Skip to main content


Blake Henderson

Published on

March 24, 2022


content marketing, copy, copywriting, creative, creative copywriting

I’d known for weeks that I had to write this blog post. It seemed easy, as I could choose the topic myself. I’m a creative copywriter, so I had a general sense of what I wanted it to be about. First it was “How to Write Compelling Ad Copy.” Then it was “The Value of a Short Sentence.” Soon “Crafting a Good Headline” was the big idea, which quickly morphed into “Creative Copywriting Tips” before becoming “Nailing Brand Voice.” However, all these topics felt tried and true, and I really wanted to try something new.

But I was still stuck. There were no boundaries — I was careening from idea to idea and the due date was looming. Then I remembered what I do when I’m stuck on a client project:

I make lists.

These lists originate from my short-lived — and unsuccessful — pursuit of a stand-up comedy career. I first learned of this method when a teacher of mine elegantly broke down how jokes generally work: you find the connections between seemingly disparate ideas and then weave them together to (hopeful, rare) laughter. He recommended finding these connections by creating lists around the things you wanted to intertwine.

Graffiti "good joke. thx" on gray wall

Related: Content Marketing Funnel Themes to Reach Every Customer

How Do These Lists Work?

One column is all the words you can think of around a topic. For this example, let’s go with the recent Winter Olympics. A second column is for, let’s say, out-of-control inflation. [As a note, you can make as many columns as you want, depending on how ambitious you are and what the task at hand is.]

And with that, I made some lists. Just a stream of consciousness around the words on top. Some good, some bad, some “what?” But that’s the point, there’s no bad ideas. Let it all out.

List comparison between Winter Olympics and inflation

After all this creative listing, you get to the juicy part: the connecting. Maybe there’s something between ports and sports? Maybe something else between supply chain and gold medals? You get to really flex your imagination muscles here.

As you can see, I circled, arrowed and chicken-scratched all over this to uncover these (however tenuous) connections to find some fodder for a joke. And because it wouldn’t be fair to you as a reader for me not to take this exercise full circle, here is an attempt at a joke connecting the Winter Olympics and inflation.

So, the Winter Olympics just ended. At a cost of $4 billion, they were the least expensive of all time — when taking into account inflation. Which is funny, because when also taking inflation into account, I paid what feels like $4 billion for groceries last week.

Remember, I said unsuccessful comedy career. But hopefully you get the idea: connect two or more things that people wouldn’t expect to be connected, and you can hopefully surprise and delight them.

How Can This Apply to Effective Copywriting?

Half-formed jokes aside, I quickly realized that this process of listing things could be helpful in all areas of my life, particularly in my work writing compelling copy. But how?

Creative copywriting is about finding the common threads between topics, products, audiences, holidays and more to succinctly tell the story you’re trying to get across. It’s the distillation of complex and sometimes-opposed ideas down into a phrase or a sentence that is easy to understand, riveting, (sometimes) humorous and — when successful — memorable.

In my experience, I have found that the best way to get to the highest quality results is by parsing out all of the components that the client is trying to communicate, making lists of these and then finding the common linkages between them with some creative thinking. Then the copywriting can begin.

Mic stand against orange and purple gradient lights

Related: How to Improve Your PR Writing

Further Connections

Since finding this connective groove here, I couldn’t help but think back more to my comedy-chasing life. The anxious days leading up to the terrified nights on stage. The ill-fated New York-to-LA move. The much smarter and funnier people chasing the same dream. The fear of a joke falling flat. The memories of a joke falling flat. The constant psychic toll of a joke falling flat. Okay we can stop thinking about this now.

But during this reminiscing I was struck by the sense that there were more connections across comedy and creative copywriting than I ever could have thought. So, what did I do? I made a list and tried to find these deeper connections. Take a look.

List comparison of comedy and copywriting

Whaatttt??? Samesies!!

It was then that I realized how I ended up in this career. Creative copywriters, at least this one, are just more risk-averse and job-stable versions of comedians. And we also enjoy significantly lower odds of being heckled by mean audience members (we’re still vulnerable to social media backlash, however). But I digress.

So, what can you take away from this perfectly balanced, two-columned list?

Be Unique

One linkage that deserves to be called out is the importance of being unique. Even if it’s accidental, stealing jokes is essentially a criminal act. You can build off other people’s ideas for sure, but it’s imperative to keep your point of view and your joke unique. For writing good copy, it’s the same thing. There are a lot of shared baselines to work with in the marketing space — with the very real possibility for parallel thought happening — but it’s critically important to always incorporate your own POV into your work, in both approach and execution, to find ways of standing out from the crowd. This is important because by putting your personal twist on things, it helps you better refine your own brand voice while also keeping things more fun — something we can all use more of right now.

Self-Evaluate, Self-Critique, Self-Edit

However, I think the biggest and most important connection I found between these two seemingly unrelated areas is self-editing. Yes, having a great Creative Director and teammates to give you insightful feedback and get you on track is very important, but constant self-refining is the key for creating effective copy and avoiding unnecessary words.

In comedy, a joke can take months or even years to refine to a point where you’re happy with it. You may say the first iteration one night at an open mic to a void of laughter from the audience, but if you believe there’s some nugget of gold in there, you might stick with it and slowly build the joke up. A tweak here, a twist there, a different set up maybe. Over time, the joke may evolve into something totally different than how it began — to become actually successful on stage — but it would never have happened if you didn’t start with that first bad joke and commit to making it work.

The same is true when making creative copy, or in really doing anything, as there’s no perfect final form. But you can work hard to get as close as possible to that form. And while a copywriting job at an agency likely – I mean definitely – doesn’t allow for a timespan of years (or even months) to get to a product you’re happy with, the same self-editing practices apply as much as it does for someone who crafts jokes for a living. It’s just about constantly questioning and stress-testing all that you create, so as to make it better.

Concluding Connections

I could go on expounding about the parallels between what we thought were two seemingly unconnected vocations, but I think there’s enough here already to prove two things:

  1. I created copy for a (hopefully) memorable and unique-to-me product that I self-critiqued and self-edited until the very last minute, all while transparently utilizing the list-making method that was the driver of the whole post.
  2. I wrote a pretty bad joke.


Looking to refine your marketing copy and copywriting skills? Our creative copywriting experts are ready to help. Reach out today!


Get in touch