How to be witty and off-the-cuff as a slow deep thinker

How can you be witty and off-the-cuff, if you like to think deeply? As Winston Churchill once said to an aide – "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.

I do this too. Maybe you've noticed :)

This is where regular writing becomes a superpower for deep thinkers. You develop ideas in the quiet of your room when the muse strikes, which is every day at 7am. Then you hit publish and get feedback.

Over time you develop a core set of anecdotes and metaphors that you know will land and resonate. The perfect thing to say when someone asks "So how do I know when to pass an object or a value?" or "How do I turn a blob of a project into a roadmap?" or "What is the airspeed velocity of an unladen swallow?.

You sound off-the-cuff, but it's deep thinking that got you there.

Cheers,
~Swizec