Dear Greg, I bought a piece and now I don’t like it. What now?

Dear Greg, 

A couple of years ago, I bought a painting through a gallery I know well. The owner is a sort of friend and after a very passionate sales pitch and hearing the artist’s story, I felt emboldened to buy even though it was not my usual type. I am usually a prudent person, but this felt impulsive. Now, having lived with the painting for a while, I’ve realised I really don’t like it. It’s not a bad painting, it’s just not me and it feels like a complete anomaly amongst the rest of my art. I feel bad and a bit ashamed; I want to continue working with the gallery and don’t want to jeopardise the artist’s market as they’re still relatively emerging, but I really want to move on. How do I handle this well? 

It begins with a flicker of doubt – that painting, the one you were once so pleased with, now feels wrong. It’s too loud, or too safe, or perhaps just no longer relevant. You bought it with conviction, and it made you feel progressive and attuned to the life you were building. But now, you pass it daily and feel something more complicated – an unwelcome recoil, even embarrassment.

This kind of reversal is more common than most collectors admit. Unlike clothes or cushions, art resists being demoted. It hangs and confronts, announcing to all your tastes and ambitions, so when you fall out of love with it, it feels more like a failure than a change of heart.

But it shouldn’t: tastes change. Collecting isn’t a fixed state. It’s a conversation with yourself and time and the world around you. To find yourself out of sync with a work is not a failure of judgement, it’s evidence of evolution. What excited you once may now feel like an echo from a past self – like a voice note from another life.

So, what do you do? Sometimes, the answer is simply nothing. Keep it. Taste has seasons and what irritates you now might, with time, become interesting again. Rehanging an artwork elsewhere or putting it away for a while can be a kind of silent negotiation – a break, not a breakup. A painting moved out of sight isn’t lost; it’s just paused.

And some works are worth keeping precisely because they don’t sit easily. Art isn’t only there to please. Some pieces challenge us and stretch the edges of what we understand. If the discomfort is aesthetic, maybe sit with it, but if it’s ethical –if something about the artist, or your understanding of them, has shifted – then it’s reasonable to move on. There’s no virtue in keeping what makes you uneasy.

Collectors often ask how to avoid this, how to buy well, and the truth is, you can’t, and you probably shouldn’t. Regret is part of the education. It’s how your taste deepens – how your understanding gets keener. Every serious collection contains at least one misfire – and often, it’s that misfire that teaches us what really matters.

Art is not static, and neither are we. What you hang on your walls is a moving self-portrait, so to edit is not failure; it’s refinement. Letting go of a piece that no longer fits can sharpen the rest – and sharpen you.

So, if you’re ready to move something on, you have options. If you bought through a gallery and the artist is still on their roster, start there. A discreet resale may be possible, especially if the gallery has collectors looking for earlier work. But understand the economics: if the gallery sells from their own stock, they earn 50% commission; if they sell your piece, they typically take only 20%. So if they hold a lot of work, or if the artist is hard to place, they may quietly decline. Unless they fear you’ll take it to auction – with the potential damaging consequences of a low sale or a no sale.

Auctions can be tempting but they are treacherous. If the artist doesn’t have an active, robust auction market (which is true of most artists), results can be sobering – a low sale damages both your return and the artist’s reputation. Worse, not all auctions are equal. Some houses will accept anything; others are more selective. As Groucho Marx almost said: you don’t want to sell through any auction house that would have you too easily.

You could work with a secondary market dealer or advisor who may be able to place the work quietly with the right buyer. This preserves the artist’s market and avoids public exposure, but success depends entirely on their network – and, bluntly, your piece’s desirability.

If it’s difficult to sell, you could turn to strategic generosity. Gifting is not just sentimental; it can pay dividends. An institution, a residency programme, or a private collection might value your piece in a way the market doesn’t. But be aware that major institutions (yes, including Tate) are inundated with offers and accept almost nothing. Private gifting – to a friend, a younger collector, a residency – often has a quieter, more satisfying afterlife.

Whatever you decide, consider keeping a record of why you bought the piece, and why it stopped working for you. You’re building your art-historical diary – a map of how your tastes sharpen and mature. Regret is rarely comfortable. But it isn’t a waste. It’s useful and is the price of paying attention.