In a recent LinkedIn post, Justin Oberman delves into the nuanced art of copywriting, specifically exploring how and why breaking established rules can lead to compelling and effective communication. Oberman uses a classic Western Union advertisement as a case study to illustrate his points, emphasizing that not all rule-breaking is created equal.
Oberman begins by posing a fundamental question for copywriters: how does one discern between rule-breaking that enhances a message and rule-breaking that falls flat? His central thesis is that effective rule-breaking stems from the constraints of other, more fundamental rules. In contrast, ineffective rule-breaking occurs when such limitations are absent.
“Good copy rule-breaking occurs as a result of the limitations imposed by other rules. Bad copy rule-breaking occurs when limitations from rules aren’t imposed at all.”
The Principle of Engaging Contrasts
To elucidate this concept, Justin Oberman introduces the ‘rule of engaging contrasts.’ He explains that for an advertisement or any piece of content to be engaging, there must be a dynamic interplay between the copy and the visual elements. According to Oberman, if the copy is interesting, the visual should be simple. Conversely, if the visual is compelling, the copy should be straightforward. He warns that when both the copy and the visual vie for attention, the overall impact is diminished, leading to a lack of engagement.
Oberman applies this principle to the Western Union ad, which features a simple image of a telegram. The accompanying copy, however, is strikingly unconventional: “Ignore It.” This starkly contrasts with the visual, creating the engaging contrast he describes.
“The Western Union product demonstration ad below the image is simple. It is a picture of a telegram. The copy is interesting. “Ignore It.””
When Negativity Serves a Purpose
The choice of the word “Ignore” presents a clear violation of a common advertising adage: always stay positive. Oberman anticipates the potential client reaction, humorously noting the likely request to rephrase the headline to something more positive. However, he argues that in this specific instance, the negativity is not only acceptable but instrumental.
As Justin Oberman points out, the negative headline strengthens the ad’s adherence to the rule of engaging contrasts. This deliberate deviation from positivity serves a higher purpose, making the overall message more impactful. He elaborates:
“But in this case, the negativity is ok. Why? Because it breaks the rule of negativity to make the rule of engaging contrasts stronger. And as a result, its negativity has positive results.”
Recognizing and Applying the Principles
Oberman acknowledges that such effective rule-breaking often happens organically rather than through conscious deliberation by the original creators. He suggests that by studying examples like the Western Union ad, professionals can develop a keener eye for recognizing these underlying principles in other forms of communication.
According to Justin Oberman, the ability to identify what makes ads work can be transferred to understanding the effectiveness of content on platforms like LinkedIn, in newsletters, or on webpages. He concludes by encouraging readers to cultivate this analytical skill to improve their own communication strategies.
📝 About This Content
This article is based on insights shared by Justin Oberman on LinkedIn.
📅 Originally posted on August 8, 2026 | View original post on LinkedIn →