The Art of Gift Giving

Why the best gifts might be the ones we never thought to ask for

There are many Christmases I don’t remember, and I couldn’t tell you what I received. 

But I remember one Christmas vividly.

I can still picture the tree in the corner of our great room, decorated by my mother, a remarkably talented artist who could paint, draw, design theater sets and decorate a Christmas tree better than anyone I’ve ever known. I remember the burgundy velvet tree skirt, and the enormous box underneath with my name on it.

Inside was the retro pink jam box I’d specifically asked Santa to bring me.

And I remember feeling disappointed.

It was exactly what I’d wanted. So why wasn’t I delighted?

Looking back, I wonder whether I wanted something more than the jam box. Perhaps I wanted to be surprised. To discover something I hadn’t thought to ask for… To be seen a little deeper.

That’s the curious thing about gift giving. We make lists of things we want, but the gifts we remember aren’t necessarily the ones that satisfy those requests.

Which brings me to the wonderfully presumptuous act of giving art.

Unlike a sweater or a gift card, an original work of art, handmade ceramic or needlepoint pillow requires us to make a judgment about someone else’s taste.

We’re effectively saying, I saw this, and I thought of you.

But we shy away from choosing art because, well, what if we’re wrong?

Perhaps that’s exactly what makes giving art worth considering. It requires observation, curiosity, and a little courage.

So how do we choose art for someone else?

Start with the person, not the walls.

Think about what captures their attention. What are they curious about? Where have they traveled? What stories do they tell over and over?

Consider the difference between choosing something because it matches a friend’s living room and choosing something because it reminds you of a conversation you had years ago. One is decorating. The other is storytelling.

Make size less of a consideration.

Art doesn’t have to dominate a room to make an impression. An original work measuring 8 × 10 inches can find a place in a hallway, on a bookshelf or above a desk without requiring someone to rearrange the furniture.

A tabletop easel offers even more flexibility. The idea is to give something meaningful without asking the recipient to make a major decorating decision.

Don’t confuse your taste with theirs.

This may be the hardest part. We naturally gravitate toward things we find beautiful, but giving art requires a different kind of discernment: recognizing something wonderful that we might never choose for ourselves.

Sometimes the most thoughtful gift is something you admire precisely because it belongs in someone else’s world.

Don’t be afraid to ask for help.

Artists and gallery owners can help you explore possibilities within a budget, introduce you to unfamiliar mediums and suggest works you might otherwise overlook. Original prints, small paintings, photographs, ceramics and handcrafted objects offer many ways to begin.

Give the story along with the art.

Tell the recipient what caught your attention. Share something about the artist, the materials or the circumstances in which you discovered the work. Explain what made you think of them.

That story becomes part of the gift. Over time, it may become as important as the object itself.

I’ve been thinking about this as we approach the holidays at Four Stories, the art gallery I recently opened in Libertyville. Every day, I see how differently people respond to the unexpected things we carry with delight.

It’s a reminder that the real opportunity in giving art is giving them a surprise that sparks their imagination and feels deeply personal. Because that’s where memories are truly made.