Originally published September, 2022. Updated October, 2026.
At Maestro Group, we remind folks that sales is both an art and a science. We point out that the art of sales is grounded in authenticity. But let’s go deeper. What does “authenticity” look like in a sales context? Some qualities we might include are projecting informed confidence in your skills, making personal connections, and showing a creative spark.
This series explores the full potential of calling sales an “art.” Artists have long talked about entering a “flow state,” a period of heightened productivity and intense focus in the present moment. The task that once seemed laborious now performs itself.
The blank page fills with words; paint overtakes a blank canvas. Psychologist Mihaly Csikszentmihalyi devoted a 2004 TED Talk to flow state, describing it as a “secret to happiness.” Research continues to highlight “the experience of being deeply immersed in an activity” as a predictor of well-being.
Is this concept useful in sales? Absolutely. Flow state and authenticity go hand in hand. The flow state represents peak ability to take cues, engage with others’ ideas, and come up with original solutions. To your prospect, client, or partner, these are the qualities that register as being authentic.
The result? A deal that might have previously seemed unlikely now sells itself.
Show Me the Money
Every artist figures out, somewhere along the way, that they must be their own best advocate. Successful artists also realize that no one should be embarrassed by looking to make a sale. Those who tell you that art should be “above money” are usually speaking from places of privilege.
The authors Charles Dickens, Alexandre Dumas, and Gustave Flaubert all serialized their novels in newspapers and literary journals. Songwriters such as Carole King flocked to New York’s Brill Building not just because it was a catalyst for 1950s and 1960s pop hits, but because the labels housed there offered steady paychecks.
“I started as a commercial artist, and I want to finish as a business artist,” declares Andy Warhol in his 1975 book, The Philosophy of Andy Warhol (From A to B & Back Again). “Making money is art and working is art and good business is the best art.”
When Warhol first arrived in New York City, having left his Czechoslovakian immigrant family in Pittsburgh, he was determined to make a living. He freelance-designed album art for Columbia and RCA Records at a starting rate of $50 apiece.
Glamour magazine took a chance on his cold call and commissioned a drawing. His playful interpretations of women’s fashions soon earned him a dedicated client base that included Tiffany & Co. and I. Miller Shoes, which used Warhol’s art in their advertisements. His album covers yielded iconic images for The Velvet Underground and chart-topping work with the Rolling Stones.
Even after Warhol launched his “Pop” persona and his work became more abstract and experimental, he remained frankly enthusiastic about commercial brands such as Brillo and Campbell’s. His signature techniques—stamping, silkscreen, lithography—remained rooted in the industries of mass production, which he recognized could also yield multiple generations of licensing and income.
This fascination with the public vernacular also shaped his takes on fine art portraiture, as he meditated on how something as small as shifting the palette could create an editorial statement about the familiar face of a celebrity or politician.
Ice-Breakers and Deal-Makers
I live in Washington, D.C., a city somewhat notorious for how many conversations start with the question, “What do you do?” People hold this up as proof that our city is dry and humorless, filled with bureaucrats and strivers.
But people’s disdain for the question is misplaced. There’s nothing dry or humorless about the question; in fact, it’s a question that can open doors. The problem is when the answer is dry and humorless, and that’s on you.
When someone asks, “What do you do?” find a way to reply that isn’t cloaked in jargon. Reframe the question. If you say you had a “good day at work,” what accomplishments made it feel good? Who did you help, how did you help them, and what were the dividends? Don’t be afraid to mention money—again, no one should be embarrassed by looking to make a sale.
How would Andy Warhol answer, if asked, “What do you do?” He’d probably say, “I make art, and I sell art.” And he’d be ready to talk about both halves of that equation.
Coming from a Real Place
For the Florida Highwaymen, a cohort of about two dozen African-American painters active from the 1950s through the 1980s, every sale came from having the courage to not only present their art, but to ask for money.
They painted on inexpensive Masonite and fiberboard, often working with sturdy palette knives rather than brushes, and priced their pieces modestly. Then they went door to door, up and down the Atlantic coast, pitching themselves on-site to hotels, offices, and families who might not otherwise splurge on original artwork.
The Highwaymen were a subset of the Indian River School, those mentored by a naturalist and self-taught artist named A.E. “Bean” Backus. Although Backus traveled to New York to study for a few summers at the Parsons School of Design, he ultimately chose to spend his life in his birthplace of Fort Pierce.
Backus encouraged his students to paint landscapes that were genuine and unique to the region. One recurring motif was the brilliant, sprawling red of the Royal Poinciana tree. Crashing waves and wind-blown palms could have veered into generic beauty—at which point, why not go for a pre-framed print?
But viewers reacted to these coastlines, which felt recognizably local, and they opened their wallets. A painting first sold for $25, signed by Alfred Hair or Harold Newton, might be worth $5,000 to $10,000 today.
Why do we emphasize “authenticity” as the art of sales? Because you have to be clear on what you do and why you’re doing it, and you have to communicate openly with prospects, clients, and partners. You have to embrace the hustle.
Otherwise, you’ll never free up the essential resources you need to get into your flow state. Next week, we’ll talk about sharpening your visual intelligence to pick up on all the cues made available in conversations and meetings.
We can help your team with both the science and the art of sales. Reach us at mastery@maestrogroup.co for more information on training, coaching, and consulting.