5 New York Times bestsellers - Outliers, Blink, The Tipping Point, David and Goliath, and What the Dog Saw - are all the proud work of the celebrated eccentric writer Malcolm Gladwell. Not only is he an author, he is also the co-founder of the audio content company, Pushkin Industries, where he hosts his very own podcast, Revisionist History. He also co-hosts on the famous podcast, Broken Record, where he, along with Rick Rubin, and Bruce Headlam, interview musicians about their lives, inspiration and artistry. 

As an author, Gladwell centres his writing on psychology and history, motivational speaking and outside the box thinking, business, marketing, human behaviour and everything in between. Let’s just say, he is passionate about nudging his readers toward fresher perspectives and reshaping their minds in order to help them grow both personally and professionally, and this list of books will help you do just that.

The Tipping Point: How Little Things Can Make a Big Difference

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In this book, Gladwell explains how a single idea can snowball and turn into an empire - the same way a small spark can turn into a raging field fire. 

According to Malcom, the tipping point is the moment where our ideas go from a mere thought we bounce round from friend to friend, to a well sought out must-have for everyone. But in order for us to ‘spread the fire’ we need to have connections. This is where Pareto’s Law comes into play, where we find the 20% of the carriers to spread 80% of the idea. If we want our idea to go big and beyond, we need to involve 3 major players - Connectors: the networkers, Salesmen: the sellers, and Mavens: the advisors. However, if our ideas aren’t ‘sticky’ enough, that is, memorable, then no matter how much of the idea is spread around, it won’t grow.

Outliers

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Who we are cannot be separated from where we’re from.

According to Gladwell, there's no such thing as a ‘self-made man.’ He believes that it’s through chance, once in a lifetime opportunities and factors that are out of our control that are the true secret to success. 

In this book, we learn how our background - our culture, family, financial disposition, even the year we were born - all contribute to our success rate. He shows us how those who come from lowly backgrounds grow to be big names while those who grew up in financially sound homes sink into the shadows. He also explores why some people, cultures and groups are the way they are - how most “Asians are good at math”, why soccer players are good at what they do, and he even tells us the secret to becoming a software billionaire.

David and Goliath

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For those of us who love a good underdog story, this is an eye opening take on our own underdog experiences. In the original story, David defeats Goliath with a simple sling and stone. Impossible right? Wrong.

In his take on the story of David and Goliath, Gladwell confronts our comfortable view on how we deal and handle challenges and disadvantages, shedding new perspectives on why underdogs win in situations where the odds are not exactly in their favour. He teaches us that instead of cowering in the face of adversities, we need to tackle them head on, like a child who has to work hard to come up in the world - such experiences toughen us and as a result, contribute to our success in the future. Instead of focusing on the strength of our ‘problem’, we need to think about what we are good at and how we can use that to our advantage. 

Blink: The Power of Thinking

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We’ve all had that sickly gut feeling that something is wrong, only to find out that we were right all along and something was actually wrong. Or how we make a choice by chance and it turns out to be the right choice. How? 

Through his book Blink, Gladwell explains how making decisions in a ‘blink of an eye’ and trusting our gut results in more wins than not. But he also explains why some decisions crash and burn. We get to learn the ups and downs of decision making, when to trust our instincts, how our brains really work in stressful situations and why the best decisions we make are often the hardest to explain. Blink reveals how, in order to make good and even great decisions, we need to have perfected the ability to cut out all the noise and focus on factors that really matter when weighing the best course.

Talking to Strangers

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“Don’t judge a book by its cover” is a fitting statement for this book. We all meet people and make assumptions based on what they look like; the energy they give off or some other wild reason. But reading Talking to Strangers gives us a new perspective on meeting new people and will help us understand and judge better and more accurately the people we meet while keeping our heads cool, not losing our patience and actually tolerating others.

Throughout the book, Gladwell offers valuable lessons and insights that challenge abilities we think we have, such as:

1. How we are not actually good at reading people’s thoughts and emotions as we thought we were- it’s just overconfidence in an ability that doesn’t actually exist.
2. How people aren’t good at telling when someone is lying. As much as we think we are human lie detectors, we need the assistance of triggers and tells to tell when someone is lying, and even then, it might now work.
3. How people show and express themselves in different ways, thus making it hard to ever really figure out what they are truly thinking and going through, no matter how much we try to understand them. We can only truly know someone’s thoughts and emotions when and if they tell us.

The Bomber Mafia

In his newest 2021 release, Gladwell examines the Bomber Mafia of World War II, relaying how technology and good intentions colliding in the heat of war resulted in a more ‘moral’ way to bomb people - precision bombing. But when does bombing ever end well?

Gladwell mashes up stories of a Dutch computer genius, a band of brothers from central Alabama, a British psychopath, and a pyromaniacal chemist from Harvard all together to examine one of the greatest moral challenges that America faces. This is a riveting story of persistence, innovation and the do or die calculations of war taken from original interviews and archival footage from Gladwell’s very own Revisionist History podcast. One could say this is a podcast turned book. 

For more dramatic, controversial yet illuminating reads, visit Uptime and get access to all your book hack needs.

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