Issue #48: The Pros and Cons of Thinking
​Read this on my website​

I started writing this at around 10pm my time on Friday night, which is awfully late for a newsletter that was supposed to go out in less than 11 hours. I had a conversation with someone late this afternoon, though, that compelled me to scrap this week's topic and write this.

The call was just to catch up. We've known each other for several years. This person, who understand the industry back-to-front and subscribes to my newsletter, said something immensely gratifying:

“I learn a lot from you, and I really like the way you think.”

I'm paraphrasing, of course, because had I know this person was going to say this I'd have recorded it for posterity! It took him about 30 seconds to get the full thought across but the gist of it was this:

“You think in an complete and organized way. It is rare for me to read your writing and think ‘yeah, that's interesting, but I kind of already knew that.’ Instead, there is a fullness and depth in your writing—and thus your thinking—that is unusual and genuinely insightful. I am constantly learning from you.”

And, as has happened to me so often before, I basically spent the rest of the day thinking about this. Thinking about thinking.

What does it mean to “think’?

I don’t really care what the dictionary says. I always thought people were good thinkers if they did three things in increasingly larger circles:

1. Within their specialism, they were able to develop a framework that allowed them to make sense of their area of expertise. The framework was robust enough such that it could even handle unknowns and new topics.
2. Outside their specialism but still within their broader domain, they were able to extend that framework that allowed them to make sense of that domain. The framework was also robust enough to handle unknowns and new topics.
3. They were able to connect their domain to the wider world, thereby creating a worldview linked to a lived reality, from which they could envision an endogenous push and pull by which external events impacted their domain, and vice versa.

Doing the first of these is not very difficult. Doing the second takes time, but can be accomplished over the long arc of one’s career. Doing the third is hard. Doing the third means you’re talking about states of nature and macro-level truths about occasionally micro-level behavior.

There is also a fundamental need for receptiveness to criticism. A framework doesn’t become truly robust unless it can withstand both legitimate and illegitimate challenges. This is also hard, if only because it bruises one’s ego when someone dismantles your argument with an angle you hadn’t considered.

The bottom line is that thinking is about adding and subtracting, of converging and diverging, of constantly challenging what you think you know. In my experience, real advances in thinking, unsurprisingly, become possible when you are in over your head. My own ability to think in ever larger circles started in graduate school as I pursued my doctorate. I would have been unable to consume, much less integrate, the requisite literature without this capability. It was hard at first, but it allowed me to graduate with distinction. As I made my way into the business world, I found that the same capacity to organize information and make connections within and outside my domain was crucial to my success.

The Pros of Thinking

Some people will equate my conception of thinking to being good at strategy. It’s certainly close. I find that strategy is one of those terms that is used too casually in business, and whose meaning is poorly understood. I have met countless people who believe that strategy is merely the sequencing of multiple tactics to achieve an outcome. It may in fact be the right strategic move to pursue those tactics, but for me the difference lies in understanding WHY it should work, WHY a set of actions makes sense in the broader scheme of things.

The key benefit of thinking is that, once you have a worldview, it becomes far easier to know what to do. The paths narrow. The choices diminish in number. Clarity emerges. The more you refine your thinking—the more you iron out the wrinkles and dissonance—the easier it becomes to do your job, and especially to navigate business cycles and periods of uncertainty.

The Cons of Thinking

I remember the first Myers-Briggs test I ever took. I was an INTJ, or what they call a Mastermind. I was pretty pumped about this. Not only was it a rare set of skills, I thought it was super cool to be called a Mastermind. Then I read the primary weakness of this trait: finishing. It turns out Masterminds aren’t intrinsically great doers, and that described me to a T for the first ten years of my career. I got super excited about putting the plan together, but lost interest as we ground through the details of its implementation. The larger the organization, the harder things were to do.

I have changed all that. What once was a huge weakness is now, according to one recent former colleague, my superpower. He told me I get even the “hardest shit” done. But therein lies the challenge to thinking. But therein lies the challenge to thinking. At some point you need to do. At some point, all the thinking in the world will not get you over the hump of a decision, or tell you how to respond in a crisis. In fact, during times of crisis and enormous complexity, sometimes you have to throw all that thinking out the window and rely on instinct and the people you’re with to get you through.

When I look back at the best executives and leaders I’ve worked with, this is what I see. I see people who understand how the pieces fit together. I see people who use that thinking to know what to do. And I see people who know when they need to put all those principles aside and just get shit done.