Artists vs. Creative Entrepreneurs – Which Best Describes Freelancers and Why Does It Matter?

Certain beliefs about money, art, and everything else aren’t formed through a linear, reasoned train of thought and can be difficult to unwind.

“Art and commerce don’t mix” is one such belief. It’s like an old coin that found its way into our cultural purse of axioms, along with others like “Pigs don’t fly.” The laws of gravity and the limits of porcine physiology don’t leave us much room to argue, but what about art and commerce?

Without too much effort, we can find artists from various time periods, countries, and artistic movements who didn’t profit monetarily from their talent, including these poets and writers: Zora Neale Hurston, John Keats, Edgar Allen Poe, Emily Dickinson, Henry David Thoreau, Stieg Larsson, Sylvia Plath, Franz Kafka, and John Kennedy Toole.

Does that mean all artists are doomed to scrape by? Not necessarily. We can find counterexamples of artists who did quite well for themselves:

• When Pablo Picasso died in 1973, he owned five homes, including two chateaus. He had $4.5 million in cash, $1.3 million in gold, and an undisclosed number of stocks and bonds. A court-appointed auditor estimated the value of his estate at between $250 million and $500 million.
• Gross revenue from Harry Potter book sales was around $7.7 billion last time I checked. J.K. Rowling would no longer qualify for welfare.
• At the time of writing, Lin-Manuel Miranda’s Hamilton had grossed over $612 million. His net worth is somewhere north of $90 million.

With the cliché of the starving artist on one end of the spectrum and wealthy outliers on the other, where do freelancers fall?

People obviously value art in its many forms and are willing to pay for it. Some artists struggle financially, and others don’t.

Talent and critical acclaim can certainly help artists get paid through and with their art. Would Hamilton have had its astonishing commercial success if the themes, script, and songs? That’s doubtful.

However, talent and critical acclaim don’t guarantee that any artist “makes it” financially. The short list of poets and writers above includes talented, celebrated artists straight out of the Western literary canon.

In short, factors other than mastery of craft, relative level of talent, and approval from gatekeepers and tastemakers influence how much money an artist makes. Let’s look at a couple of them before we get to the real point.

One slap-you-in-the-face factor that helped Ernest Hemingway was other sources of income. Hemingway clearly had the talent. The Pulitzer and Nobel Prize he won attest to that. And how did he pay his bills all those years while writing? He made some money as a journalist and correspondent, but in Paris, while he was finishing his first novel, The Sun Also Rises, he and his first wife Hadley Richardson, lived off her small trust fund.[1] His second wife, Pauline "Fife" Pfeiffer, came from a wealthy family and supported them and their two sons for thirteen years of marriage, from 1927 to 1940, while Hemingway published the eight novels in that cemented his literary career.[2]

In the five years leading up to his death in 1961, more of Hemingway’s income came from his investments, including blue-chip securities, than from book royalties.

We can speculate whether Hemingway would have written or published as much without financial support. It’s logical to think that if he’d had to put royalty money toward living expenses all those years, instead of investing it, he wouldn’t later have had the investment income to live on.

How many any artist makes eventually depends on how much they keep along the way. Hemingway left his widow, Mary, an estate worth $1,410,310,[3] or over $12 million.

Another factor is timing. In an episode of his Daily Stoic podcast Ryan Holiday chatted with James Clear, author of Atomic Habits. Both authors have sold millions of books, and Holiday commented on the role that timing can play with the successful launch of any creative project:

“What if your book [Atomic Habits] had come out the day of a terrorist attack or my book had come out the day of a hurricane and it just all got wiped away and you lost that moment? And you just didn’t get it [the attention, momentum, and commercial success]? That happens too.”[4]

Good timing probably won’t help a bad book, but it can help turn a good one into a perennial seller.

However, before we drift too far into the wrong debate about whether most artists are doomed to starve, let me tease out crucial differences between artists and creative entrepreneurs like freelancers.

