I've been hosting 1:1's for the @beondeck writing fellowship and the common question I've been getting is "How to write funnier?" Here's a short, common, and hopefully useful response:
Step 1: Have a sense of humor. If you already laugh at things, you probably have one. If not, find the things that make you laugh.
Step 2: It's easier to be funny about the things that already make you laugh, so find what's common/or a pattern/topic/trend/format that makes you laugh and start creating material with it (supplant it, add more and so on)
Step 3: start writing, practicing, tweeting (and not just retweeting everything you find funny). This is hypocritical, I know, but I'm trying to be better.
Step 4: Workshop/find your people/find your writing groups/ find spaces where your work can be understood (I happen to exist in the Venn diagram overlaps of a variety of writing and other communities, so I'm always worried who my audience will be. So I'm still learning)
Step 5: Can't find things to laugh? Here's a small and incomplete sampler: @ankurcomedy @Jest_Iris @shadesofgreaves @showmetheyamz @masiragz @jennycavallero @hijennieblair @bambiambi313 @amsuchanass @ngocbbuii @GeorgiaShenk @bossy_dawsey @rajandelman
/ that marks the end of this unfunny but hopefully useful thread. It is not comprehensive, and perhaps obvious to comedy friends. I'm mostly summarizing the work of fantastic teachers. None of this content is meant to be perceived as didactic thought leadership