Monday Morning Edge (8/3/2020)

🎉Welcome to all 17 new subscribers who are reading their first ever Monday Morning Edge newsletter!🎉

Greetings from Chandler, Arizona!

Welcome to the 10th edition of Monday Morning Edge!

While celebrating the 10th newsletter seems a bit trivial, I think it’s important to recognize this achievement in the context of today’s world. 

With so much uncertainty about the future, I create this newsletter to help coaches and leaders like yourself continue to grow in spite of the very real daily challenges we face.

While major league sports are back on TV, many coaches still find themselves reserved to sitting in front of their computer on Zoom calls, watching games on TV, and dreaming about getting to work with athletes in-person again. While I can’t fix those problems, I hope this newsletter leaves you with a fresh glimpse of hope and excitement about the important work you do.

Today’s newsletter is no different.

In a time like this, positive thinking about the future seems highly contrarian. But as Morgan Housel points out, optimism is the most reasonable stance.

Which is why now seems like as good of a time as ever to devote an entire newsletter to thinking about (and building) a better future.

I hope you’re excited for today’s topics, which include:

  • What it means that software is eating the world
  • Why having a positive vision of the future is the first step of actually building one
  • Why nothing in life can be decontextualized (from Pep Guardiola’s mentor)
  • Why you should stop chasing “productivity”
  • And how coaches can (and should) use content as leverage to grow their careers

Book of the Week

This week’s book of the week is Breaking Smart by Venkatesh Rao.

We don’t have to look far to see the technological revolution that’s shaping the future of sports. Everywhere we look, coaches use technology to help their teams get better. But even though technology seems ubiquitous in sports, we still struggle to grasp what this technological revolution is about and how the software we work with each day is changing the entire world.

Marc Andreessen (the guy who basically invented the web browser) famously said that “software is eating the world.”

This 22-part essay series is a thorough analysis of what software eating the world means, how it came to be, and how the software programs we use everyday ushered in a new way of living.

The essays are available for free over on, or you can purchase them as a Kindle eBook.

With that being said, I wanted to pull out two interesting themes from the series that I think especially apply to coaching.

#1 The Serendipity of Streams

All realtors know that finding a home is all about location, location, location. ​In ​Breaking Smart,​ Venkatesh Rao points out that the software-driven world we all inhabit is all about connections, connections, connections.

When it comes to our working lives, we’ve been told that we need to focus. We’re instructed to focus on the one thing, do an essentialist purge, schedule time for deep work, and become a digital minimalist. But Rao argues that this is an inferior model of work.

A better approach to solving the problems you face is to open yourself up to streams–a diverse flow of information such as a social media feed, your email inbox, or a curated resource list. Immersing yourself in streams of information allows for serendipity in your life as you can test all kinds of information against your problem to find a workable solution.

I admit that this probably isn’t true all of the time (you do still need to focus), but knowing how to benefit from streams are one of the best ways to think more creatively and come up with better solutions.

#2 Tinkering versus Goals

As we recognize the importance and benefits of stream-driven serendipity, it leads us into an appreciation for what the author calls tinkering–“a process of serendipity-seeking that does not just tolerate uncertainty and ambiguity, it requires it.”

If your approach to problem-solving is to lay out a plan for how the problem will be solved, you will be constrained into your plan. There’s little (or no) room to make changes to the process when you’ve laid out the process beforehand. Rao points out that this model (called authoritarian high modernism) worked in the past, but is quickly being “eaten” by software.

In a software-driven world, you actually benefit from keeping yourself open to tinkering and serendipity.

This probably seems abstract, but coaches do this every single day when we work with players. We do something, see how it works, and then adjust our future course of action. That’s tinkering.

If we’re not willing to be flexible in the dynamic player development process, we’re never going to succeed.

But we need to consider the other areas that this mindset might be useful: our careers, creating content online, habit-building, relationships, and any other pursuit we’re after.

Articles of the Week

The Brain in Spain by Sid Lowe

This is one of my favorite coaching-specific articles I’ve ever read. It’s mind-expanding, challenging, and contrarian.

The article is an interview between Sid Lowe and Juanma Lillo, Pep Guardiola’s mentor. Trust me, it’s worth your time. Lillo’s insights are timeless in nature, which makes them perfect for any coach looking to think about the future of his or her work.

Here’s one of my favorite quotes as a preview:

“I actually try to make sure that a player doesn’t have a pre-established plan, because it might be that it is of no value. If you isolate variables and maximise one thing, you minimise the other. If you focus on a player being fast, you subconsciously weaken his ability to do other, equally necessary things. That’s not a good idea: humans are constructed as a complimentary network of qualities, not a hierarchical pyramid of them.”

Definite Optimism as Human Capital by Dan Wang

“I wonder if economists overrate the easier-to-observe policy factors and under-theorize the idea that positive visions of the future drive long-term growth. To put it in a different way, I wish that they would consider definite optimism as human capital. In addition to education levels, human capital models should consider factors like optimism, imagination, and hope for the future.”

A huge (underrated) part of building a better future is simply believing that you can play a part in building it. As Tim Urban of Waitbutwhy writes, Elon Musk is the world’s raddest man. But the thing that enables his ultimate radness is that he truly believes the future can be better than the past. This vision for a positive future is what Peter Thiel calls an effective truth, and is a key part of making tomorrow better than today.

On Productivity by David Heimann

My perspective on productivity was forever changed when a co-worker with the Angels told me, “We didn’t hire you to learn. We hired you to be productive now.”

I had always viewed productivity as checking boxes in to-do lists and optimizing minutes for the sake of efficiency. But like most people who have gone down the route of hustle culture will tell you, I found it unsustainable and unsatisfactory. No matter how much I got done in a single day, I always felt like I could be more productive. I suspect you might know what I’m talking about.

Which leads me to my main point. Human productivity isn’t as simple as a single metric like GDP. Software is changing how the world looks at almost every level, and one of the largest shifts going on right now is a redefinition of what it means to be productive. Instead of one that’s focused on raw output, productivity is shifting towards an optimization towards flow states. â€‹Here’s Heimann:

“I really don’t like the word productivity or the discourse that has emerged around it…It’s the classic Apple thing, if you’re constantly look at the data, you’ll optimize whatever is in front of you. If you’re constantly chasing productivity, you’ll optimize time spent producing. But, I’ll argue that what you want to optimize for is time in flow.”

Thought of the Week

One thing that stood out to me from last week’s Building Your Competitive Edge workshop is that if you’re looking to grow your career, you need to help other coaches in addition to helping players.

Many coaches are so focused on helping players that they never realize that players aren’t the ones who have jobs to offer.

If you’re looking to grow your career, you need to do work that reaches the people who have jobs to offer–College Head Coaches, Athletic Directors, private facility owners, and the coaches and/or executives of professional sports teams.

For example, let’s say you’re an underpaid assistant at a mid-major D1 school with few technological resources. You want to get a job that allows you to better support your family. What should you do?

First, you should help the players you’ve been given. You need to get players better. Don’t forget that.

But helping players isn’t enough.​ To get a better job, you also need to help other coaches. As Seth Kindig pointed out on Twitter, “Coach development is player development.”

If you write a great blog post about how you helped players get better despite having constrained resources, a professional coach or front office member might read that and be impressed.

When a job opens up, he is going to rack his brain for who he should contact to fill that spot. By writing something that reaches him, you improve your chances of being at the top of his mind.

This is the essence of using media as leverage, which was a major focus in last week’s workshop.

In today’s world, you can create something once and share it an infinite number of times. And when you do this, incredible doors of opportunity swing open because you increased your surface area of luck.

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,