Using Metaphor In Strategy
It's an inaccurate but powerful thing to do.
October 28, 2025 - Medellín, Colombia
Today:
More speakers announced for The Sweathead Do-Together - November
Using Metaphors In Strategy
New YouTube: Learn Storytelling from DJs, Memes, and Songwriters
Meet more Medellín friends
Have you read: Is “Strategist” A Personality Type?
Things to do:
Get tickets to November’s The Sweathead Do-Together (NYC, Chicago, online)
Come to our A.I. Show and Tell - Thursday, October 30 - with Natalia Cristin,
Come to my strategy masterclasses in the Middle East and Africa in December and Asia in January and February.
Add me on LinkedIn - I opened my profile after having it closed for years.
Interested in strategy training for your company anywhere in the world or online, find out more here.
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Speaker Announcement:
The Sweathead Do-Together
New York Speakers:
We’re hosting our fourth strategy conference The Sweathead Do-Together this November. In the face of the batshit crazy stuff happening in the world, we’ve decided to do the event in person and online.
Chicago happens on Wednesday, November 19, 2025, from 1pm – 5pm Central Time.
New York happens on Thursday, November 20, 2025, from 1pm – 5pm Eastern Time.
If you buy a ticket to an in-person event, you’ll get access to both days - one online.
But you can also watch both days online with a ticket or a Sweathead membership.
Earlybird tickets are available until October 31.
Bring your team. It’s a great way to re-energize them after what has probably been another intense year.
Here’s our first batch of speakers and our hosts:
New York
Jenny Chang - Cultural Strategist (Host)
Anibal Casso - CSO, Ogilvy North America
Joe Burns - Strategy Lead, Quality Meats Creative, NYC
Geno Schellenberger & Jack Westerkamp - Co-Founders, Breaking and Entering
Madison Giller - Strategy Director, Arnold Worldwide
Sharon Panelo - Founder, Stories & Strategy
Chicago
Pilar McQuirter - VP Strategy, Current Global (host)
Ambika Pai - Head of Brand, TIAA / Podcast Host
Michelle Gerstin - VP, Strategy Director, Critical Mass
Kieran Ots - Founder & Creative Partner at Make No Small Things
Doug Malcolm - Founder, Pale Blue Dot Strategy
Stephanie Kelly - Head of Brand Strategy at Doner
We’ll add a couple more speakers soon.
Find out more here.
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Using Metaphors In Strategy
There are two truths about metaphors that are awkward bedfellows:
Metaphors are useful when it comes to strategic and creative thinking, and
Metaphors can confuse strategic and creative thinking.
I’ll explain after you read these metaphors:
Metaphors For Strategy Careers
Find these in our free ebook “The Sweathead Career Planning Toolkit.”
Chris Charles, Freelance Commercial Director
NOW: A surfer at the top of a massive dam, in control of the flow of the water.
THE FUTURE: A captain in a great ocean, catching the wind in my sails.
Jaymie Rubiano, Director - Marketing, Strategy, & Planning, American Eagle Outfitters Inc.
NOW: An old beloved car that’s stalled out in the driveway.
THE FUTURE: I own the road. I’m in the driver’s seat. I call the shots.
Kat Richards - Associate Director - Experience + Strategy, Digitas North America
NOW: A baby sea turtle wandering into the big ocean.
THE FUTURE: A phoenix that is constantly reborn and re-evaluating where our passions and values lay.
Kavinda Welagedara - Chief Strategy Officer, Fudge
NOW: A one-man-band playing music .
THE FUTURE: Conductor of an award-winning orchestra.
What Is A Metaphor?
A metaphor is “a figure of speech in which a word or phrase is applied to an object or action to which it is not literally applicable.” It’s a symbol.
For example, “freelancing is limbo.” To say this isn’t to say that freelancing is literally a place between Heaven and Hell. It’s to make the point that some people freelance without committing to a more long-term direction. They freelance to bide time. While this can work for some people, it can also prevent more ambitious action such as setting up a company.
