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Why Is Writing Funny So Hard?4 Min Read

Why is Writing Funny So Hard?4 min read


Quick, answer this question: “When you think of a stereotypical salesperson, what do they sell?”

Scroll down to see the answer virtually everyone gives.

I’ll wait.

Human Interest

Used cars right? Gee, did I give it away? I have no idea how that picture got in there.

Anyway, to most people, selling is synonymous with the not-so-noble profession of selling used cars.

OK, next question. When I say, “I help self-employed people write funny emails that get more attention and meetings.”

What do you think the immediate response is?


Well, when I said this to many people last week at Social Media Marketing World I got one response only:

“That’s really hard!”

Yes, nobody thinks writing something funny is easy.

Everyone seems to think that it’s a mysterious process and that either you’re funny or you’re not.

And writing funny is hard, difficult, impossible. So why even bother trying?

Why is this? Well, armed with my fake doctorate in psychology, I’d surmise that at an early age you were punished for laughing, ridiculed for being silly, or denigrated for your Jim Carey impersonations.

And you never fully recovered from the humiliation.

I hope you can get beyond all that because it’s truly a worthy pursuit to learn how to write funny.

The purpose of humor in writing is to change/alter/modify the state of the person reading your email (or other marketing materials).

You want to lighten things up.

Look, you’re going through your email inbox and almost everything you see is either serious or boring. What to keep, what to discard? It’s a slog.

And then you hit an email that is different, unexpected, absurd, silly or wacky.

And if it’s done well, it elicits a laugh.


The reader can’t help it. It’s unexpected. It just comes. Pow!

And now the reader is immediately in a different state. He or she is smiling and wondering what this is all about.

It’s unusual, different, and provokes curiosity. “What the hell is this?” you think. And so you start reading.

And if the rest of the email incorporates a little more humor here and there, it keeps you reading.

And this is the big challenge of emails, isn’t it? To get you to actually read the damn things.

But if the email is fun, entertaining, different, it stands apart from everything else in your inbox.

Now you are engaged, open, curious, and feeling good about the message.

The whole purpose of any kind of business-related email is to both inform and to nudge the reader into taking action.

And when also you interject some humor, the chances of that happening increases dramatically.

Back to those responses to writing funny being hard.

There are actually some pretty simple formulas that are easy to emulate with a little practice. They make funny writing easier.

The most fundamental is called “The Reverse.”

You create a mental image and then you shatter it.

Here’s an example I liked:

“It has been a few months since we last spoke.  I have been colluding with the Russians. I know, I know, that is not in style these days but I just couldn’t help it. They have such good caviar and vodka.” (by Paul Johnson)

Selling techniques

That’s a reverse.

It’s like calmly walking down the hallway in your office and then falling headlong into a vat of lime Jell-O. Not expected.

The reverse is a perfect device when contacting a past client whom you know.

It’s not unexpected to say you are following up. But it’s completely unexpected to say you’ve been colluding with the Russians.

But it could be anything:

You were kidnapped by a tribe of rogue tax accountants.

You contracted a rare disease that made your skin glow.

Once you have the formula, you just try a number of things until one makes you giggle.

It needs to be unexpected, silly and fun. If it conjures up a visual image, so much the better.

The reverse can be your primary tool for getting laughs from your emails.

But you only get good at it with practice.

One way to do this is by first writing an ordinary email. One that is completely straight-forward and sane:

“I’ve been really busy the past few weeks but wanted to get back to you. I’ve been thinking of some ways we could improve that plan to get even better results.”

That’s expected, normal, and boring. So change the second sentence into a reverse.

“I’ve been really busy the past few weeks but wanted to get back to you. My nefarious plans for world domination took an awkward turn when my cellphone was hurled into a wood chipper. But now that I’ve recovered the data, let me share some ideas with you.”

It’s not boring anymore. It’s fun and a little wacky.

Human Interest

And guess what? People love to work with fun people. The above guy excepted. Avoid him at all costs.

However, if you are determined to maintain your staid, cool demeanor, be my guest. But I’m afraid your emails won’t be getting a lot of attention.

Cheers, Robert

P.S. If you have the courage to actually try this, let me know. What response did you get? I take no legal responsibility for outraged ripostes.

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