break remote work rules

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.

Courtesy of GIPHY

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 People are ditching outdated, rule-based mindsets, excelling for themselves and not organizations, and being the artist of their own lives.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.

Courtesy of GIPHY

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?


  1. I hate working and I can’t understand people who like it, I tried to be the star employee, tried to be the mediocre, tried to be the average, nothing works for me. And don’t tell me you need to do something you love, work with something you love and you will no longer love it.
    At the moment I want to do nothing and get paid the highest salary possible.
    I know a lot of people in my carrer that managed to do that, they have pretty strong social skills, an infinite set of excuses and can bend people at their will, they may well start a carreer on politics, lol.
    That being said I work in IT, but from all areas inside IT, programming is the most difficult one to have multiple jobs because you’re expected to produce working and reliable code. While functional QA’s is the best one because they can say they’re testing but actually are doing nothing and can come up with a hell of excuses such as lazy devs, infrastructure problems, bad written user stories.
    I know a QA guy who have more than 7 jobs and guess what, he doesn’t do anything in any of them and when questioned he knows how to pull out the excuse deck of infinite cards.
    Cow milking several companies is morally wrong, yes, but so is to work for just one and slack the whole month off.
    That’s why I believe that all this capitalism game would end if people were paid by productivity rather than by hour, which means, you could do more in less time and go home, have more free time to do whatever you want, but we all know the system wants you to do more in less time but get paid the same to ramp up their profits.
    So in this sense, if it’s ok for the system to cow milk you why not you cow milk the system back ?
    One issue though is the poisoning of the well effect, if a company discover your wrong doings and get really mad at you, you could potentially be left out of market if they have connections with other competitors and warn them to not hire you, or even worst, take you to court, which I’ve seen already both cases. But I also have seen just a termination on contract and nothing more happens so the risk is possible there, be warned.

  2. Lame ass millennials who just want to play video games and get paid. No work ethic, not real Americans, just a bunch of weak ass wimps. Milking the system as some form of silent protest? You don’t have any ethics or morals, and one day your time will come. But until then enjoy hiding in your room, Karma will get you, don’t worry.

    1. Wrong, they don’t share YOUR backwards morals. Have fun killing yourself for an employer who doesn’t care about you. The karma is that working people finally have some leverage.

      I can tell from your post that you think there’s nothing more to life than your job and bet you are a blast at parties…

    2. So working 2 jobs = no work ethic and “milking the system”?

      Damn, I better start working 4 jobs…

  3. Over my experience, I tried to be the star employee in order to be promoted, so I took way more responsibilities than I had to and set incredible goals for myself just to get that pay rise. On my review day, I was reminded how an amazing asset I am for the company and how greatful I have to be that I have achieved so much. I received an amazingly small pay rise and was told to continue towards my next promotion, where, guess what, I have received nothing.
    So, since that day I left them and found a J1 and J2 and now I am your average employee that finishes the tasks on time and nothing more. They can keep their “greatful” pay rise.

  4. I do 3 jobs at a time, I earn 20000€/month, my house will be payed in 2 years (a big house)… So yeah it worth it. And I’m from home so I am a lot with my family.

  5. Based on these replies above, maybe it would be best to stress the importance that the OE are not elite entitled tech workers, we are picking up the slack for the job market that demands our skills. We are not taking away jobs, we just do them better than everyone else. Including people who do one job at a time.

  6. In regards to rules 2 and 4, I think it depends on the job. My current J1 is very, very badly run and 4 or 5 exceptional employees are doing almost all the work of the department of around 80 people. There’s one person who the staff regularly describe as awful at his job and he’s been there for six years, he’s been passed by for promotion repeatedly but he does just enough to stay. (Which is almost nothing)

    The opposite can be true as well as I previously worked for a pair of sociopathic managers who expected 90 hours a week on the pay of 40.

  7. Been doing this already for more than the last 10 years and I can testify to the validity of the authors statements. Many many in IT have done this for along time already as well. A lot of commenters here have a closed mind set. When I do a second gig as a consultant I can make money in a single month than I can in my annual bonus on my regular W-2 job . All of my bills are paid and I have college accounts set aside for all my kids, in a good year for me I’m sure I make more income than any of my managers.

    To the haters in the doubters I say this WILL fast become the norm for IT workers. And why shouldn’t it ? If you have a very special set of skills and you’re good at what you do able to multitask and at the end of the day accomplish both jobs why should you not get paid 2x ??!

    As far as workers or people who do the bare minimum, take a look at any large corporation in America and you see those people all around you.

  8. Ha.
    This article almost fooled me.
    Advocating for getting another job is just advocating to get more productivity instead of using the extra time you get from “bending the rules” to invest in yourself.
    What really threw your cover away was “moving outside your comfort zone”, it doesn’t get more corporate bullshit than that.

  9. Dude, you’re the problem ^^^ and you don’t even see it. 😂 P.S. learn to write a sentence, you over achieving fuck 🖕

  10. This is good advice. It’s important to blend in. And if you can blend in, stay middle of the pack at multiple jobs, you’ll be in a better position than management. 😉

  11. The attitude in your comment leads me to believe that YOU are a member of the entitled elite club and don’t want others to get ahead, especially hard working employees. I myself juggle 2 jobs and am always looking to improve my position, as we all should. Why shouldn’t I be able to work remotely and produce for ME?

  12. Just a heads up if you actually listen to this article then you may as well start looking for a nice cardboard box cause your gonna lose your job why would anyone employ or bother keeping an employee who dose the absolute bare minimum and Dosent care about the job at all your getting paid do a good job and you get paid do a poor job you get laid off people are so entitled these days

    1. In my experience of working, the last 10 years, I routinely see employees doing the bare minimum and staying employed or even getting promoted because their manager needs to look good by promoting someone. Maybe it’s wrong but this is the new approach I am taking. I do only what is asked. I do it slow. My manager sent me something to look at in which if said manager had looked at it themselves before sending they would have realized the email didn’t need to be sent. She said it wasn’t a priority and then a week later was like we should get on this sooner rather than later. I sent an email back a day later stating the obvious. These jobs are just a means to an end. They are not life.

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