What Failed Attempts at Writing Humor Can Teach Your about Living Authentically

Gillian Sisley

When people are used to seeing you in a certain light, they feel utterly bamboozled when you flip the script on them.

Photo by Ayo Ogunseinde on Unsplash

I’ve been challenging myself recently to live more authentically ‘me’. Live my truth, every glorious cell of it, and the more I reflected on my online writing the more I realised,

“This isn’t entirely who I am. When did I get so serious in everything I write?”

I’m known on this platform for being an advocate for women, a sexual assault survivor, and a social justice warrior.

The pieces I tend to write are quite heavy — from trauma healing, to living with diagnosed PTSD, to commentaries on problematic behaviours in our culture… the list goes on.

Definitely not topics you can call warm and fuzzy. Important? Yes, absolutely yes. Casual and fuzzy? Absolutely not.

This isn’t necessarily a bad thing, mind you. I write and execute these topics well — they’re my niche. But being as heavy as they are, they also weigh heavily on me as if a writer.

There is a lot of emotional burden involved in writing a social justice piece.

I’ve been looking for a way to lighten the load a bit.

And so, I’ve been asking myself recently, “How can I bring some more joy, wit and laughter into my work?”

I ask myself this mainly because while I’m a serious activist, I’m also a playful, quirky weirdo who loves to laugh and loves making other people laugh.

I have the utmost respect for wit in writing, and creating clever sentences with multiple depths to them.

And thus, in an effort to be more authentically me, all of me, I decided to test out a style of writing I hadn’t really tried online before:


I’m not going to sugarcoat things— people didn’t get the joke. At all.

There’s no other way to put this — half of the readers of these pieces just didn’t realize that I was writing (attempting) humor.

No matter how outlandish, over the top and exaggerated my narrative felt to me, to them I was just being an a**hole, which contradicted what they believed to know about my character and integrity.

And that reaction is not their fault — if anything, that onus is entirely on me as the writer.

I tried to deliver humor, and simply failed at it. Rather spectacularly, in my opinion (which is based on the horrifying comments and shocking feedback I received).

There were a lot of reasons that contributed to why my humor pieces fell a bit flat. The most notable miscommunication that happened here is that the change in tone was too shocking, too unexpected. I write about serious issues related to gender equality, violence against women, and global injustice almost 100% of the time.

There’s not one single thing about any of those subjects that’s cute or funny.

I have built an audience that expects me to write serious, critical thinking pieces — so ‘humor’ just came out of left field and simply didn’t compute with many of them.

The feedback and data would honestly say that I’m just not all that good at humor writing — but I’m working on it.

There’s a good reason humor is considered one of the most difficult art forms to land.

Standup comics? Geniuses in my eyes.

Kyrie Gray? The Queen of Satire writing on Medium. Flawless. All hail Kyrie!

Well-delivered humor is a truly tricky skill, and it’s not one easily learned. But that doesn’t mean it isn’t worth giving a go. Just recognize that in the beginning, just like me, the joke might not land. There might be confusion. You might just publicly flunk it.

I’ve always (playfully) said that one of the biggest reasons I married my husband is that he laughs at my jokes.

I’m going to be very honest with you all — not that many people laugh at my jokes. A select few of my friends think I’m funny, but if I try to land a joke with a wider audience? Well, I usually get crickets.

Now, I know what you’re thinking!

“Wow, Gillian, if you’re really THAT bad at humor you should probably quit it while you still can.”

I mean, you’re probably right.

But the reason I’ll keep trying to fine-tune this not-so-funny bone of mine is because I find humor and wit delightful. And while I haven’t quite hit the mark yet with delivering that to an audience, I’m going to keep practicing and keep trying.

Because being playful and cracking bad jokes is honestly authentically part of who I am.

That may sound odd, knowing me as a serious activist writer, but it’s true.

And I want to be more authentically me this year — and this is part of that process, starting with my writing.

I can’t promise that I’ll hit my next humor piece out of the park (the proof is in the pudding!) but I’m certainly willing to give it a good, honest go.

And whether that authentic part of me is accepted or not? Well, we’ll just have to wait and see.

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