The Startup
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The Startup

An Entrepreneur’s Guide to Following and Breaking Rules

True entrepreneurs know when to follow established rules and when to create their own

Photo by Clint Patterson on Unsplash

I was one of those kids that got busted on even the smallest misdemeanour. I once got written up in a waitressing job for shoving a spoonful of cake in my mouth. I should add it was after a double shift, all the customers had gone, I was one of 5 other members of staff to do it and it had to be binned anyway because the following day it was out of date. I’m over it, honest.

Episode after episode of this type of scenario was enough to keep me in the camp of full-blown rule followers.

I led the geek squad.

But when it came to work something else shifted in me. An itch at first. Then an irk. Then a progression to what I’ll call a professional level of rage. What was fuelling this?

Blind acceptance that the standards and norms in my profession were the limit of what was possible.

People were too exhausted/inexperienced/indoctrinated (insert any other number of mindsets) to believe in something else or design anything different. Breaking rules (and mindsets) ended up taking lead times down by two-thirds, conversion rates down to 1 :1.5 and income doubling year on year.

So am I about to encourage you to break the rules?


Come on, it’s never as clean cut as that. Let me unpack a simple guide for what you really need to know.

Your skill as an entrepreneur is knowing when you need to follow the rules and when you don’t

I know that most articles like to polarise this debate and get you sat in team ‘rule breaker’ or team ‘rule follower’ (I have a good T-shirt for this team), but the answer is more sophisticated and actually, I think a lot more beautiful.

Stewart Dreyfus, a professor at University of California, Berkeley looked into how we acquire skill as human beings, I want to adapt it to flesh this discussion out.

Trial and error is inefficient if there is an answer

Dreyfus argued that we can work instinctively, imitating and using trial and error as we go, but that this is full of inefficiencies. Think about copying another organisation’s marketing without understanding the principles of audience segmentation. You likely waste your entire budget, time and reputation.

Know the rules

Can we be honest? Despite your niche, thousands have gone before you in multiple parts of your business. Think customer-orientated design, marketing, sales, supply chain, leadership and management, financing, compliance, preparing to sell your business…you know the list and the rules that are out there. Heck, there are degree courses for most of them! And if there aren’t explicit sets of rules, 99.9% of the time there will be people who have been through it who can offer you advice close enough to a set of rules to get you there. And these rules are there for a reason. People lost a lot of money and time by taking different paths and they want you to succeed. They want to help you. I know that seems crazy, but there really is gold in them there hills.

Let’s go back to that marketing example. If you don’t a) have a target audience and b)know that audience inside out there is absolutely no way you can design attractive messages or place them in spaces your target audience will see them. Needle in haystack. Wasted time and money. Thank you rules of marketing for saving us! There are great building blocks of knowledge packaged up in rules. Yes, they change over time, but there really are no excuses any more for not being aware of them.

So instead of trial and error, work to find the rules that are out there to help you. You can think of these rules as the building blocks of knowledge that get you out of blindspots where you are feeling your way forward in the dark, into more efficient spaces.

Implement them accurately

Now you can know about these building blocks, but whether you actually implement them into your business is another matter and that is Dreyfus’ next key behaviour in how we acquire skill. I’ve met leadership that could recite building blocks of strategy and plans but had absolutely no idea how to actually implement them into their businesses. Strategies that had no data, no analysis, but a beautiful SWOT analysis full of completely irrelevant or superficial information. You cannot fake the rules and be successful, you need to actually use them. For two vital reasons.

  1. You want to reap the efficiencies of these rules
  2. You want to be able to see when it is time to break the rules

Create your own rules

Only when you actually use the rules, can you see their limitations. You see what they can achieve for you in your quest to creating your vision and you see what they cannot. And it is in this boundary that you find the territory of needing to break away and create for yourself. It is a beautiful liminal moment. If you get a chance, check out the history of electricity. From the Ancient Egyptians right up to the electronics producers of today, each person of curiosity, each researcher, inventor, designer has taken the building blocks of knowledge from the one before and looked for the boundary in the rule, found it and built on it.

Think of any of your entrepreneurial heroes. They held steadfast on to their visions of what they wanted to create, they used the rules where it served them and they broke new ground when it needed to be broken. Apple certainly think about market orientation and getting customer input to their designs…

…until the customer input is the limitation.

Customer insight could not have designed the smart phone alone. Vision and imagination were also needed to design it and a new set of actions were needed to deliver it to us.

Make it your culture to use the rules AND break the rules

Read this quote with care.

“Some people say, “Give the customers what they want.” But that’s not my approach. Our job is to figure out what they’re going to want before they do. I think Henry Ford once said, “If I’d asked customers what they wanted, they would have told me, ‘A faster horse!’” People don’t know what they want until you show it to them. That’s why I never rely on market research. Our task is to read things that are not yet on the page.” Steve Jobs

Don’t be mislead into thinking Apple doesn’t use market research. It knows the building blocks of understanding its consumers and it works this data beautifully. It just doesn’t use it everywhere. Apple know how far the rules take them and they know when it needs to venture beyond them. They understand this very well and it is a part of their very identity. That is how they play at Dreyfus’ Mastery level.

How do you know as an entrepreneur that you are at this boundary of using the rules or preparing to break them?

  1. You have a vision of what you want to create
  2. You have found the rules that help you to create this
  3. You have applied the applicable rules correctly
  4. You have found a point of conflict — i.e. you want to achieve something you are not getting with the existing rules or the rules don’t fit your circumstances. This is the part where you get the niggle. That little voice that just says, ‘it has to be more than this’.
  5. You know you don’t have the answers and no one else does either, but you hold a mindset of finding them. The beautiful territory of inspiration combined with motivation that causes creation.

Quick Tip:

If you are looking for a short-hand way to make this process happen then make sure your mindset is set to ‘learning mode’. Staying curious about what is out there to help you and then staying curious about how it could be done better is the fastest way to navigate this exciting space.

Also, don’t be tempted to eat forbidden cake.



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Kim van Niekerk

Kim van Niekerk

Explorer of mindsets. Writing about leadership, start ups, teams and organisational culture.