Breaking the rules
Before they break you
Yo Ho Ho And A Bottle Of Rum
“When have you broken a rule and been really proud of it?”
This question, or some variant of it, is put to every guest on the ‘Be More Pirate’ podcast by Sam Conniff and Alex Barker. In fact they ask it of every group they speak to at a talk or in a workshop.
One of the tenets of ‘Be More Pirate’ is ‘break and replace the rules’ but most of us stumble at the first step. The question is intended to get us thinking about rules, which ones we can challenge and how. Then we can start to develop rule-breaking as a habit. It’s a lesson from the Pirates of the Golden Age, who broke free of the rules of their society and made better rules to create an alternative society.
However, it’s always been one I’ve struggled with a bit. You see, I don’t mind rules. In fact, I sometimes get annoyed when others break them. Some rules help us rub along as a society, they keep us safe (i.e. driving on the left hand side of the road!), they are social lubricant. Some rules help things work better, and I’ve made up plenty of rules as I’ve developed processes and systems for the products and services I’ve created. I’ve even been known to police them (until I realised that was pretty fruitless and not what I was about).
So rules are OK. And people who wilfully break the rules, for no other reason than they just don’t like being told what to do, well, I find them infuriating. Children pretending to be adults, their selfishness and arrogance a shield for their insecurity (any relationship to former PMs called Johnson is entirely co-incidental). And I don’t want to be like them.
But then, some rules are just bloody stupid. Or unnecessary. Or repressive. So those rules I bristle against. Those rules I am more than happy to challenge, to try to change or, failing all else, get around in some way. I’m much more likely to subvert them than to directly disobey or ignore them.
In fact, I realise on reflection, I have a long history of avoiding rules I disagree with and coming up with better alternatives. It starts with curiosity, asking “Why do we do it like that?”. And then ideas, like “Have we though about doing it this way?”, or “Would it make more sense to do x?”. And then, if told “We’re not allowed to”, asking why. Then keep asking it until I get an answer, get a change made, or get told to shut up (which has happened on more than one occasion).
I just see this as what I do. Find a better way, a more elegant solution, and push for it. Rules that stop it happening don’t deserve any respect, they are just obstacles to be overcome. I don’t see it as rule-breaking per se, it’s just one of the means to the end.
So there’s a fine judgment here, a nuance to the way that rule breaking is applied. Be More Pirate adds the qualification that you break the rules and ‘replace them with better ones’ but I don’t think that’s enough. You see, if you read the paragraph above, it could just as easily be used as justification for Trump’s actions, and for those of all the corporate tyrants and despots that leave a trail of chaos and harm in their wake, for all the TechBros-archy and their ‘fail fast and fail often’ nihilistic business approach.
The additional qualification has to be who the rule-breaking benefits, who the new rules help. Is it the individual or the collective? For pirates, it must always be the collective. It has to be for the benefit of, if not all, then of many. That was how, in an age of kings and queens and ultimate power, they were so revolutionary and ground-breaking.
New Rules
The biggest set of rules, however, are the ones in your own head. All the musts, shoulds and oughts that we’ve either made up for ourselves, or have ingested through socialisation.
Those are the hardest ones to break. Most of the time we don’t even realise they are there, so we have to work to identify them. Breaking them is a real personal challenge because we can feel they are part of our identity, that breaking them could undermine our very sense of who we are. It won’t, of course, but we won’t know that until we’ve broken one of them.
That’s why we have to develop our rule breaking muscle and make it a habit (if I’m not mixing my metaphors up too much there. Well, if I am, sod it, who said I can’t?).
Rules can also give us a sense of safety, and they help us conform with our peers, also building safety. Breaking them carries a risk of alienation and abandonment. No wonder we succumb to them, that’s why we fall in with corporate norms even though we don’t really like them. We’re pre-programmed to fit in for our own safety.
If you are stuck in corporate life, feeling like you are going nowhere at best, slowly dying inside, then your only way out is to start breaking some rules. Starting with those internal ones. Start small and grow. Think of it like digging a tunnel out of prison. It starts with a shovelful, then another, and another. You just have to keep going.
And if you’ve been jettisoned from corporate life and are wondering what happens next, it’s even more important because all those internal rules were for a world you no longer inhabit. If you continue to hold onto them then you won’t be able to go forward, you won’t be able to re-imagine yourself and write a new chapter.
So, how would you answer that question? What rule have you broken and been really proud of?
This train of thought was prompted by the last Be More Pirate podcast with the independent singer-songwriter, artist and producer Storry. Go and have a listen and check out the other great guests they’ve had recently.
Falling Down
Did you get affected by the internet outage recently? Were you starved of retail therapy and cat videos when Amazon AWS service suffered a major outage?
If you’d looked up at the sky (well, you might as well have gone outside for a change, what else was there to do?) you would have seen it darkened by flocks of chickens coming home to roost.
