Improvisation is all about sounding natural. Listen to the way Jack Kerouac talks. Listen to the flow, the rhythm of his speech. Like he’s just making it up on the spot and it’s coming out in these long beautiful phrases with perfect balance and control.
Kerouac is known for a style that is influenced by jazz improvisation, it’s cadence mimicking the freewheeling flow of 50s-era bebop. It feels relaxed and full of life, each phrase swinging and rolling down a bumpy road, evoking the raw energy of live improvised music. Composed and performed all in the same breath, one graceful motion.
There’s just one problem– he’s not actually improvising. He’s reading from a page.
You think it would have been as smooth and cool if he had actually improvised? Not a chance. Had he tried to really improvise by composing a passage aloud on the spot, it would have sounded terrible. It would have been stilted, crude, and unpoetic.
(Yes, I know he supposedly wrote On the Road on one long piece of paper. But it was heavily edited before publication.)
This is the great myth of improvisation. Improvisation of any kind is all about sounding natural, and it’s commonly accepted that the best stuff happens when you just wing it. Let it all hang out. Just chill out, man, and be yourself. It’s a romantic idea, and it’s fitting in a country that so esteems individuality, spontaneity, and innovation. Unfortunately, it’s also bullshit. The truth is that behind a veneer of carefree emotion and unbridled enthusiasm is preparation, pure and simple. Lots and lots of boring preparation. There is a paradox at play: to sound natural and carefree, you have to put in the hours and meticulously perfect your craft. If you try to wing it like you think you’re supposed to, you will sound like horse shit. But in everything, we tend see the end product and we fail to notice the work that made it possible.
What does preparation look like? When jazz musicians improvise, they use old show tunes for inspiration. They can take any melody, turn it inside out and upside down, and play a brand new one in its place that still fits into the harmony. Fast and complex, or sweet and lyrical; anything is possible. Think of how impressive this is. They’re basically composing a piece of music in real time. I’ve met musicians who can improvise a better piece of music on the spot than others can compose alone in their rooms after hours and hours of work.
But it’s all a deception, my piano teacher once once told me. When you listen to the masters, you think they’re making it up, but they’re really just rearranging phrases that they already know. They’re not playing anything they haven’t played before in the comfort of their homes. Sure, jazz musicians never play the same song the same way twice, but it’s not like they’re composing a symphony from scratch every time they play. They’re riffing, playing with ideas that are already floating around in their heads.
You and I are improvising every minute. I don’t know exactly what I’m going to say when I engage you in conversation, but I have a general idea of the direction it’s going to take and the topics that will be discussed. I just say the words that feel right at the moment. I’m winging it, like jazz.
One of the ways jazz musicians practice is by memorizing improvised solos of the greats. Miles Davis, Charlie Parker, Herbie Hancock. It’s called transcription. You listen to a particular recording a million times over until you can replicate your hero’s playing note for note, mastering every tiny nuance and inflection. You experience the awesome feeling of what it’s like to have those notes flow through your fingertips or through your horn. But you never play this solo in the real world when you’re with other people. Fragments may come out here and there, but never verbatim. Your own unique twist will be stamped on it, indelibly filtered through your own personality. Yet it still sounds like you’re making it up on the spot, 100%.
Use this information. Apply it to your life. People assume you improvise when you speak, but that doesn’e mean you have to. Job interview? Write your responses in advance and memorize them. Don’t just sketch them out roughly. Do it word for word. Once you have it memorized, it’s easier to riff on. Your actual response probably won’t be exactly what you memorized, but it will be damn close. You may say, “I don’t want to sound like I’m delivering a phony elevator pitch!” But you won’t sound like that if you’ve practiced enough and internalized the words fully. Done right, it will sound a natural and effortless. The preparation will be invisible.
This works for conversation of any kind. Ramit Sethi talks about having a set of 3 to 5 stories that you’ve perfected and can whip whenever you need them. People think they’re spontaneous, and in way, they are. The precise wording and delivery may change, but the foundation does not. People are entertained and are none the wiser to your careful preparation, and it makes you a better communicator. Everyone wins.
Look behind the curtain, and you realize that there’s nothing natural about improvisation at all. I love the irony. Improvisation, the soul of jazz and the foundation of America’s greatest art form, born in a country that esteems originailty and spontanaeity above all else, is only possible through hours and hours of not-so-sneaky plagiarism and endless preparation.
The most impressive people in the world are the ones that make their facility look easy, like they were born to do it. But it’s a lie. Throw away the desire to look like a natural, and focus on preparation instead.