Write about things that confuse and bother you
Author Tim Kreider: "Distinguish what you actually think, and how you actually feel, from the things you know you're supposed to think and feel."
I once took a writing class with author and cartoonist
(a great essay by him) and he wrote this in our first assignment email:I tend to think something might make a good essay if I haven’t figured out what to think of it, or how to feel about it. Things that confuse and bother me. (Maybe the sine qua non for a writer is being able to distinguish what you actually think, and how you actually feel, from the things you know you're supposed to think and feel, the opinions and reactions that are publicly sanctioned, and being brave enough to admit to them in print.) It’s more interesting for me as a writer—and also, I suspect, for the reader—if, in the first draft, at least, if I’m not sure where I’ll end up when I start out.
Love that. Great advice for writing interesting jokes too. Find out what you’re unsure about and explore both sides of it. Argue with yourself (and conventional wisdom). Give voice to the opposing view of mainstream society. Find the spots where what you think and feel is different than what society tells you you’re supposed to think and feel.
The great thing about this approach is the premise will hook people in immediately. Doug Stanhope and Bill Burr are both great at using this approach to set up a bit. “Wait, he doesn’t think we should support the troops!? Can’t wait to hear how he explains THAT…”