The Joy of Giving: What I’ve Learned After Years of Watching Generosity at Work

Giving is rarely transactional — it’s emotional, personal, and deeply meaningful. This post explores the joy of giving and what years of witnessing generosity have taught me about why people give, especially during the holiday season.

Holly Kobia

12/3/20253 min read

December has a different kind of weight to it.

It’s festive and joyful, yes — but it’s also emotional. For many individuals and families, this is the time of year when generosity feels closest to the surface. Memories are stirred. Gratitude is heightened. Reflection comes naturally. And for those who choose to give, the act itself often carries far more meaning than the dollar amount suggests.

After years of working as a fundraiser, I can tell you this with certainty: giving is rarely transactional. It is deeply human. And when it’s done with intention, it can be one of the most gratifying experiences a person or family has all year.

Giving Is Emotional — and That’s a Good Thing

From the outside, fundraising can look structured and strategic — campaigns, appeals, deadlines, goals. And while all of that matters, it’s only part of the picture.

What I’ve witnessed, again and again, is that giving is often rooted in emotion:

  • A loved one who benefited from a program

  • A family tradition of generosity

  • Gratitude for a season of abundance

  • A desire to honor someone’s memory

  • Hope for a better future

For some donors, giving is carefully planned and highly structured. For others, it’s spontaneous and instinctive. Neither approach is better than the other — they’re simply reflections of how different people process meaning, values, and connection.

The Privilege of Being Close to Generosity

One of the greatest privileges of my career has been being invited into these moments.

I’ve sat across tables from families making gifts together for the first time. I’ve listened as donors shared stories they’d never told anyone before — stories that explained why they cared so deeply. I’ve watched people light up when they realized their generosity could truly change something.

Those moments are humbling. They’re also a reminder that fundraising, at its best, is not about persuasion. It’s about creating space for people to express what already matters to them.

Joy Doesn’t Always Look the Same

The joy of giving isn’t always loud or celebratory.

Sometimes it’s quiet — a check mailed anonymously, a monthly gift set up and never mentioned, a simple “this felt right.” Sometimes it’s deeply emotional, even tearful. Sometimes it’s joyful in the traditional sense — a family gathered around a table deciding how they want to give together.

What unites all of these experiences is meaning. Giving allows people to align their resources with their values. And that alignment — especially at the end of the year — brings a sense of purpose that’s hard to replicate anywhere else.

Why December Matters So Much

December giving isn’t just about tax deadlines or year-end goals. It’s about reflection.

People are naturally asking:

  • What mattered most this year?

  • Where did we feel grateful?

  • How do we want to show up in the world?

When organizations honor the emotional nature of this season — when they approach donors with gratitude, humility, and respect — they create opportunities for giving that feel authentic, not pressured.

And that’s where joy lives.

A Reminder for Nonprofit Leaders

As fundraisers and nonprofit leaders, our role isn’t to manufacture emotion — it’s to honor it.

To recognize that giving is personal.
To leave room for different styles of generosity.
To say thank you often and sincerely.
To remember that behind every gift is a story.

When we do that well, we don’t just raise funds. We steward something far more valuable: trust, connection, and the joy that comes from being part of something bigger than ourselves.

The Takeaway

The joy of giving isn’t found in the size of a gift or the structure behind it. It’s found in meaning.

And after years of witnessing generosity in all its forms, I can say this with confidence: the ability to give — thoughtfully, intentionally, and from the heart — is a gift in itself.