We artists and gallerists work hard to ensure buying a painting is easy. Yes, we’ll take your credit card; yes, we’ll pack and ship it.
Living with the painting you bought is the real test. I have a houseful of paintings myself; some have endured the test of time, others I hardly notice, and still others have quietly left the room. Even with a strong background in art I still make mistakes.
Sentiment plays a big role in art purchases
Sentiment is not a weakness. My house is full of portraits of people and dogs, and I wouldn’t have it any other way. A painting that’s tied to a memory, place or moment has staying power. That said, sentiment can work for you or against you.
At its best, sentiment deepens your relationship with a painting. Maybe you bought it on a trip or it reminds you of a landscape you love. Or, you met the artist and you clicked. Those layers don’t disappear. Twenty years on, they are a marker of who you were and what mattered to you at that time. That kind of resonance is impossible to fake.
Sentiment can cloud your judgment
A common mistake is buying something solely because of what it represents, rather than its formal qualities. A great example is the multitude of bad paintings of lighthouses in this world. The problem isn’t the subject; it’s that they’re so emotionally-resonant and easy to sell that artists of all abilities paint them.
If the composition is weak or the values are muddy, you will find yourself disengaging over time. The emotional hook got you in the door, but it didn’t keep you there.
Paintings must stand on their own, with strong design, clear value structure and a sense of intention. They also need to speak to you personally. When those two things align, you get something rare: a painting that is both visually compelling and emotionally durable.
Paintings that last
Paintings based on trends tend to fade fast. Trends may carry a piece for a moment but can’t sustain long-term interest. Instead, look for work that has depth, subtle shifts in color and a sense of intelligent decision-making. These hold your attention because they don’t give everything away at once.
Strong paintings are built on good bones. Even if you don’t know the formal language of composition, you can probably educate yourself on the subject (starting with this blog). Does your eye move through the painting, or does it get stuck? Does it feel balanced without being static? Are there areas of definition and areas that aren’t spelled out? A well-designed painting will continue to engage you because your eye can travel it in different ways over time.
Paintings with clear, intentional light patterns read well from across the room but also reward closer inspection. That keeps them alive in your space.
The paintings that last are the ones that leave room for you. They suggest rather than insist. They allow your mood, your memory and your changing perspective to interact with them. In twenty years, you will not be the same person you are today. Your painting should be able to meet you there.
Finally, if you can (and it’s not always possible), walk away and come back. A painting that still pulls you in after a day or a week is worth serious consideration. The initial spark matters, but so does the slow burn.
Hey, painters!
If you’re ready to sharpen your eye and start seeing your paintings with more clarity, I invite you to join my Fresh Eyes Critique Zoom class on Tuesday evenings, 6-9 PM on April 14, 21 and 28. After that, you’re on your own for a few weeks, because I’ll be in the Cotswolds.
Registration is now open for workshops in 2026! Reserve your spot:
- Find your Authentic Voice in Plein Air | Berkshires, MA, August 10-14, 2026
- New! Color Clinic 2026 | Rockport, ME, October 3-4, 2026
- New! Composition Week 2026 | Rockport, ME, October 5-9, 2026
Can’t commit to a full workshop? Work online at your own pace: