> I'm truly impressed about others who can just come up with interesting or funny things to say on the spot.

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

I’m one of those weirdos who does public speaking sometimes. Even 8 hour workshops. 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.

You can build frameworks that are similar to code. Prepared functions/coroutines/objects that you run in appropriate situations. Works pretty well especially in mentoring/teaching/consulting situations. This is also how comedians prep their sets.

The key is that things you say are new to the audience, but not to you. It can be the same metaphor you’ve fine-tuned over dozens of interactions. And the person you’re talking to thinks “Wow that guy is so quick on his feet, how did he come up with that so fast!?”

You can also spot this if you watch talks by popular presenters (Simon Sinek is a good example). You’ll notice the same 2 or 3 core stories getting polished and fine-tuned over years of talks and interviews.

When I was super young, I used to think my dad (who everyone I met seemed to think was extremely funny) had a huge repitoire of hilarious stories, but after a few years I noticed him repeating them and realized he just had a few specific ones that he would re-use with new people, like you mentioned. As someone who tends to be pretty slow to learn how to navigate new social situations, it was eye-opening when I recognized this was something I could do. What's amusing to me at this point is that I'm still not sure he fully realizes that this is something he does sometimes, because he'll still sometimes try to whip out one of the stories when talking to me and then genuinely be surprised when I remind him of some very minor detail about it that he forgot to mention this time he told it.

Jeremy Vine once wrote a story about Boris Johnson which I thought was the pinnacle of this. It was published on his Facebook page and I've since lost the link, so you're going to have to read it on Reddit where someone has posted the whole thing again.

It is uproariously funny and very relevant.

https://www.reddit.com/r/ukpolitics/comments/c1korj/jeremy_v...

It tells the tale of how the man who was going to become Prime Minister of the United Kingdom used to play the improviser and ex tempore comedian, in a practiced and automatic way.

  > “Oh just preparing my off-the-cuff remarks for tomorrow”

  | "Shower thoughts only work, when you put in the work." You have to actually spend time trying to brainstorm something, trying to think of something, and at the end of it you'll've made no progress and be discouraged. But then randomly, later, in the shower, doing something completely unrelated, the idea hits. 

I think we would be naive to assume quick responses are a good measure of one's intelligence[1]. I know this is common, but I think it is missing the same thing that quick responses also tend to miss: depth. You can be fast and deep, but more often people are fast and wrong[2]. More complex the topic the easier it is to be unaware of how wrong.

[0] https://youtu.be/9FL7IZavt1I?t=93

[1] https://news.ycombinator.com/item?id=45242293

[2] https://0x0.st/KcAU.png

[Edit] I wanted to add that I found this method highly effective during my PhD. It requires a balance of churning the wheels and walking away. Progress is invisible until the finish line is in sight, so you need to spend time pushing even if it looks like you are getting nowhere. But at the same time, you need to walk away. If you keep pushing you'll never have that time for those random thoughts. There's a laundry list of famous physicist[3] who used to "only work" for a few hours a day and then do things like go on long walks or play tennis. I think that fits into this model. It seems to be a critical aspect for any creative work. Honestly, I would find that the most common mistake I would make is sitting at my desk for too long. It results in a narrowing of focus. There's a lot of times we want that narrowing, but there's also plenty of times we want to think more broadly. I think this is very true for programming in general. I can sympathize with managers who look at people doing these things and interpret them as being unproductive. But I think the reality is that productivity is just a really hard thing to measure when you're not a machine stamping out well defined widgets. I think this ends up with us just making fewer "widgets" and of lower quality. I mean it isn't like you can measure quality by anything as simple as the number of lines of code or number of Jira tickets knocked off. Hell, if you are too narrow your solutions are probably creating more tickets than you're knocking off! But that's completely invisible, only measurable post hoc, and even then quite difficult to measure (if not impossible).

We often talk about current "titans" and all of them boast their long hours and "dedication." People like Elon suggesting 120hrs or the growing 996 paradigm. But I'm unconvinced this really checks out. If anything, it appears much more common that Nobel scientists worked fewer hours, not more. We're all not working on Nobel level work, but it does beg the question of what the most effective strategy actually is. Certainly we can't conclude longer hours at the desk yields better output. We can't counterfactually conclude that Dirac would have been even greater had he spent 16 hrs a day working rather than a handful. "More hours" just seems to be a naive oversimplification, highly related to these "shower thoughts"

[3] Dirac is a famous example, who colleagues would also jokingly use the unit "Dirac" in reference to "one word per hour". Notoriously "slow" thinker, but a surefire candidate for one of the smartest humans to ever exist. Poincare famously worked 10am till noon then 5pm till 7pm. Darwin followed a similar model.

I once had the opportunity at a comedy festival to see John Mulaney’s same set twice, and it’s pretty wild to see with your own eyes.

Do you have any advice for accumulating and sharing relevant anecdotes? I struggle with sharing anecdotes that have an "Aesop", or directly relatable point, even if I've lived such experiences.