The Art Of Fresh Thinking: How To Create Obvious & Non-Obvious Content

Don't be too Obvious. And don't be too Non-Obvious.

Dear Friend, Subscriber, and Category Pirate,

What is “thinking?”

According to Roger Martin, arguably the world’s #1 management thinker, “thinking” is when you look at the world through an existing model. It’s how we use learnings from the past to make sense of the present—which is critical when you’re, for example, driving down the highway. When another driver cuts you off, you instantly apply your past experiences to the present and swerve to avoid an accident. Your reflex saves your life. 

But here’s the rub: almost all thinking is what Roger calls “reflexive.” 

Which means our mental scaffolding for thinking is the past. 

Let’s play a game:

Read the following words (slowly) and just notice what happens in your brain. 

• Guns

• Abortion

• Flat earth

• Billionaires

• Democrats

• Republicans 

• Free-speech 

• Climate change

What did you notice? 

Did you have any immediate reactions? Do you already have an opinion? 

Almost all thinking is reflexive (having an unconscious “reflex” in response) versus what Roger calls “reflective” (taking a moment to consciously reflect on how the past may have created a preexisting mental model keeping you from considering a new and different future). 

For example, someone says: “If you’re not for the 1st amendment, then you’re anti-American.” 

The recipient of this opinion experiences a reflex—like when a doctor slams a tiny pink hammer against your kneecap and your leg jolts upward—and they immediately say in response, “I’m not anti-American! You’re anti-American for even thinking that about me!”

This exchange is more akin to the mental Retweeting of information we agree with or disagree with—without any meaningful reflection.

Which causes a scarcity of fresh thinking in the world.

Actual “thinking” is not reflexive. It’s reflective.

You are presented with information.

You become conscious of which model you are using to evaluate the information (which “lens” you are looking through).

And then before you react, respond, or give in to your reflexive nature, you pause and first consider which mental model you’re using to examine the information being presented. You train yourself to be curious, to ask why, to suspend your past opinions, beliefs, and mental models, and to open the aperture of your mind and consider something different.

That’s “thinking.”

(Which is very different from what most people do, which is play a game of  “I’m right, you’re wrong Ping-Pong—you talk, I talk; you talk, I talk—no one really listening or actually thinking.)

Remember, what most people call listening is actually called “waiting to talk.”

The Art Of Strategic (Fresh) Thinking

With the above in mind, then “strategic thinking” (which is maybe one of the most overused yet misunderstood phrases in all of academia and business) is not what most people think it is. 

The vast majority of strategy is thinking “what has been true” about the past. 

• Harvard Business School students read ~500 case studies (about the past) during their 2 years of study.

• Good to Great by Jim Collins is all about comparing similar companies (from the past).

• McKinsey’s own website says that strategy is based on the past:
  
  “Creative data mining enables us to produce privileged insights and finely calibrate strategies that we know work; these are not simply theoretical claims backed by a few cases but rather statistically valid ones based on large-sample learnings from nearly 100 years of experience.”

The vast majority of content about strategic thinking comes from academia and strategy consulting firms. And thinking about “what has been true in the past'' is deeply rooted in their DNA. When you hire (most) management consulting firms, what you’re really buying is a detailed analysis of what worked yesterday. This is exactly what technology analyst firms like Gartner do. They explain the past. 

Academia takes it one step further. Academics can’t publish without extensive research about the past. And any new information has to be rigorously peer reviewed by other professors who are experts about the past. The pinnacle of being an economics or business school professor is winning the Nobel prize. But the Nobel prize in economics is typically awarded for work completed decades ago (based on analyses of data even before that)!

Neither of these are accurate (or effective) definitions of truly strategic thinking.

Strategy, in its purest form, is the art of the possible. 

It’s the process of considering “what could be true.” 

• What new mental model would have to be invented for this to work? 

• What if people moved from the way it is, to a new different way?

• What if a new outcome (an outcome we haven’t considered before) was possible?

