Seven Essays to Improve Your Thinking in 2020

7 essays to improve your thinking in 2020
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Every year I save dozens of articles for offline reading in Instapaper. This year I did a review of them for the first time. The best ones are timeless essays from independent online writers that helped me improve my thinking. Here are my top seven to help you decide what to read in 2020 to improve your thinking. 

These articles cover topics ranging from personal finance to China, from our history as humans to where we’re headed as a society, and from understanding systems to understanding the flow of information within them. I hope you find as much value in these as I did. 

Climbing the Wealth Ladder, by Nick Maggiulli

“If I gave you $100, would that change your life?  What about $100,000? How about $100 million? Your answer will depend on many things including age, family situation, and your current net worth.  More importantly though, how you change your behavior after receiving such money can tell you a lot about your current financial standing.”

Key Insight: Imagining what you consider a trivial financial decision (e.g., buying new shoes, ordering at a restaurant, or booking a flight) can be a proxy for thinking of your overall wealth and what effort it would take to move up the ladder. 

This article helped me identify immediately where I am and where I want to be from a financial position for our family. Applying the semi-log scale graph below then helps put into perspective the effort required to move up levels. 


Wealth levels based on net worth
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I found this simple heuristic clear and incredibly motivating. 

The Psychology of Money, by Morgan Housel

“Grace Groner was orphaned at age 12. She never married. She never had kids. She never drove a car. She lived most of her life alone in a one-bedroom house and worked her whole career as a secretary. She was, by all accounts, a lovely lady. But she lived a humble and quiet life. That made the $7 million she left to charity after her death in 2010 at age 100 all the more confusing.”

Key Insight: How you think and behave with money is more important to master first than what you do with it. 

This article pairs really well with the first one. Housel lists 20 common flaws and biases he has witnessed through his experience investing. It’s like an anthology of financial advice and I’ve read it countless times, applying so many principles to my own life.

The advice is applicable to more than just finance too. Take this quote on why we struggle to capitalize on the power of compounding:

“Too much devotion to one goal, one path, one outcome, is asking for regret when you’re so susceptible to change.”

This is a good reminder as set out on a new decade and all the reflection and forward planning that inevitably comes with it. 

What is Game B? by Jim England

“If we don’t consider alternate forms and social structures, many worry these problems could accelerate into a civilization-collapsing event.”

Key Insight: The current way we live as a global society is characterized by competition among ourselves, a rivalry that values growth above all else without factoring in the negative externalities of our actions. This will inevitably lead to total destruction. To prevent this, we need to rely on collective sensemaking to create a society that gets stronger through challenges and results in win-win scenarios for all. 

This is a bold vision, still very much under development, and recently popularized by the likes of Eric Weinstein and Jim Rutt. England does a great job introducing the concept and then pointing you to a range of resources for further reading and, critically, getting involved in the movement. 

One of the central points in the article is the concept of collective sensemaking as a superpower, “helping us develop situational awareness and understanding in environments of high complexity, ambiguity, or uncertainty.” 

A key challenge moving forward is to figure out how to incorporate collective sensemaking beyond the Dunbar limit of 150 people (historically, the maximum size a group of humans can reach before cohesion breaks down).

If Sapiens Were a Blog Post by Neil Kakkar

“Future-me should be happy to read this once future-me forgets how we evolved.”

Key Insight: Humans are the only species capable of organizing millions of individuals toward common goals using intangible ideas and incentives. 

This is a great effort at summarizing an important book, Sapiens, by Yuval Noah Harari. I love the idea of condensing 9 hours of material into a 30-minute blog post to refer back to, but what I love even more is how Kakkar has segmented the content and made it interactive by creating clickable images for you to navigate through history. 

This is no substitute for reading the book but once you have, future-you will be happy to have this to refer back to. 

What is it Like to Work in China? by Zara Zhang

“Although it feels like you are scrambling and hustling from meeting to meeting every day without end, the learning and growing are also happening at a rapid pace. China is one of those places where just being there is an educational experience.”

Key Insight: If you think life in the West is a never-ending firehose of information, messages, meetings, and movement, you haven’t seen anything yet. 

Zhang relocated from a busy life in Silicon Valley to Beijing and does a fascinating job describing the difference in this article. Her insights and observations are descriptions of everyday life, but she draws out consistent themes that paint a very real picture of life in China. 

I’m including this article because I think it’s important to study China and I learned a lot from it:

  • Working in China means processing a much higher volume of information, people, and deals on a daily basis.
  • WeChat is the primary source of this.
  • Chinese business communication is very straightforward.
  • People are always late and many things get scheduled or cancelled at the very last minute.
  • Numbers (scale) in China are much bigger.
  • Information overload is the norm.

What the Hell is Going On? by David Perell

“By understanding information flows, we gain a measure of control over them.”

Key Insight: The shift from information scarcity to information abundance is transforming commerce, education, and politics from a centralized, Mass Media dominated environment, to one where information is decentralized and new technology is changing the way we communicate ideas.  

Perell analyzes the flow of information through a media lens, shedding light on why trust in higher authority is corroding, how control of the narrative is dispersing and what this means for uncovering truth. 

A takeaway of mine through the lens of what I am working on is that the keys to success for any information distribution strategy are (1) decentralize information, (2) connect directly with your audience, and (3) reach them via one platform that everyone already uses.

Leverage Points: Places to Intervene in a System by Donella Meadows

“In the end, it seems that mastery has less to do with pushing leverage points than it does with strategically, profoundly, madly letting go.”

Key Insight: This reflection, from the late Donella Meadows, centers on an epiphany she had during a meeting about the new global trade regime at the time (NAFTA, GATT and the WTO). She found herself getting worked up about this new system people were inventing, it’s monstrous scale, and how nobody could predict how it would behave (even though they all talked as though they did). The result is a superb meditation on the relative pros and cons of intervening at the various leverage points of a system. It’s a must-read for anyone new to systems thinking (as I was at the time), and infinitely more useful than what it first appears. 

For instance, in response to the question, how do you change paradigms?

“Keep pointing at the anomalies and failures in the old paradigm, keep coming yourself… with assurance from the new one… don’t waste time with reactionaries; rather work with.. the vast middle ground of people who are open-minded.”

Or this insight into power, control, and resistance to change:

“The higher the leverage point, the more the system will resist changing it — that’s why societies have to rub out truly enlightened beings.”

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