A student at Shipley from seventh through twelfth grade, Armstrong came to school from his home in West Philadelphia with plenty of artistic talent, but got off to a challenging start, repeating the seventh grade. He persevered, though, and the influence of his teachers—particularly the indomitable Chris Wagner—developed his skills and dared him to be better. “The worst thing an artist can be is convinced of his own greatness, and I walked into her classroom utterly convinced of my own greatness,” says Armstrong, “I had never even heard my work referred to as anything other than fantastic.” Chris Wager, who has led the Shipley art department since 1977, challenged Armstrong’s preconceived notions about his artwork and pushed him to trust his creativity and develop an original style. “She woke me up out of a slumber,” says Armstrong. “She would do anything to get the best out of you. Chris Wagner is a marvel in instruction.”
A Real-Life Jumpstart
In addition to helping him develop his artistic voice, Armstrong also credits Shipley with his professional start. “Every person who aspires to be published—whether in cartoon or writing—needs to have a history of published work. That’s the catch-22,” he says. With Armstrong’s contributions to the Beacon, he became a published cartoonist as a teenager. Then, during the then-required “mini-term,” an internship-like program, Armstrong had the opportunity to work with editorial cartoonist Signe Wilkinson, who was with the Philadelphia Daily News at the time and is now the first female cartoonist to win the Pulitzer Prize for Editorial Cartooning. Shadowing Wilkinson gave Armstrong incredible insight into the profession. “She was smart and critical and showed me how to loosen up my style and think for myself.” Thanks to Wilkinson, who remains a friend to this day, Armstrong was able to learn how to pitch his work to newspapers—which is exactly what he did at the Philadelphia Tribune to become a political cartoonist at just 17 years old.
After graduating from Shipley, Armstrong attended Syracuse University, where he earned a Bachelor of Fine Arts in 1985 and advanced his career by publishing cartoons in the university paper, The Syracuse Daily Orange. The experience and confidence Armstrong earned at Shipley enabled him to be published right away, “all because Shipley gave me a leg up on everybody else my age. I never encountered a true contemporary—at my level, at my age—until much later in life,” says Armstrong. “When I signed my deal for Jump Start, I was the youngest cartoonist in the country, and one of three African Americans,” he says.
Motivated to Succeed
For Armstrong, though, the Shipley advantage runs deeper than professional gains. “The greatest thing that happened to me [at Shipley] is that I actually became part of the world. Shipley gave me an all-access pass into the real world,” he says. Daily travel to and from the contrasting worlds of Armstrong’s West Philadelphia home and the Shipley campus broke down fears of social interaction. He developed an understanding of and appreciation for people from all backgrounds. “Now, I step right into all environments,” says Armstrong, which is incredibly helpful in his career as a motivational speaker. His calendar is filled with speaking engagements at locations from Kindergarten classrooms and universities, to retirement homes and prisons. He aims to motivate with the story of his own success, adapting lessons he has learned to his varied audiences. “Being a public speaker and a motivational speaker, you have to be intimately involved in what’s important to the audience anywhere you go. To be effective in a prison and also in a prep school, you have to understand that it’s about them,” he says.
Armstrong applies almost that same principle to the creation of his daily strip—although instead of a live audience, he looks to his long-time characters, Joe and Marcy Cobb, to guide his voice. “If I don’t have ideas for them, the characters can speak to me. I have to work really hard to relate to these characters, almost the same way I try to relate to an audience. I try not to think about myself, but think about them,” he says. But his hard work has certainly been rewarded, as Jump Start has appeared in hundreds of newspapers over the course of its 23 years in print. But Armstrong doesn’t let that longevity influence his daily grind. He always strives to look forward and be original, just like he learned from Chris Wagner. “A lot of cartoonists do have brief careers. If it happens to anyone, it’s special,” he says. “To keep the career moving forward, it always has to be better the next day, but you can’t stop and think about that too much.”
Wherever his talents take him in the future—he has recently been doing some acting, too—Armstrong looks back on his years at Shipley with remarkable gratitude. The lessons he learned, both personal and professional, have guided him throughout his life. “I’m extremely fortunate to have started off as a lucky little boy,” he says. And while some artists might name a first contract or publication as their break into the creative world, Armstrong simply says, “Really, my big break was Shipley.”