Now, I'll be honest with you, folks. I hate terrible writing. (You should see me debate the logistics of awful characterization in Japanese giant robot cartoons.) Naturally, I hate what I perceive as terrible comedy writing, and so I've always strided to create the best writing possible.
This Became A Problem.
I mean, this is perfectionism. It's always a problem. Yeah, a desire for excellent quality will ensure you strive to write the best material possible, and I love how that anal-retentiveness keeps me on autopilot. But then you get too anal and it becomes a self-doubting war of "is this good enough" and "I should make this even better" and blah blah blah. We've all been here before.
But writing humor is a double perfectionist sword in that it's easy to obsess over writing amazing articles AND amazing jokes. There's enough material out there to cover perfectionism for other types of writing, so I won't get into that. But since it's tempting to keep fiddling with a joke until it's "perfect"...how do you know when a joke is good enough?
Personally, the easiest way for me to consider a joke "finished" is to match it next to my goal for the piece. Usually when I write comedy, I want the humor to unfold in a certain way. Sometimes it's observational, sometimes it's bizarre, sometimes it's character-driven...things like that. So I look at these jokes after the initial revision and think, "does this joke match the tone I'm trying to set?"
This is important. Because sometimes you WANT the joke to feel basic. There's a real risk of alienating your target audience through clever wordplay, so sometimes you need to ask yourself, "is this enough for my readers to get the point?" And then, I push it a LITTLE bit more, just to satisfy my need for cleverness. But anything after that is overworking it, and I'm much better off moving on.
Like dealing with other forms of perfectionism, this takes practice and awareness. With enough effort, you'll learn when to press on for this as well. (Though that little technique called a "deadline" is always helpful!)