Monday Morning Edge (08/10/2020)

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Greetings from Chandler, Arizona!

Before we get into the newsletter, I have one thing on my mind that I want to share with you…

I know it can be hard to handle all of the reading recommendations you get on a weekly basis–including the ones from this newsletter.

From time-to-time, we all face a common enemy: information overwhelm.

If you ever feel overwhelmed by the volume of information being thrown your way, I want to suggest an article I wrote called Building a DIY Second Brain.

Inside the article, you’ll find a sign-up box for a free email course to learn how to master information overwhelm once-and-for-all.

It’s the most popular article I’ve ever written, and I want to make sure it gets in your hands.

Now, onto the rest of the newsletter…

New Essay of the Week

Coaching from First Principles with Jack Han

I recently had the chance to sit down with former Toronto Maple Leafs coach, Jack Han. Jack is one of the most insightful coaches I know and his newsletter doesn’t disappoint (even though I’m not much of a hockey guy).

I’ve been drawn to Jack’s work because of his unique blend of first principles thinking, analytics, and personal development.

We talked for close to an hour, and in my recap post, I highlighted the best of Jack’s wisdom.

Our conversation covered a wide range of topics, including:

  • How to use video games to build better players
  • The three-step process all great coaches follow (you’re probably forgetting #3)
  • Why Jack chose to write a newsletter when he left professional hockey (instead of going to get a different job)

Read Coaching from First Principles with Jack Han​.

One common theme throughout our conversation was inversion, which is best explained with this Charlie Munger quote:

“It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent. There must be some wisdom in the folk saying, `It’s the strong swimmers who drown.’”

When we try to achieve success, we often think about adding new habits, goals, and pursuits. But inversion requires us to think backward. It leads us to the insight that sometimes the best thing to do is to subtract the unnecessary.

For coaches, inversion looks like focusing less on what will make us a “successful” coach (whatever that means), and instead ask, “What will make me a horrible coach?” and avoiding those things.

In a phenomenal interview with Shane Parrish, Daniel Kahneman shares an illuminating story about the power of inversion.

“What we tend to do when we want to move people from A to B is we push them. We add to the driving forces. Kurt Lewin’s insight was that this is not what you should do. You should actually work on the restraining forces and try to make them weaker. That’s a beautiful point…but it’s like you have the plank and it’s being held by two sets of springs. 

You want it to move one direction, and so you could add another spring that would push it that way, or you could remove one of the springs that are holding back. 

The interesting thing, and that’s the striking outcome, is when it moves, if it moves because of the driving force—you’ve added to the driving force—then at equilibrium, it will be in a higher state of tension than it was originally. That is because you’ve compressed one spring and so it’s pushing back harder. But if you remove a restraining force, at equilibrium, there’ll be less tension on the system. I must have been 20 years old, but I thought that’s just so beautiful.”

I’ve spent a lot of time thinking about inversion lately.

From asking myself, “How do I avoid a miserable 2021?” to “What would I have to do to have my newsletter fail?”, nearly every time I reverse the question and think backward, I end up finding a better answer than when I was thinking forwards.

I’ve found inversion to be one of my greatest thinking tools and because of that, I want to share some of the best articles to help you use inversion to give yourself an edge.

Articles of the Week

Inversion: The Power of Avoiding Stupidity

A perfect introduction to inversion by the team over at Farnam Street.

“It is not enough to think about difficult problems one way. You need to think about them forwards and backward. Inversion often forces you to uncover hidden beliefs about the problem you are trying to solve. “Indeed,” says Munger, “many problems can’t be solved forward.”

Avoiding Stupidity Is Easier Than Seeking Brilliance

Another article from Farnam Street, this time applying the mental model of inversion to playing winning tennis.

“In expert tennis, about 80 percent of the points are won; in amateur tennis, about 80 percent of the points are lost. In other words, professional tennis is a Winner’s Game – the final outcome is determined by the activities of the winner – and amateur tennis is a Loser’s Game – the final outcome is determined by the activities of the loser. The two games are, in their fundamental characteristic, not at all the same. They are opposites…

… if you choose to win at tennis – as opposed to having a good time – the strategy for winning is to avoid mistakes. The way to avoid mistakes is to be conservative and keep the ball in play, letting the other fellow have plenty of room in which to blunder his way to defeat, because he, being an amateur will play a losing game and not know it.

Sam Hinkie by Mike Dariano

One of the great things about sports is that they’re full of great case studies to learn about risk, uncertainty, and decision-making–things we all could become better at.

One of the best recent examples is Sam Hinkie’s 3-year tenure as 76ers’ GM.

Hinkie regularly employed inversion to help him make better long-term decisions to build a championship contender.

This article is one of the best pieces I’ve read breaking down Hinkie. Drawing on Hinkie’s resignation letter, Dariano breaks down who he is, how he thinks, and why he lead the team the way he did. It’s a tremendous read and even though the article is about Sam Hinkie, I wanted to pull out this quote about Bill Belichick to tie it into our theme of inversion:

“One of the adages Belichick always subscribes to is called the inverse theory by Charlie Munger. Instead of saying, ‘What will it take to win?’ you ask the question, ‘What can we do to avoid losing?’ and Belichick always takes that approach.”

The Basic Laws of Human Stupidity by Carlo M. Cipolla

I can’t talk about inversion and avoiding stupidity without sharing one of my favorite essays of all-time.

The author defines a stupid person as someone “who causes losses to another person or to a group of persons while himself deriving no gain and even possibly incurring losses.”

Cipolla then goes through the five basic laws of stupidity which we would do well to avoid.

The Five Basic Laws of Stupidity

  1. Always and inevitably everyone underestimates the number of stupid individuals in circulation.
  2. The probability that a certain person be stupid is independent of any other characteristic of that person.
  3. Human beings fall into four basic categories: the helpless, the intelligent, the bandit, and the stupid.
  4. Non-stupid people always underestimate the damaging power of stupid individuals. In particular non-stupid people constantly forget that at all times and places and under any circumstances to deal and/or associate with stupid people always turns out to be a costly mistake.
  5. A stupid person is the most dangerous type of person.

Thought of the Week

We overestimate the importance of the technical knowledge to work in professional baseball.

Don’t get me wrong, having strong technical knowledge in biomechanics, statistical analysis, or any of the various technologies that are used in the game is important. You could argue that it’s essential to getting a job in the first place.

But one thing that most coaches don’t seem to recognize (or be willing to admit) is that technical knowledge becomes less important than communicating well almost immediately after you get hired.

I put out a mini-thread on this idea last week, and you can check it out here if you missed it.

That’s all for this week. Thank you so much for reading.

If you want to discuss something in this newsletter with me, reply to this email or DM me on Twitter.

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Thank you so much.

Until next week,


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