Find the second right answer
Your first ideas probably won't be your best, so go ahead and beat a dead horse.
"Coming up with great, innovative ideas usually involves much more brainstorming than people think,” according to Loren Nordgren, a professor who’s studied comedians.
“Most people consistently underestimate the value of persistence in the creative process,” writes Nordgren…[He] talks about a fallacy called the “creative cliff illusion,” which is the belief that creativity drops off over time. In one study, they worked with amateur comedians for a caption-writing contest. They surveyed them about how creative they felt over time. “We found that the comedians who were more certain that their early ideas would be their best ideas stopped ideating sooner,” the researchers reported. “These comedians ended up submitting fewer jokes and, importantly, fewer of the jokes that these comedians did submit were rated as being highly creative.” This suggests that if you think your first ideas will be your best, you’re more likely to stop coming up with ideas before your actual best ideas are uncovered. Nordgren and Lucas explain, “it’s only by digging more deeply that more novel, creative ideas finally emerge.”
Your first idea for a punchline probably won’t be your best. Write a list of dozens of possible punchlines and you’ll be much more likely to come up with a twist that’s genuinely surprising/funny.
It can also be helpful to snooze a premise for a bit and then come back to it. Often, your subconscious will keep working on it in the background and a good line will pop into your head later.
“The Second City Way Of Better Brainstorming” offers this tip: Find The Second Right Answer.
Despite the old adage, sometimes it is good to beat a dead horse. You may have come to a few cursory conclusions and found some good-enough solutions, but that's not good enough. Early solutions often aren't the strongest--and they've probably been thought of before. Your job is to go deeper. [Look] for the second right answer. "It takes a little bit of discipline because we tend to jump on the first, obvious solution to a problem."
Again, the first “right” idea is often a somewhat obvious one that goes from A to B, which means an audience will see it coming. But the second (or 3rd or 200th) is more likely to be an A to C one that sparks laughter.
Nina Sunday also argues the second right answer is often the most elegant and offers this advice:
For solution generating use the 20 possible ways method.
Record every idea as it comes to you. Don’t censor ‘silly’ ideas. Record them anyway and then use them to springboard or trigger yet another idea.
Compare the process of writing freehand on paper vs. typing on a keyboard at a computer. Freehand uses a different part of the brain and may generate a different style of thinking.
Plug: Central Pennsylvania! Like a NYT reporter looking to discuss politics with white working class voters in a diner, I'm coming for ya. I’ll be doing two shows in Hershey, PA on Nov 26: Misguided Meditation, my one man show on mindfulness (Misguided Meditation tickets) and then a straight up standup show later that night (standup tickets). Come give me a (Hershey) kiss.