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How a Cartoon Caption Contest Can Make You a Better Writer

Peter Boumgarden

July 21, 2015

On the first day of my undergraduate marketing strategy course, I show my

students one of my favorite New Yorker cartoons. It is an image of a familiar

red-and-white-shirted man with matching cap and wooden cane. He sits at a bar.

The caption states, Nobody ever asks How s Waldo? It s sharp. It mixes

familiar and clever. It s classic New Yorker humor.

While a good number of my students chuckle to themselves, few if any are

regular readers of the New Yorker. Many have not even heard of the magazine,

let alone its famous caption contest. But I d like to think unfamiliarity is

par for the course, as even fewer of them expect a weekly humor competition to

be a graded portion of their capstone marketing class.

Each Monday of the semester, I send that week s New Yorker caption contest to

my students, who have until Friday at 5 PM to come up with their own

submission. When all the entries are in, I send them to a team of friends who

work in comedy full- or part-time, asking them to pick the top four. I then

take those four back to the class to have the students choose their favorite.

When done well, the exercise drives a lively class discussion on language and

meaning, and generates a wealth of implications for future marketing

professionals.

The idea first came to me when I read a post on the New Yorker blog by Cody

Walker, a University of Michigan creative writing professor and New Yorker

caption contest winner. Walker started his own contest a number of years ago

with a group of his students at the University of Washington. As a creative

writing professor, Cody s goal is to fix the broken assumptions of the

inexperienced writer. He suggests that inexperienced writers sometimes imagine

that good writing comes from good ideas. But that s not right: good writing

comes from good sentences.

I would frame my goal a bit differently. One thing I have learned through the

discipline of writing is how rarely I can assess the quality of my ideas (or

lack thereof) until I write them down. For marketers, it is easy to rest in

abstractions. Making general statements like I think we can connect to

Millennials with authentic branding is a whole lot easier than writing a pitch

that achieves the goal. This work of moving from general idea to powerful copy

at some point requires the discipline of pen hitting the page, then revising

what s there again, and again, and again. And I would argue the same clarity of

thinking is required outside marketing too, for the entrepreneur or corporate

executive designing a new strategy, for example. We need good ideas in

business, and an important part of producing them is learning how to expose

flaws in our thinking.

In the fall of 2014, one of our judges, Matt Sterenberg, was picked as a

finalist for the real New Yorker caption contest. His entry catered to an image

of two fish swimming in the sea one as a set of bones and one in more

full-bodied form. Matt s caption read, The relationship was less symbiotic

than I d hoped. He ended up second in the public vote. His selection and

overall finish created a lively debate among our judges and students on what

worked or failed to work about Matt s caption versus that of the public winner:

He only wanted me for my body. Was Matt s too obscure, too intellectual?

Could he have framed his joke in a way that was more accessible? It is these

kinds of discussions that help us better understand and work through the power

and flexibility of language.

This playfulness with words is at the core of combining disparate thoughts, of

standing ideas on their head, and it has a great deal to do with the

right-brain/left-brain integration required in a business vocation. In my

experience, business students and leaders too often rely on a style of thinking

that seems cut-and-pasted from some first-year MBA case or bland management

theory, or that s generated creatively but without a corresponding rigor of

thought. To the extent that we think in words, cultivating the discipline of

writing is one practice toward clear and creative thinking. This is true

whether we work in writing or business, live in for-profit or nonprofit worlds,

make our home on Wall Street or Main Street.

While asking a busy business executive to flesh out a creative long-form

article or book chapter is a bit unrealistic, a weekly discipline of submitting

for a caption contest is a move in the same direction. Returning every week to

the journey from an image to an idea to a punchy joke is a great way to train

playful and disciplined thinking, and it has value whether done individually,

within a classroom, or across a larger organization. In this way, I find the

caption contest to be a helpful pedagogy in the most unlikely of places. And

if, in the end, what results is merely a future of business with a splash of

New Yorker humor, then I would venture we still all come out ahead.

Peter Boumgarden is an academic entrepreneur, a professor of management at Hope

College, a faculty affiliate at the William Davidson Institute at the

University of Michigan, and an independent consultant on topics such as

cultivating innovation in an organization s strategy. You can follow him on

Twitter and sign up for his monthly newsletter on business, creativity, and

culture.