Once upon a time, we were alone, plying our OE trade in secret. Well, no more! Many companies have embraced remote work. So, we figured it’s time to share our biggest OE lessons learned from the school of hard knocks. Who knows, maybe you’re an OE old hand who will find this entertaining.
Just a fair warning to the OE newbies, nothing is ever written in stone – bending and breaking norms is second nature to OE. Use what works for you, and discard the rest. The OE life is a continuous grand experiment. Embrace the uncertainty.
Here’s the OE scripture (and by no means religious in any way, shape, or form just having fun):
1. Thou shalt have many other jobs besides this Job (J1)
This goes without saying, OE is a lifestyle. There’s no going back. Life before OE was financially risky, professionally mundane, and personally unfulfilling. Having two jobs unlocks unexpected mental health benefits by reinvigorating our desires to learn and grow. While J1 is easy, we need J2+ for intellectual challenge and life fulfillment. The money is not too shabby either.
Once freed from the anxieties of a single job, many OE newbies stop overworking and start prioritizing life and family. OE also forces you to be more business-minded and disciplined. After all, you’re forcing yourself to do more in the same or less time (just as how companies do all the time). But make sure to interview and job shop every six months to stay sharp.
Hence our first commandment: hold a minimum of two jobs and always be interviewing. You’re more than welcome to do more than the minimum. 3-4Js is the sweet spot for many in our community.
2. Thou shalt not share the same devices across multiple jobs
Sometimes it pays to keep it simple, stupid (KISS). I know it’s hard. We all have a little optimizer in us. Most of us are engineers after all. But for heaven’s sake, keep the hardware of all Js separate. Don’t get all cute and think you’re a genius. It’s a recipe to get caught by the security department. Use the tech setup we recommend and stay away from getting caught.
DO NOT mix the hardware. This includes your mobile phone (don’t be a cheapskate, use an old phone or buy a prepaid phone, or risk your cash flows). Enough said. You’ve been warned.
3. Thou shalt not take the OE name in vain (and not do your jobs)
Ah the good ole churn and burn aka fast “money” OE versus slow “sustainable” OE debate.
First, do your jobs well enough so you get paid every two weeks.
Second, burn and churn is not sustainable because you then need to always interview and onboard – a recurring overhead. However, burn and churn may be necessary if the jobs turn out to be an OE nightmare. Quit while you’re ahead and save your own sanity.
Finally, OE is like running a marathon. Don’t burn out after the first couple of miles by running too fast. Take your time and find the ideal OE jobs. Plan to work these OE gems long-term until you reach financial freedom.
The goal of OE is to finish the race and get to financial independence (FI). No one said you have to do it in record-breaking time. Power walk instead.
And oh, if you OE with 5Js for six months and then burn out, that’s not OE. It’s called a cash grab at the expense of long-term physical and mental well-being.
Long-term thinking > short-term thinking. Think about it (pun intended).
4. Remember the Sabbath day and keep your boundaries
Sabbath – the day of rest. If you’ve been OE for a while, you know how important it is to set hard boundaries. If you don’t, then your Js will eat you up and spit you out. And once your brain is fried, good luck getting back into the OE game.
Practically speaking, this means building up good start and stop work routines:
- Write down in advance what you’ll accomplish for the day. Our favorite is the 5-year journal
- Writing serves as a morning routine and cue for the reward of work – cash flows and intellectual challenge
- Build in structured breaks – kids and pets are good excuses. So is working out and having lunch like a normal person
- Set a wind-down routine like reading and responding to the last batch of emails and then shutting off for the day. Stand up and walk away from your OE battle station. You’re done.
Remember, you OE so you don’t have to compromise on boundaries. Don’t ever let your bosses encroach on your boundaries.
5. Thou shalt honor thy calendars
If you have problems managing 5-10 work and personal calendars at the same time, then you have no business in being OE. Keep other calendars separate, J1 on J1’s laptop, and J2 on J2’s laptop.
Refer back to commandment #2 and try not to get cute with aggregating calendars and optimizing. Our simplest solution is to cross-check calendars via your mobile phone’s native calendar app.
