 West Red Oak Lane
White Plains, NY 10604

2024 Featured Speaker: Scott Rudin '03

Scott Rudin is the Creative Director of the Ralph Lauren Agency.  In his role, Scott is responsible for all the Global Advertising at Ralph Lauren.  Scott oversees the advertising for all Ralph Lauren brands including: Purple Label, Collection, Polo (men’s, women’s, kids, baby), Lauren, Home and Fragrance.  Scott leads a large team of creatives who are responsible for delivering world class campaigns that set the image for the Ralph Lauren brand.  Prior to being the Creative Director of the Agency, Scott spent 14 years in Men’s Design. As Vice President of Concept Design and Brand Creative, Scott oversaw the seasonal conceptual direction of all Ralph Lauren Men’s clothing.  Scott has been at Ralph Lauren for 17 years.  In addition to his role as Creative Director, Scott is also an accomplished fine art photographer, and has shot several Ralph Lauren campaigns.  He has also had his work displayed in notable galleries.

Prior to joining Ralph Lauren, Scott Graduated from The George Washington University in 2007.  Scott lives in New York City with his wife Jessie and his 3 sons.  When Scott is not at work, there is nothing he loves more than being at the beach surfing with his family.

Scott attended The Windward School from grades 3-5.

Past Dream Big Featured Presenters Include:

2011 – The Kings Speech Screening
2012 – Dannel Malloy, Governor of Connecticut
2013 – Screening of The Big Picture: Rethinking Dyslexia, by James Redford
2014 - Ben Foss, Lecturer, Teacher, Founder of Headstrong Nation
2015 – Meryl Davis, Olympic Ice Dancer and Dyslexic
2016 - David Flink, CEO and Chief Empowerment Officer of Eye to Eye National
2017 – Jack Horner, Paleontologist
2018 – Meryl Davis, Olympic Ice Dancer and Dyslexic
2019 – Robert Carroll ’04, New York State Assemblymember NYC
2020 - Denis J. O’Leary, III ‘06, Senior Investment Associate at Bridgewater Associates and Member of The Windward School Board of Trustees
2021- Julie Schechter ‘06, Criminal Defense Attorney
2022- Reed Switzer, '19, Co-Founder and CEO of Hopscotch
2023 - Patrick Ewing Jr. '02



Learn More & Support Future Dream Big Programs

Michelle Spino Andruss
Alumni Relations Director