Parent & Family
EDUCATION SERIES
Workshops & Resources to Help You Make Informed Choices on Your Student’s Education
Cheshire Academy provides several complimentary resources for current parents and guardians hoping to find answers and guidance on education and financial considerations and build strong school-home connections. Topics include:
- School Readiness
- Screen/Life Balance
- AI & Protecting Your Child
- College Financial Aid & Scholarships
- Healthy Boundaries & Consent
- College Loans
ISACS PARENT SERIES
A year-long program offering six exceptional webinars designed for independent school parents & caregivers in all stages of their children's growth.
The ISACS Parent Series is a year-long program of six evening conversations with some of the most respected voices in education, child development, and parenting. Each session is a one-hour webinar held in the evening over Zoom. Every session is recorded, so you can watch live, catch up later, or revisit a conversation whenever you need it.
The 2026-27 Series
School Readiness: The Skills Behind “Doing School”
with Sarah Ward, executive-function expert
Tuesday, September 29, 2026, 7:30 p.m. ET
Planners, folders, and checklists only work when the skills beneath them are in place. Sarah Ward moves past the tools to the executive-function skills — working memory, time awareness, task initiation, and organization — that students need to get out the door with their materials, record and finish homework, and follow through on their own. Expect practical strategies for starting the year strong.
Most helpful for: families with children in grades 3–12
The Power of Beliefs
with Shawn Achor, positive-psychology researcher and New York Times best-selling author
Tuesday, December 1, 2026, 7:30 p.m. ET
What a child believes about themselves and their world shapes what they see as possible. Drawing on research from more than 50 countries, Shawn Achor shares seven core beliefs — among them “I matter” and “I have something to give” — that predict resilience, happiness, and long-term success, along with concrete ways parents can help strengthen them, even amid the pull of social media and technology.
Most helpful for: all parents and caregivers
Screen/Life Balance: A Family Guide to Tech & Kids
with Catherine Price, science journalist and best-selling author
Wednesday, January 13, 2027, 7:30 p.m. ET
What if the battle over screen time could become a conversation instead? Catherine Price offers a hopeful, practical approach to technology at home — how to set healthier boundaries, encourage kids to delay smartphones and social media, and think through newer questions around AI and chatbots — so families spend less time fighting about devices and more time actually living.
Most helpful for: especially helpful for families with children under 13
Protecting Your Child in the Age of Deepfakes
with Evan Harris, expert on emerging AI risks in schools
Tuesday, February 9, 2027, 7:30 p.m. ET
AI-generated images, scams, and manipulated media are turning up in the apps and games children use every day. In plain language, Evan Harris explains what these tools can do, where kids are most exposed, and how to respond — and makes the case that the single most protective thing a parent can do is make sure their child knows they can come to them without fear of judgment.
Most helpful for: families with children in grades 4–12
How Temperament Shapes Who We Become
with Aliza Pressman, developmental psychologist and host of the Raising Good Humans podcast
Thursday, April 8, 2027, 7:30 p.m. ET
Every child is wired to experience the world a little differently — some feel everything deeply, others seem unfazed, and most fall somewhere in between. Aliza Pressman offers a science-backed lens for understanding your child’s temperament and knowing which stresses build resilience, which call for support, and which need protection — so children feel seen for who they truly are.
Most helpful for: all parents and caregivers
The Power of One
with John O’Leary, best-selling author and speaker
Tuesday, May 4, 2027, 7:30 p.m. ET
A close to the year that no one forgets. Burned over 100% of his body at age nine and given little chance of survival, John O’Leary tells an unforgettable story — really a story about the people who showed up for him — about gratitude, courage, and the truth that one person can profoundly change another’s life. A moving reminder that our small, everyday moments of connection with our children matter more than we know.
Most helpful for: all parents and caregivers
QUESTIONS?
Do you want to know more about the ISACS Parent Education Series partnership with Cheshire Academy? Contact Sarah LeBlond at communications@cheshireacademy.org.
COLLEGE FUNDING WORKSHOPS
The Financial Literacy Series: Funding a College Education with Confidence
This program offers guidance with an increasingly challenging part of the college process: creating a plan to fund college.
