Why the Cartoons, Cy?

The Art of Insight: How The New Yorker Cartoons Shaped My View of Cybersecurity

You might have noticed something a little different about my approach to cybersecurity – a touch of humor, a dash of irony, and soon, perhaps even some stylistic cartoons in my books. It might seem unconventional for a field as serious as cyber risk management, but for me, it’s deeply personal and profoundly effective. The root of this lies in a childhood fascination with those single-panel drawings from The New Yorker magazine.

The Rube Goldberg Conundrum: A Child’s First Encounter with Complexity

Every week, as a kid, I’d pore over the New Yorker, not just for the sophisticated humor (much of which went over my head then), but for the cartoons. There was one particular Rube Goldberg-esque drawing that flummoxed me. It depicted an impossibly complex contraption designed to perform a simple task, with every absurd lever, pulley, and falling object intricately connected. I spent hours trying to understand the “joke”—how each piece led to the next, why it was so convoluted, and where the inherent absurdity lay.

That drawing was my first unwitting lesson in systems thinking, in cause-and-effect, and in dissecting complexity. It taught me to look beyond the surface, to trace the connections, and to find the point of critical failure or ingenious (or ridiculous) design. This, I later realized, was the foundation of what would become my passion for security.

Spiderman’s Web and the Art of Protection

Like many kids, I loved superheroes. Spiderman, in particular, resonated with me. He wasn’t just strong; he was intelligent, agile, and constantly analyzing threats. His “Spidey-sense” was an early warning system, and his web-slinging wasn’t just cool—it was about control, containment, and protecting the innocent by dissecting dangerous situations. The idea of using clever solutions to secure and protect, even if I wasn’t swinging from buildings, appealed to me deeply. The security of things, of people, of systems, even of a complex cartoon’s inner workings, became a fascination.

Humor as a De-jargonizer and a Catalyst for Understanding

Cybersecurity is often portrayed as a terrifying, opaque, and overly technical field. This creates a barrier to entry, leaving managers feeling excluded from a conversation that is vital to their business. Humor, irony, and satire in the style of the New Yorker offer a powerful antidote:

My Commitment: Making Security Human

So, as I develop “The Manager’s Cybersecurity Toolkit” series, expect these elements of wit and insight. Each chapter will feature a cartoon designed not just to entertain, but to subtly (or sometimes overtly) encapsulate the lesson, the moral premise, or a key commandment of storytelling within the context of cyber risk. It’s my way of making cybersecurity human, relatable, and, dare I say, even a little bit fun.

Because ultimately, understanding security doesn’t have to be a chore. It can be an engaging journey of discovery, where a well-placed drawing can illuminate a complex truth, just like those childhood cartoons did for me.

Join me, and let’s find the humor and wisdom in securing our digital world.

Best regards,

Cyrus ‘Cy’ Berger

Author & Cybersecurity Expert

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