The Future of Freelance

For Collegiate senior William Bennett (‘16), drawing has been a hobby for as long as he can remember. Personally, I have gotten to know William as a friend and been able to witness him develop as an artist, from Lower School when we first became friends, to the present, as we serve as captains together on the Cross Country and Track teams at Collegiate. It was obvious William had found his passion for drawing and art at a young age and was encouraged by his parents early on. He comes from a lineage of artists, including his father, Charlie Bennett, and his grandmother, Joan Bennett, who was a professional painter. William’s mother and Collegiate 4th grade teacher Julie Bennett says, “Whether it be firemen or dinosaurs or later baseball players, he would look at photographs of them and notice the striations in the arms and try and replicate that at such an early age. He was completely transfixed with image and figure and trying to represent that. From a very early age, that was something that interested him, and constantly that would be his free time and that would be his choice.” As William has developed new techniques over the years, many of his skills have been self-taught, either through the practice and experience of trying new things or reading books and researching online. Most of William’s early work took the form of pencil and paper sketches done in his free time, but it wasn’t long before he began tackling new mediums.


William working at his desk. Photo courtesy of William Bennett.

In Middle School, William got his first Wacom tablet, a small graphics specialized tablet with a stylus for converting drawings to digital images. At about the same time, William took a newfound interest in Adobe Photoshop and the boundless possibilities that the software unleashes for artists. Commenting on the changing landscape in art today, graphic designer and Adobe Community Professional Rafiq Elmansy says, “digital arts is a natural extension of traditional arts due to the digital evolution in human civilization. In an age when everything around us becomes digitalized, the arts are taking this step towards the digital world as well.” In the general art community, however, there has been an ongoing debate about digital art and whether or not it qualifies as “real art.” Some traditional artists emphasize the importance of physical interaction with a piece, and that by editing on a computer, you are losing that personal touch. Others claim that less effort goes into digital artwork, but many of today’s younger artists, including William, would argue that digital art is just as difficult, if not more so than traditional art, to develop the proper skills and use the technology effectively. Just as painting with water colors, for example, may take hours of practice to become comfortable, working with specialized art applications takes practice and experience to master as well. Monika Zagrobelna, a Polish artist who offers online courses and tutorials in Adobe Photoshop, commented on the debate, saying, “You get a set of tools, but they don’t have any technique assigned to them. What’s more, the techniques of sculpting, drawing and painting are the same between traditional and digital media.” As society continues to move towards the digital world, many artists find it important to not only move on with technology, but also stay in touch with traditional art forms, as they believe both styles complement one another. Zagrobelna says, “You can have great artistic skills without ever touching the paper with a pencil. That’s why good artists have no problem with switching among different media—the soul stays the same while the technique is being changed.”

William's workspace

William’s workspace. Photo courtesy of William Bennett.

For William, as he began broadening his focus from basic sketches to illustrating comics and working on other projects, he found the use of technology to be extremely helpful in expediting the process and making it easier to organize and tell stories. “Once I began working on graphic narratives, that’s when it really became handy… It was a lot quicker and easier to arrange things on the page.” Now, William relies heavily on Adobe Photoshop for the drawing and coloring, and Adobe Illustrator for the lettering, but outside of his main projects, he loves the ability to revert back to pencil and paper drawing whenever he has the time.   

Now that he is a senior, several people at Collegiate and in the greater Richmond community have reached out to William with projects to help design logos, t-shirts, and even book covers. William has been more than happy to help the community while using the opportunities to expand upon his own skills. Since starting Upper School, he has illustrated logos for the Interact Music Festival, the Deb Angstadt Wiffle Ball Tournament, Smash Cancer, the Dover Hall 2015 Collegiate Prom, his band Paddle Faster, The Match, and is currently working on a logo for a Richmond triathlon group. Classmate and fellow band member Jimmy Melnick (‘16) said about William, “He designed a killer t-shirt for our band. He’s truly very talented in both music and graphic art.” During William’s sophomore year, legendary Collegiate Middle School English teacher and Varsity Cross Country coach Weldon Bradshaw was in the process of publishing his book, My Dance with Grace, and called William into his office one day to see if he’d be interested in illustrating the cover. William sent in a few concept drawings, and ultimately Mr. Bradshaw and the people at Brandylane Publishing decided to go with one of William’s illustrations for the final product. William says, “I was happy to be there for Mr. Bradshaw and collaborate on his project.”

Over the years William has been involved in several art classes and programs, but most of what he knows and excels in has been self-taught. At Collegiate he has taken two drawing classes and a painting class with Upper School Visual Art teacher Mrs. Pam Sutherland, who commented on William as a driven and gifted student in illustrating the representational world. She said, “I’ve tried to help him improve his sense of realism, but in a way, he is naturally gifted and has worked so well on his own that in a sense he doesn’t need me.” She has seen William carve his own specific path and succeed to an extent so early on that it almost makes her job difficult as a teacher, but, in turn, allows her to appreciate the work he has done for the Collegiate community. “I honestly think his greatest contribution to the school is how he has elevated all of the graphic design elements of the school in the time that he has been here. I love that he is really entrepreneurial in that way, and he has raised the bar in that respect.”

A sample from The Savage Lyrics

A sample from The Savage Lyrics. Image courtesy of Sink/Swim Press.

