How to become a better writer? Fail like a comedian.

The best comedians are often not that funny. The reason you see Chris Rock and Aziz Ansari perform hilarious routines with audiences laughing for an hour or more is because that routine is practiced and polished. You never see the duds.

Friends of mine are big fans of Aziz and they’ve seen him perform a handful of times. Once, they caught him in a really small club where he was testing jokes from his cell phone. He was on stage, literally reading jokes from his phone that he had typed out earlier.

Chris Rock does this too.

In gearing up for his latest global tour, he made between forty and fifty appearances at a small comedy club, called Stress Factory, in New Brunswick, New Jersey, not far from where he lives. In front of audiences of, say, fifty people, he will show up unannounced, carrying a yellow legal note pad with ideas scribbled on it.

…he will talk with the audience in an informal, conversational style with his notepad on a stool beside him. He watches the audience intently, noticing heads nodding, shifting body language, or attentive pauses, all clues as to where good ideas might reside. In sets that run around forty-five minutes, most of the jokes fall flat. His early performances can be painful to watch. Jokes will ramble, he’ll lose his train of thought and need to refer to his notes, and some audience members sit with their arms folded, noticeably unimpressed.

…Often Rock will pause and say, “This needs to be fleshed out more if it’s gonna make it,” before scribbling some notes. He may think he has come up with the best joke ever, but if it keeps missing with audiences, that becomes his reality. Other times, a joke he thought would be a dud will bring the house down. For a full routine, Rock tries hundreds (if not thousands) of preliminary ideas, out of which only a handful will make the final cut.

Peter Sims, Little Bets

One of the ways I’ve improved my writing is simply by practicing it in front of others before you get a chance to read it. I’ll find questions on forums like Hacker News, Reddit, or a StackExchange site. And I’ll make answering the question practice for writing a blog post.

I won’t just rattle off a reply in a couple barely intelligible sentences. Instead, I’ll spend a good 30 to 60 minutes crafting something thoughtful. I’ll create multiple versions in a tool like Draft. I’ll reach for thought provoking quotes or personal stories I haven’t told before.

Some of my best posts started this way.

My thoughts on Pricing in Reverse started from an answer to a StackExchange question. Three mistakes I see web designers make was something I’ve practiced responding to over and over again when people wanted design feedback on Reddit.

The external feedback can be useful, but the core reason I’m doing this is to find questions people actually have on their minds and to give myself a chance to fail or succeed in answering it in a unique way. Writing is hard. It’s tough to be creative. It’s tough to find things that still sound useful to me after I’ve written them. But these practice replies give me a chance to experiment with my thinking before I share it with you.


P.S. I’d love to meet you on Twitter: here.

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