Raising Empathy: How Andi Sklar Inspires Philanthropy in the Next Generation

In a world where busyness is a badge of honor and digital distractions often dominate, Westport’s Andi Sklar has quietly built a legacy that’s anything but ordinary. Her work as a community advocate and fundraiser is well known throughout Fairfield County, but what makes her story especially compelling is the way she has seamlessly woven philanthropy into the fabric of her family life—raising not just funds, but the next generation of givers.

For Sklar, philanthropy isn't a side project or seasonal effort—it’s a way of living. From lemonade stands in her driveway to large-scale hospital initiatives, she brings her children along for the ride, teaching them that making a difference doesn’t require wealth or perfection—just intention and heart.

Modeling Service at Home

Andi Sklar’s philanthropic philosophy starts at home. Rather than waiting for the perfect time to introduce her children to giving, she integrated it into their lives from the earliest age. That mindset helped shape the creation of Angel-ade, a community lemonade stand initiative that benefitted Al’s Angels, a local nonprofit supporting families battling life-threatening illnesses. With her kids at the forefront—mixing lemonade, greeting neighbors, and collecting donations—Sklar turned a simple summer activity into a lesson in compassion.

“The idea wasn’t just to raise money,” Sklar explains. “It was to show my children that they could be part of something bigger than themselves.”

And it worked. Through these experiences, her children not only learned about the causes their mom supported, but they saw firsthand what it looks like to give time, energy, and care to others. The message was clear: philanthropy isn’t just something adults do—it’s something families can do together.

Creating Space for Conversations

One of the most powerful tools in Andi Sklar’s parenting toolkit isn’t a spreadsheet or a planner—it’s conversation. In her home, discussions about helping others are as commonplace as talking about school or sports. From explaining why their family supports breast cancer patients through PinkAid, to conversations about pediatric heart health and Long QT Syndrome through the Hearts in Harmony Foundation, Sklar never shields her children from the realities of life’s challenges—instead, she equips them to respond.

“I want my kids to grow up understanding the world is bigger than their own experience,” she says. “The goal isn’t to make them feel guilty for what they have. It’s to help them feel grateful—and to see the privilege of being able to give back.”

These conversations often lead to real action. When helping organize “Check Your Beat,” an event offering free EKGs to children, Sklar involved her family not just in setup and logistics, but in understanding why it mattered. She encouraged questions, explored their ideas, and made sure they felt like participants, not spectators.

Philanthropy as a Family Value

What sets Andi Sklar apart is how consistently she centers family in her charitable work. Whether she’s raising awareness for Connecticut Children’s Medical Center or co-hosting events for local nonprofits, her children are never far from the mission.

“We don’t separate giving from our day-to-day life,” she says. “It’s not something we turn on during the holidays or a crisis—it’s something we’re always looking for ways to do, even in small ways.”

From making cards for hospital patients to helping pack care kits for families in need, these hands-on acts have created a culture of empathy in the Sklar household. Her kids have grown up understanding that generosity isn’t just about money—it’s about presence. It’s about showing up for others, listening, and lending what you have, whether it’s your time, your talents, or your voice.

Inspiring by Example

In today’s social media-driven world, many young people grow up believing that philanthropy has to be performative—something you post about, hashtag, or brand. But Sklar offers an alternative vision: philanthropy as quiet, consistent action. And this, too, is something she teaches by example.

Her work is often done behind the scenes: coordinating vendors for events, guiding families through the donation process, working late nights on logistics. Her kids see it all. And in seeing it, they’re absorbing something powerful—that impact isn’t about attention. It’s about intention.

“Andi doesn’t do what she does for recognition,” says a longtime friend and collaborator. “She does it because it matters. And that’s the lesson her kids are learning every single day.”

A Blueprint for Future Changemakers

Andi Sklar’s approach to raising empathetic, socially conscious children offers a blueprint for other parents who want to instill those same values. Her advice? Start small, stay honest, and let your kids lead when they’re ready.

“Giving back doesn’t have to mean creating a nonprofit or leading a massive campaign,” she says. “It can be a conversation at dinner about a cause that matters to you. It can be volunteering for an hour. It can be making one donation. And when kids see you do it, they start to understand that they can too.”

As her children continue to grow, so does their confidence in their ability to help others. Whether or not they choose careers in philanthropy, Andi knows she’s laid the foundation for them to live meaningful, compassionate lives. That, she says, is the greatest legacy she could hope for.

“I want them to grow up believing they’re capable of creating good in the world—and that they have a responsibility to try,” she says. “That’s what giving is really about.”

And thanks to her example, they already are.