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last updated:
March 26, 2021


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Hey! Ashlyn here, OG copywriter for creatives—reporting for duty. 

Let's get you a message so tight you can bounce a quarter off of it. Around here, we serve up science-based storytelling strategies the creative set.  Even while raking in more than 1.26M in agency work since I've been at it, I firmly believe working from a place of rest (not hustle) IS possible—and I want the same for you. Words matter. Best be sure they work (and oui, with math) ... and know how to party while they're at it. 

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Reading time: 10 min.

There are soooo many terrible ways I could start this post—BUT I’m not going there. 😉 I’m just jumping in because I asked on Instagram this morning what you wanted to learn from me and the *overwhelming* majority of you said you were interested in learning about how to write witty, entertaining copy even if you don’t think you’re funny. So that’s exactly why I am bringing you 6 practical copywriting exercises and tips that you can start implementing today.

And I think I’m the person for the job because I know I’m not funny. BUT I get emails saying things like “you’re emails are so funny and encouraging” from leads and email subscribers, potential clients. These are my dream boat customers—the the people I’m trying to appeal to.

How to write witty, entertaining copy | Ashlyn Writes

So here’s the sitch. I don’t know your audience specifically, but I do know this, they associate humor with wit, intelligence and relate-ability. Those are three things they definitely want to see in all the marketing messages that are flung at them day in and day out because they’re human beings.

That’s why in this post, I am bringing you copywriting exercises and tips that you can start implementing today to write wittier, funny, and entertaining email copy. And again, no, you don’t need to feel like you’re funny to be an entertaining writer for your creative small business.

Make sure to read until the end because I’m sharing one thing that you can start implementing in your email marketing strategy and in the next piece of email copy you have to send out—I promise it’s going to make at least one person chuckle.

I just wrapped up an SEO Copywriting series that you guys loved, so we’re gonna kick off in the next few videos I’m focusing specifically on copywriting tips that you can start implementing. So hit the subscribe button on my YouTube channel to make sure you don’t miss out on those.

Don’t forget to click here or down below to grab your FREEBIE: Find Your Brand Voice Guide


No. 1 | Understand why you’re trying to be funny in the first place & establish YOUR brand of funny.

Maybe humor and funny copywriting IS the best way to convey your message—but—maybe it’s not. After all, we know in copywriting that clarity trumps clever any day.

So I wanted to start, before jumping into the rest of these copywriting exercises and tips, with a little come-to-Jesus mindset session and make sure that we’re on the same page about why and when you want to be entertaining…and when you need to not do that at all.

Here’s a quick list of yes, no, and maybe places where I think you can afford or at least most people can afford to be more entertaining or lighthearted in the messaging and when you don’t need to do that because it needs to be clear.

6 copywriting exercies-ashlynwrites

You *never* want to let humor take precedence over clarity.

But here’s my pitch on getting you to listen to these next five copywriting tips and copywriting exercises, like I’ve said multiple times, I don’t think I’m funny but I sought to at least figure out some sort of way to try to be entertaining in my messaging and here is why.

We know that reading or watching something definitely increases our energy levels. You’ve seen this in action in your own life but reading or watching something that you find entertaining increases your energy levels. It reduces and turns down negative emotions and increases people’s perception of you. And I mean, come on, what’s not to love about that list?

Those are things that we absolutely want people to feel and have emotions about as they’re interacting our brand messages. After all, most people do think a marketer is out to separate a fool from his money. So here’s how you can kind of come in and soften it and get people to like you as they read your copy.

The second warning label, though, is that there are different brands of funny. And again, you probably know that. My husband will show me a video that I don’t’ think is funny at all, while he’s off snickering and I’ll be watching some TikTok and he has no idea why I’m cackling, I show it to him. He doesn’t think it’s funny. Some of us like Parks and Rec, some of us like Schitt’s Creek. There’s different brands of funny.

Why does this matter? Because you need to know enough about your brand messaging and brand voice to establish your own brand of comedic voice through brainstorming, trial and a decent amount of error along the way.

