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Seow Yan Yi
Seow Yan Yi

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Why More Knowledge Isn’t Making Your Conversations Interesting (And How Associations Can Help)

Last week I purchased a particularly nice 24 piece set of pale blue plastic Tupperware containers. It was financially reckless of me but they were in a 25% discount sale. Also it IS summer, can I not let my hair down a bit?

I brought the pack home and arranged the containers on the kitchen table in descending size order, using the bubble sort algorithm. It was at this point I discovered to my delight that there must have been a labelling error at the factory, for there were in fact 26 pieces not 24! I nevertheless felt obliged to check my excitement and call up the manufacturer to warn them of a potentially serious commercial oversight. I spent the next three hours carefully labelling each container and placing them inside one another, testing the interplay between each and writing down the best stack combinations, scoring them out of 10. Two containers in particular have a very impressive flush when the smaller is pushed into the larger. I was in fact so impressed by this that I took said containers to work the following day to show my colleagues this particular example of fine plastic manufacturing. But they just weren’t that interested, I think it’s because they have kids. It’s having children that makes a person boring I am afraid. When you have children you don’t have time for Tupperware anymore.

I came across this amusing answer on Quora a few years back about “What makes a person boring”.

How would you feel if you were in this conversation?

It’s not about how much you know or how much you talk

Most people think that being a good conversationalist means being able to talk at length about anything under the sun.

Engineers would decide to handle this logically and read more books!



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You can talk on and on and yet you’re going to find people dozing off beside you.

You also need variety

Imagine you are in a basketball game. Sometimes you dribble, sometimes you aim and shoot, sometimes you intercept the ball.

Good basketball players have a variety of moves they can play. And they can transition between moves seamlessly.

Associations add that variety

“I don’t know what to talk about” isn’t the real problem.

The problem is you don’t know what topic to transit to after the current one has reached its expiry.

And you don’t know how to do it elegantly.

It might another topic altogether, or a deeper level of the current topic. It can go broader or go deeper.

Understanding the concept of association means you will never run out of things to talk about.

Take a piece of paper and write a word in the middle

And for the next one minute, write as many associations to the word you can think of, forming a mind map. Don’t filter yourself.
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If the word is “raining”, you might think of a huge thunderstorm. Or you feel like snuggling in bed. Or the time you saw a tree collapse during a storm.

Suddenly you have at least 8 more associated topics you can talk about!

Associations don’t have to be logical

They can be stories, your personal experiences, and even how you are feeling right now.

All these are associations stemming from just one topic. Being able to quickly draw links on the fly expands your conversation range tremendously.

Instead of getting stuck with a topic that is running dry you now can transit to another “somewhat related” topic.

Instead of your conversation being like a PhD thesis – linear, logical, technical, it now sounds like an exciting comic book

But why do I still feel like I’ve got nothing to say?

Many years ago when I first started to improve my conversation skills, I didn’t have the confidence to fully be myself.

I was afraid of saying the wrong things. I was too self-conscious and closed off all the possible conversation topics.

I censored myself way too much.

What should I say next?

Will they like me?

Should I bring this up?

Truth is, maybe it matters, maybe it doesn’t. But what got me out of this trap was not wanting to live in hesitation and fear anymore.

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The next time you are in a conversation, try letting down your guard. Open up and explore the associations your mind and heart tells you to.

You might just discover something new about yourself 🙂

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