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:

  • When average people like me are wondering how to invest, the best answer is usually “set up automatic contributions to an index fund”.
  • When setting up a budget, it’s more important to pay attention to the Big Picture than it is to fret over details. Follow the balanced money formula and you should do okay.
  • When you want to get out of debt, use the debt snowball method. If possible, pay high-interest debts first. Many folks (including me) have more success, though, if they pay off low-balance debts first. And still others use a debt snowball approach in which they start by tackling the debts with the greatest emotional weight.
  • If you’re going to use them, know how to use credit cards wisely. If you’re unable to use credit without digging yourself into debt, then throw away the “shovel”.
  • And so on.

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.

  • What happens if I add more bacon? (Deliciousness!)
  • What happens if I add more garlic? (Deliciousness! But too much garlic makes things worse…)
  • What about more onions or clams or potatoes? (More onions are good, but the potato ratio depends on the amount of liquid I use.)
  • What if I use Yukon Gold potatoes instead of russets? (Gross! Yukon Gold potatoes are awful in chowder.)

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:

  • Why do you want to break this rule? What purpose does it serve? Is it simply out of laziness? Or will breaking the rule potentially lead to some useful reward? Driving on the shoulder because you’re inconvenienced by slow traffic is not a valid reason to break the law. But adding bacon to clam chowder because it’s delicious is a good reason to change things up.
  • What are the consequences of breaking the rule? Will it harm anyone else? Will it harm you? Take the Balanced Money Formula, which says that you shouldn’t spend more than half of your take-home pay on Needs. If you do, you put yourself in a precarious financial position. You could really hurt yourself (and your family) if something goes wrong. On the other hand, you’re not going to hurt anyone by jaywalking on an empty street at midnight.
  • For some rules — office rules, personal rules, family rules — it’s useful to ask what the new rule will be if you break (or change) the old one. If you decide to withdraw from your retirement accounts to fund a purchase — a financial rule I don’t suggest breaking — is this a one-time thing? When will you allow yourself to do the same thing in the future? How will you replace those funds?

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.

24 Replies to “When to follow the rules — and when to break them”

  1. Dan says:

    Thanks for this. I’ve long said that I don’t like “personal finance” rules of thumb, because personal finance is… wait for it… personal.

    I broke the rules.

    I turned 40 this year and last month, I had $500 to my name outside of my 401k. I’ve traveled to 30 countries in the last ten years, graduated college with $92k in student loan debt and have no emergency fund. Six years ago, I had just gotten laid off, divorced, and started my current with $20k in credit card debt. In the months between getting divorced and getting laid off, I bought a new-to-me car.

    Sounds like a wreck, right? Could I have skipped all of that foreign travel? You betcha I could have. But I wouldn’t trade it for the world.

    Today, I’ve got $220k in my 401k, my student loans are down to $50k, the car is paid off, and the $20k in credit card debt is long gone. But I still have $500 in liquid assets. My credit score is 820.

    I made the choices I did for several reasons:

    1. The credit card debt was financed with 0% APR balance transfers. I paid a 4% fee to carry the debt at that rate for 18 months at a time. (Paying $800 flat to carry $20k for 18 months is not a bad deal.)
    2. The car cost me $13k — a 2010 Nissan with 20k miles when I bought it.
    3. The foreign travel was largely covered by frequent flyer miles obtained by credit card signups. If I would have taken those trips later after I followed the rules, I would have paid multiples for them.
    4. My student loan interest rates were never terrible, but I just refied them down to 1.9%. My interest payments for that $50k are $90/mo.
    5. As far as my e-fund, this is the big one: My employer matches my 401k contributions at 25% up to *10%* of my total salary.

    A few years back, I had a choice: max out my employer contribution or pay down my debt at a faster rate. We’re talking $400/mo here, which isn’t chump change. Mathematically, the choice was easy: Max out the match. That $400/mo was costing me less than dollar per month ($400*.04/18). For the cost of $1, I was getting $100 from my employer match + earnings growth. I made this choice back in 2016, and the credit card debt was paid off this year.

    In addition, my e-fund would have been further 0% APR balance transfers if necessary. Not ideal, but I had the credit line if necessary.