In addition to cost, the financial aid landscape has changed and colleges are reassessing how they provide assistance. Paul Martin, founder of College Money Method, provides expert guidance for families, building an earlier understanding of how schools award assistance, making them better equipped to make wise decisions.
The series is built on six hour-long workshops, followed by 30 minutes of Q&A. This second component allows for parents to hear how other families are navigating the same challenges and provides expert guidance in real time.
The program also includes a School Resources Center, a dedicated hub of college funding and financial aid information and resources prepared specifically for Cheshire Academy families.
A registration link will be sent directly to parents in advance of each event.
The 2026-27 Workshop Series
Applying for Financial Aid and Scholarships in Senior Year
Monday October 5, 2026, 7 p.m. ET
A guide through the senior-year financial aid application process, including how to research and apply for merit aid
Most helpful for: recommended for 12th grade families
Loans and Borrowing for Your College Investment
Wednesday, November 11, 2026, 7 p.m. ET
How to determine the right amount to borrow and evaluate lending options
Most helpful for: 11th and 12th grade families
Navigating Today’s College Pricing and Financial Aid
Monday, January 25, 2027, 7 p.m. ET
An overview of how colleges price education and award financial assistance today
Most helpful for: recommended for 9th and 10th grade families
Understanding How to Qualify for Financial Aid and Scholarships
Tuesday, February 16, 2027, 7 p.m. ET
An inside look at the financial and academic factors colleges use to determine your need-based aid and merit scholarships
Most helpful for: 10th grade
Comparing Your Awards and Strategies for Appeals
Tuesday, March 30, 2027, 7 p.m. ET
A framework for comparing aid offers and knowing when and how to appeal for more
Most helpful for: 12th grade families
Evaluating Schools for Award Opportunities and Financial Fit
Tuesday, April 20, 2027, 7 p.m. ET
The tools and resources to evaluate how generous colleges will be with aid and calculate your expected costs
Most helpful for: 11th grade families
PARENT TALK WITH THE CENTER FOR RESPECT
"Creating a Safe, Respectful Community: What Families Need to Know"
Oct. 12
6-7 p.m. | Richardson Lecture Hall
Cheshire Academy is hosting Hall of Fame speaker and author Mike Domitrz, founder of The Center for Respect, for a program built specifically for parents and caregivers. In one hour, you’ll walk away with practical, real-world tools for talking with your teen about respect, consent, boundaries, dating, and intimacy, and for helping them make safer decisions, without the awkwardness these conversations usually carry.
Mike has spent more than two decades helping schools and families build cultures where respect and safety are part of everyday life. The presentation is approachable and responsive to your family’s own questions, not a one-size-fits-all lecture. He has been featured as an expert voice in The Wall Street Journal and on Dateline NBC’s “My Kid Would Never Do That” series.
This program follows an interactive assembly for CA students earlier that same day, so the conversation your teen starts in the Dining Commons can continue at your own kitchen table.
Refreshments will be provided.
Our School Resource Center
A huge asset of the College Money Method program is access to a dedicated hub of college funding and financial aid information and resources specifically for Cheshire Academy families. Our School Resource Center gives you multiple ways to engage with the materials and resources to create your college funding plan.
- Learn by Grade organizes all program content by your student’s grade and specific topics that matter most at each stage
- Attend a Workshop hosts all workshops with chapter-marked recordings, key learnings, and resources organized by the specific action items from each session; You can prepare, review, or catch up on your own time
- Find a Resource is a searchable, filterable collection of calculators, guides, and worksheets, built and curated and updated regularly to reflect changes in financial aid policies and scholarship opportunities; Search by keyword or filter by grade or category to easily find exactly what you need
Check out this 4-minute video tour.
You can access our School Resource Center and register for workshops without creating an account. A school password will be emailed to all parents.
QUESTIONS?
Do you want to know more about the College Money Method workshop series partnership with Cheshire Academy? Contact Madeleine Bergstrom, Dean of College Counseling, at 203-439-7550 or madeleine.bergstrom@cheshireacademy.org.