6. Thou shalt not kill mental health by onboarding multiple jobs at once
A common mistake by OE rookies with multiple offers. While it might be tempting to accept all the offers, take time to consider your mental and physical health first. Read our success stories first before pulling an OE stunt that lands you in hot waters.
Our advice is to start slow. Take a couple of weeks off from J1 to onboard J2. Try the J1 and J2 together for at least a couple of months before scaling up.
If you feel the urge to break this commandment, we understand. You worked hard at landing these jobs and the money can be tempting. Do save your sanity by spreading your onboardings at least one week apart. Mistakes get made when you rush.
7. Thou shalt freeze your TWN to avoid getting caught
Cover your bases. Freeze your TWN here. Not sure if your current J1 or past Js submit data to TWN? Find out.
Practice good privacy hygiene and exercise your privacy rights. Lockdown as much of your data floating out on the internet.
Read our article on how background checks work and find out all the places to freeze your data. It’s your data and none of anyone else’s business.
8. Thou shalt stay off LinkedIn and social media
Along the same line as freezing your TWN and credit agencies, minimize your social media and online presence and guard your data privacy closely. Check out more on our FAQ.
If you’re an experienced tech worker, like many who OE, jobs will still come to you. You have to do outbound job applications instead of relying on LinkedIn’s inbound job opportunities. Also, by staying off LinkedIn and keeping your resume private, you save yourself from all the recruiter InMail noise and constantly being marketed to by various social media platforms.
So, think of Commandment #8 as mental health cleanse to reduce your digital footprint:
- Start with a Google search of yourself and set up an alert
- Hibernate or delete your LinkedIn account
- Set all social media accounts to the strictest privacy settings or delete them
9. Thou shall not bear false witness on someone who is OE
Ok, let’s get this one out of the way. Is OE lying? Not really. It’s being practical.
First, lying by omission cuts both ways. If you, the employee, are expected to tell HR (whose job is to protect the company) you’re OE, then companies should tell you six months in advance when they plan to lay you off. But does that happen? Almost never.
Just ask anyone who has been laid off right before their annual bonus or stocks vesting. We’ve been there. Companies don’t play fair.
Second, companies get into contract disputes with other companies all the time. That’s why they’re staffed up with in-house lawyers. Now, think of OE as your business, and you’re the CEO running your company-of-one. Contract disputes happen. But that doesn’t mean OE is illegal. Most NDAs (non-disclosure agreements) and one-sided employment contracts are paper tigers: not enforceable in court and not worth the time to try.
Just remember, companies’ outside employment policy and conflict of interest guidelines are just that, policy and guidelines. They are NOT “laws” that give companies and bosses the right to own you or all of your time.
Finally, this goes without saying, don’t be nosy and go snitching on others who may or may not be OE. Whether you choose to OE or not, it’s none of your business how others make their money and vice versa.
10. Thou shalt not covet another OE-er’s lifestyle or income
This is a classic scare mindset at play. “You’ve got yours, now I need to get mine.” Coveting what others have is the start of an ugly road down a life of unhappiness. Instead, just focus on yourself and run your own marathon.
We get it. To compare is to be human. Our brains are hardwired to gauge our standings in the OE pecking order. There will always be someone who OE and makes more than you, as well as others who OE and earn less.
Be content and happy you’re OE-ing in your own way, and finding your own path to financial freedom and happiness. Remember it’s more about the enjoying journey than reaching the destination faster.
A mindset of scarcity (which breeds jealousy and unethical behavior) is due to a disdain for those things easily obtained.
Seneca
What OE has taught me
What OE has taught me is anything is possible if you’ve got the right mindset, imagination, and attitude. You CAN choose to live a new and better lifestyle, it starts with having the guts to admit the old way (work until retirement) isn’t working and the OE way is better.
We’re only at the beginning of a new way of working, one which unlocks the 4-Hour Workweek lifestyle in a massive way. I’m already looking forward to my next challenge: going on repeated mini-retirements with my family (yes, do get envious and motivated to do the same).
What OE has revealed is mindset and imagination are all you need. The simple act of choosing to OE has led me to endless possibilities of what’s next. OE is the new nouveau riche (new, new “stealth” rich) accessible by many.