    I’m sure many in the PF community will criticize my choices for not following the “rules”. I took calculated risks, and they paid off. Things could have turned out differently, but they didn’t. Again, the risks were calculated. I lived *my* life according to *my* rules, and hindsight being 20/20, here’s the rub: I wouldn’t change a thing. I enjoyed all of the travel that I did, especially for the price I paid. The car? I needed to replace the old one, and I got a great deal on this one. It’s got 65k miles on it now, and easily has another 10 years left in it.

    My goal this year is to build a $20k e-fund. It’s not going to be that hard.

    It paid dividends for me to break the rules (and I did so wisely.)

  2. Dan says:

    I don’t mean any snark by this, but why? Isn’t that true for everyone who has found success?

    There are a number of things in my story that could have gone different ways and I recognize that. But I worked with what I had and my risks weren’t wreckless.

  3. Marla says:

    As a fellow rule follower, I loved this post. Lots of food for thought. Also, as a Canadian, we are known for being rule followers: my fave joke in this regard “Q: How do you get 100 Canadians out of the pool?…A: Please get out of the pool”. I definitely see the benefit of breaking a few rules/taking a few more risks as I become more expert. Happy holidays my friend!

  4. Jeff says:

    Great post. I really like the frame.

    The lessons learned from mistakes along the way could be a way to learn faster but why not absorb the knowledge that is already published first.

    I love those thought provoking articles that question the status quo. Kudos for pushing against and beyond the standard answers.

  5. Andy Locatelli says:

    Actually, I think the criteria used for deciding who should break the rules are wrong for many situations.

    People who become experts in a given field or subject often become the worst people for seeing why a process or outcome should change. People become so invested in being experts that it is difficult for them to allow change to happen, which could result in them no longer being as competent (at least from their perception of things). For instance, an organization’s directors can often be resistant to changing anything unless the signs are dire enough that change must happen. Their schooling, training, and experience have all led them to be the movers and shakers in their particular organizations and/or fields, and their ideas tend to become unquestioned by others and themselves. It takes someone who is not beholden to those ideas or processes to introduce a new solution to problems. This happens on so many levels in organizations, groups, and more generally in society that needed change simply doesn’t happen, or the solutions offered tend to just be a different take on existing processes and ineffectual or not far-reaching enough to get to the heart of the issue.

    In an era when the old rules for governing, conducting business, and personal growth seem so antiquated and ripe for change but so very ingrained that change just never really happens at a fundamental level, I’m not sure that arguing that only experts should break the rules rings true.

    I understand that the article is focusing on rules for financial management, but it seems that the claims are broad enough that readers could easily extrapolate the message to think it applies to other situations as well.

    • FoxTesla says:

      Agreed, where is the line of the expert accepting the “fresh voice/outside the box thinking” vs “you just don’t know enough yet, go study some more”.

      I’m reminded of my senior coworker’s quote from 5ish years ago when SpaceX started presenting its plans to reuse rockets – “Why are they wasting time trying to do this? I’ve done the back of the envelope calculations, you can never land a rocket that just launched.”

  6. Brooklyn Money says:

    I was literally just thinking about this topic this morning. I’m sure a rule follower sometimes I miss simple solutions like the one Kim proposed because it doesn’t cross my mind. Guess count me in as another rule follower.

  7. S.G. says:

    DH and a coworker were discussing a problem once and he coined the phrase “I’m sorry, I don’t have a PhD. So I can’t break the laws of physics.” He isn’t an expert producer.

  8. FinanceFTW says:

    One of my favorite rules to break is to invest in your own business(es) vs. investing in a portfolio of stocks/bonds/real estate. Most wealth of the richest people in the world comes from the businesses they’ve built (or their families built), not from investments following traditional investment advice.

  9. DJ says:

    Excellent post, JD.

    Happy Holidays and please keep posting – especially cause studies from folks living in FIRE! All thE best,

  10. fatdaddy says:

    Great piece, loved it.

