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How to Start Collecting Art

Writer's picture: Diamond ZhouDiamond Zhou

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SATURDAY EVENING POST

February 22nd, 2025



“I thought you’d appreciate a painting that [we] could not resist acquiring recently. It’s by an artist named Ryan Dineen, called “Collector.” It comes from the most fleeting of contacts. I had gone back to Clint Roenisch’s gallery to sit for an hour while the gallery was quiet and contemplate a gorgeous large scale abstraction by Niall McCllelland. [We] wanted to acquire it and we did acquire it, but first I wanted just return to the gallery and to tarry with the piece for a while. Clint kindly gave me a chair and left me alone with the work. As it happens, during the time that I was there, Ryan came by briefly. We had never met, but of course introduced each other to each other, chatted momentarily about the show, and then he was gone, leaving me to return to my reverie. Two years later he captured me seated in front of Niall’s chrome red canvas, unbeknownst to me. [We] love the wry ironies of the title, and how the image captures the strangeness and singularity of finding oneself in front of a painting, as if under its gaze rather than the other way around. And of course there’s avoiding the vertiginous pleasure of collecting a painting of a collector who is you, or of a painting of a painting under whose contentless eye we fall every day.”

 

We could not help but to share part of this beautifully written email with our audience. The moment a collector discovers that an artist has quietly immortalised him, transforming a simple act of looking into an enduring portrait, invites a reflection on the reciprocal nature of collecting. In microcosm, how the collector’s gaze can be turned back upon the collector, revealing deeper truths about why we acquire art and how artworks, in turn, acquire us.



Níall McClelland, Repression Cypher, 2023, oil and sand on burlap over canvas, 198.12 × 152.4 centimetres. Photo: LF Documentation. Courtesy Clint Roenisch Gallery, Toronto.
Níall McClelland, Repression Cypher, 2023, oil and sand on burlap over canvas, 198.12 × 152.4 centimetres. Photo: LF Documentation. Courtesy Clint Roenisch Gallery, Toronto.

Ryan Dineen, Collector, 2025, Oil on canvas, 16 x 12 in. Image courtesy of the artist and the collector.
Ryan Dineen, Collector, 2025, Oil on canvas, 16 x 12 in. Image courtesy of the artist and the collector.


In Renaissance Florence, the Medici family championed emerging artists such as Michelangelo, not only as a means of decorating their palaces but also as an expression of civic pride and family prestige. A few centuries later, Gertrude Stein’s Parisian salon gathered Picasso, Matisse, and others around her in an ongoing dialogue that shaped the trajectory of modern art. Whether for personal enrichment or genuine aesthetic admiration, collectors have always played a pivotal role in determining which artists flourish and which works endure.



The Steins hosted salons in their apartments and introduced friends and friends of friends to avant-garde art. The small apartment was also a place where the artists could meet, and be influenced by one another. After a decade of collecting art with his sister, Leo Stein moved from Paris to Italy in 1914. © San Francisco Museum of Modern Art.
The Steins hosted salons in their apartments and introduced friends and friends of friends to avant-garde art. The small apartment was also a place where the artists could meet, and be influenced by one another. After a decade of collecting art with his sister, Leo Stein moved from Paris to Italy in 1914. © San Francisco Museum of Modern Art.

Gertrude Stein at 27 rue de Fleurus with her portrait by Picasso on the wall, May 1930. By Wide World Photos - This image is available from the United States Library of Congress's Prints and Photographs division under the digital ID ppmsca.30616.
Gertrude Stein at 27 rue de Fleurus with her portrait by Picasso on the wall, May 1930. By Wide World Photos - This image is available from the United States Library of Congress's Prints and Photographs division under the digital ID ppmsca.30616.


The drive to collect can be seen as a means of forging identity. There is a certain sense of control over one’s space, with carefully chosen objects that speak to one’s tastes, values, and aspirations. There is a certain comfort in possessing something that resonates with us on a visceral level. Yet as philosopher Jean-Paul Sartre reminds us, the gaze is never unilateral, the objects we choose to live with can, in effect, “look back,” influencing how we see ourselves.