So that said, if you have never started creating some sort of mood board for the words that you’re using to describe your brand and the words that you’re using to market your brand, absolutely get started on that. I have a Freebie, it’s a brand messaging style guide starter to help you figure out where your voice lands on the spectrum and how you can start to incorporate that into your brand messaging. It’s an 11 page guide, I know we’ll help you out—you can grab it here. 

Now that we’ve thought through why and where we can actually afford to be funny let me get into some practical tips.

Related:What Is a Brand Story? The ULTIMATE Guide for How to Create Yours (+ Examples)

No. 2| Copybanking.

I want you to start something I call copy banking anddd I want you to do it all. the. time.

A study published in the journal of Consumer Research found that nostalgic feelings make people more willing to spend money on consumer goods and purchases.

Think about some of these car commercials that you see that are playing  sixties and seventies rock music and you can kind of tell who they’re trying to appeal to. People’s sense of humor is so personal because it’s tied to all of our different layers. So you really need to know your audience. And this is why I love my number one go-to copy hack.

Copy banking—this is a complete Ashlynism—but basically study it and load up your ammo. I talk to you about your brand messaging style guide but I also recommend a student’s inside Copywriting for Creatives that you have a copy bank set up, a place where you can file words and notes and messages and gifts and names and things that pop into your world that make you smile or make you think and have some sort of database where you can come back to and pull when you’re stuck.

Related: 3 Hacks to Build Your Copywriting Swipe File

Here’s the kicker—copy banking only works if you’re doing it outside of your industry/your bubble. It’s always going to work best if you’re just being a noticer of life and you’ve got your eyes and your ears open maybe it’s something that someone says a certain way in a sermon or a podcast or in a book that you see.

Here are some ideas to get you started with this copywriting exercise:

  • Quotes
  • Memes
  • GIFs, duh
  • Stories
  • Catchy phrases <<< just make sure they’re from somewhere completely not in your world/bubble … that’s what makes it entertaining … more on this at the end
  • A list of websites that make you laugh to put you in the ~mood~ … Ex. McSweeneys Internet Tendency, Betches,

“Humor is subjective, and comedy is trial and error” – TED Talk. But it’s worth it to eases tension and anxiety and can bring in nostalgia ~feels~ and activates the part of our brain that’s associated with happiness and fulfillment.

No. 3| Drop your reader in the middle of the action.

When you’re telling a story in your marketing make sure that you drop your reader in the middle of the rising action.

Comedic timing is ultimately in the mind of the joke beholder but one of the biggest things that can kill the funny or even just the entertaining factor is when the wind-up takes forever and ever and your audience or your reader is thinking, “Oh my gosh, just say it already, just get to the point.”

Watch any Netflix special about comedy and you can see how much timing and pausing are essential in the delivery of a joke.

So here’s a pretty quick copywriting exercise that you can implement this week for your next social media caption or email that you have to write. If you’re sharing some sort of an anecdote or story don’t wind-up so much before— just drop into the action. Let me show you two examples of this so you can see what I mean from two email campaigns.

The first one is from my friend, Justin. He is such a brilliant writer. Can you see how he doesn’t wind-up too much in advance?

6 copywriting exercies-ashlynwrites blog

And then the second example I have is where I was trying to implement this myself. You can see a little bit of what I mean here—I don’t want to oversaturate with details. I just want to kind of get to the point more quickly.

6 copywriting exercies-ashlynwritesblog

Now timing is ever changing from audience to audience. You’ll learn your flow and your style as you start to write. This is just one simple quick tip that I see all the time. It also helps elevate the energy of the copy a little bit when you’re getting to the point faster and dropping them in that rising action.

While we are on the subject, don’t belabor a point. I’ve learned this from experience just less is more. Little snippets of copy to make people smile can be like ghost peppers, a little goes a long way. 😉

Related:Find Your Brand Voice: How to Add Personality to Your Copywriting

No. 4| Use Microcopy to surprise and delight.

Aristotle said “the secret to humor is surprise”—he wasn’t talking about microcopy buttt he could have been.

