12 rules for working remote jobs

12 Rules For Working Two Remote Jobs (WFH)

The concept “x” rules for “y” have been popularized by books for almost any domain or niche. Here we will introduce our own 12 Rules for working two remote jobs (WFH). Just remember, these are guidelines more than hard and fast rules. But for newbies, you should heed these rules closely.

As with any “x” rules for “y”, we’ve come up with these rules through our community’s collective shared experience, taking note of what works and what failed along the way. You may also want to dive into the successful traits of someone working two remote jobs. Here are our 12 rules, in no particular order.

1. Don’t Talk About Working Two Remote Jobs

The golden rule. First and foremost, don’t talk about working two remote jobs, not even with family members outside of your household. If you can’t keep a secret to yourself, how can you expect others to do the same when they’ve no skin in the game? We made this rule for your own protection. Most who got caught working two jobs were because of a shared connection inside their network. Remember, loose lips sink ships.

Here’s a prime example from the New York Times, and why you should never tell anyone, ever. Not even your dog. Ok, we went too far there. But you get the point.

2. Don’t Fall In Love (with your second burner job)

Don’t fall in love with your jobs, specifically your second job. It is harder to make logical decisions when there is attachment. This attachment includes the role itself, the company brand on your resume, and coworkers. The more attached you are, the more you make emotional rather than rational choices. For example, decisions you might make on what job you want to show on your LinkedIn, whether to leave the job, or whether to stay. You want to be deliberate in your career story and how each job will fit (or not) into your timeline. If you start off with a 2nd job for money and then want to list it on your resume for the brand name, you’re not going to have a good time.

3. Do Your Own Research (DYOR)

No one has skin in the game more than you. As you’re considering Overemployed, filter the signal from the noise, and watch out for confirmation bias (rationalizing to reinforce how you feel). People will give you advice based on their own experiences. And everyone will think they’re right. This includes what you read on this website. It’s always better to have more inputs, but don’t go paralysis by analysis. You should have already done your own research. Now ask hard questions no one else is asking to see if you have missed anything.

4. Have A Clearly Defined Goal

Go into two jobs with a goal and operate off of that goal. Is it early financial freedom? To pay off some debt and buy a house? Being indecisive and losing focus is a recipe for anguish, burnout, and stress. The greatest tragedy is you let lifestyle creep lock you into working two jobs indefinitely. Ouch.

Don’t start this journey without knowing why you are doing it in the first place. Remember yourself of this goal every day.

5. Have An Exit Strategy

Having an exit strategy is complementary to having a focused goal. Things are not always going to turn out the way you want. Having an exit strategy helps you stay ahead and save you from a lot of stress, like when a co-worker is about to rat you out. It will help you stay calm and composed as the juggling act is about to blow up.

Know what you want (goal) and determine in advance when you’ll bail once you’ve hit your goal. It’s no different than going to the casino with a set plan to call it quits when you’re ahead. Don’t let the house take your money.

6. Get What You Want By Giving People What They Want

Success in two jobs is all about perception. If you feed into people’s perception of what they want from you, you’re more likely to get what you want from them. It may be the job, a promotion, or in our case, keeping the job. Act, say, and do things with purpose and give people what they want so you can get what you want from them.

For example, a hiring manager will want someone that is confident. What they’re really looking for are cues that they associate with confidence. Whether you are confident or not, you just need to feed them those cues and give them what they want to see/hear. They get the signals they want, but on the back end, you’re merely decoding and feeding them that perception. Think from their angle to see what they care about so you can send the signals and reap the rewards. Fake it till you make it. Is it manipulation if you know how people tick?

7. Be Average

Don’t cause attention. Try not to be recognized. Don’t add more work for yourself. Think about work dynamics from your experience. The more attention you bring to yourself, the more people will remember you. Going back to rule 1, you don’t want people talking about you and tripping on a common connection to your other job.

8. Take Care Of Yourself First

No matter what, you should prioritize your health. If the pandemic has shown us one thing, it is that life is full of unknowns. Know the reason why you decided to do two WFH jobs. Is it for money? Happiness? What is happiness? It’s all worthless if we do not take care of ourselves to enjoy the outcome. It’s important to always remind yourself of the tradeoffs of the why and what you are doing.

9. Have No Ego; Be Wrong To Be “Rich”

Ego is the Enemy of good leadership” so says HBR. This is true for being the captain of your own life. For example, are you afraid to be laid off? Being told you need to improve? Can you stomach just doing a mediocre job and being judged by your peers? Will you be willing to resign after 2 weeks if the new job is too demanding? Would you worry about what people think?

You have to leave that ego aside and remember your mission – using the 2nd job as a means for money. Think about your personal ROI: Salary / Time Worked. Realize your salary will not scale with the amount of work you do, which leads us to the next rule.

10. Live To Work Another Day, “Another Day, Another Dollar”

Taking a book from Trading Psychology. The rule here is “survive” to work another day. Do your work, meet expectations, don’t do extra, and don’t get terminated. Need I say, “another day another dollar” or “another day 2x the dollars” in our case.

11. Always Seek To Self Improve

Success in two jobs is similar to a field agent in a foreign environment. You’re alone, self-reliant, and you have to figure out problems alone as they come. Having a mindset of self-reflection and constant improvement will get you out with a successful mission. You’re constantly facing new unique challenges and have to devise crafty solutions to get you out of a tough spot. Conflicting meetings, overlapping deadlines, Linkedin management are all unique challenges you will have to figure out. Constant learning and development will get you out of the next situation.

12. Don’t Talk About Working Two Remote Jobs

Rule #12 is don’t forget about rule #1, bringing it to full circle. Don’t talk about working two remote jobs with anyone. If you tell your spouse, think through the expectations and fear they may have.