To understand Sartre’s notion of “the gaze”, it is described as a person suddenly aware of being watched through a keyhole. In that instant, the observer realizes that he, too, is an object in someone else’s field of vision. A painting or sculpture in one’s home is not just a passive decoration, it holds a certain agency over its surroundings, shaping the ambiance of a room and subtly reflecting back onto the collector. We may wake up each morning and catch a glimpse of the artwork from across the room, only to sense it quietly “judging” us, an experience that can prompt self-reflection. One might even find that the changing light or the differing emotions of each day cause the work to “speak” differently, gently shifting the collector’s self-perception. By granting art a permanent place in homes, we invite this unspoken dialogue, a communication rather than a monologue that allows for light to shine on hidden facets of ourselves.



Maxwell Bennett Bates, Circus People, 1972, Oil on canvas, 19.5 x 23 in. Work available.
Maxwell Bennett Bates, Circus People, 1972, Oil on canvas, 19.5 x 23 in. Work available.


The unexpected inversion that occurred when Ryan Dineen captured the collector in front of McClelland’s painting crystallizes this truth: as collectors, we shape our surroundings, but these surroundings also shape us. What could be more delightful than owning a painting of yourself as a collector, of a painting of a painting that once held you captive? It’s a mise-en-abyme of artistic experience, a meditation on perception, and a love letter to the strange intimacy we form with the works that move us. When the collector became the subject of another artist’s work, the dynamic was reversed in a highly literal way: the act of contemplation that he believed to be private and one-sided was reframed as an exchange in which he, too, could be looked upon and interpreted.


Walter Benjamin’s notion of an artwork’s “aura” refers to its unique presence in time and space, an authenticity rooted in its provenance, physical condition, and the moment of creation. Digital reproduction undermines this aura, reducing art to an endlessly accessible image. By living with an original piece, however, we reclaim that singular presence, letting shifting light, texture, and colour continually renew our sense of wonder. It is one reason art collecting endures, especially for those seeking experiences beyond mere commodification.


As the late art critic John Berger observed: genuine looking demands sustained attention rather than fleeting glances – a willingness to pause and let an image reveal itself through time rather than mere seconds of distracted attention. A painting or sculpture within one’s own environment encourages this sustained reflection: each day presents a fresh invitation to rediscover the subtleties of brushwork, tone, or composition. By returning to the piece under different moods and lights, we enact a kind of gentle conversation with the artwork, allowing it to question our assumptions or emotional states as much as we question its formal and conceptual properties.


For those seeking to advise or begin a collection, always try to collect a major work by an artist. However, selecting “major” works, for instance, is not merely about purchasing what is most expensive or of highest investment potential but about securing a piece that demonstrates the essence of an artist’s vision. A “major” work can be defined in multiple ways: sometimes it is the large-scale painting or the iconic sculpture that encapsulates the artist’s core style; other times it may be a smaller, rarer piece that marks a pivotal moment in the artist’s development. These works essentially best represent the vision of the artist. In either case, the notion of collecting the most meaningful piece within your budget ensures that you are focusing on quality rather than quantity, imbuing your collection with greater coherence and depth. Such selectivity does require patience, especially when an artist has produced many works across different periods, but it rewards you with acquisitions that are potent distillations of the creator’s broader vision.



Installation view of Jack Bush, Spin-off Yellow, 1976, Acrylic on canvas, 67 x 140.5 in. Work available.
Installation view of Jack Bush, Spin-off Yellow, 1976, Acrylic on canvas, 67 x 140.5 in. Work available.

Installation view of Jack Shadbolt, Dog in an Empty Room, 1976, Acrylic and oil on canvas, 53 x 215 in.
Installation view of Jack Shadbolt, Dog in an Empty Room, 1976, Acrylic and oil on canvas, 53 x 215 in.

Jack Shadbolt, Bird #11, 1965, Ink on paper, 25 x 19 1/4 in. Work available.
Jack Shadbolt, Bird #11, 1965, Ink on paper, 25 x 19 1/4 in. Work available.


Equally important is identifying a gallery, or a network of galleries that can serve as a trusted partner and advisor in this process. A reputable gallery does more than sell art, it provides context, facilitates introductions to artists, and can advise on the relative significance of particular pieces in an artist’s career. Establishing this relationship often involves visiting exhibitions regularly, engaging in conversations with gallerists, and allowing them to understand your personal tastes, interests, and budget. Over time, a gallery that genuinely understands your collecting goals can alert you to works that align with your evolving vision, rather than pushing you toward pieces that merely fit your wall or market demand. This guidance becomes particularly valuable when navigating the fine line between investment potential and genuine aesthetic resonance.


Building a collection is also not a venture that should be hurried. The strongest collections are often built gradually, as collectors collect together works that resonate with different facets of their intellect and emotions. Being in a rush to “fill a wall” can result in haphazard acquisitions that dilute the overall power of a collection. By contrast, taking the time to research artists, revisit their works, and let each piece “speak” to you fosters an internal dialogue between you and the art itself. Sometimes, you might find that a painting which initially struck you as unremarkable or difficult deepens in intrigue on a second, third, or even a fourth visit, suggesting new layers of meaning. On the other hand, sometimes an initially “pretty” or palatable work might lose its lustre upon revisiting. This slow, reflective process guards against impulsive choices, ensuring each work holds enduring value and significance.


Our initial reactions, whether awe or ambivalence, may change dramatically once we have had the chance to see the piece in different lights or after absorbing some background on the artist’s conceptual concerns. What appears visually striking in a gallery setting might feel overpowering or incongruous at home, while a subtle, understated piece might reveal layers of beauty that unfold slowly in one’s personal space. Sitting with a work, contemplating its surface treatment, thematic intricacies, or delicate composition ensures that the choice is grounded in lasting appreciation rather than fleeting excitement. This unhurried engagement also dovetails with the gallery relationship, as knowledgeable gallerists are often open to extended viewings or the option of temporarily reserving a piece while you consider it.



Robert Kelly, Mimesis XV , 2025, Oil/mixed media on panel, 22 x 17 in. (29.5 x 24.5 in. with frame). Work available.
Robert Kelly, Mimesis XV , 2025, Oil/mixed media on panel, 22 x 17 in. (29.5 x 24.5 in. with frame). Work available.

Robert Kelly, Mimesis XVI , 2025, Oil/mixed media on panel, 22 x 17 in. (29.5 x 24.5 in. with frame). Work available.
Robert Kelly, Mimesis XVI , 2025, Oil/mixed media on panel, 22 x 17 in. (29.5 x 24.5 in. with frame). Work available.


The impulse to buy quickly because of market hype, social pressure, or because your friend has one, risks reducing art to a mere commodity. Courage is integral to this process. To acquire a work of art because a friend has one is to risk relinquishing the deeply personal nature of collecting. The moment you base your choices on today’s trend or on external validation, you lose the very spark that makes an artwork uniquely yours. True collectors, those who shape rather than follow culture, bring an independent eye and an unshakable sense of self to their pursuits. It is precisely by daring to buy something unendorsed, untested, and perhaps misunderstood at first glance that one can open new pathways of appreciation, both for oneself and for the wider cultural conversation. In this sense, to collect bravely is to affirm that your sense of taste and judgment matter, that you matter, and that you can influence rather than be influenced. Just as early patrons of Picasso took a leap of faith before he was canonized by critics, so can today’s collectors champion artists. Such a stance demands both curiosity and resilience: curiosity to discover creative voices beyond the obvious, and resilience to stand by a piece that may initially provoke scepticism from peers or advisors. But it is in these moments of risk that collecting transcends mere consumption. It becomes an act of individual expression, of quietly yet decisively shaping the narrative of contemporary art. Collecting, at its best, calls for the confidence to say “yes!” only when a work resonates on a deep aesthetic or conceptual level. This is how collectors become stewards of culture rather than mere consumers in a cycle of passing fads.


This slow accumulation also lets collectors grow alongside their acquisitions. Our tastes and perspectives shift over time, influenced by educational forays, travel experiences, and changing personal circumstances. The art we choose to bring into our homes can serve as a record of these evolutions, each piece forming a chapter in the ongoing narrative of who we are and what we value. Rather than a static display, the collection becomes a dynamic conversation, capable of surprising us when we turn a corner or re-examine a painting in a new season of life.


History teems with examples of collectors who allowed art to reshape their environments, from Peggy Guggenheim to Albert C. Barnes, the collector’s personal journey was as integral to the story as the art itself. Behind every famous painting that hangs in a museum or private collection stands someone who, at some point, paused to look more carefully, to feel a shiver of recognition, and to decide that this work ought to become part of their world.



Peggy Guggenheim at home with Jackson Pollock in front of his Mural (1943), New York, ca. 1946.
Peggy Guggenheim at home with Jackson Pollock in front of his Mural (1943), New York, ca. 1946.

Barnes Foundation’s main gallery.
Barnes Foundation’s main gallery.

Paul Cézanne (French, 1839–1906), The Card Players, 1890-1892, Oil on canvas, 53 x 71 in. Barnes Foundation, Merion, Pennsylvania. A great admirer of Post-impressionism, Barnes acquired nearly one hundred Cézanne works over his lifetime. The Card Players became one of the jewels in the Foundation's collection.
Paul Cézanne (French, 1839–1906), The Card Players, 1890-1892, Oil on canvas, 53 x 71 in. Barnes Foundation, Merion, Pennsylvania. A great admirer of Post-impressionism, Barnes acquired nearly one hundred Cézanne works over his lifetime. The Card Players became one of the jewels in the Foundation's collection.


Of course, any serious collector must also consider budgetary boundaries. The trick lies in balancing financial realism with the aspiration to acquire meaningful art. If a monumental piece by a blue-chip artist is out of reach, a smaller yet equally representative work, perhaps a drawing or print, can still convey the artist’s defining qualities. Moreover, many collectors discover that working within budget constraints can spur creativity, such as learning about worthwhile prolific and rising artists, follow them through different stages of their careers, and in some cases, secure works of considerable future importance at accessible prices. This approach can yield a dynamic, ever-evolving collection that grows in step with both your taste and an artist’s rising profile. The key is not to equate a restricted budget with settling for lesser art, but rather to use that budget as a framework for informed decision-making and deeper exploration.



Daniel Mullen, Slouching Towards No. 2 (Future Monuments Series), 2021, Acrylic on linen, 79 x 75 in. Work available.
Daniel Mullen, Slouching Towards No. 2 (Future Monuments Series), 2021, Acrylic on linen, 79 x 75 in. Work available.

Pablo Picasso, Profil et femme nue, 1944, Drypoint etching on paper, 13.75 x 10.5 in. Work available.
Pablo Picasso, Profil et femme nue, 1944, Drypoint etching on paper, 13.75 x 10.5 in. Work available.


One persistent misconception is the idea that auctions alone set an artist’s true value. While auction results can generate high-profile headlines and serve as indicators of market interest, they are also susceptible to speculation and trends that fluctuate wildly. A record-breaking price under the auctioneer’s hammer does not necessarily bestow enduring stature on an artist, particularly if their primary market, driven by gallery representation and critical support, has not been developed over time. Indeed, it is typically the sustained efforts of galleries, curators, and informed collectors that establish an artist’s reputation and financial standing in the long run. Galleries invest in nurturing talent by promoting the artist’s work, securing exhibitions in reputable institutions, and facilitating scholarly discourse that bolsters credibility. When these elements are in place, the artworks accrue a deeper, more stable value than a single auction result can confer. Buying directly from the primary market, then, is often a way of supporting not just the artist but the ecosystem that ensures their meaningful contribution to culture, while also safeguarding a more reliable sense of long-term worth.



Tony Scherman, Woman in Bar, 1988, Encaustic on canvas, 54 x 72 in. Work available.
Tony Scherman, Woman in Bar, 1988, Encaustic on canvas, 54 x 72 in. Work available.


The decision to collect art can be a kind of creative act in its own right, an extension of one’s personality and intellectual curiosity. The story of being caught unaware, of becoming a subject in an artwork, is a potent reminder that this relationship is never a one-way street. The collector may choose the painting, but the painting also, in some sense, chooses the collector. If there is a lesson to be gleaned from the anecdote and the centuries of collecting that precede it, it is that art demands reciprocity and a willingness to see and be seen. To collect art, then, is not simply to own objects but to participate in an ongoing dialogue with beauty, history, and our own sense of self.




 


Current Exhibition




Installation view of “Jack Bush: Flaunting the Rules”. Copyright (C) 2025 Paul Kyle Gallery. All rights reserved. Photography by Kyle Juron. Left: June Lilac; Middle: Pink on Red (Thrust), Right: Spin-Off Yellow
Installation view of “Jack Bush: Flaunting the Rules”. Copyright (C) 2025 Paul Kyle Gallery. All rights reserved. Photography by Kyle Juron. Left: June Lilac; Middle: Pink on Red (Thrust), Right: Spin-Off Yellow




A message from our Insurance Sponsor for this exhibition:

At Acera Insurance, we’ve been serving the fine arts community for decades. Partnering with the world’s leading insurers, our advisors provide comprehensive, customized solutions to protect your valuable collections.


Contact: Farzina Coladon

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