Why It’s Sometimes Necessary to Break the Rules

Caroline Leon
5 min readAug 3, 2021

“Learn the rules like a pro, so you can break them like an artist.”

~ Pablo Picasso

As a business coach, I’m often asked about the rules we need to follow in order to become successful in business. It’s not uncommon for people to begin a question with “am I allowed to…?” or “is it acceptable to…?” or “Is it okay if I…? Questions around how to connect with clients, how to create and share content, how to price offerings, how to do just about anything within the context of building and growing a business.

It surprises people often that I rarely come down on the side of any given rule. I realised early on in my entrepreneurial journey that whilst we are constantly bombarded with different rules we should follow in order to be successful, there are in fact no rules. Allow me to explain.

When it comes to creating content, for example, we’re overwhelmed with rules from how many words to use to what kind of headlines work best and to the absolute necessity of using images, after all “a picture is worth a thousand words” so they say. In this article, we’re helpfully told the ideal length of everything online, backed by research including the fact that the ideal length of a blog post is 1,600 words. Any longer and people’s attention span can’t bear it, too much shorter and we risk not getting ranked by google and missing out on sales conversations and subscribers. That’s a pretty daunting word count for a newbie entrepreneur trying to figure out what the heck to write about in the first place.

But I have good news. For every so called rule we can find, it’s possible to find a rule that argues the opposite as well as someone who broke the rule and succeeded anyway. It’s my pleasure to introduce you to some of my favourite, highly successful, rule breakers.

There’s Seth Godin who regularly posts articles with a super short word count. You can read one here that comes in at a measly 76 words but has had to date well over 7000 likes. Or Mark Manson, who has a readership of “millions”, whose post clocked in at 4,442 words.

It has often been argued that we should publish blog posts daily. While this article from another well respected expert on blogging vehemently argues the opposite. It never harmed Seth to post daily and there are countless others who have succeeded just fine without doing so.

Then there’s Authentic Business Coach George Kao, with more than 8000 followers on Facebook, who flouts the “a picture is worth a thousand words” rule and rarely uses images in his Facebook Posts and/or (shock horror) his Facebook adverts and gets a great deal of traction regardless. In fact he argues that he actually gets better engagement by not using images, because the people who interact with his posts do so, not because they like a pretty picture, but because they appreciate the content.

Another area where people like to spout out rules like they are sacrosanct, is pricing. We’re told by some so-called experts to never discount our products or services as it devalues our work, yet the highly successful, Kelly Rae Roberts, holds sales frequently and I personally (and gratefully) have bought ALL of her painting courses at sale price! And heaven help anyone who breaks the charge what you’re worth rule and offers pay what you can pricing like established business experts, Tad Hargrave and Mark Silver do.

And then there’s branding. How often are we told that in order to succeed we must cultivate the perfect image, have the perfect website and a carefully crafted brand. Check out Steve Chandler, a renowned and highly successful coach and author whose website clearly hasn’t had a branding makeover any time recently (sorry Steve!) or back again to successful, Business Coach, George Kao who openly admits that he hasn’t paid any attention to branding as he’s built and grown his 6-figure business.

There are countless more “rules” and successful rule-breakers I could share but hopefully that’s enough to make the point that there are, in fact, no real rules to follow and more importantly that when we try to follow the rules, we end up tying ourselves in knots because when we focus on the rules, oftentimes, what we end up doing is give ourselves an out.

I would write a weekly post but I don’t have time to write 1600 words.

I would post on social media every day but I struggle to find nice images.

I would share my website but I’m waiting till I can afford to pay for branding.

Sound familiar? So what are we to do if we don’t follow the rules?

Instead of trying to follow a gazillion, conflicting and oftentimes, unhelpful set of rules instead we can tune in to what feels right for us. We can embrace the adage “better done than perfect.” We can ask ourselves, what rules am I trying to heed that are actually holding me up? We can embrace values and principles instead like integrity and connection. Like putting the person before the sale, like being of service and producing meaningful content. These are the things that hold up in the long term, not a cleverly crafted headline or slick branding. If we struggle to even adhere to the so-called rules, then you can bet that our audience tire of being on the receiving end of them.

Consider forgetting about the rules and create meaningful content (at whatever length your heart desires!) and share it with love. Price your offerings from the heart, with your clients and customers best interests in mind and above all be authentic in your business. Show up genuinely and with honesty and that will serve you and your bottom line far greater than any silly rule will. Having said all that, if there is a rule that you’ve been following in your business that is working for you, great keep at it. Heaven forbid that I should create a rule about breaking rules here!

What do you think about what I’ve shared here? Are there any rules you’ve been trying to follow without success, have you found certain rules have been stifling your ability to show fully in your business? Or have you found certain rules helpful? If so, please share them in the comments, I’d love to hear your perspective.

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Caroline Leon

Business Coach helping conscious change makers to build and grow sustainable businesses, using strategies rooted in integrity. https://carolineleon.com