So, I’ll leave you here with my 10 OE commandments. Do as you wish, but don’t let others tell you “OE cannot be done” or “it’s impossible.” Your life. Your call. Welcome to the OE lifestyle.
Hardware: how about multi VMs on single hardware? Just alt tab to another os?
VMs vs PiKVMs for remote access. Choice is really depending on mobility, flexibility, and redundancy/backup requirements. Also, depends on how many Js you’re trying to scale with.
Curious if any NetWorking/Systems/InfraStructure/DataCenter/etc type guys are OE’ing out there, and how do you manage it w/ on-call unexpected emergencies any time of day or night? Personally, after decades in the IT racket, EMERICUS DURDEN above makes the most sense when he says IT is just too much work, and that OE should all be about the EASY money, and lots of it. To me, this translates to getting away forever from TECHNICAL crap and just do FUNCTIONAL roles, which are usually bullshit excuse-laden subjective-accountability roles that can easily be avoided, circumvented, and talked-around when something goes not quite right. TECHNICAL roles deal with black-and-white problems, something is either working or not (server, router, database, etc) and has to be addressed NOW regardless of your OE plans in place. So, again, any NetWorking/Systems/InfraStructure/DataCenter/etc type guys out there OE’ing, and how do you manage networking OE with it’s endemic 24 x 7 x 365 troubleshooting and problem-laden nature?
You are just stealing from employers and other employees who have to take on the work you avoid! Shame on you!
You guys do realize that not every business is a large evil corporation? Most of the small businesses are bootstrapped by the founders or owners who take risks. By doing only half or 1/3rd job, you are actually hurting small entrepreneurs? When job market becomes tight, you are also hurting other candidates (like me) who need that first job for survival?
I understand there is no such thing as loyalty by employers but OEs are taking it too far! I am pretty sure organizations will eventually catch on but this is just sad!
I need some advice. I have two computers that need to be on two different wifi connections. Is there a device that would allow me to work on the same monitors and keyboard? I am currently using my laptop to connect to the other job using their VX connection and the other is using a velocloud connection. Any tips?
Hello, this is awesome, I worked as a medical biller/manager and as a server at a wealthy resort for 9 years, I did have permission from both employers, I had 3 at one point. So, I begun a remote position last year and I been thinking about a 2j and to be OE lol, but I was thinking of getting a job at a restaurant, then I though I can do a basic PT billing remote positions, is super easy when you know what your doing. So, I saw this on the news, about this lady that has 11j. Wow, then I said YES I can do this FT, so I’m her and I love it.
But do I leave my present job of the resume? do I say I will leave it?
Why would they not agree if employers in Californians know we work multiple, hard physical jobs at that, and I understand they want our mental health well being nowadays but, we as human being are capable of this and more.
Thank you all.
This is all great advice. I agree with it because I know following it cannot hurt, and yet, strangely enough, I’ve followed very little of it since 2017, the year I started doing two or three jobs full-time. Nonetheless, I’ve never encountered a single problem. Actually, in my case, it’s almost been like having two or three full-time careers: management consulting, corporate internal communications, and private equity analysis.
I suppose I’m a bit of an oddball around here because I have no coding or IT background, nor do I have any interest in acquiring one. My own opinion is that tech stuff is just too much work. My goal has always been EASY MONEY. I use my intelligence to pull all the cash I can from the companies I work for. Currently I earn about $350K a year in total, and I still feel like I have a LOT of time on my hands.
I do all of this work from home, always have, on my own personal computer, even though every company I work for issues me a company computer. I put those company computers in my closet. Whenever I have a meeting conflict — it’s rarer than you might think — I simply tell a lie to one of the companies — “Oh, sorry, that totally slipped my mind” or “Sorry, I won’t be able to make it, there’s xxx going on in my life right now” — and I personally have no moral qualms with this. I have NO social media footprint, and I haven’t had one for several years. I use an alias in everything I do online, including this post, so that’s not an issue.
Now here’s the thing: all of that extra income I earn from those jobs I have invested in the stock and bond markets, in dividend-paying and interest-paying financial assets. Nothing too fancy. No crypto assets. No options trading. As a result, I now easily have more than a million in assets that generate six-figures of passive income on top of those salaries. This is separate from 401K and IRA. So this financial independence means that I could take all kinds of risks at those companies (though I don’t), and if they fired me, I wouldn’t even care. I would still be able to pay all my bills for the foreseeable future.
