While interning in a state legislature, he said nearly everyone he approached said almost to a one: "Don't go into law."
Plus, he said, "pushing papers in the backroom didn't appeal to me." Instead, Schillerstrom went a drastically different route, honing his love for drawing into political cartooning. He decided to study at the American Academy of Art in Chicago, where, he said, it was the only place he could go where he could concentrate solely on drawing.
In the spring of 1982, on one of his last days at art school, "one of the ladies who was in my class had seen me doing cartoons in my class. She said, 'You know my husband is an editor at Crain's Chicago Business, and they're looking for a cartoonist.'"
He said CCB, a sister publication of Pensions & Investments also published by Crain Communications, wasn't impressed with his first batch of cartoons. But he worked at putting together a second batch and got the job. While Schillerstrom worked freelance for Crain's Chicago Business and worked part time in the customer complaints department at the Chicago Tribune, other Crain publications began to show interest in including his work, and he began drawing for P&I in the fall of 1982. He eventually joined the staff of Crain Communications in 1989 and worked on half a dozen publications for over 20 years.
How does he manage to capture P&I's arcane subject matter? First, he said he "strongly relies on the expertise of you guys."
Given an editorial or opinion piece in advance, Schillerstrom said, "I'll go through the article as it's been edited and pick out a couple of key phrases. Then I'll basically say, 'OK, this is what's good or this is what's bad' or this is what we're addressing, and I'll refine it down to one or two points and then I'll come up with art ideas." Sometimes it's as simple as realizing an editorial is "Humpty Dumpty on the wall" or "two guys in a rowboat sinking."
If the visual metaphors just aren't coming, Schillerstrom has relied on his wife. He also noted that he will usually present the editors with at least two ideas, and he and his wife will have a personal wager on which cartoon they pick.