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What do you do when your favorite painting isn’t the smartest buy?

It’s a question more collectors are asking in the 21st century, as the art market has become a curious battleground between passion and performance—between the heart and the spreadsheet. The art world today is flush with hedge-fund logic, blue-chip rankings, and portfolio talk. But behind every collection worth remembering is a moment of connection, an instinct, an irrational desire. And therein lies the dilemma.

Can you collect with both your heart and your head? And if so, how?

The Romantic Collector vs. The Strategic Investor

Let’s be honest—collecting art used to be romantic. You saw something, you loved it, you bought it. End of story. There was no immediate concern for future liquidity, resale performance, or how many Instagram followers the artist had.

Fast forward to now: art is a recognized asset class. Collectors attend auctions with advisors, track indices, and compare ROI across artists the way you might compare tech stocks. Art fairs look increasingly like private equity conferences in disguise.

And yet, for many of my clients—especially those who began collecting in the 1990s and early 2000s—there’s still a lingering nostalgia for collecting based on feeling. They’ll tell me about the first Kusama they bought for $18,000 or a Nara they stumbled upon before the market frenzy. None of it was calculated. They simply fell in love. Today, those works are worth millions. But at the time, it wasn’t about the money.

When Love Fails the Ledger

But what happens when the opposite is true? When you fall in love with a painting, but your advisor tells you it’s overpriced, overhyped, or impossible to resell?

This is where the collector’s dilemma gets real.

I remember a client in Paris who was absolutely enamored with a painting by a young figurative artist from Eastern Europe. The work was raw, emotional, and brilliantly executed—but the gallery was asking €150,000 for it. The artist had no major institutional backing, no auction history, and the price had skyrocketed in just 18 months. From a market standpoint, it made no sense.

I advised caution. He bought it anyway. And you know what? Two years later, he still tells me it’s the piece he thinks about most when he walks into the room.

Did he overpay? Probably.

Did he make a mistake? Not necessarily.

Because some purchases aren’t about exit strategies. They’re about identity, taste, memory. And that, too, has value.

Collecting with Both Intuition and Insight

The best collections, in my view, are built with a balance of emotion and expertise. You can—and should—follow your gut. But also understand the broader context of your choices.

That means asking:

• Is the artist represented by a credible gallery with long-term vision?
• Has the artist been collected by institutions or major private collections?
• Is the price consistent with comparable works in size, medium, and date?
• Is this purchase part of a coherent collection narrative, or a random indulgence?

I often tell clients: buy emotionally, but justify intelligently.

The Rise of the Hybrid Collector

Interestingly, a new type of collector is emerging: the hybrid. These are individuals who understand the financial mechanics of art but still collect based on feeling. They’ll buy a rare early Christopher Wool because the brushwork reminds them of their father’s calligraphy. Or they’ll acquire a piece by Lynette Yiadom-Boakye not just because of the upward market trend, but because her figures evoke a presence they’ve never encountered before.

The hybrid collector is thoughtful, informed, but not emotionally numb. And they’re redefining what it means to be a serious collector today.

Final Thought: The True ROI

At the end of the day, art isn’t stock. It hangs on your walls. It lives with you. It witnesses your life.

There will always be smarter buys. There will always be trending names. But there are few things more gratifying than waking up every day to a work of art that stirs something in you—regardless of what the charts say.

And in that sense, the truest return on investment may be emotional after all.

Daniel Turriani