For example: in 2008, the idea of Airbnb made no sense when evaluated through old mental models. As a result, nearly every venture capitalist said, “No way. You can’t rent out your living room as if it’s a hotel. That’s insane. Probably illegal. What if someone gets killed in their sleep, or raped? And you really think people are going to want to share a kitchen, or a toilet, with someone they’ve never met before?” Only a very small handful of investors (including the world-class firm, Sequoia Capital) had the courage and mental awareness to ask a different question—a “thinking” question: “What would need to be true for this idea to work?” And what they ended up concluding was that the idea of Airbnb didn’t make sense when evaluated through previously established mental models—but it did make sense through the lens of a new model (a model that was not unfathomable). In fact, it was likely a decade away from being completely acceptable—and thus, “worth the risk” (which helped Sequoia turn roughly $280 million invested over multiple rounds into more than $12 billion). 

(Every legendary business is a dumb idea. Until it isn’t.)

But these moments are rare. Most people (whether they realize it or not) are trapped in backward-looking reflexive thinking. As a result, their “strategic thinking” regresses into an exercise of evaluating the future against the past (this is how management consultants put “food on the family”). But there is no thoughtful, reflective discussion about what “could” be true (the art of the possible). Only reflexive Ping-Ponging monologues about how hypotheses about the future do not make sense against the mental models of yesterday.

Remember: everything is the way it is because somebody changed the way it was.

Some of the “smartest” people on planet earth lose this thread. Some of the smartest people stopped reflective thinking a long time ago. We would even go so far as to say that being declared a smart person is almost certain to make you stupid. Because when you get called “smart,” you become entrenched in your comfortable past. When you’re smart, you know things. And most people who know things are called “experts.” Which means they already know. And when you already know, by definition you are using old mental scaffolding to consider new and different futures. 

Which makes you stupid.

So, don’t strive to become an expert (ever!).

Because being an expert is the enemy of fresh thinking. 

In martial arts there is a manta called “white belt for life”... because fighting is like life. You’ll either be humble in life, or humbled by it.

How To Create Obvious & Non-Obvious Content

In order to build the skill of coming up with fresh, new ideas, we have to first define what it means to “think.”

And here’s why:

• Obvious Content = The art of speaking to what people already think and believe (catering to the reader’s reflexive nature).

• Non-Obvious Content = The art of educating people on what they haven’t thought about or decided they believe yet (requesting their reflective nature).

It’s crucial to understand which of these two consumption states you are creating for, and where you are “meeting the reader”—long before you write even a single word. Because if you try feeding Non-Obvious content (that requires reflection and a challenging of one’s own mental models) to someone in an Obvious (reflexive) state, you will fail to get their attention and/or they’ll likely become frustrated at your inability to cater to their preconceived notions. And conversely, if you try feeding Obvious content to someone starving for Non-Obvious insights, you will burden them with boredom and/or they’ll likely become frustrated with your wasting their time, even insulting them (“This is so Obvious! Make me think!”).

Reflexive readers want Obvious content.

Reflective readers want Non-Obvious content.

Knowing who you are creating for, what their expectations are (and why) is half the battle to becoming a legendary writer, creator, and/or entrepreneur.

The Obvious/Non-Obvious Spectrum

We Pirates are Non-Obvious thinkers, Category Designers, and writers—and are clearly biased in “thinking” in Non-Obvious ways.

However, we want to emphasize the importance of Obvious thinking. In fact, when you are a beginner (trying to learn anything), Obvious action steps and incremental insights are exactly what you need. If you are trying to learn how to play the piano and a world-class pianist sits down and starts explaining Non-Obvious ornamental variations, you will have no idea what to do with that information. Furthermore, you’ll become frustrated. You’ll feel as though the person you sought out for (Obvious) education wasn’t meeting you where you are—triggering all your existing fears and further reinforcing your “newbie” nature. 

Obvious and Non-Obvious thinking (and content) exists on a spectrum.