Pie in the Sky: Why You Should Join In

Every fall, hundreds of people across Greater Boston reach out to friends, family, and colleagues with a special message. “There’s this amazing nonprofit called Community Servings. For just $35, you can provide an entire week of medically tailored meals to a neighbor in need – and get a delicious Thanksgiving pie for your generosity.”

Last year alone, these personal asks – shared through texts, social media, and conversation — raised over $1 million in just eight weeks. Those funds supported, as they do every year, Community Servings’ medically tailored meal program, fueling meal deliveries to individuals and families who need access to healthy nutrition and are living with critical and chronic illnesses, such as cancer, diabetes, HIV/AIDS, and others.

Pie in the Sky, our annual peer-to-peer fundraiser, thrives because of the volunteered time and passion of the entire community. Literally. When you ask people why they participate year after year, the answers are often deeply personal. For many, it’s a way of connecting with neighbors on a deeper level. It’s a way of doing something positive. It’s a way of changing the world for the better. Pie in the Sky has a low barrier of entry, but the rewards, for volunteers and for Community Servings, are extraordinary.

Sarah

Sarah Clausen of West Roxbury works as a realtor for Coldwell Banker. She first heard of Community Servings from her supervisor, a long-time Pie in the Sky supporter. With this intro, she gathered her friends and together they volunteered on-site in Boston, preparing and packaging meals. The effect on Sarah was immediate. “I feel so appreciated in the kitchen. I meet all sorts of different people. The staff, everyone. It’s just a feel-good experience. You feel like you’re making a difference. It makes you want to work for Community Servings.”

Sarah Clausen (center) kicks off Pie with fellow volunteer fundraisers

And work she does. Every fall for 10 years now, Sarah reaches out to friends and colleagues, tells them about the agency, and asks them to donate to Pie in the Sky. While she recognizes the science of the medically tailored meal intervention, Sarah keeps her pitch simple: It’s all about “compassionately providing care to those who are going through a tough period and need nutritional and emotional support.” She saw this first-hand when she volunteered a few years ago as a delivery driver. It was the first time Sarah met Community Servings’ clients. And it was unforgettable. “It felt like Community Servings took care of them, gave them dignity. It really was eye-opening in many different ways and really inspired me to do whatever I can to help.” She saw how significantly people in her community needed the support. Many had difficulty moving and couldn’t meet Sarah at the door. Many lived right in Sarah’s neighborhood. “Community Servings gives you a real connection with the community that needs the support. I think that’s kind of unique.”

Regan

The uniqueness is by design. A tremendous amount of labor goes into the Community Servings experience — the aesthetics of the experience we provide volunteers, event guests, and clients. Few people know that better than Regan Winkler of Arlington, who has partnered with us since the early years. “It was so easy to be part of that community and be a cheerleader,” Regan says, remembering first working with now Chief Development Officer Tim Leahy and Chief Executive Officer David B. Waters. “I admired how clever they were with finding that motivating factor for the volunteers, making it simple, clean, and clear, and also giving their donors an experience, something special, something they could be proud of and talk about.”

“And the mission made so much sense to me,” Regan adds, “the fact that food is nourishment and health.” Once you’ve been involved once, “you’re hooked. You can’t walk away from that experience and not see how you can continue to help.” That hook, in Regan’s opinion, is “the desire to do something helpful in this world. That’s something people are searching for in general. You can help out 50 people if you sell 50 pies. The bite-size commitment of it is a great way in.”

Jacob

Jacob Miller of North Cambridge has long been a fan of Jacques Pepin, watching the celebrity chef on public television and following his foundation on social media. When Pepin was recently in Boston, visiting Community Servings’ Teaching Kitchen program, Jacob took notice. “What is this place?” he wondered. “Then I remembered: The day before I had listened to an hour-long podcast on medically tailored meals.” It was, Jacob recalls, a sign from the universe. He had to get involved.

He volunteered with Community Servings Young Leaders (CSYL), coming on-site to package meals. “I was struck by how serious everybody was about doing things the right way,” Jacob remembers. “I was very impressed with the way the whole operation worked. It really struck me how good the process is and how precise and how much people care who work there in the kitchen.”

While not a fundraiser by personality or training, Jacob took on Pie in the Sky as another way of contributing to something he cared about, another way of sharing his passion. “I made it very clear to people that this matters to me. It’s not convincing them that they should care. It’s convincing them that I care — and you should too.” Jacob led the CYSL team for Pie in the Sky in 2023 and he’s returning to fundraising for Pie in the Sky this fall.

A Snowball Effect

How does this happen? Why do people stay involved year after year?

“The world’s a crazy place and we have to do whatever we can to make it better,” Sarah says. The problems of the world can be paralyzing. Sarah gets that. “I don’t know what I can do, so I don’t do anything. Which doesn’t feel good. But then you do a little something. Like I did one day in the kitchen at Community Servings. And I think oh yeah, this is fun, I can do that. And it sort of snowballs.”

In her current season of life, Regan is carrying a lot: a full-time work schedule and caring for kids. But Pie in the Sky stays in the picture. It’s manageable, it’s fun, and her friends love supporting her. “I feel committed and I don’t want to walk away,” Regan says. The fundraiser is “something I can’t ever imagine not doing. It’s just such a pitch-perfect idea. It just feeds everybody joy at all different levels.” 

When Jacob was growing up in Connecticut, his mother would scratch-make “the best chicken soup you’ve ever had” any time he or a family member got sick. And it worked. They healed. “So the Community Servings ‘food heals’ line I think really resonates with me,” Jacob says, “because that was how we nourished ourselves and tried to heal when we were sick.” Jacob reflects how fortunate he’s been to always have access to good food.

“If I can say to someone, you give Community Servings $35, you can help someone access these meals, that’s really powerful and emotional.”

Want to share that experience with someone who needs it? You can in two easy ways:

  1. Spread the word about Community Servings and sell Thanksgiving pies to your friends, family, and colleagues through Pie in the Sky.
  2. Donate to Community Servings through Pie in the Sky. $35 funds one week of meals for a neighbor in Massachusetts and Rhode Island! All pies are baked by a local Boston business and are available for pickup at a location around Greater Boston the week before Thanksgiving.
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