When to follow the rules — and when to break them

by J.D. Roth

Last night’s HelloFresh recipe was Bulgogi Pork Tenderloin. As always, the instructions were clear and easy to follow. As always, it took me about twice as long to prep things as the recipe card said they would.

HelloFresh instructionsI chopped the vegetables, boiled the rice, seared the meat, made the sauce. But when I reached the final step — “finish and serve” — I hit a wall of sorts.

“Ugh,” I said to Kim, who was playing with our three cats and one dog simultaneously. “The recipe calls for a tablespoon of butter in the rice. I hate adding butter to rice. It makes it gummy and gross. But HelloFresh always wants me to do it.”

“I like butter in my rice,” Kim said, throwing a bacon ball for the dog while kicking a catnip toy for the cats. “But if you don’t like it, don’t add it.”

I sighed. Of course, she was right: Just don’t add the butter! Such an obvious solution, right? Yes — and no.

You see, I am fundamentally a Rule Follower. When I’m cooking, I follow the recipe exactly. When I’m building an IKEA desk for my new office, I follow the instructions exactly. On the road, I generally stick to the speed limit (which sometimes drives Kim nuts). I used to take pride that never once did I cheat on my homework or tests in high school and college — and I never helped anyone else cheat either.

As I said: I am, fundamentally, a Rule Follower.

This has been true when it comes to managing my money too. Since beginning my quest to become the CFO of my own life fifteen years ago, I’ve surrendered to wiser minds than mine. I tend to heed the time-tested “rules of money”, rules like:

Following these rules has proved profitable. These “rules” are rules for a reason. Because they work. They allow folks to get out of debt and build wealth. Crazy, right?

Here’s the thing, though. As effective as these financial rules have been for me, as much as I like strictly following a recipe, I’ve also come to realize that sometimes it makes sense to (gasp!) break the rules.

The challenge, then, is determining when to follow the rules — and when to break them.

Chesterton’s Fence

Some people chafe at rules. They instinctively want to rebel against them. My old friend Sparky, for instance, never met a rule he didn’t want to break. It was just part of who he was.

From my experience, though, rules generally exist for a reason. They’re not arbitrary creations meant to frustrate and hamstring people. Rules are an attempt to create order and help life run more smoothly. Sometimes, though, people and institutions evolve. Old rules that once proved useful become outdated and ought to be discarded. But it’s dangerous to mindlessly break rules (or to discard them).

G.K. Chesterton’s 1929 book The Thing includes an essay entitled “The Drift from Domesticity”. While I haven’t read the entire essay, I’m fond of the intro, which describes the danger of discarding rules without careful consideration:

In the matter of reforming things…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.”

This paradox rests on the most elementary common sense.

The gate or fence did not grow there. It was not set up by somnambulists who built it in their sleep. It is highly improbable that it was put there by escaped lunatics who were for some reason loose in the street. Some person had some reason for thinking it would be a good thing for somebody. And until we know what the reason was, we really cannot judge whether the reason was reasonable.

It is extremely probable that we have overlooked some whole aspect of the question, if something set up by human beings like ourselves seems to be entirely meaningless and mysterious.


This principle applies to a thousand things, to trifles as well as true institutions, to convention as well as to conviction.

I learned about this concept — colloquially referred to as “Chesterton’s Fence” — last March from a GRS reader named Marc. “With an old house,” he wrote, “I have found the principle of Chesterton’s Fence to be invaluable. When renovating or repairing never rip something out if you don’t understand why it is there.”

In the nine months since I first heard about this idea, I’ve thought about it often. I think it’s important. It applies to many aspects of our lives. And it’s directly applicable to the question of when to follow rules and when to ignore them.

From Amateur Spectator to Expert Producer

Earlier this week, David Wells (who runs the excellent Fifteen on Friday email newsletter) published an article on the four steps to expertise and meaningful contribution. These steps seem like a natural fit for a discussion of knowing when to follow (and when to break) rules.

According to Wells, there are four steps to moving from a “spectator” to a “producer”.

  1. The first step is becoming an “amateur spectator”. At this stage, you’re new to whatever it is you’re experiencing. You don’t know the rules, but you’re able to enjoy the process. This is me when watching cricket. I have zero clue what is going on, but I’m entertained by the sport.
  2. The second step is becoming an “expert spectator”. Here, you do understand the rules. More than that, you know why the rules exist and how they influence whatever it is you’re experiencing. I’d say I’m close to being an expert spectator when it comes to film. I have an appreciation for film history, and I’ve read a lot (and watched a lot) about how films are made. This helps me appreciate the movies I see, but I couldn’t make one of my own.
  3. The third step is becoming an “amateur producer”. (Wells calls this an “amateur professional”, but I think he actually means producer.) At this level, you have enough knowledge of your subject, of its rules and conventions, that you can participate and create. An amateur producer, Wells writes, “is not someone who just undersands that something happened, but can explain to you why it did.” I’m an amateur producer when it comes to photography. I know the hows and whys of writing with light, and have even sold a few photos.
  4. The final step is becoming an “expert producer” (or “expert professional”). Wells writes, “At this level, you not only understand why something works, but you are able to deploy various tools to accomplish a desired end.” I like to believe — although you might argue the point — that I am an expert writer. (Or, at any rate, an expert blogger.)

