Which rules to break and when: a personal disruption guide

rules break
Photo: Brent Payne via Flickr

Breaking rules is necessary, because if you follow all the rules to the letter, you’ll never accomplish anything new and original. Ironically, though, every piece of advice on the Internet — including my book and my blog — is setting up new rules  (“Avoid the passive voice! Build your personal brand! Floss!). So should you break the rules or obey them?

I will provide a map to help you steer a path between horrifying consequences (jail, getting fired) and stifling conformity. There’s a flowchart at the bottom.

For example, here are some rules you might encounter:

The first step for rule-breakers: ask “why”

Every rule is in place for a reason. If you don’t understand the reason, you’ve got no business breaking the rule.

For example, the rules I listed about insider trading and vendors exist to insure integrity. Their existence helps either the market or a company to function fairly.

The lawmakers in North Carolina created the transgender bathroom rule to protect women in bathrooms; you might find this reason justified, or you might decide it’s not a good reason because of the problems it creates for transgender people.

The rule about corporate innovation exists to make a company easier to manage. You might or might not find this to be a worthwhile reason to follow it. And the advice rules exist to further your career; you might easily decide in a given situation that you’re better off doing the opposite of what they say.

Once you know why a rule exists, you can determine if it is a just rule or a stupid one, a personal rule or a societal imperative. When a rule exists for a good reason, you’ll need an even better reason to break it.

Then, quantify the risk

Rule-breakers pay a price. In the case of laws, you could end up in jail. In the case of policies, your management may reprimand or fire you. And in the case of career advice, you’ll be undermining habits intended to help you get ahead.

With the risks calculated, you can go on to assess if the benefits outweigh them.

When assessing benefits, concentrate on new creative paths

Breaking some rules just makes your life more convenient, or gets you more money. You’ll benefit a bit if you go faster than the highway speed limit, for example, or fail to pay sales tax on a yard sale.

If the benefits to you in breaking a rule are only tangible and personal, the decision is straightforward — and boring. Break the rule if you think it’s worth it.

It’s the intangible, creative benefits that interest me. In fact, here’s a principle for you:

[tweetthis]The only good reason to break a rule is because it opens up new creative possibilities.[/tweetthis]

For example, you might elect to bypass the corporate innovation process to investigate a new product idea so compelling that you feel you must explore it. You may decide to spend your hour per day writing poetry instead of on your career.

If the creative opportunities are more compelling than both the reason for the rule and the consequences, go for it. (But don’t blame me for what happens next — you’re the one taking the risk.)

Rules I broke and why

I broke a lot of rules to get where I am now. The main one was, you don’t quit a secure job for risky one. I tried to quit Forrester once to write books — the CEO offered to support me as I wrote books for Forrester, and Groundswell was the result. When I actually did quit in 2015, I left stock options and a salary behind and started a blog with a curse word in the name. That looked stupid, but it allowed me to engage my creativity, and it has worked out pretty well so far.

Breaking rules and disruptive innovation

Many of the most innovative companies that have succeeded in the last decade have broken rules along the way.

AirBnB often breaks local hotel and tax policies, and Uber violates taxi regulations. Tesla’s direct sales model violates the rules mandating independent car dealers in many states.

These companies determined that the creative possibilities of their new models outweighed the existing rules. The risks were (and remain) huge, but the payoffs were bigger. And their CEOs would tell you that the reasons for those regulations were obsolete.

I’m not suggesting that you behave like Tesla or AirBnB, but it wouldn’t hurt to recognize the value they created by breaking rules to create something.





Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.


  1. I enjoy every one of your daily blogs. I have preordered your book and I cannot wait to get it. This blog says so much. I have shared this with my entire Customer Experience team. I LOVE IT! Thank you for taking the risk that you took.

  2. Josh,
    All my life I have struggled with stupid rules, and when I see one, i am almost compulsively motivated to break them, particularly corporate ones that just protect the status quo. I guess that is why I became a corporate refugee 20 years ago.
    I rarely break laws, and never more serious than a few Kms over the speed limit, but have never really thought about it through the lens of risk/reward.
    So thanks.