Sometimes, despite knowing full well that we must create motion, we are unable to do it. Sometimes our minds go blank. The next couple of sections deal with this specifically—how can you think more quickly on your feet? This requires practice; no one who manages it consistently is truly born with such a quick wit. And so how do you practice it? With free association, by simply taking a word and naming a few words or concepts that it reminds you of. The important part is to train your brain’s quick response reflex and break through any mental filters you might possess. You can also choose two words and relate them with a brief story, or flip to random words in the dictionary and use them to create a story.

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Think on Your Feet
Now we know we need to create motion, and yet still, there are times when we are just stuck. Our minds go blank. When we try to think of different things to talk about, our dilemma becomes even worse, like trying to climb out of quicksand. The struggle just makes it tougher. Before you know it, anxiety and pressure start to build, and you’re beginning to sweat on your upper lip.
So let’s simplify conversation.
Conversation is a series of statements, stories, and questions. After one person contributes one of those elements, the other person responds in kind, either on the same exact topic, or a topic that is in some way related to the original one. That’s really it. Sometimes we’ll have trouble thinking of what to say on the same topic, or finding a connection to another subject.
That’s where free association comes in. Isn’t conversation just a series of free-association exercises?
For instance, if someone started talking about motorcycles and you had no experience or impression of motorcycles, then what is your response going to be? You might not have anything to say about motorcycles, but what if you took away the statement and context and focused on the word and concept of motorcycles?
With simple free association, you can find a way to quickly and efficiently breathe new life into the conversation, regardless of how deeply stuck it may feel.
Just free associate five things about motorcycles. In other words, blurt out five things (nouns, locations, concepts, statements, feelings, words) that flashed into your brain when you heard the word “motorcycles.” Allow your mind to go blank and zero in on the word “motorcycles.” Stop thinking of the word as a trigger to past experiences and memory. Instead, start looking at it as a fresh concept unconnected to what you’ve experienced before.
Play a word association game with yourself. What does “motorcycles” make you think of? We’re just talking about purely intellectual connections.
It doesn’t matter what you feel, what your emotions are. It doesn’t matter what your experiences were, whether you were traumatized or not. It has nothing to do with that. This is just a purely intellectual challenge to try to rapidly fill out a list of what “motorcycles” as a concept can connect to.
Let’s switch words. For most people, when the word “cats” is mentioned, they think of kittens, cuddles, sand boxes, cheetahs, lions, fish, sushi, fur, dogs, allergies, the musical, etc. Keep in mind that there is no right or wrong answer here. It’s all free association. What’s important is that you’re rapidly filling out that list of things that you can intellectually connect with the word “cats.”
You’ll notice that doing this is much easier than coming up with a responsive statement or question to the declaration, “I love cats.” Yet, your task and challenge is exactly the same—where do you go with what the other person said? With that framework and perspective, it’s much easier to disassociate from the actual statement and free associate with the subject matter.
Doing this will train your brain to think outside the box, approach conversation in a non-linear way, and see the many possible directions one simple concept or word can take you.
Now suppose that someone proclaimed their love for car racing, and suppose that you know nothing about that either. What are the top five or six free associations that come to mind for car racing?
For me, it’s a mixture of (1) NASCAR, (2) gas, (3) tires, (4) The Fast and the Furious movies, (5) Japan (don’t ask me), (6) Mustangs. Here’s the magic part: each of these six associations are perfectly normal topics to switch to while remaining in the flow of the conversation.
“I love watching car racing! It’s so fun!”
“You mean like NASCAR, or illegal street racing?”
“I always wondered what kind of gas mileage those cars get.”
“Do those cars have specialized tires? I don’t think my car’s tires could take that!”
“So are The Fast and the Furious movies your favorites?”
“I heard they do some kind of drift racing in Japan—do you mean like that?”
“I always imagine car racing happens with huge, powerful Mustangs. Is that the kind of car races you watch?
Try free association with the words “coffee” and “trains” and think about how much easier it is to construct questions and generally converse about something once you can form a mental map of the topic and its related topics.
You just feel unstuck.
Of course, the best way to do this is not to try it for the first time when you’re in an actual conversation. Practice free association consciously several times throughout the course of a week. The more you do it, the better you get at it.
Here’s how to practice: on a piece of paper, write five random words. They can be anything—a noun, verb, memory, or even an emotion or feeling. Suppose the first word you write is “napkin.” As quickly as possible, write three associations for that word. Take the last word you came up with, and then as quickly as possible, write three associations for that new word. Repeat three times, and then move to the next set of words.
Napkin -> table, spoon, fine dining.
Fine dining -> France, Michelin Star, butler.
Butler -> Jeeves, white gloves, Michael Jackson.
And so on.
Or pick a word at random from a dictionary, and list out fifteen words in a free-association word chain as quickly as possible. Then, do it again and again—verbally, because that will require the quickest thinking.
After you grow more comfortable with random free association with words, you can take the next step and choose two random words from a dictionary and pretend they are the name of a company. Then, create a short story about what that company does, as quickly as possible.
For example, the two random words you pick are: bottle, Africa. The short story I would construct about a company named “Africa Bottle” is that they import African homemade liquors.
The final step of this set of free-association exercises is to choose five random words from the dictionary and make up a story that involves all of the words, as quickly as possible.
Again, these exercises are intended to train you to think quickly and be creative, so it’s imperative that you do these exercises at “full speed.” They’ll be tough, and at first, your responses might seem terrible. But, imagine how big the difference will be between your first day and your tenth day, for example. That’s the power of free association, and practice.
If you also care to analyze the similarities between free association and conversation, you might find that they are virtually the same. In conversation, you’ll reply to someone on a topic, a slightly related topic, or a new topic. That’s exactly the type of thought process that free association takes. In a sense, free association trains you to come up with conversation topics quickly.
Practicing free association is an excellent foundation for good conversation because conversation is about relating unrelated things, making connections, and going with the flow of topics. Next time you’re struggling for something to say, take a step back and tap into your previously practiced free-association skills.
Just as with every other aspect of conversation skills, you can only master it if you try it enough times. The best part of all this is that you can do it instantly. You get caught in a stream of consciousness flow. Always remember there is no right or wrong answer. If you believe there is, you’ll be putting unnecessary pressure on yourself.