Sign up right now for email updates and get two free ebooks:

Breaking the Rules for Fun and Profit

I joke that I am the most conventional unconventional guy you might ever meet, but it is true in a way.

When we think of unconventional we often think about specific things. Going off to live on a commune might be a big one, having tattoos and piercing might be smaller “bucking the system” type ideas.

Anyone who knows me at all will know I am not the extreme kind of unconventional, and I expect you will be somewhere on the spectrum too.

So what makes me a “rule-breaker” and why might you consider breaking some rules yourself?

The Rules Have Changed

I don’t need to tell you that some of the rules we were raised on have changed.

For example “Work hard. Get a steady job. Be loyal to your employer and they will give you a job for life and treat you well in return”.

Yeah, that one didn’t work out so well did it?

I landed my first dream job, ย working for an internet consultancy with some pretty sweet clients, in 1998. In late 1999 after my daughter was born and fighting for her life they made me redundant. You can imagine how hard it is going for interviews out of telephone contact and knocking on doors applying for jobs knowing that while you are away your child might die.

Yes, I did as I was told, I worked hard, was loyal, and still didn’t last more than a year.

So that is one rule we are often raised to believe that just is no longer true, if it ever was. There is no such thing as job security apart from what you create for yourself.

Sky Diving Without a Parachute

I am pretty risk-averse, and I am not a natural entrepreneur by any means. Unlike some of my friends, I did not sell baseball cards in the playground, and without the experience I mention above and others like it, I would probably never have started my own business.

Oh, I had side “hobby” businesses occasionally through my career, but I made the real leap in 2005. I quit my (pretty good) job working for a marketing and advertising agency and struck out into the world of self employment and business ownership.

Not so unconventional because many people do that every day. But pretty weird for me to do because business was not in my DNA. Both my parents worked for the public sector. In fact my brother, my wife and I all started out our careers working for the UK National Health Service – you can’t get much less of an entrepreneurial family.

But I quit, and I quit with no plan-B and less than no money in the bank. I felt the company was shrinking so much that there was a good chance I might not have a job to go to again, I was not enjoying the work I was doing, and an opportunity to work with a cool startup came along that would just about fund our bills for a while.

(Don’t do what I did – make sure you have at least a few months salary in the bank before you give up your day job)

Thankfully I was pretty well established by the time the startup collapsed, but then and now a lot of people think I was crazy to make that change, and probably still think I am crazy.

Let You Be Your Guide

The point?

Sometimes you just have to learn the rules and then break them.

I am not saying all rules are made to be broken, but some rules don’t apply to your specific circumstances.

Very often we regret the opportunities we DON’T take more than the mistakes we make.

Work out what is best for you and your situation, and put your all into it.

(Mitigating the risk with a plan-b is a smart idea too).

What rules have you broken? Are you glad you did it? Please share in the comments …

Sign up right now for email updates and get these
two free ebooks

"Creating Killer
Flagship Content"

"Authority Alliances"

Just enter your primary email address in the form below and hit the button!

Before commenting, please read my Comments Policy - thanks!


  1. My father had a saying “It Doesn’t Hurt to Ask”. Thus, I named my award-winning book “It Doesn’t Hurt to Ask.” The premise is that sure there are the standard rules, but hey…..ask and you might be surprised what happens. He quietly told us, there are a reason for rules, however, they can be broken when you give people the why. I’ve used this all my life and many wonderful things have happened… yes, call me a rule maker and I’m proud of it.

    • I like that, thanks Kathy!

      Yup, sometimes good things happen when you go against “how things are done”. I was just thinking that a lot of rules are to keep us safe, so knowing the risks can be a reason to break the rules.

      • Absolutely agree—thank goodness we have rules for driving. On the other hand, rules for customer service often do not even make sense. Thank goodness for “out-of-the-box” thinkers/rule breakers for we would not have a world where ideas flow….think about countries where they are not allowed to break rules.

  2. I am running Thesis – why would I want to switch?

    I wish I had a Plan B

  3. Awesome article Chris. You know I have broken a few rules. One rule says that you should always have a “plan b”. I don’t always follow that rule. Another rule is that you should never rely on one source for your income. I didn’t follow that rule either.

    Sometimes, we break rules and learn that we needed to break the rule to learn a really good lesson; not saying the results are what we want, but it’s a lesson nonetheless.