• Some freelancers are artists, and they produce art for clients—for example, a photographer capturing stunning images of Yellowstone in winter.
• Other freelancers produce excellent, effective work that doesn’t qualify as art. Art was never the aim for the UX writer who picks words that will make the client’s software more intuitive to use or the marketer who puts together an effective strategy.
• Art is art because of what it does. Art moves and provokes us, inspires and elevates, sobers and humbles, excites and entertains. The purpose of art can also be as simple as putting beauty where there was none before. A mural transforms an old warehouse wall into a funky, geometric background for an urban garden.
• On the other hand, creative entrepreneurship, of which freelancing is a subset, has an entirely different set of qualities, purposes, and outcomes. Creative entrepreneurs solve problems. They make their client’s businesses more profitable. They make their customers’ lives better or easier.
• An entrepreneur provides a service, product, or experience, and if customers don’t find enough value in it, the entrepreneur fails. A freelancer can think and act like an artist and create a thing of beauty that fulfills its purpose as a work of art and yet her work of art can still fail to fulfill its other purpose of helping the client meet her goal, to fix, enable, persuade, instruct, or sell.
• If a freelancer lines up enough project flops like that, she’ll run out of clients. She won’t make much money, and her business will fail, not because there’s no money in art but because the art she produced was at cross purposes with the client’s goals and her own business and financial needs. There’s a difference between quality and efficacy.
• Some freelancers are artists, and all freelancers are entrepreneurs. Until artist-freelancers learn the skill of making money, they will struggle to build a profitable and sustainable business. They’ll falsely attribute their struggles to the industry—“people just don’t value art”—instead of their own reluctance or refusal to acquire business acumen.

The “I am an entrepreneur too” identity represents a paradigm shift for many artists. We must give ourselves permission to acquire not one but three sets of skills required to thrive as a creative entrepreneur:

• Those required for the art, craft, or discipline.
• Those required to build a creative business.
• Those required to keep and grow money.

Believe it or not, this is very good news.

Even if you aren’t a once-in-a-generation, world-class talent with writing, filmmaking, design, illustration, development, you name it, you can still build a profitable freelance business.

Other freelancers may respect your work, but that doesn’t mean clients will pay a premium for it. Or perhaps your peers dismiss your work as sub-par, say you represent everything that’s wrong with freelancing these days, and grumble that you don’t deserve clients.

As long as your clients are pleased with the experience of working with you—how you manage the project and make them feel along the way, as much or more than the subjective quality of the deliverables listed in the Exhibit A of your contract—there’s nothing the self-appointed critics and naysayers can do.

In “Make Good Art,” Neil Gaiman encourages freelancers to not underestimate the value and staying power of being pleasant and punctual:

“People keep working in a freelance world and more and more of today’s world is freelance, because the work is good and because they’re easy to get along with and because they deliver the work on time and you don’t even need all three. Two out of three is fine.”[5]

So let’s replace the worn “Art and commerce don’t mix” coin with a better, more nuanced set of assumptions you can bank on.

Art and commerce often mix, and many factors other than aesthetic prowess, originality, and positive reviews come into play.

The logic implied by “art and commerce don’t mix” doesn’t fly, just like pigs. The connection between “good” art and commercial success has always been tenuous. We’ve got critically acclaimed commercial flops and critically acclaimed commercial successes, commercial successes panned by critics and commercial flops panned by critics. There simply is no pattern or prescription for artistic excellence or commercial success or both.

Despite “a resounding lack of critical acclaim,” Danielle Steel has sold over 800 million copies worldwide.[6] All of her novels have been bestsellers, including those issued in hardback. She’s judged for putting out formulaic fiction, and yet she’s the bestselling author alive.

Are her books not “art” because critics pan them? Are critics the only ones who get to decide? As long as you enjoy creating it, does it even matter what they say? History forgets critics, after all.

Do I dare point out Steele Effect? If you find your audience, give them what they want, and get the commerce side right, the art side can slide. All the writers who turn their noses up at pulp and all the artists striving for a singular vision may not like that observation, but the evidence is there in abundance.

How much money you make long term as a creative entrepreneur has more to do with your business savvy and financial literacy than with the likelihood your work will end up in a museum.

Creative skills are especially valuable when combined with other aptitudes and advantages: consistent marketing, strong positioning, juicy offers, well-defined process and timelines, above average results, and an overall satisfying experience for clients.

It simply isn’t realistic to think that you can make a comfortable living creating whatever you like whenever you like.

What makes art “good” has always been up for debate, and we can find plenty of acclaimed artists and less celebrated ones too who did quite well. Achieving financial stability doesn’t mean tainting your artistic expression or vision.

Even Michelangelo had to take commissions he didn’t particularly want—namely, painting the ceiling of the Sistine Chapel.

• ^{[1] https://www.biography.com/authors-writers/ernest-hemingway-wives}
• ^{[2] https://www.grunge.com/188914/the-truth-about-ernest-hemingways-many-wives/}
• ^{[3] https://archive.nytimes.com/www.nytimes.com/books/99/07/04/specials/hemingway-estate.html}
• ^{[4] https://youtu.be/0QKd-ulbH5E?t=2912}_‍
• ^{[5] https://youtu.be/ikAb-NYkseI?si=xotTV2_WPTdjQg5-}
• ^{[6] https://www.publishersweekly.com/978-0-312-11257-8}