A former CEO of Singapore’s National Volunteer & Philanthropy Centre reframes the season of giving, arguing that the greatest gift is a relationship, not a transaction

It’s the season of lists. Gift lists, guest lists, and last-minute donations to optimise one’s tax ledger. But in the quiet lull after the carols fade, a more profound question lingers: what are we truly building with our generosity?

We often narrate giving as a linear act: a need exists, a resource is transferred, and a problem is solved. It’s a satisfying story we tell at fundraisers. Yet from my vantage— raised at the confluence of generational wealth, then leading the National Volunteer & Philanthropy Centre—I saw a more complex truth, starkly revealed during the pandemic: philanthropy is a double-edged sword. One edge can cut a path to a better future; the other, wielded unwittingly, can leave a deeper wound.

This is the chasm between what philosopher Martin Buber called an I-It transaction and an I-Thou encounter. One sees a problem to be fixed; the other, a person to be met.

Years ago, I spoke at a Day of Service for an elite school. I shared the story of a lonely auntie in a rental block, waiting for visitors who never came. A nearby institution, seeking to help isolated seniors, had installed motion detectors in their flats. “A good idea?” I asked. The students, clever and compassionate, agreed it was.

Then I asked the better question: “Who thinks this is a bad idea?” After a silence, a brave soul whispered: “Because they are still lonely.”

Exactly. We saw this writ large during COVID-19. Good ideas are not complete ideas. This is I-It giving: well-resourced, efficient, and ultimately, a bandage over a festering wound of loneliness. It provides data, not dignity. The giver gets a report; the recipient gets monitored.

So, if this is the shadow, where is the light? How does giving become a transformative I-Thou encounter that benefits the giver in ways that matter?

The first benefit is influence. The minister’s table, the named wing, the backstage pass to conversations that shape our city’s future. This access is real. But it can distort, inflating the ego into a ‘saviour’ complex—the ultimate I-It trap.

My counter-move? Spiritual hygiene. At a recent gala, I asked not to be seated at the VVIP table. Puzzled, they obliged. I dined with beneficiaries and frontline workers, gaining grounded insight into the root causes of the issue I was there to support. The food was the same; the perspective was transformative. True influence isn’t about prestige; it’s about the precision that comes from true understanding.

We are drowning in information, most of it noise. Strategic giving is an antidote. It grounds us in reality, breaking our privileged echo chambers. For deeper impact, I recommend a cluster strategy: funding a portfolio of linked, mutually reinforcing initiatives. Think of it as a thematic investment fund for social good. This is where philanthropy becomes high-risk R&D for a better world, often uncovering the redemptive business models of tomorrow—profitable solutions to the problems of people and planet. The ultimate sweet spot is not just giving money away, but investing it in a future where your wealth and the world’s well-being are aligned.

Finally, the most profound benefit is spiritual. An entrepreneur friend once told me: “Whenever I feel poor, I give something away.” Her logic was flawless: it’s a visceral reminder that no matter her temporary cash crunch, she still holds the power to improve a life. Gratitude, it turns out, is a remarkable antidepressant.

This is the ultimate statement of value. No one wants to die rich and alone, a will read in a room thick with entitlement. Giving breathes life into a purpose beyond the self, knitting families together with conversations that transcend “What’s in it for me?”

Everyone, including the giver, is better off. Numerous studies confirm the mental health benefits. It begins with the smallest of habits: an extra tip, a sincere thank you looking someone in the eye, helping your helper with matched savings. I have a friend who transformed her doom-scrolling into micro-giving on Giving.sg. “It just makes me feel more human,” she said. “Like I belong here.”

Perhaps that’s the spirit of Christmas, the final item on the only list that matters: a sense of knowing who and what we are connected to, and living it out in our choices, large and small.

Merry Christmas.

Some useful links
A great place to start: MyLegacy@LifeSG
Legacy giving initiative by Community Foundation of Singapore here
For contributing to local charities and causes: Giving.sg