Outside of school, William has participated in a few summer programs, including a month-long illustration class at Maryland Institute College of Art (MICA) and a class in drawing and painting at VCU. Some of the specific techniques he picked up were useful, but William considers those classes more helpful in a broader sense, allowing him to determine what he is not interested in and narrow his focus of work. The class William considers to be the most influential in Upper School, though, was actually the Graphic Novel English elective he took as a junior with Upper School English teacher Vlastik Svab. As a part of the class students were required to write their own graphic novels, which allowed William to really dive into some projects and explore what he was capable of with both his writing and illustrating skills. William says he owes much of his current success with Sink/Swim Press to the class, as he showed his graphic narrative work to the publishing company, ultimately allowing him to get a deal for his most recent book, The Savage Lyrics.

When he’s not illustrating, writing, or spending time on his other school work, William can often be found at a local 3Sports at River Road Shopping Center in Richmond, where he works on the weekends. William’s love for running and biking initially brought him to 3Sports, but what he didn’t know was that this job would later lead to his connection with Sink/Swim Press, a small publishing company located in Richmond. William had been a follower of Sink/Swim on Instagram, and one day at 3Sports he noticed a co-worker wearing a Sink/Swim t-shirt. Shortly after discussing some of their work, William learned that this coworker, James Moffitt, turned out to be the owner of the publishing company. William later showed him his graphic novel and other work from his own portfolio, and no more than a few days later he found himself waking up at 6:30 to get started on a script Moffitt assigned to him.


More of William’s work from The Savage Lyrics. Image courtesy of Sink/Swim Press.

Communicating exclusively over Facebook Messenger, William contacted writer Ian Bodkin almost daily, asking for his input and suggestions. He said, “That was one thing, working on a comic, that was really knew for me–the collaborative process and working with other people to tell a story in the best way possible.” William started the project in July 2015, and from then until the end of August, William said the process moved fairly slowly. He experimented with several different ideas and was somewhat apprehensive early on, but he soon gained confidence in knowing what both Ian and James were looking for and knowing that he could consistently produce valuable work. Because of the slow start, he had to devote more time from September through December to meet the January deadline. With all of his other school work and daily sports practice, he would have to drop an extra art class just to make room in his schedule for the project.

Bringing his laptop and tablet to school and working through free periods, William was eventually able to get through the brunt of the work and increase his pace to where he could finish two to three pages per week. After finally completing the publishing process for The Savage Lyrics in January, William is thankful for the opportunity and the connections he has made through the project. “It has been fun sometimes and at times really different. Doing things in the art community is really different than doing things in the Collegiate community, just in terms of the types of people you see at some of these comic book stores, but sometimes it is really cool to have a different perspective on things or to share ideas with people you wouldn’t normally talk to.” Throughout the process, William has had the opportunity to meet several artists, including Chris Visions, a local Richmond graphic designer who has done work with DC Comics, Marvel Comics, and Cartoon Network to name a few. Now, after having done a book signing in downtown Richmond and having given talks at John Tyler Community College, William says, “It’s always cool to see people come out and listen to your book and support what you are doing.”

William at his book signing

William at his book signing with writer Ian Bodkin. Photo courtesy of William Bennett.

Having been with William throughout the process, his mother said, “What strikes me the most is the amount of time he has quietly put into this. He probably put in 25 to 30 hours a week since May, while handling all the other things he did as a rising senior and during his senior year. I’m just in awe with the dedication and time that he puts into it when he doesn’t have to. This is his choice and his passion, and I can’t really take much credit for it, but of course I’m proud!”

William has since signed into a contract with Sink/Swim to illustrate four or five more books as a part of The Savage Lyrics series, and he hopes to continue with other local projects. “I’ve met a lot of cool people in the Richmond community, but I would love to be able to send my portfolio out to some larger publishing companies as well.”

William’s immense success has been in large part due to his independence and personal drive as an artist. His various logos and illustrations that can be seen around Collegiate School and the Richmond community, or his first comic book, published at only age 18, serve as microcosms of the growing entrepreneurial economy we live in today. In an annual study conducted by MBO Partners, the independent workforce in America has both grown immensely and gotten younger in the past five years. In the coming five years, the number of independent workers is expected to grow by 24.5%, which combined with “occasional independents” would make up roughly 45% of the private workforce. More data from the National Endowment for the Arts (NEA) shows that artists specifically have a higher tendency to be self-employed and have a higher education than the general workforce. According to Fast Company, these trends have to do with a rapid change in society. The expansion of technology has generated newfound accessibility and availability of platforms for businesses and independent workers to communicate and find one another, ultimately making it easier for freelancers, like William, to find opportunities for work.


Photo courtesy of William Bennett.

With all of the time William puts into his art, he still views it as an outside project, second in importance to his core classes in school. It seems for now, and at least through college, he will continue to focus on majoring in some discipline other than art as a way to reach his career pursuits. He said, “A lot of people have asked me if I’m going to study art in college next year, and to be honest I plan to major in something else entirely. I think business and writing majors can both contribute to long-term success as an entrepreneur in many career avenues, especially in the art community. I feel confident enough in my knowledge and abilities as an artist that I don’t need to study art — at least as a major — and  sacrifice other educational opportunities that I value just as much as the arts.”

Featured image courtesy of Sink/Swim Press.

About the author

John is a senior at Collegiate School.