
The most important skill I’ve learned in the last decade
And more importantly, two ways to sharpen it
Over the last decade I've started a tech company, built 2 top 25 apps, self published an award-finalist book (didn’t win 😔) and helped another startup triple their monthly average uniques.
In that time I have, as I’m sure some of you have as well, received tons of advice from different people. I’ve also scoured the internet with a fine-toothed comb for the latest thought leadership in relevant fields. I’ve always believed that if I mentally downloaded as much information as possible it would all come in handy later.
Acquired knowledge, however, is just knowledge. It may sound obvious, but unless you apply your own critical thinking to it — it’s useless. Without thinking for yourself, you’re merely another mime, repeating and regurgitating what you’ve heard in an effort to sound intelligent.
I’m guilty as charged — I’ll often repeat news headlines just to sound smart at dinner. But then I’ll meet someone who actually knows what they’re talking about, and to avoid looking like a fool I’ll just pretend I’m taking an extra long sip of my drink.
The cost of the problem
The societal cost is a generation of people who are complacent in their understanding and apathetic in their action. Look around! You’ll see people blindly voting for a political party without understanding their platform, or using the latest business strategy without knowing if it really fits their context.
The smartest people understand this and question every assumption. They hold extreme points of view that cut through assumptions others take for granted. However, if you manage to dislodge their thinking with a new insight, they’ll change their minds incredibly quick.
Strong opinions, weakly held. — Paul Saffro
If we agree that it’s a problem, what’s the solution? Can we learn to be better at thinking for ourselves?
Entrepreneur and outspoken venture capitalist Peter Thiel is often asked what’s the formula he uses for starting businesses. The reply? There is no formula. The only formula is to think for yourself, unbiased by the socially-derived opinions of everyone around us.

This is nothing new — we all know that assuming and regurgitating others’ opinions isn’t the smartest thing to do. The real difficult part then, is how we go about doing it. The unfortunate reality is that it’s not easy! If it was, flawed assumptions would never happen and we’d live in a world where everyone understands everything that comes out of their mouths.
From personal experience, that’s not the case. There are few things more entertaining for a third party than to watch two people discuss a topic that neither really understands. And there’s nothing more awkward than being one of those two people, which I often am.
Solution 1
Find really smart people who disagree with each other.
To sharpen this skill, all you have to do is find really smart people (they’re not too difficult to find, they’ve usually written popular books or have public blogs) and read their arguments against other people. Then, when they cite who they’re arguing with, find that person and go read what their original thesis was.
There’s plenty of examples of this. Take Peter Thiel, who we were just talking about. If you’re familiar with tech startups, I’m sure you’ve heard of an execution framework called The Lean Startup. It’s super popular, and has been used by the likes of Facebook to build products. Thiel is an ardent opposer of the framework. A quick Google will yield this:

Or, here’s another one of my favorites, the work hard vs work smart debate. On the one hand, here’s Mark Suster, a successful venture capitalist who argues hard work is the key to success. The harder you work, the more opportunities you open yourself up to. The more times you roll the dice, the more chance you have of bending luck to your will and reaching the “overnight success” that so many seek. That’s some sound logic no?
And then here’s DHH, co-founder of Basecamp. He argues that Darwin worked 4 hours a day, and that was enough for him to have an accomplishment that dwarfs the many companies that have 100-hour-work week-founders. Instead of working more, to increase productivity Darwin had to rest for the remaining 20 hours of the day.
Both pose interesting perspectives and logic, both are smart people. Want to improve your “think for yourself” skills? Take a side! Read their arguments and take a side, understanding why it is that you are taking the side that you are taking.
The next time someone talks about working smart vs working hard over dinner (if that’s what you enjoy discussing over food), you’ll be able have a constructive conversation about it. Not only that — but you’ll be developing the one skill that I believe can transform your career, and in many ways your life. That and pear juggling. But I’ll discuss why pear juggling will change your life later.
Solution 2
Another technique I’ve found effective in sharpening your critical thinking skills is to live with a contrarian mindset. Every time you read something, think about a reason why the author is wrong. Treat everything you read as an opinion. If it’s true, great. What are some reasons why it could be false? if there are none, move on!
You may find yourself being super cynical about everything, but if that’s really the cost — I still believe society would be better off with a group of cynics than a group of yes-men, bobbing their heads together like Elvis dolls.
This technique is really effective in spotting critical thinkers vs blind followers as well. Want to ensure that you’re hiring the right product people for your startup? Instead of asking what books candidates have read and what blogs they follow, ask them why they disagree with their favorite authors.

Imagine being on the other side of the table and applying for a job where the recruiter asked you that in your interview. How would you answer?
Personally, I find that an incredibly challenging state of mind to be in. With it though, comes a realization of a. how much I assume things to be true simply based on what others tell me, and b. a sort of liberating thought that almost everything is an opinion and can be challenged.
It takes effort, no doubt. It’s not a natural state of mind to be in and you really have to force yourself to question the tidal wave of information that is unloaded on you every day. The result however is someone sublimely confident in his or her opinions, and is able to make sound decisions and judgement as a result of them.
It’s not a matter of being an entrepreneur or having career success. The skill is the most important one to me because I believe that if a generation of people thought critically about half the things they say — the world would be a much better place as a result.
It’s not that we are dumb, it’s that we’re lazy. We blindly follow what the general consensus is not because we understand it, but because it’s too much effort to unearth why it should be true.