Here’s the thing to note about these four stages of expertise. Folks at lower levels ought not break the rules. Hell, folks at the first level don’t even know the rules. As you become more aware of the rules (and the reasons for them), you’re able to actually create within this set of guidelines. At the very highest level — as an expert producer — you can, at times, break the rules.

And I’d argue that those at the very top can sometimes write their own rules. To wit:

Let’s return to Chesterton’s fence for a moment. I believe that Chesterton is arguing that if you’re an amateur spectator, you have no right to ask for the metaphorical fence to be removed. As an expert spectator, you at least appreciate why the fence exists, but you probably shouldn’t be the one to remove it. Only if you’re a producer — and preferably an expert producer — should you actually remove the fence.

Once, about 25 years ago, I decided to bake some brownies. Although my wife was an expert baker (and a chemistry teacher to boot!), I was not. As I mixed the ingredients, I realized that we were out of baking soda. “No worries,” I thought. “We have baking powder. I’ll just use that.”

My brownies were a disaster. They didn’t rise. Turns out you can sub one for the other, but you have to know what you’re doing. It’s not a one for one equation. I didn’t have a clue why this “fence” existed — I was an amateur spectator in the kitchen — and I paid the price with bad brownies.

Obviously, some “fences” (and some rules) are more important than others. When I don’t follow a brownie recipe correctly, there are no real consequences other than losing a small amount of time and money. But if you were to, say, disregard the rules for operating a nuclear power plant, you could end up with the Chernobyl disaster.

When you’re dealing with trivial matters, it’s less important that you follow the rules. When you’re dealing with larger issues — marriage, firearms, vehicles, politics — knowing the rules and adhering to them becomes more critical.

Learning to Break the Rules

Now, there’s no doubt that sometimes a fence — or a rule or a guideline — outlives its usefulness. Sometimes when a person complains that a fence serves no purpose, she’s right. And sometimes, as in the case of recipes or financial rules of thumb, it’s okay to stray from the path — if you know why you’re straying.

Let’s use that Chesterton passage above as an example. The quote I published in this article has been altered. The original was a wall of text, two ginormous paragraphs with odd punctuation. This worked fine in 1929 when Chesterton published the piece. It does not work so well in 2019 when people are reading on computer screens.

So, I took the liberty of re-formatting the quote to make it more readable for modern eyes. A minor thing, perhaps, but it’s still a case of me altering Chesterton’s Fence. (Literally!)

Actually, I can think of many examples of how I break the rules of writing. I didn’t always do this. In fact, I used to be a strict prescriptive grammarian. I believed that the rules of writing were immutable and ought to be learned and followed.

Today, I don’t see grammar rules as black and white. After decades as a writer, and after working with professional editors for the past ten years, I’ve come to understand that the purpose of writing is effective communication. Our grammar rules are useful guidelines because they tend to promote effective communication, but once you know them (and know why they exist), it’s okay to break them.

Last night’s dinner is another great example. Over the year that I’ve been using HelloFresh, I’ve followed their directions for rice many times. I know how they want me to make it — and why. In that time, I’ve learned one very important thing: I don’t like the tablespoon of butter they ask me to add at the end. It serves no functional purpose. Kim likes the taste; I don’t. (And I hate the texture.) Because I understand how the rice is prepared, it’s okay for me to omit the butter.

My clam chowder is an even better example. My source was a recipe published in the November 2000 issue of Bon Appétit magazine. I’ve probably made this chowder fifty times since I first discovered it. At first, I was slavish to the recipe. (I’m a Rule Follower!) In time, I began to experiment.

Today, nearly twenty years since I first made the chowder, the recipe I use is mostly my own. I started by following the instructions exactly. At the time, I was a clam chowder “spectator”. Eventually, I gained the confidence to “break the rules”, to adapt things to my own preferences. As I gained competence, as I became an “expert producer” of clam chowder, I could play with the recipe.

When to Break the Rules

Breaking the rules can lead to innovation. Breaking the rules can let you build a life that is truly your own. Breaking the rules can produce better clam chowder. But in order to break the rules, you have to understand them. More than that, you have to know why the rules exist.

“Learn the rules like a pro,” painter Pablo Picasso is reported to have said, “so you can break them like an artist.”

I think it’s also vital to ask yourself a few questions, such as:

It’s not bad to follow the rules. In fact, as a Rule Follower, I think it’s generally a smart thing to do. When you follow the rules, you usually get good results.

Twenty years ago, I didn’t understand the rules of money. I was violating the rules without even realizing it. As a result, I was deep in debt and living paycheck to paycheck.

In 2004, I surrendered to the idea that what I was doing wasn’t working. I was playing the game without understanding the rules. As a result, I was losing and I knew it. So, I decided to teach myself how money works. I learned the rules. More to the point, I started following the rules. Surprise! My financial life improved. (In a way, this is what’s happening with my friends Wally and Jodie. It’s fun to watch them learn the rules of money — and to start winning the game.)

All the same, sometimes it pays to break the rules — if you do so wisely.

Credit cards are dangerous, yes, and ought to be avoided if they’re going to lead you into debt. That’s a solid rule. But if you’re disciplined and sophisticated, you can use credit cards as tools to unlock all sorts of rewards.

And in a way, the modern FIRE movement — that group of folks who wants to achieve financial independence and retire early — is built on “breaking” the rules of retirement. The folks who pursue FIRE not only understand the “rules” of money, but understand why those rules exist. And because of this, they’re able to re-write the rules to achieve something truly remarkable.

Updated: 20 December 2019

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