Penny’s Legacy – Love and Hugs

Show Up Like Penny

Because she gave the best hugs, she had a mega-watt smile & the world needs a little more of Penny’s spirit.

A life fully present. A heart turned toward others. A legacy that keeps showing up.

Penny DePhillip traveled to Cuba four times in five years with Shared Resolve friends—returning not simply because she loved the place, but because she loved the people she found there & she gave regularly to make life a little easier for them.

She planned to return again in 2027. Unfortunately, Penny passed away in the summer of 2026. Now, the relationships she built, the generosity she began, and the way she lived are inviting the rest of us to carry something forward – To show up like Penny.

Give in Penny's Memory

THROUGH NOVEMBER 30, 2026, Shared Resolve will be matching donations in Penny’s honor. To be a part of this matching, simply add “Show Up Like Penny” to the note on your donation!

She kept coming back.

Some people take a trip and bring home photographs.

Penny brought home relationships.

Over four trips to Cuba, she experienced the country with different groups of travelers. She returned to familiar faces, made new friends, shared meals and conversations, laughed, danced, dived, hugged, listened—and became part of a community that stretched far beyond geography. She made friends with artists and brought home their art to weave into the fabric of her everyday life. She had a quiet but unmistakable way of giving 100% to everything she did.

That was Penny.

She had a way of being fully present. Her unmistakable smile and generous hugs made people feel seen. She didn’t simply pass through people’s lives.

She showed up for them.

And she intended to keep doing exactly that.

When people become friends, need becomes personal.

As conditions in Cuba grew increasingly difficult, the people Penny had come to know were no longer simply people living through a humanitarian crisis thousands of miles away.

They were friends.

Families were struggling to afford and find basic necessities—food, medicine and everyday essentials.

So when Shared Resolve’s first round of food assistance began, Penny was there.

She gave.

But then Penny asked a question that revealed something deeper:

“How can I give every week?”

Penny wasn’t looking for a one-time response to a difficult situation.

She wanted to keep showing up.

From compassion to commitment.

“How can I give every week?”

That question captures so much of what Shared Resolve exists to make possible.

We encounter another person’s need.
We allow ourselves to care.
And then we decide to do something about it.

Penny’s compassion became consistent action. She wanted families she knew and loved to have food on their tables, medicine when they needed it, and the reassurance that people beyond Cuba had not forgotten them.

Her giving wasn’t about solving everything.

It was about doing what she could, for the people in front of her, again and again.

Show up like Penny...

At Penny’s memorial, her scuba instructor shared a story.

Penny had initially been timid—even afraid—to dive. But she kept at it. She pushed through the fear and eventually did the thing that had once frightened her.

It was one more glimpse of the way Penny lived.

Be present. Be brave. Keep going. Show up.

And from that came a simple challenge:

Show up like Penny did.

Show up when something feels uncomfortable.

Show up when someone needs you.

Show up when compassion asks something of you.

Show up with your smile, your courage, your resources, your time—whatever you have to give.

Because showing up matters.

Her story didn't end with her last trip.

Today, families connected through these relationships continue to receive groceries, medicine and humanitarian assistance during an extraordinarily difficult season in Cuba.

And every act of generosity extends something Penny believed deeply enough to practice:

People are worth showing up for.

Her friendships continue to matter.

Her generosity continues to inspire generosity.

And a life characterized by presence is becoming an invitation for others to be present, too.

We keep showing up.

Penny planned to return to Cuba in 2027.

There is something poignant about knowing there was another trip she expected to take, more people she expected to see, more hugs she expected to give.

We cannot take that trip for her.

But we can carry forward what made those trips matter in the first place.

And together, we can show up like Penny.

Her legacy becomes someone else’s hope!