Open Note from the author

This book is very much a work in progress. In its early stages it is going to include a lot of rough wording, some direct quotes from various sources with little or no context to the larger project, and many things that end up getting cut before the final edit (assuming there is a final edit).

If you have thoughts about anything I'm writing, suggestions for how to improve the content or the flow, or if you think I am completely missing the boat, I would love to hear from you. You can find me on LinkedIn or by email at gbrett@hey.com.

-- gBRETT miller, 2025.05.13

Open About this book

Love them or hate them, rules are inescapable.

As individuals we are subject to rules created and enforced by others, and as managers and leaders we subject others to the rules we create (or that have been given us from “above”). In this book we will explore the role of rules in our daily work and our relationship to them, as both individuals and as leaders. We’ll discuss why you should always follow – and enforce – the rules, except when you shouldn’t.

Or, if you prefer, why you should never follow – or enforce – the rules, except when you should.

image courtesy Dave Gray

Although the ideas in this book have been rattling around inside my head for the better part of two decades, I am sitting down now and writing it all out as part of The School of the Possible, an incredible gathering of ridiculously talented, creative, and generous humans who have encouraged me to

Open The question that started it all

The Question That Started it All

"Do you always follow the rules?"

I was sitting with some other team parents, planning out a Trampoline and Tumbling meet that we were hosting later in the year. We were at the point where we were laying out the competition floor, figuring out how to arrange the equipment, where to set up the judges tables, the flow for the athletes as they went from the staging area to the equipment where they would compete.

The question caught me a little off guard. My first thought was, "Well, yeah, we have to follow the rules here if we want this to be a sanctioned event that counts for the athletes who are competing." Which is basically how responded in the moment.

On the drive home from the gym that night, the question was still bouncing around in my mind. I eventually realized that the question wasn't really about the specific situation at hand.

"Do you always follow the rules?"

I don't know if the emphasis I placed in that sentence quite conveys it, but the t

Open Some rules about rules

Some Rules about Rules

The tl;dr of my exploration of the rules and my relationship to them can be summarized in these four rules:

1. Learn the rules, including their purpose and their history
2. Imagine the consequences, imagine the possibilities
3. Always follow the rules (except when you shouldn’t).
4. If the rule needs to be changed, change it.

My rules about rules have evolved a bit over the past 15 years or so. The bulk of the rest of this book is an exploration of these 4 rules.

* Like all rules, these rules are subject to rule 4 above and are hence, subject to change.

Open Leonardo on rules

Leonardo On Rules

My introduction to mind maps came from Michael Gelb‘s book, How to Think Like Leonardo DaVinci: Seven Steps to Genius Every Day. After a brief description of Mind Maps, Gelb lays down the rules of Mind Mapping before presenting exercises. What really grabbed me was his “justification” for using rules, a quote from DaVinci’s Treatise on Painting:

These rules are intended to help you to a free and good judgement: for good judgement proceeds from good understanding, and good understanding comes from reason trained by good rules, and good rules are the children of sound experience, which is the common mother of all the sciences and arts. (emphasis added by me)

Throughout my adult life I’ve had a “glass half full” perspective on rules that somewhat mirrors DaVinci’s sentiments. This comes from the scientist and engineer in me. To paraphrase another great mind, Richard Feynman, it is important to know what has been done before so that you can build from it.

As any

Open Shu Ha Ri

Shu Ha Ri

I first came across the concept of Shu Ha Ri in, of all places, the book Scrum: Twice the work in half the time.

quote from book

Actually, I had been familiar with the concept for quite a while, I just never knew that it had a name. I had the opportunity to practice Aikido for a while in the 90s, where the concept was embraced, if not explicitly named. The rough translation given on Wikipedia is:

Follow the rules, break the rules, transcend the rules.

(fwiw, I never got out of the "follow the rules" phase; even if I had practiced for the past 30 years I'd probably be just barely in the "break the rules" phase.)

A more detailed description comes from Aikido master Endō Seishirō shihan, as quoted on Wikipedia:

It is known that, when we learn or train in something, we pass through the stages of shu, ha, and ri. These stages are explained as follows.

In shu, we repeat the forms and discipline ourselves so that our bodies absorb the forms that our fo

Open Chesterton's Fence

Chesterton's fence:

In the matter of reforming things, as distinct from deforming them, there is one plain and simple principle; a principle which will probably be called a paradox. There exists in such a case a certain institution or law; let us say, for the sake of simplicity, a fence or gate erected across a road.

The more modern type of reformer goes gaily up to it and says, "I don't see the use of this; let us clear it away."

To which the more intelligent type of reformer will do well to answer: "If you don't see the use of it, I certainly won't let you clear it away. Go away and think. Then, when you can come back and tell me that you do see the use of it, I may allow you to destroy it."

Open Finite and Infinite Games

Open Why was the rule written?

Why was the rule written?

Open Who wrote the rule?

Who wrote the rule?

Open Who enforces the rule?

Who enforces the rule?

Open Who benefits from the rule?

Who benefits from the rule?

Open In what context was the rule implemented?

In what context was the rule implemented?

Open Is there a process for updating the rule?

Is there a process for updating the rule?

Open When was the last time the rule was updated?

When was the last time the rule was updated?

Open Consequences - Breaking the rule

When people think about a rule and whether they should follow the rule or not, the most common question they ask themselves is:

What happens if I get caught breaking the rule? What are the consequences for me?

Open Possibilities - Following the rule

Not nearly as many people consider the possibilities that may be available if they follow the rules.

Open Possibilities - Breaking the rule

Along with considering the consequences of not following a rule, many people think about the possibilities available to them by not following the rule. In fact, it's probably safe to say that this is the main reason that people choose to break a rule, either consciously or unconsciously.

Open Consequences - Following the rule

Even following a rule has consequences.

Open How do I decide?

It's one thing to say, "You should always follow the rule, except when you shouldn't," and something entirely different to be able to figure out if you should follow it or not.

Open Cynefin

The Cynefin framework offers decision-makers a "sense of place" from which to view their perceptions.

note: this idea needs to be developed further

Open On Obedience

From the description of On Obedience: Contrasting Philosophies for the Military, Citizenry, and Community by Pauline Shanks Kaurin.

This volume is designed to be an in-depth and nuanced philosophical treatment of the virtue of obedience in the context of the professional military and the broader civilian political community, including the general citizenry. The nature and components of obedience are critical factors leading to further discussions of the moral obligations related to obedience, as well as the related practical issues and implications. Pauline Shanks Kaurin seeks to address the following What is obedience? Is it a virtue, and if it is, why? What are the moral grounds of obedience? Why ought military members and citizens be obedient? Are there times that one ought not be obedient? Why? How should we think about obedience in contemporary political communities?

Open For rule followers / breakers

Open For rule enforcers

Open For rule makers

Open Bibliography

Open About the author