Episode 5 – The Art World Demystified by Brainard Carey / The Right Questions


The interviews at the beginning of this book are a prime example of two major figures in the art world who aren’t pulling any punches and are saying truly useful things for artists. Conversely, the less accomplished the artist or administrator of whom you ask questions, the more likely you will get a response that is the opposite of helpful. It can be summed up in the paradigm of scarcity versus abundance: if you are afraid there will not be enough career opportunities for you, then you will think it is not helpful to share; and if you think there is plenty for you (as evidenced by success on your terms), then you will be happy to share knowledge and expertise. So perhaps the art world is seen as a mysterious place because many people in it do not understand what is happening there, and worse, they are insecure about the power of their artwork or their job, and thus they purposefully mystify a situation to feel more powerful.

It is a strange behavior, but a common one—when in doubt, act arrogant. It works on a superficial level, but soon it wears thin, and no level of arrogance can replace real knowledge and real connections with people who care about you and want to see your art career grow. As you search for answers and information, asking the right questions is important, as well as sensitivity and generosity.

The Right Questions

In most cases, if you ask a question very directly, after a few preliminary questions to break the ice, you can get almost any information you need. It is a technique used by people who are pros at asking questions, like Oprah or Barbara Walters. Their technique is to first build trust. Ask a few questions that are easy to answer and are genuine and sincere. Then slowly but directly move to the harder questions. In the case of major celebrity interviews, the celebrities are often well prepared to deflect a question, and it is usually asked again if it is not answered.

Raising Money

I once worked with an artist who also happened to be a private banker and owned several companies, but couldn’t get his art exhibited or sold. His job, not unlike some artists, was to raise money. Unlike artists, he raised money for companies that he thought needed more funds for research on scientific ideas he thought would be profitable. His job was to find people with money to invest and then “ask them the right questions.” The reason that he could not just tell them about the exciting research, and ask if they would be interested in investing, is that he would sound like every other person wanting money and it would not be persuasive enough. To improve his chances, his strategy was to ask the “right questions” and get the person he was after engaged in a conversation, thus building a relationship and giving him the opportunity to present his idea and ask for funding. Of course you are wondering what the right question is. That is the area where my client had to be creative. As a side note, I have to say working with this particular client taught me a lot about how creative the business world is, especially on the highest levels of financial engagement. For this particular man, the first step was not convincing the person he wants to meet to invest or watch his presentation, but to simply engage him in a conversation. As Dale Carnegie said, “You will make more friends in two months by taking an interest in someone then you will in two years by telling them to take an interest in you.”

The right questions tend to begin with what truly interests the person you are asking. The more research you do on them (via the web), the better prepared you are for developing the right questions.

Business World vs. Art World

Even though this person was in the high-level business world, it is no different for artists because it is not enough to just have great art, or a great business investment; you must also be able to engage a potential gallerist, curator, or art buyer with the right questions. We will get to those questions soon with specific samples, but it is up you and your personality to create questions that reflect who you are and what you want to accomplish. And it comes down to a personal style that is truly sincere when asking people questions about who they are and what they do.

I was working with a young emerging artist who would go around meeting gallerists and after asking about their gallery and what they did, he would go home and take notes about details—like the names of their children, favorite artists they mentioned, and other tidbits. Then when he would see them again at an opening he could say, “How are the twins?” and that got a very warm response indeed!

Am I Good Enough? Do You Like my Work?

The artist that I mentioned who was a successful business manwanted to exhibit and sell his work. He hired me as a mentor. At first the answer seemed obvious to me—if he applied his business skills to his art, he would be very successful. If he used his charm, his good questions, and his huge beautiful

Manhattan studio, he would get far. However, things did not progress that easily. He found many stumbling blocks in his way. When he had calls to make or galleries to visit, he often was too busy to do it. When he did meet people and introduced himself, it started off well, but he tended not to follow-up, and even when he did, rather than “asking the right questions” he would ask the person he was talking to if they liked his work.

They would not know what to say, and then he faltered and became less interested in networking. He would say, “I didn’t like their response, they didn’t seem to like my work enough.”

One reason is that the absolute wrong question to ask is,“Do you like my work?” Because it does not matter initially if the collector or gallerist likes your work, what matters is if they want to buy it or, in the case of a gallery, if they want to sell it. The other reason this man was retreating was that his self-esteem was getting lower every time he went out to meet people and didn’t get the answer he wanted. When I explained to him that he was getting in his own way, he recognized that and we worked hard to move through that by examining what he was doing and carefully changing the language he was using. Once he began asking the right questions, not the wrong ones, and presenting plans and ideas, his success grew dramatically.

Building Your Own Hurdles

What was he doing wrong? What did I mean when I said hewas getting in his own way? In that case I meant that although he was doing all the right things, he was undermining his potential success by self-sabotaging his situation. This is not uncommon for artists to do, or, for that matter, anyone to do, but it is particularly common with people in creative fields.

Unlike most jobs, being an artist means you have to believe in your own work, and you have to truly believe that it is good and worthwhile to pursue. In the case of the businessman, he seemed to have no doubt that his work was good, even great—but did he really believe that? I feel that he did not believe in his work entirely. In some respects, this is the job of the ego and how it gets in the way or helps. We all have doubts about one thing or another and sometimes, to compensate, we act as if we have no doubts at all, perhaps even acting arrogant in some way. That is natural,but can also be problematic because underneath what appears to be a confident ego is a doubt, a crack in the façade that is being generated, and when that is exposed we retreat. This is most likely familiar to the reader, if you are an artist. The businessman/artist was acting confident, but did not truly believe his work was valuable, unlike his belief in the companies he represented.

Personal Strategies

I have noticed a similar pattern with many artists that I work with. At first when I design a strategy with them to reach their goals, which may be getting a gallery show or a grant, everyone is excited and ready to do the work. As they put themselves out into the world, and begin to apply for grants or submit work to galleries or invite more people to their studios, inevitably it begins well—and then there is a rejection.

The rejection may be subtle, like an email or phone call not returned, or less subtle, like not getting the grant, or a gallery that says they are not interested at this time. This can cause a tailspin, and all the energy they had to go out into the world fades. If they were selling cupcakes they might not feel so bad, because sales involves rejection, any salesperson knows that, but in this case it is their own art and it is so closely associated with the artists’ personalities that the rejection is taken personally.

The crack is then revealed—you have a doubt—and the ego protests and fires back that there is no doubt, it is the gallerist that is wrong. The conclusion, even if not consciously revealed, is that the world is against you. You react so strongly because the mistake you made in thinking about yourself seems to have been revealed. That is a painful experience that everyone has felt. It is also a mistake in thinking, because the galleries and granting agencies are not rejecting you—it is not personal, and it is not a judgment on the quality of your art.

Confidence Game

Confidence is one of the more profound aspects of building your career; how do you get out of your own way? How do you shatter your own glass ceiling? It is an issue in practically all fields of commerce, and the methods to move forward and up in spite of yourself are various and often culturally-specific.

An artist’s worth in terms of prices that artwork has sold for, is a barometer of how the artist perceives the marketplace of art and their place in it. However, we have all seen artwork that you know to be substandard, fetch huge prices and vice versa, so there is something more at play in terms of how an artist prices their work and gains confidence. Consider the following case history of one artist I worked with.

Case History #1

Jim is an artist that made small paintings on wood panels.He worked at more than one job, working at a restaurant, at a bar, and as an artist’s assistant. He lived in a borough of New York City and found a gallery that sold his beautiful small paintings for about 1,200 each. The gallery would sell three or four a year, sometimes more, which made him happy at first, but was hardly a salary. He assumed the rate of sales would naturally increase. He would ask the gallery to raise the prices but they said customers wouldn’t pay anymore. The gallery began selling fewer paintings as time went on and Jim got frustrated. His jobs were not paying much and he moved back to his hometown in the Midwest. He felt that he had not “made it” in New York, and just wanted to live an easier life with his wife and children.

Bold Move

Back at home he became a carpenter’s helper. A friend came byand looked at his work and asked how much a small painting was that he had recently finished. He thought about the sales in New York and what he really wanted, and he thought about how good that little painting was, and he said confidently, “That painting is eight thousand dollars.” As he told me, he thought, “What do I have to lose?” The friend said he wanted to think about it, and thanked him. Jim assumed that was the end of the sale, especially since the friend did not have much money, but he felt good about saying what he thought it was worth.

A day later the friend came back and bought the paintings for the eight thousand dollars that was asked. That friend was not rich, and had to figure out how to get the money for something he really wanted. And if you really want something, you can usually find the money, even if it is by using a credit card or getting a loan or liquidating an asset. Isn’t that how so many go to college and afford new cars? In this specific case, the friend liquidated some of his retirement savings. Since then, Jim’s career has grown and his prices have not gone down. He does sell original wood block prints for under two hundred dollars, but the paintings remain the same price or higher. The turning point for Jim was not just raising his prices but feeling good about it. I often work with artists to raise their prices, but if the artist is not ready they will not do it. They might feel that they will lose customers or simply not make sales anymore, but unless you really want to change your prices, it won’t happen on its own. His old gallery would not raise the prices because they did not have the ability to sell at that range or the belief in his work. He had no choice but to leave that gallery.


The game of selling art is not so mysterious, but our personal reasons for lacking confidence often are. As you read on, you will see various institutions and jobs within the art world deconstructed so you can navigate this world easier. There will also be more help in discovering and overcoming your own mysterious issues that come from unknown sources, but as sure as there are words on this page, your career can be remedied with patience and practice. The case I just mentioned was unique and special, just as yours is. What is not unique is a lack of confidence and overcoming it. Patience is needed because it doesn’t happen overnight, and practice is needed because it takes doing a task repeatedly to make it work and to believe in it—like raising your prices. In this case, practice comes in the form of asking multiple galleries over and over if they want to work with you.

One common myth that will be explored is the idea that a gallery can do it all for you and then you are set and sales will roll in. In reality, you do most of the work, because you do not want one gallery, you want several galleries representing your work in different states or countries. When you have several galleries selling your art, it is easier to actually make a living—whereas one gallery, even if it’s successful, can ruin your career if it closes. The mystery of the inner workings of sales is easy to dispel, but the hard work on your part comes in the form of building new relationships—and many of them. Museums are a world that seems inaccessible to most artists, and the hardest to break into, so next I will talk about exactly how to do that.

To learn more about Brainard Carey and his services for artists, or to take a class from him, click here.  To join one of his free weekly webinars, click here.


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