You see, Amazon had been aggressively pursuing two policies of a 5-days-a- week Return to Office policy and a headcount reduction to thin middle management and make them work more like a startup. Many felt that these were two cheeks of the same arse (to use a favourite phrase of Frankie Boyle’s), in that the RTO policy would cause people to leave and that those middle managers ‘reduced’ would be the ones reluctant to enforce the RTO policy.
A great wheeze, eh, to get the profit number singing once again? CEO Andy Jassy and his board must have been ordering doubles all round at that one (or new private jets, more likely).
You’ll never guess what happened next. Well, obviously Jassy and co didn’t but many commentators did point out the inevitable consequence of this, if not how it would manifest itself.
Whilst these policies made people leave, they couldn’t control which people left. Mostly, they would be the best people who had options. The ones who resisted RTO were probably those who knew they could get jobs elsewhere. If you make work less hospitable, the talent flees and you end up with the rest who have nowhere to go, the mediocre.
Shortly afterwards, AWS fell over, causing huge expense and reputational damage to the company. And probably hurting Andy’s bonus. It’s the corporate equivalent of stepping on a rake. Twice.
There’s no proof that the flight of talent is linked to the AWS failure. It’s one hell of a coincidence, though, along with other signs that Amazon’s service levels are falling away.
There’s further irony in that the internet exists because the US government wanted a data network that would survive in the event of a nuclear attack. The fundamental design principle was resilience, which led to multiple nodes using packet technology so it could route around damage and have 100% uptime. And Amazon, a company that only exists because the internet, has created a huge point of vulnerability on the internet and to its business, in order to save money (big data centres have major economies of scale).
The internet can survive a nuclear bomb but it’s much more vulnerable to CEO ego, it seems. And there’s a lot of unexploded CEOs out there…
Back To Life
A look at the brighter side now, and whilst many US corporations are playing ‘follow the idiot’ by cutting staff, dragging people back into the office and hoping the AI fairy is going to come along and make it all better, some are making the most of this period of disruption(s) to remake themselves into something better.
Bayer took decisive action to halt what they saw as a slow and inevitable decline by hiring Bill Andersen as their CEO to do what he had done at rival Merck and remodel the business. Anderson came up with ‘Dynamic Shared Ownership’, a model where thousands of teams operate like startups (not dissimilar to Haier’s model).
As Micheal Zanini explains in this LinkedIN post:
Bayer is executing one of the most important business transformations happening anywhere in the world right now. Instead of the usual corporate shuffle, they’re stripping leadership and management models to the studs and rebuilding them, recognizing that anything less won’t deliver the step-function change in performance they need.
The changes run deep: management layers dropped from an average of 12-13 down to 6-7, annual budgets gave way to dynamic resource allocation, and the culture shifted from hierarchy and bureaucracy to entrepreneurial drive. These moves are having a meaningful impact on performance.
They aren’t just moving the deckchairs around as the iceberg approaches, in the forlorn hope that if no-one’s looking directly at it, it might disappear. They’re changing course and rebuilding the whole ship in the process. Stripping it all back to the skeleton and building something fit for today’s world.
In the process, they are breaking rules left right and centre and putting better ones in place. And fewer of them, too.
The reason some organisations are struggling with hybrid working is because they are forcing it onto the existing organisation. The reason cutting headcount doesn’t deliver efficiencies is because they’re just trying to do exactly the same things with less resource. The reason AI isn’t delivering any benefits is because it’s being jammed into the same old machine. The reason change programmes don’t change anything is because the same old rules are being left in place.
There’s a reason why my little logo says “Decrapify Work Or Die”. I think organisations like Bayer are going to outcompete the ‘follow the idiot’ crowd.
The message is be bold, go back to first principles and redesign from there. There are enormous advantages to be gained, for everyone. It’s what the Golden Age pirates did back in the 1600s, breaking all the norms of the time to build a new way of being and a society based on freedom, equality and fellowship. (Ever wondered where the French got it from?)
The first step has to be a rejection of the Status Quo. Perhaps it’s just that moment when you decide “Up with this, I will not put!!”. That’s a rule broken right there. Then you just have to look for what would be better, and start doing that instead. Even if it’s just sticking to your boundaries around working hours. Or taking all your holidays. Take the first step, then keep going.
Or it could be remodelling the entire organisation. If you can do that, start there!! And tell me about it. I like good news.



The Madagascar Golden Age lasted around fifty years, and the Lunar Society a little longer. Both fulfilled the same social; and economic function as catalysts that didn’t survive the reactions they initiated. That doesn’t make it a bad thing, just a fact. I think the distributed network is vital, and it asks the questions why do we need large organisations to make the most of it? If we’re going to break rules, let’s start there.
And it you like the pirate metaphor, I found Graeber’s work on it brilliant. Harder read, greater depth. https://davidgraeber.org/reviews/book-review-pirate-enlightenment-or-the-real-libertalia/
Great article! We, the world of work is in the midst of change. The old rules no longer provide guidance. It's time to re-think business and break the existing rules. The first rule to break is 'command and control'. We go further as a team.