The Rules of Rule-Breaking

Are Rules Really Meant to Be Broken?

If you are an entrepreneur/freelancer, you already understand that some rules need to be broken to create your best work. What many rule breakers don’t understand is that to effectively break the rules, you first have to understand the rules.

When I say understand the rules, I don’t just mean know what they are. I mean know why they are. Rules are usually put in place for a reason. I say usually because, let’s face it, some rules really are just stupid. In general, though, rules serve a purpose.

Whatever market you want to enter has a set of rules that have been created, meant to lead towards success. Before you can really decide on your plan of action it is a good idea to make yourself familiar with those rules.

Since I have chosen writing as my path, I will use this for my example.

Understanding the Rules:

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In writing, there are a set of rules that have been created for engaging your reader and marketing your work.

  • Show don’t tell
  • Use the active rather than passive voice
  • Use simple sentences and simple language
  • Don’t use a word if you don’t understand its meaning
  • Avoid using market jargon
  • Avoid abstract concepts

These are just a few of the rules you can find linked to the art of writing. These are some of the rules that apply to any type of writing, but other rules can be added depending on the genre you choose. This leads to another big rule in writing:

  • Stick to a specific genre.

These rules all serve a purpose in creating material your audience will want to read. That’s another rule;

  • know your audience and write to what they want to hear from you.

See, I can come up with rules all day long.

If you are a creative person, this can seem daunting and frustrating. Can’t I just create what I want to create? Do I really have to follow all these rules to be able to follow my craft?

The answer to this is simple yet complicated: yes and no. Let’s take a look at one of the big rules of writing to explain this, show don’t tell.

Yes, you need the rules:

These rules were created by looking at what worked in marketing books and articles. They have been tested and proved repeatedly. So, why do these rules work?

Show Don’t Tell:

If you have ever joined a writing community, read a writing article, or just skimmed the internet, you have come across this rule. Why is it important?

People want to have a picture in their mind of what you are expressing. By using descriptive words and, where possible, dialogue, you paint this picture for them.


John is a large man.

John and Eric stood next to each other. At six-foot, Eric seemed like a dwarf in comparison to his companion.


The women stood around gossiping about the latest exploits of Janet.

“Did you hear what trouble Janet got herself into this time?” Ann directed this question to the group of women she had assembled around her.

A chorus of “No, what?” came from her audience.

“Girls, you didn’t know her husband had left her? He’s been staying at the Three Crowns for two-weeks now.” Ann paused before going on, satisfied with the reaction she was creating. “I overheard him telling her he could never forgive her for what she’s done. You know what that must mean don’t you?”

Many of the assembly nodded their heads in understanding of the implications. Obviously, those words could only mean one thing.

These are rough examples, but you get the picture. It is clear that “show don’t tell” serves a valid purpose.

No, you don’t always have to follow the rule:

Is it important to always follow this rule? Not necessarily. If you understand the purpose of this rule, you can skirt around it, creating a hybrid or throwing it out if you deem necessary.

I wouldn’t recommend always ignoring the rule, but there are some instances where it would serve a purpose to ignore it.

For instance, let’s say you are creating a dream sequence. You may want to avoid going into detail, as dreams are often hazy, and avoiding the rule of showing will actually give a clearer picture to your audience.

Notice the theme though: You need to understand the point of the rule to break it effectively to get the most out of your work.

Know Not Everyone Will Respect Your Rule-Breaking

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If you are going to be a rule-breaker, you will get a lot of criticism. People love rules. They’ll tell you they don’t, but they do.

Rules give them a parameter to work within, they make it easier to create wholesale because you have a structure in place. There is nothing wrong with this.

But, sometimes if you want to stand out, or if you have an idea that doesn’t fit the parameters of the rule, you will have to be willing to break, or at least bend, some of them.

Not everyone is going to appreciate you for this. This is where you will better define your audience. If you know the reason for your rule breaking, those who understand you, will respect and continue to follow your work. Those who don’t, were not your target audience to begin with.

Don’t Just Break Rules for the Sake of Breaking Rules

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I know the idea of the rebel is a fun one. If you are striking out on your own, you have a little rebel in yourself. While this is good, and I am always willing to applaud the person willing to question things, remember that some rules may be necessary to follow.

This goes back to understanding the rules. It is important to understand them so you know which ones you can break, but it is equally important to understand them so you’re not just breaking rules for the sake of it.

Remember, these rules of the trade have been created over the years based on what works.

While you never want to get stale and just do something because everyone else is doing it; let’s face it, you wouldn’t be striking out on your own if you were that person; breaking rules just for the sake of it can actually hurt you.

If no one is sure what to expect from you, it will be harder to create a following. People want to have at least an inkling of an idea what they’re getting into. Some of the rules help create this assurance for your audience.

You don’t want to alienate your audience just to be a rebel.

You also don’t want to alienate those who came before you. The people who have carved out the niche you’re working in, many of whom have been involved in setting the rules for that niche, are not going to be welcoming towards a blatant disregard for the work they have put in.

You may be able to find a way to improve something, and that’s great and could be welcome after a time.

A certain rule may be unhelpful to your specific situation, and that’s fine too.

Most pioneers will understand these scenarios and remember the time that their situations led to a need to bend some rules.

If you just come in with the attitude “Rules! I don’t need no stinkin’ rules!” you will not find people as willing to embrace your ideas; not others in your niche, not your audience.

I will leave you with a personal example:

I worked as a conference coordinator several years ago. This involved, among other things, organizing and shipping the materials needed at conferences. In order to make this process easier for myself, as well as make it easier for the sales people on the other end, I created an organizational chart to keep up with what items were being placed in what boxes.

This process took me a couple of conferences to get perfected, but it became a valuable tool for myself as well as the conference team.

Eventually my role in the company changed, and it became time to train a new person to take over for me. I created a binder for this person with all the information needed to do the job, including my finely crafted organization chart.

I presented this information, discussed it and went over where all the files could be found. They seemed to understand, so I left them to it, reminding them to come find me if they were confused about something.

This person, for reasons never made clear, decided to change my organization chart. I have no problem with the idea of innovation, the problem was, they didn’t take the time to learn my chart, and more importantly why my chart was organized the way it was, before they set out to create a new one.

This meant all the work I had put in to understanding the needs of the sales people at the conferences, the best methods for packing with minimum boxes, etc. was just thrown out, and they started from scratch.

Guess how well that worked out for them?

Had the person taken the time to look at my chart, to understand why I had set it up the way I had, or even come to me and said they wanted to change it, they would have saved themselves a lot of time.

They didn’t do any of these things though. This person thought they would show off, prove they were better at the job than me.

If they had taken the time to understand why I did things the way I had, they may have succeeded in standing out. Instead, they caused confusion and stress.

What’s the point of this story?

Even if you have valid reasons for breaking established rules, you want to make sure you fully understand the rules first. This will save you a lot of time and effort in the long run.

Breaking rules can be necessary, and it is definitely fun, just make sure you are breaking the rules for the right reasons.

Have you found it necessary to bend some rules along the way? How did you go about it? Let me know in the comments.


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