The Catch-22 of Writing Funny

Jason Falls
4 min readNov 13, 2023
Photo by Glenn Carstens-Peters on Unsplash

Note: This is a revision of a piece I allegedly wrote in 2007, but have no recollection of. It felt like it needed a facelift. So here goes:

In my opinion, I am not an attractive person. Yet, for some reason, I seem to attract people. To panhandlers I look generous. The lost assume I have directions. My neighbor thinks I’ll smile and wave in return. Each of them soon experience the full emotion that comes from a scowl.

While I wouldn’t lay claim to much expertise outside of a few areas of work, I have piecemealed together a modest level of experience as a writer, both for work and play. Occasionally, I’ll attract those with similar interest seeking advice or inspiration.

I’m no Hemmingway, mind you. But when you are ballsy (or stupid) enough to write stories about aliens extracting your sperm for cloning purposes or grabbing evangelical Christians by the nipples, a couple folks might ask how you pulled that off.

(For those wondering, it was a silly humor column and a lifetime ago.)

Being sought after for pointers is awkward for me. A writery type friend of mine named Bill could dance around stories like Baryshnikov, all while cultivating excellence in others willing to ask or listen. I’ve not been that qualified or effective.

Once upon a time, though, an old high school friend blogged about my writing. It was by far the most flattering thing anyone every wrote about me. Part of what she wrote included:

So, I like to read blogs. It makes me happy. However, I have this buddy who makes me feel like a first grader in a Shakespeare class. For one thing, his writing is bang-up funny and interesting. That’s okay. I can compete with that. Here’s the real problem. He writes what he wants to write — whatever that may be. I’ll have to say that I’m a little bit jealous.

That certainly hasn’t aged well. This venue (Medium) is the only place I do that now. That is, if I do it at all.

I’ve sold out. I mostly write marketing drivel, ad copy and press releases for clients and prospects. The hope all along was that each tome made more money to support my family. Then later, my divorce. The writing “for me” never did and wasn’t likely to, regardless of how much fun it was.



Jason Falls

Writer & published author. Marketing strategist & podcaster. Dad. I think I’m funny, too.