  11. Joe says:

    Good post. I used to be a rule follower. Now, I enjoy bending the rules a bit. It’s good learning experience. Great example with cooking too.
    At first, you need to learn the basics. After years of experience, you’ll learn to make it to your taste. The same applies to almost everything in life. Experience is the only thing good about getting old…

  12. Jim Wang says:

    I fully subscribe to the copy and innovate strategy. We have some family favorites (recipes) in our home where we use a recipe but it’s mostly to refresh our memory on the ballpark timing. Flavors-wise, we try to keep the ratios relatively similar but otherwise we just kind of wing it. I think once you get a feel for something, you can take liberties that won’t get noticed and you can innovate in ways that you will notice.

    As for butter in rice, consider using chicken stock instead of water when you cook it. We buy rotisserie chickens from Costco and always turn the bones into chicken stock (45 minutes in the Instant Pot!), so we always have a ton of it on hand. It contains less sodium than the traditional store-bought kind and it adds a nice flavor to rice (and stir-fry vegetables) without the heavy caloric burden (or stickiness).

  13. J.D. Roth says:

    Hilarious example of my innate Rule Follower tendencies (contrasted with Kim’s tendency to be a Rule Breaker). We both wanted ramen for lunch. To prep mine, I followed the instructions on the package EXACTLY. She did not. She just kind of made things up as she went along. I got so tense! Silly, yes?

    • El Nerdo says:

      Yes! Relax! Have a cocktail or something haha. It’s just ramen. We sometimes make lo-mein with it instead of a ramen bowl. Also, cacio e pepe. Yes, we’re heathens, we have little respect, lol.

      Look, you’ll never learn the rules of cooking via paint-by-numbers. This service you’re using might destroy your mind.

      Butter in rice is delicious, but works better when you use it for cooking rather than add afterwards— ghee works even better.

      Anyway, butter might be a bad match for a Korean dish. Try sesame oil, or better yet, plain white rice, let the rest of the food be the spicy seasoning that soaks i to the rice. There’s a why to these traditions. Figure them out.

      In order to change rules successfully, you have to understand the whys. And discovery requires experimentation…. Hail Hydra! XD

      Go check out Kenji at Serious Eats. He does the science and explains the whys, so you can play, and have a blast.

      Goodbye Fresh! 😛

      Now put a little salt on your ice cream. Yeah, you know you wanna 😉

    • Joe says:

      My wife is a rule follower too. She cringes every time I jaywalk. 😀

  14. Adam says:

    Oh man, this hits home so hard. I wish I’d read it ten days ago when you published it.

    I’m a classically-trained musician. All four years of a performance degree are spent learning The Rules. By the end you have some idea of why these long-dead composers did what they did, and how it works, and how to make it happen to the best of your ability… and you realize just how much you don’t know, and why there are so many varied interpretations by so many conductors who’ve done this thing for decades upon decades. I’ve got friends with doctorates who do things that are almost unrecognizable as “music” — but hoo boy, they sure know what rules to break for maximum effect.

    In cooking, I’m right there with Kim and her ramen. In driving, I believe that folks who neglect turn signals or headlights in the rain should probably be crushed with their cars into small cubes. Rules are weird. To me, consideration (for the listening audience, for those who will eat your food, for other drivers) should be the deciding factor.

  15. squire says:

    “Rule Following” is “doing what you have always done and expecting different results” unless of course you are already seceding following the rules.

  16. Mark Campbell says:

    I am similar to you in following the rules. But I remember reading the book Chicken Soup for the Soul where they explained it’s okay to eat ice cream for breakfast on occasion.

    I don’t remember eating ice cream in the morning but once or twice, but I will experiment when preparing food or grilling.

  17. Kim @ The Frugal Engineers says:

    My advisor in grad school told me “you have to know which rules apply to you and which ones don’t”. Great advice since I’m a self-proclaimed rule follower with a rebellious side 🙂

  18. Financial Mechanic says:

    I wonder if this is a common balance in relationships. My SO is a rule follower– he hates it when I “wing it” when it comes to recipes, and most recently, the methods of training our cat to do fun tricks. (He’s waiting until the training clicker arrives, and I’m starting without it). This article is awesome because I didn’t know about Chesterton’s Fence or the four steps to being an expert producer. Thanks for sharing!

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