An insightful comment on Hacker News about optimizing for serendipitous conversational insights.

"As Winston Churchill once said when asked 'what are you doing' –> 'Oh just preparing my off-the-cuff remarks for tomorrow'

You cannot prepare for an 8 hour speaking engagement. Not really. But you can accumulate a plethora of anecdotes, metaphors, and remarks that you weave into the narrative or in response to questions.^[af]

You can build frameworks that are similar to code. Prepared functions/coroutines/objects that you run in appropriate situations.

The key is that things you say are new to the audience, but not to you."

The "new to the audience, but not you" is the magic trick.