Malcolm Gladwell is the author of six New York Times bestsellers. He has been a staff writer for the New York Times since 1996 and is named a three-time top global thinker.

He is one of the New York Times’ Hundred Most Influential People and the co-founder and president of Pushkin Industries, an audio content company that produces the podcast Revisionist History. 

Gladwell’s books were of significant influence to Jay Shetty throughout his early teens and twenties. They helped transform the choices he made. It is not every day that a person gets the opportunity to sit down with someone that had such a profound impact on their life, but Jay Shetty got the chance to do just that.

In a recent ON Purpose episode, Malcolm Gladwell joined Jay Shetty to dive into ways you can effectively communicate in overwhelming situations. They touched on Gladwell’s current book, Talking with Strangers. The book examines how we interact with others we do not know and how those interactions differ from our interactions with the people in our circle. It breaks down the tools and strategies we currently use to communicate with strangers and explains how those strategies invite misunderstanding and conflict into the situation.

Exploiting Contradictions

What does it mean to exploit your contradictions? Gladwell and Jay Shetty unpack the answers to that question. 

“I always find that when you get to know someone, when you really listen to someone, what you discover about them and then ultimately about yourself, is that we’re full of contradiction,” Gladwell explains.

Using himself as an example, Gladwell reveals to Jay Shetty that his father is English and his mother is Jamaican. He has a foot in two very different heritages. When asked which he identifies with, his answer is, “I don’t. I’m both.” 

“Being both is a contradiction,” Gladwell explains to Jay Shetty. “I’ve written a lot about racial issues in my books, and one of the reasons I’m drawn to them is I feel and I see both sides of them. There’s a part of me that’s white. I sometimes see the world through the lens of a privileged white man. Part of me is black, and I sympathize with the other side of the equation very easily and readily and appreciate it. Those two things exist inside of me.”

When Gladwell gets to know people, he can see which parts of their characters conflict, even when they are not in conflict. As humans, we navigate our way around disputes and differences that pull us in different directions. We calculate who and what we need to be in different situations. 

Jay Shetty relates his experience of living as a monk for three years and his life now as a contradiction. As a monk, Shetty spent most of his time in India working on his inner self and serving others. Now he lives in Los Angeles and is a content creator and producer. He loves to embrace the different polarities while implementing the practices he learned in monkhood into his modern daily life.

People ask Jay Shetty how he intertwines monk life elements into his current life driven by external things?

“I don’t see them even as transitions,” Jay Shetty explains. “I see them as a paradox, and I love being a paradox. I enjoy the paradoxical nature of how my mind can go between the two and find connections.”

Too often, contradiction is seen as weakness or controversial. Why is contradiction looked upon as a character flaw? The world has this idea that it can reduce a person’s identity into something singular. 

When someone is a Republican or a Democrat, they become just that. Nothing else about their life matters in the eyes of the world. If you are a trans person, the world identifies you by your sexuality in a public debate, but there is much more to a person than a label. When your mind simplifies something or someone to a singular box, that is when all you see is the contradiction or controversy.

Practicing Tolerance

How can you open your mind to entertain opposing ideas without feeling the pressure to choose or define yourself by them? 

Gladwell shares his definition of tolerance with Jay Shetty. 

“Tolerance is giving people room to live their contradiction,” Gladwell explains. “It is accepting the fact that those things may be a group of identities, responsibilities, and roles that we may be unfamiliar with that may trouble us and cause discomfort or strike us as weird. It’s our job to get over that.”

Jay Shetty adds that tolerance allows people to live in a world where they can be authentically who they are and express every part of that. Being a tolerant person means being kind and embracing people in their complexity. 


A stranger is anyone who is not a member of your intimate circle, and communicating effectively with a stranger is a struggle for many people.  

Humans are built to communicate with loved ones and those in the inner circle. We have an enormous advantage when we have context, meaning the better acquainted you are with someone, the easier it is to communicate. You do not have the luxury of context with someone outside your circle. When you use the same communication tools on strangers as you use with those in your inner circle, the general outcome is a failure to communicate as effectively. 

Gladwell shares an example with Jay Shetty of the Sandra Bland incident in Texas. 

Bland was a young black woman who was pulled over by a white police officer. As he observed her behavior, he thought she was behaving in a suspicious and dangerous way, but she was the furthest thing from dangerous. She wasn’t acting suspiciously. She was upset. She was mad because she got pulled over for no reason, and he didn’t understand that. He confused her being upset with her being dangerous, two very different things.

“If you’re a police officer about to make a consequential judgment about how to deal with someone, if you confuse those two emotional states, you’re making a huge error,” Gladwell explains to Jay Shetty. “All of a sudden, the things he’s holding in his head, the assumptions he’s using to understand her, and the biases he’s carrying are super consequential.” 

The officers found Bland hanging in her jail cell three days after her arrest. The backlash that ensued included protests, and the police officer was indicted on perjury charges and fired from his job, permanently ending his law enforcement career.  

The wrongful death suit that Bland’s family raised against the county jail and the police department resulted in a $1.9 million settlement and procedural changes in the department. 

The knowledge of how to communicate with a stranger could have helped to prevent this regrettable event. Gladwell explores the tools you need to communicate with strangers in his book Talking to Strangers.

Key Mistakes in Communication

What are some of the biggest pitfalls and assumptions made when first meeting a stranger, and how do you avoid making those mistakes?

“Human beings place a great deal of emphasis on that kind of evidence,” Gladwell explains to Jay Shetty. “We use that evidence to send people to jail, to judge guilt or innocence, to figure out whether someone likes us or not. People are pretty confident in the judgments that we make based on that kind of evidence. The truth is, we’re terrible at decoding people’s emotional states from observing their outward map.”

Drawing conclusions based on body language and facial expressions can lead to an astounding number of misjudgments. You are merely making an assumption about someone with no contextual evidence to back it up. 

Digital Communication

In this digital communication era where text messages, Snapchat, and Instagram reign supreme, the conversation’s tone can become lost in the translation. People feel no remorse for saying things that would not be appropriate to speak to your face. It removes the tenderness from the conversation.

Conversations happen differently when you are in the physical presence of another person. 

“We’re probably going to hang out less than if I had come to your office,” Gladwell tells Jay Shetty. “We might have chit chatted before our interview, we might have chit chatted afterwards. If we’d got along, we might have had a meal. Imagine if we’d gone for a walk. Instead of talking face to face, we’d have spoken side by side. Now that sounds like a trivial thing. It’s not a trivial thing, different conversations happen when you walk with someone, because you’re not looking at them. You can have a different conversation.”

Jay Shetty agrees and believes that in-person conversation is something that is missing today. The accountability you feel when you communicate in person is far greater than when you are behind a keyboard. 

While in-person communication may be difficult in the age of a pandemic, making a conscious effort to communicate with respect and understanding will elevate your digital communication experiences. 

There is no way to accurately judge a stranger. We are programmed to take people at face value, and in a functional society where civility is needed, face value is the default. 

No one is transparent and behavior can be tied to unknown circumstances. It is not anyone’s job to judge based on outward appearance. Empathy and understanding can go a long way in communication with a stranger. Put yourself in their shoes. A walk in another person’s shoes is often the shortest distance to understanding where they come from.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode with Malcolm Gladwell on “How To Communicate Effectively During Overwhelming Situations and Mistakes You Make Reading People” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at

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