Why Metaphors Are Useful
1. Metaphors create new meaning and new meaning creates new energy
An idea brings at least two topics together in a novel way (Topic A x Topic B). Ideas create new meaning. They help us see to ourselves and the world around us differently. Metaphors are ideas. “Strategy is an act of confusion.”
2. Metaphors drag people out of corporate speak
Most business documents I’ve seen in the past decade - yes, including documents from the biggest, coolest companies around - are very hard to understand. They’re riddled with poor writing and business speak. A simple metaphor about an urgent problem that needs solving or about how to reposition a brand can grab people’s attention and make action easier.
3. Metaphors are memorable
As emotional, mental shortcuts, metaphors get stuck in our minds. Getting people’s attention and getting your ideas stuck in people’s minds are the two main jobs of communicators.
The Issue With Metaphors
1. Metaphors are inaccurate because they’re not literal
I remember seeing a LinkedIn debate years ago between strategists in which one said to another, “You’re cherry-picking how you mean the metaphor.” Umm. Yes. A metaphor isn’t literal. So, yes, we need to cherry-pick its meaning.
For the metaphor “freelancing is limbo”, this is what I mean:
i. It’s a place that people go when they’re inbetween directions,
ii. They can get stuck there if they’re not careful, and
iii. If they get stuck there, it can suck there.
This sort of exercise in which you write your metaphor and then write the 3-7 ways in which it is true or in which you are using it is helpful.
2. Mixing metaphors is confusing
If I say “freelancing is limbo for a lot of people” and someone respond, “Sure, freelancing can be limbo, but I just keep swimming toward the next opportunity,” this is a mixed metaphor. Unless limbo is a pool.
3. Using metaphors on creative briefs is risky
A CCO I worked with once loved this single-minded proposition: “Brand X is Aladdin’s Cave.” He knew what to do with it. He knew he needed to capture how incredible it was to enter this store and marvel at what was inside. Sometimes, a metaphor can work on a creative brief. But, usually, people will ask, “What do you mean?” and this is a sign that the proposition isn’t clear.
So, metaphors are worth toying with as ways to reframe problems and brands and as ways to grab attention in a presentation, but make sure you can also explain what you mean.
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New YouTube: Learn Storytelling from DJs, Memes, and Songwriters
What do songwriting, meme-making, and DJ-ing have in common with great strategy?
They’re all forms of storytelling - rhythm, structure, emotion, and timing.
In this episode of Cuts on Craft, three strategists break down how they use music, memes, and story to move people. From emotional hooks to cultural drops, we explore how strategy and creativity share the same beat.
Featuring
Matthew Ryan - Sr. Director, Creative Strategy, Universal
Hayley Truncali - Director of Cultural Insights, Fact & Fiction
Luis Miranda - Group Strategy Director, Critical Mass
Watch now.
More Medellín Friends
Luisa and Manu run Medellín design agency This Is Haww (see their work here). We had a small meetup in June - maybe 15 people. Three of those people are now their clients. So they must be doing something right.
I’ve spent about three months in Medellín this year. The local creative industry doesn’t seem to have a center of gravity here. I could be wrong but I mostly spend time with local friends and I constantly ask them about this.
Having said that, I think it will be interesting to watch how Medellín grows in the coming years. The city has been inundated with tourists, retirees, and digital nomads in the past 5-7 years. This does create jobs but it also makes things more expensive for locals.
For the sake of comparison, Medellín has a population of around 2.5 million and Bogotá, the colder capital, has a population of nearly 12 million (which surprised me). Bogotá has much more industry there - including advertising. It hosts a lot of industry events for Colombia and LATAM but it can also feel closed.
Anyway, watch my Instagram stories for travel content. Medellín has been super interesting to try to understand.
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Peace
Mark
@markpollard
Now
Find out about our strategy classes at Sweathead
Follow us @markpollard and @sweathead
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Find my book “Strategy Is Your Words” here