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How to Get Started Painting Portrait Commissions

How to Get Started Painting Portrait Commissions

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Wende Caporale and John Ennis describe their journeys into the business and share tips for getting started.

By Meredith E. Lewis

To hear portrait artists John Ennis and Wende Caporale tell their stories is to learn about artists who clearly are doing precisely what they’re meant to be doing. Ennis is an acclaimed portrait artist with more than a dozen national awards for his work, including 11 from the Portrait Society of America.

Each depicts his or her sitter in a distinctly personal style with a confidence born of equal parts skill and experience. Their success seems so natural—so nearly inevitable—that it’s easy to overlook the fact that it has taken both artists an extraordinary amount of work to get to where they are today.

Circuitous paths to success

As with many of their peers, their career journeys were long and winding. While Ennis began his career as an illustrator, Caporale initially chose a “practical” path in business. Unfortunately, relegating her practice of art to nighttime classes left Caporale feeling frustrated that she had so little time to develop her talent. It was not until a serious car accident, however, that she re-evaluated her priorities and decided to study art full time.

“Once the decision was made,” Caporale says, “I was so determined that things began to fall into place.” She ultimately received a bachelor’s degree in fine art illustration and also worked as a freelance illustrator for 12 years before turning her attention to portraiture full time.

Gritty determination

Caporale’s early business training gave her an edge as she was building her career as an artist. “Being an independent contractor, as most working artists tend to be, we have to be conscious of the cash flow,” she remarks. “When working for someone else, you can depend on regular paychecks and maybe even health insurance.”

Being self-employed has its own benefits, such as writing off expenses connected with one’s business, but Caporale cautions, “It also involves being scrupulous about accounting and being prepared for the lean times. After many years in business, I’ve discovered the phrase ‘feast or famine’ could not be more apt. I’ve learned ways to navigate through and even benefit from these types of circumstances and always feel that it’s just a matter of time before the phone will ring with a new opportunity.”

Organization, the key

There is, perhaps, no other artistic profession that more poignantly illustrates the artist’s dilemma than portrait painting. It allows artists the chance to render a likeness in one’s own signature style for a paying audience, a seemingly perfect mix of opportunities. The more successful an artist is with commission work, however, the more commissions he or she receives, and the less time is left for other types of art.

“Balance is the struggle,” remarks Ennis. “It’s hard to get to my gallery work when there’s always a long list of commissioned work to be done.” Staying organized, he says, is the key. “I often have many projects going on at one time, involving clients, subjects, agents, galleries and travel—and staying organized has been a big challenge.”

Agency and gallery routes

Getting started is the major concern of the emerging portrait artist. As Ennis remembers, this can take some doing. After placing several failed advertisements in local magazines and realizing that there was little market for commissioned work in his native Bucks County, Pennsylvania, he went to a national conference of the Portrait Society of America, where he found himself surrounded by people with similar interests.

He was approached by an agency with which he signed, and the commissions started pouring in. Now when people employ Ennis to do a portrait, they’ve already gone through a vetting process and are not only familiar with his style but have chosen him for it. Ultimately, this allows the artist more creative control over the painting.

Caporale is represented by a number of portrait galleries that help their artists generate commissions. Before she became connected with the galleries, she approached people whose children she believed might make good subjects and asked if she could paint them. “Inevitably, I later sold many of these to the parents and built a reputation by word of mouth,” she recalls. “Every so often, I’ve had the good fortune to have my work reproduced in newspapers, which has yielded a lot of attention and subsequent commissions.”

Whether you’re a well-seasoned portrait artist or just beginning your career, continued success demands dedication and a lot of hard work. Nevertheless, resources abound to help artists of all skill levels; seeking them out is well worth the effort.

Meredith E. Lewis is a freelance writer working in Manhattan.

This article appeared in the May 2009 issue of Magazine, which is available for order as a digital download. Click here to learn more.

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