Good comedy and copy breaks the expectations of what is normal. **When I say microcopy, I’m talking about things, like eyebrow copy on your website, footer copy on your website, preview copy in email campaigns that you’re sending out—these places are a gold mine to go ahead and include some little quirky messaging.**

Remember in the first copywriting tip, when I was talking about where you can afford to be a little bit more loose and where you can’t, this is what I mean. These places are absolutely 100% places where you can include funny copywriting. It’s like Easter eggs in movies.

No. 5| When in doubt, go with self-deprecating copy.

Poking fun at yourself almost *always* will work. One of the most common denominators you’ll find in delightful copy or comedy is that it’s just relatable and it brings up something that’s common, calls attention to it.

One of the best ways you can do this is to hold up a mirror to your audience and bring up something about you that maybe is not always so flattering and they’ll be able to see themselves in that and appreciate it. I’m gonna give you an example of how you can implement this, it’s what I teased at the top of the post, but this is so easy.

Just go back to the photos of you when you were a little kid and pull out one that’s maybe not so flattering and pull that in and use it as the hook or the start to your email. Maybe it’s you surrounded with your entire beanie baby collection or like this one I used this week. Almost all of us have photos like these floating around. So, you might as well just use it as a hook in an email.

No. 6| Always test your material, just like a real comedian would.

Alright, to wrap up these copywriting exercises, I want you to test your material. You learn humor or wit or funny copywriting the same way you learn anything else, just practicing it. Especially practicing on your audience. We’ve probably all heard of some big-shot comedian who before they made it would go to little bars and practice their set over and over again, night after night until they figured out what worked and what didn’t. It’s the same kind of thing for us as copywriters for our small businesses.

It’s super awkward to watch somebody trying too hard and practicing can get it out of your system. Here’s how I’ve done this in the past.

One thing I always tell my Copywriting for Creative students is to make sure that you let something rest and look at it the next day with fresh eyes. That’s the first safeguard that you need to have—write it, let it rest for a night, and then look at it the next day.

Secondly, get someone from your team to look at it or trade with a friend. I think this is most helpful when they are the target audience or they know that target audience really well.

6 copywriting exercies-ashlynwrites

And then here’s the third tip here—this is what I think is really important—make somebody reads it that is not your target audience. More times than not I will forward an email to my husband before I send it out if I think it has something in there that I’m not quite so sure about. I’ll let him tell me if it doesn’t make sense.

This is a good safeguard copywriting exercise if you’re including some kind of pop culture reference or funny-ism thing that may be over the heads of a lot of people.

  • Does the email still make sense?
  • Does the message still make sense or is it all lost because of that one thing that you used?

Because remember we wanna use these moments very, very sparingly, like salt in your campaigns but you also don’t want to have the message lost completely because clarity is of the utmost importance.

<< Two more small bonus copywriting tips>>

I personally stay away from puns, some people love them. I find that in writing that it’s not as helpful.

Great funny copy is SHORT. That doesn’t mean it took a SHORT amount of time to create. A three-sentence paragraph on your website that brims with wit while also clearly conveying your company’s message probably took some major rewriting and a gallon of copywriter tears to achieve. Be respectful of their work.

That wraps up my 6 copywriting exercises — annnd that was a lot. 😉 If you take nothing else away, make sure that you understand that the concept of having a brand messaging style guide and a mood board for your words is imperative. You can pull into that bits about your style and the memes and gifs and whatever else you like to use in your messaging but to start that you need some sort of voice and tone guide. That’s why I have that freebie for you ready to go, click here or look down below and you can grab the link to it.

Now you have some copywriting tips on hopefully making your writing a little bit more entertaining and pleasant to read, but what about the on-page SEO copy on your website and how to make that not sound like a robot. Well be sure to watch this video next where I’m talking all about how to meld the right SEO keywords with the on-page copy that you need.




How to write witty, entertaining copy | Ashlyn Writes

Reading Time: 10 Minutes Reading time: 10 min. There are soooo many terrible ways I could start this post—BUT I’m not going there. 😉 I’m just jumping in because I asked on Instagram this morning what you wanted to learn from me and the *overwhelming* majority of you said you were interested in learning about how to write witty, […]


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