8 Remote Work Rules You Should Bend – Or Break

Are you a rule breaker? Do you find yourself constantly thinking “what if I do this” or “why haven’t I tried that”?

If you’re already working multiple jobs, chances are you’re a maverick – someone who doesn’t mind occasionally bending or breaking rules or the conventional way of doing things. In fact, rule-breaking (within the law) is practically required to live the OE lifestyle of working multiple remote jobs. If you’re not comfortable with stepping out of line, then OE is probably not for you.

Why we live in a world of rules

It’s simple: rules were introduced to keep us in line. The system as we know it today was created by industrialists. They needed a world of orderly workers who would do as they were told to keep producing results with minimum hassle.

As Seth Godin puts it in The Icarus Deception: “It’s easy to see why those in power, those running the castle or the cathedral, or even the cottage, would want to spread the word about these disloyal behaviors, to warn us off from imagining that we can walk as the gods walked.” FYI, “disloyal behaviors” here refers to anyone who dares to put a toe out of line.

Rules are designed to keep the system running like clockwork and enforced by social engineering. They’re why we work our asses off, take lunch breaks at the mandated hour, and assign a mental limit to things – such as working only one job at a time.

Breaking free of these unseen rules and living life by our own design requires a good dose of courage and creativity. As Godin says, it’s something that “requires both pride and disobedience, pride of creation and the disobedience of disturbing the status quo”.

You’re not alone. People everywhere are waking up to a new era of thinking where the old work rules are being thrown out of the window – just look at the Great Resignation and people who are publicly celebrating quitting their jobs, something that was kept hush-hush before.

Breaking rules on a massive scale is a thing that’s happening right now. People are ditching outdated, rule-based mindsets, excelling for themselves and not organizations, and being the artist of their own lives. And if you’re reading this, you’re part of that movement too.

Virtual work rules you can break

When the pandemic made remote work popular, new “rules for virtual work” were quickly spread in lieu of a formal office environment. A quick Google search reveals endless lists of such rules. Are we so uncomfortable with the freedom that we need someone to tell us how to work at home?

It’s time to shatter some of these. Here are our favorites:

Rule 1: You should love what you do

Reality: Don’t get too attached to your job(s). You are not defined by the work that you do. Be prepared to let go of things at a moment’s notice and look for something else that’s a better fit for you.

Rule 2: You should give your all to your job and devote yourself to it

Reality: Your company isn’t going to reward you or be loyal to you. Layoffs will happen to even the most devoted of employees. Give your job just enough, but definitely not all of you.

Rule 3: Climb the corporate ladder and aim for that promotion

Reality: While we’re not against excelling, we believe you should do it for yourself, instead of for the company. From an OE point of view, no pay raise is going to be as much as what you’re earning from 2Xing anyway.

Rule 4: Be visible and on the ball

Reality: “On the ball” employees tend to get more responsibilities (often without the corresponding pay) because the boss knows they can get things done. Set your ego aside and don’t try to be a hero. Blend in with the rest of the pack and do just enough to avoid being singled out.

Rule 5: You should do the job yourself

Reality: Should you, though? It’s getting increasingly common to outsource non-specialized admin tasks to a virtual assistant, whether it’s organizing your folders or helping you book a place for the team retreat. The Overemployed is a master at delegating and following up.

Rule 6: Be extra communicative and make decisions fast when you’re working remotely

Reality: You don’t have to – look at what works for you. If your objective is to save time and get things done fast, then yes, you should be decisive and communicative. But if you need to buy time on a project to work on your J2, requesting clarifications or taking a day to respond to emails won’t hurt anyone. Zero inbox is not the objective. And I’ve got bad news for you – zero inbox is fake productivity.

Rule 7: Set a schedule and stick to it

Reality: Yes and no. You want some form of predictability that shows your employer you’re working, but you also need to be hyper-flexible with task-switching between J1 and J2 during your workday. Better yet, set two to three 90-minute focus times that work for you, with built-in breaks in between.

Rule 8: Keep your camera on for meetings

Reality: If you constantly have J1 and J2 meetings happening at the same time, keeping your camera on can be tricky. Early on, try to set a precedent for not always having your camera on – you could claim your connection is slow or that you’re on limited data use. (Fun fact: Research has shown that having your camera on for 15 one-hour meetings a week can create up to 20.7 lbs (9.4 kg) of CO2 emissions per month, but switching it off reduces this number to just 0.8 lbs (377g). That way, you don’t get questioned too much when you have to switch it off to avoid clashing meetings.

Eventually, you’ll break the Overemployed rules too

Are we really advocating breaking the 12 Overemployed rules? Yes, we are. In a world where working multiple jobs is going mainstream and into the metaverse, you won’t have to stick to the rules as much. Use your own judgment and common sense.

Remember that Rule #1 about not talking about OE? Well, just like Fight Club, your curiosity and passion for OE will spread it globally, like how Fight Club became mainstream MMA. When working two or more jobs becomes the norm, you won’t have to keep it a secret – everyone will be doing it, even your bosses. Our bet is OE will become the new normal, and it’ll reshape the way we view life and work, if not already. You’re riding that big wave to come.

And the rule about remaining average? That could very well go out the window, too. You don’t have to keep yourself mediocre – you can be above average and excel for yourself, as long as you do it at your own comfort level.

Test the system (or my mantra, always be testing)

Ultimately, rules are really just guidelines that were created by others to keep the system working. To improve things for yourself, you’ll have to experiment as you would with A/B split tests – bend a rule and see what happens. If things don’t go well, try something else. Have a test goal or hypothesis in mind.

If you want to live the best OE life by design, you have to get used to moving outside of your comfort zone and changing things up to test and see what works. And if that involves shattering a few preconceptions, so be it.

What other rules did we miss that you might want to try bending or breaking?