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Greetings from Chandler, Arizona!

Happy belated 4th of July to my American subscribers. And Happy belated Canada Day to my friends up North!

For as long as I can remember, I’ve spent the 4th of July around a baseball game or at North Beach in my hometown. So, Saturday was a different experience. Instead of surrounding ourselves with friends and family, Jess and I went to our apartment community’s pool before the afternoon rush and then retired to our home where I read 100 pages of Ryan Holiday’s Conspiracy and she went to Target.

It was a good day, but I couldn’t help but think about how strange it all was.

That type of day has become increasingly common for me over the last month. While I do get bored from time-to-time, it also affords me more time to work on each newsletter – like today’s – in which we’re going to cover:

  • What all successful coaches have in common (it’s not what you’d think)
  • How we’re wrong about human decision-making (and why it matters to coaches)
  • Why founders are often so weird
  • And a 5-minute video to help you be more productive

New Essay of the Week

The Coaching Paradox

As I’ve studied the best coaches in sports, I’ve noticed that they all have something in common.

They all seem to be walking paradoxes.

Let me explain what I mean.

Take Bill Belichick, for example.

Belichick has won 6 Super Bowl titles, more than any other coach in history. That should make him a hero, widely respected by football fans everywhere.

Except in many circles, he’s a villain. Whether it’s because of Spygate, Deflategate, or his ho-hum demeanor with the media, he holds villain status in the minds of many.

This is further complicated by the fact that some people (like me) think of Belichick as both a hero and a villain at the same time. I can simultaneously appreciate his coaching genius and dislike him for the scandals that have followed him throughout his tenure in New England.

Belichick is neither hero nor villain. He’s both. And that just help might explain why he’s so dang successful.

This paradoxical pattern repeats itself over and over again with the best coaches.

  • Belichick: Hero & Villain
  • Saban: Beloved leader & disagreeable figure
  • Popovich: Nurturing leader & Authoritarian
  • Stevens: Former strong athlete & Nerd
  • Phil Jackson: Zen Master & Self-professed “asshole”

The list goes on-and-on.

I believe that success is often paradoxical. These coaches demonstrate that.So what does this mean for you?

I believe that embracing paradox might be one of the most important things you can do to improve your coaching.

Find out why: Read The Coaching Paradox today.

Book of the Week

This week’s book of the week is Rory Sutherland’s Alchemy.

I’ve written | about | this book | before. But today we’re going to talk about something new.

We’ll get started with three quotes:

1. Conventional wisdom about human decision-making has always held that our attitudes drive our behaviour, but evidence strongly suggests that the process mostly works in reverse: the behaviours we adopt shape our attitudes.

2. The error of the environmental movement seems to me to be assuming that it is not only necessary for people to do the right thing, but that they must do the right thing for the right reasons. My own view is more cynical, and also pragmatic: if people adopt behaviours that benefit the environment, we shouldn’t really care what their motives are.

3. As we have seen in this section, it is only the behaviour that matters, not the reasons for adopting it. Give people a reason and they may not supply the behaviour; but give people a behaviour and they’ll have no problem supplying the reasons themselves.

When it comes to getting people to adopt a behavior, what matters more: someone doing the behavior or someone having the right motives behind a behavior?

That’s a silly question. Of course getting people to actually do the thing is most important.

But when it comes to coaching, we’re not very good this (or maybe it’s just me).

Most people get into coaching because they have an appreciation for the finer details of sports performance. We’re perfectionists at heart. And as we should expect, that perfectionism gets transferred over to our players.

Have you ever worked with a player and gotten so detailed that you walked away from the session with your stomach in knots knowing you just made him worse?

I have. It sucks.

In those moments, I wasn’t content with getting a player to simply move the right way. I also had to get them to think “properly.”

In my mind, I wasn’t doing my job unless the player understood exactly why he was doing what he was doing.

I was like the environmentalists who insist that it’s not enough to recycle, you also have to recycle for the right reasons.

As coaches, it can be scary to allow our players to come up with their own thoughts for what they do. Knowing that our players might be doing the right thing for the wrong reasons is enough to haunt us during the wee hours of the morning.

But, I propose that we need to let go of this perfectionism and take a more pragmatic approach.

As Paul Gamble writes about in The Illogic of Being Data Driven,

“When dealing with complex phenomena such as human performance it follows we need to temper the industry drive for optimisation.”

Obsessing over optimization is the bane of the modern coach. We would do well to temper that drive and allow our players to supply their own reasons, even if their reasons are wrong.

Because if we can’t, what does that say about us?

Long(ish) Read of the Week

The Founder’s Paradox – Peter Thiel’s CS183: Startup – Class 18

Back in 2012, Peter Thiel taught a class on startups at Stanford.

One student, Blake Masters, took copious notes and turned them into a series of 19 incredible online essays. Two years later, Masters and Thiel joined together to formalize the book and turn it into Zero to One.

If my new essay on coaching paradoxy piqued your interest, you’ll want to read the essay that I drew inspiration from.

Masters’ essay from class #18 covers the rise and fall of Brittany Spears, the assassinations of Lincoln and JFK, and whether Lady Gaga was really born this way.

It’s more philosophical than your usual article on coaching, but a smart coach like yourself will see the application.

You can read the whole essay here.

Random Bit of the Week

Alive Time or Dead Time: You Choose If This Time Is Productive Or Not

My takeaway from this Ryan Holiday video isn’t anything earth-shattering. Each time I return to this video, I’m reminded of the importance of owning my time.

Choosing what I do.

Making time my ally. Not my foe.

This week, will you choose to fill your time with Netflix, Instagram, and every other distraction?

Or will you make time come alive?

Photo of the Week

Since moving to Arizona, I’ve realized two things:

1. Arizona sunsets really are the best

2. iPhone cameras are notoriously bad at capturing them

That’s all for this week. Like always, feel free to respond to this email or DM me on Twitter if you want to discuss the essay or share a link you come across that you think deserves a feature in a future edition of Monday Morning Edge.

Thank you so much.

Until next time,


P.S. – I recently sat down with Will Connerly and recorded a 1-hour podcast where we talked about a host of fun topics. Check it out on Apple Podcasts.