  4. Thanks for sharing Chris – for me this was one of those things you read at exactly the right moment! I can relate to Shane’s note on not always having a ‘plan b’. There are certain things in life (and it’s usually the big stuff) that require us to burn the bridge beneath us and not look back. Not having a ‘plan b’ can be the crucial thing that spurs us along to keep moving forward and not look back. Thanks again for the article – I found it really useful.

    • Very true – a lot of people told us to hold on to our house in the UK rather than sell it (“in case it doesn’t work out”) but I think having one foot in each country would have been encouragement to run back when things got tough. I think maybe there was an element of that thinking from some of the people giving us that advice because our moving country was not a popular decision ๐Ÿ˜‰

  5. I broke the rule that says you have to be a shameless self promoter in order to make it in the field I work in. I’m as low key as they come, but I’ve built a career for myself.

  6. Yep, I broke rules – dropped out of college 20 years ago, back when everyone thought it was thee only lifeline; thought my parents were going to die when I told them. Got married, had 9 children whom I home-school. Definitely a quiet, shy, non-wave-making person who broke some major rules right here. Thank you for writing this, I am somewhat of a lurker – I am subscribed and read quietly w/out usually commenting, but this one hit the nail on the head for me, not so much in terms of business, but life. “Sometimes you just have to learn the rules and then break them.” There are volumes of truth to that statement in these modern times. Thanks again. PS What happened to your daughter? I never knew about any of that…all the best.

    • Woah, 9 kids? Lots of respect to you!

      I try not to post details about what happened family-wise as the internet has a long memory. Suffice to say she has had some medical challenges over the years but she is doing ok now ๐Ÿ™‚

  7. I love this topic Chris… If you are not breaking rules you are not pushing hard enough. I like how you mentioned the fact that no one in your family was an entrepreneur, and the hx had been one of Gov jobs.

    So many people defer to family hx of not being this and not being that, it’s sad cause you see the potential, but they’ve believed in their self imposed stereotype for so long, their destiny is almost inevitable.

    Anyway good stuff brother :0)

    • Thanks Claudio – We tend to defer to family or impose these mindsets out of fear. “Nobody in our family has done it before so it must be genetically impossible for us” ๐Ÿ˜‰

      Someone always has to be first ๐Ÿ˜‰

  8. The important thing to rule breaking is knowing you are breaking it intentionally. I break rules all the time and am fully prepared to deal with the consequences. In fact, only those who break rules really do anything that stands out and gets noticed. Being a black and white cow gets you no where, apparently the purple ones have more to offer : ).

  9. I strongly believe that most modern societies have been shaped to believe that getting a job at a large company is equivalent to getting a job at a “safe” place (job security wise). The current economic crisis has definitely helped in waking up many people in realizing that this is no longer the case, and that rules need to be broken in order to have fun and make real money.

  10. Thanks for the mention :p Being the evil guy that made Chris redundant when our company dropped web dev back in 1999, I should like to focus on the positives and I like to think of course that we gave you an awesome grounding and set of clients to quote as back up for your awesome skills and then propelled you on to bigger and greater things for you as a person. But yeah the timing was utterly shitty ๐Ÿ™ Look at you now! Respect to ya, mush… running your *own* business is the best thing you could’ve done; you’re hugely talented and awesome and that’s why we wanted you in the first place.

    • Without getting woo-woo, I think everything happens for a reason. It all worked out well, it moved me to the next milestone which prepared me for the ones after that – I might never have moved my family to Canada if we had stuck around York ๐Ÿ™‚

      • Indeed… though I’m sure we’d now be begging you to go and open our Calgary operation to deal with the massive new Canadian retail and convenience store clients we’re about to sign up! You’d have ended up there one way or the other, the world works in mysterious ways…

  11. I was raise up with a believe that you should study hard, get good grades and get a steady job and it will surely secure your life. I study hard but unfortunately my grade was not that excellent to secure a highly paid steady job. I have to grab what ever job comes my way. With some experience, I am now working with steady job but not in a highly paid category.
    Later in my life I realize that you are not going to live a secured life unless you are doing some kind of business and to me an online business are the best way to go. If you ask me what rules have I broke? I would say I did not broken any yet.

  12. I broke the rules the first time I quit my day job. It didn’t go as planned, but it was that moment I told myself no matter what happens I must eventually own my own and be in control of my destiny. t gave me the edge. The jobs that followed were only used to fund my business and keep the bills paid until I had my breakthrough.