So please think about this: as I see it, the purpose of getting multiple, simultaneous jobs is to plow all that extra money into financial assets that ultimately make you financially independent for the rest of your life. I believe that’s the sole reason for doing it. This has nothing to do with company loyalty or being a successful entrepreneur or even having a career, believe it or not — it’s solely for the sake of being able to do none of those things for the rest of your life even while you remain well off. Again, that’s why I say that the overemployment gig only makes sense if it leads to EASY MONEY. That’s your goal! Thanks.
1000% agreed! Start up that OE financial flywheel for yourself and Family Inc. — the sooner, the better.
Truly a trailblazer. I thank you for your commitment and guidance as we navigate these murky waters.
I need little more clarification on freeze your TWN part. How does freezing help you avoid getting caught?
You need to freeze before 2nd employer start background check? Or you keep it freeze all the time?
If you freeze TWN, will 2nd employer or 3rd employer can run background check? Or you need to remove the freeze when they are running background check?
Thank you
Just freeze TWN and cross those bridges when (if) you get there.
If an employer does a check with TWN (not all of them do), AND they see your file is frozen, AND they ask you about it, then repeat after me: “my privacy is important to me.” Then go from there.
Maybe they are satisfied. Maybe they didn’t care about your detailed employment history anyway. Maybe they ask for references. Maybe they ask for paystubs to verify employment. Maybe they ask you again why you froze it, and you repeat the above. If they don’t like it, maybe you withdraw your application and go somewhere else. If they’re really looking to root out overemployment, find a different role.
Freezing TWN is a perfectly reasonable thing for anyone to do (pull your own report and see how much stuff is on there if you want to be shocked). In the multi-job world, freezing TWN buys you time and gives you options.
Great article. Words to live by.
2) On mixing devices, I think it’s a balancing act. Office 365 works great with multiple accounts provided that no more than one of them is “managed” (i.e., using intune or a device profile). I had J1 and J2 on my personal devices and it worked great—all notifications came to my smart watch. Now I have a new J2 that also wants to manage the device, so I tether an old phone when I am out and about, but I rarely remember to bring the second phone.
You’re absolutely right that having both accounts on one device creates some exposure risk: I once created a J1 Teams meeting via outlook on a personal laptop and it added a J2 teams link. Fortunately I caught it before I clicked send. If I could go back to one device I would, though, just for the convenience, even if I treated it as read-only.
8) Staying off social media for me has meant simply going inactive. I’ve found it useful to have LinkedIn visible, but I haven’t updated it since I took my first J2 (it still says I am at my J1, while my resume says I went from J1 to J2—this disconnect didn’t prevent me from landing my next J2. The key is that I am not >active< on LI. I'll toss out a like here and there, but I don't write articles anymore. Don't stay on there and astroturf for one of your companies ("so proud to work for a company like douchenugget industries that does so much to help the little starving children." Blech).
Spot on, thank you! OE is all about risks management, the commandments are conservative by nature. I thought about #11 remove yourself from all people search sites but that’s a bit of a whack-a-mole exercise.
Those people search sites have a lot of outdated or incorrect information anyway, so you have lots of deniability with them. Whitepages.com says I lived where??
Another ‘mixing devices’ comment…I’ve never listened to this and these are the mistakes I’ve made so far:
– I joined a teams meeting from an outlook calendar link when I was logged into the wrong teams account…luckily it was with a vendor, not a co-worker. They did make a comment and it freaked me out a bit
– I created an email to my manager from the wrong email account in outlook (it even had my signature in it from the other company)….somehow I talked myself out of trouble…said it was an old contract etc…but the the signature said I was a manager…not a consultant. I’ve removed all automatic signatures…but there’s still a risk
– I emailed myself from one company to the other…trying to send myself a document
One one point I did have 3 laptops…but it just makes my bag heavy and is such a hassle
I do recommend at a bare minimum having a dedicated laptop for onboarding…if you’re being trained on a system and your manager wants you to share your screen…the last thing you need showing is your outlook with 6 different inboxes.
I love this guy!
Thank you so much for every single word.