Remember that loose lips sink ships. Everyone has money scripts that could endanger your newfound fast lane to financial freedom. Unless, of course, you talk about it anonymously on the Overemployed Discord.


  1. Never start 2 jobs in the same month..
    look for 2nd job only after settling down your first job like after 3 months miniumum.

    1. Not necessarily. But certainly go in knowing what the expectations are. Hell, I picked up work with an old company I used to work for 2 or so years ago, another contract just popped up – piece of cake to take them both on, I started one last week, the other I am starting next Monday.
      I see your point, and it may be safer, but if you know the companies and the expectations, then taking the second one sooner shouldn’t be that much of an issue.

  2. I got an offer for J2 which requires MBI Security Clearance, will this cause any issues for J1 which I’ve been on the job for the past 10 years?

  3. Did anyone feel overwhelmed in the first week of taking J2 and felt like quitting? I started J2 last week and I feel so overwhelmed and feeling like quitting. I had some free time in J1 and felt I could take up J2. I got motivated after reading comments here. The problem is that I feel so lost in J2 and swamped with the workload and the past few days couldn’t even do much of J1 job, although still within normal deadline.

    Anyone in this shoe or has been through it?

    1. This is why the advice is to take minimally one week off J1 to onboard with J2. Ideally, take 2-4 weeks off if you can get away with that, so you’ve time to ramp up.

  4. I started a 2nd job on 1st November and a 3rd job on 1st December! I also changed my first job (as it was just a temp contract and I hated it) for another job (also short contract) around mid-December. My goal is to get to the end of February then leave the contract role and job 2, which is a contract job itself anyway although for a bit longer. I might consider keeping it for March as doing 2 jobs will seem a lot easier than doing 3!

    There have been some stressful moments and a couple of times I’ve had to make up an excuse to miss a meeting where there have been clashes and I’m not able to move one of them. But generally speaking its manageable and you kind of get into a groove with it. Anytime I get an email inviting me to a meeting the first thing I do is check my other 2 job calendars, and if they are free I put a ‘busy’ or ‘hold’ entry in for that time/day before accepting the invite from the other one.

    By the end of Feb, I will have made enough surplus income to totally pay off my gambling incurred debts (I have long since stopped gambling thankfully). I have been paying it off slowly through a debt management programme and doing that would take me another 5 years to finish it – yet after only 4 months (1 doing 2 jobs, 3 doing 3 jobs) I will have cleared it all. And bonus – the job I intend to hang on to will seem pretty easy when it’s the only one I have to focus on!

    I dont believe doing this is for everyone – you need to be on the ball, shrewd and not feel bad about lying to people. But the rewards are worth it. I also say don’t do it forever, as the rules here say – have a target and when its hit, bail out.

  5. Has anyone done this successfully in sales? I’m looking at J2 and although companies are not direct competitors they share some overlapping products and industry.

    1. Yes, I am currently working J2 in sales. However J1 is in construction and J2 is for nonprofit fundraising. It can be done in sales jobs too!

  6. I attempted to do this with 2 large corporations. Unknown to me how, J1 found out about J2.

    I was asked to join an HR meeting with my managers present on Zoom. I was told I was in a conflict of interest involving the theft of billable hours. I also had a fraud suit filed against me by J1.

    J2 found out about this and took the same action.

    My warning to all of you is, this is considered fraudulent in some states and is definitely easy to uncover by an employer…. Wish I wouldn’t have done this cause now I’m in a real mess!

    1. I wish you could provide more details. Im not afraid of getting fired, but this is a very real possibility people need to consider . Were you w-2 salaried in both jobs? Same industry/trade? Positions?

    2. Something in your story is missing.
      I can think of various reasons where J1 would find out about J2 and vise-versa. And all would put you as the culprit. There are some important rules you can’t violate, to some, these rules are common sense. For others, not so much.

    3. Were you salaried or hourly? If hourly and clocked in to both at the same time, I see the issue. Otherwise, it does not seem like it could be theft of billable hours if you were salaried (especially salaried, non-exempt).

  7. I have a J1 fT, but got another j2- contracting via small staffing company. I am nervous, as I dont want to put my J1 in danger, if my J1 finds out. I have a conflict of interrst form in J1, that I am thinking mentioning about J2, so that later it wont create a problem. I also wamt to inform my manager that I will br doing some freelamce work for a small friend’s company. Is it a good idea to disclose J2 in conflict of interest form??

  8. I have one full time remote job and landed second full time job that requires three days in office work. I can work from my phone for the first job. Will it be okay to work on job 1 from the office of J2?

    1. I have a question…I am currently in the works in trying to land a part time or even full time remote role in addition to the one I have now. Do you typically lie to the second company you’re looking to secure employment with about being employed? Or that you will put in your two weeks notice with your current employer?

    2. Regarding working on J1 from J2’s office — yes, you can, but be careful. You can’t use J2 resources to do J1. Get a good mobile data plan and use your hotspot for J1 work—I wouldn’t even use the J2 guest Wifi to do J1 business. Don’t print J1 stuff on J2 printers, or use your J2 laptop to conduct J1 business.

      Also, why does J2 require three days a week in the office? Is that something you can negotiate or bluff your way through? Can J2 be fully remote? With the surge in omicron cases, could you plausibly claim to be concerned for your own health or the health of those you live with? If so, they must offer you an accommodation. This three days in office thing sounds like some middle management BS.

      As for BigburgJerm, never lie. Just get your second job and keep the first. Most people interview for other jobs while they are still working.

    1. I would probably find a different J2. The risk is too high and there are plenty of other options out there.

    2. Let the reference know that you are looking for a job but not sure whether to take that new job or not.

  9. What do you do with your linkedin? majority of my connections are from my first job, however the new job cares about it way more. Any ideas are welcomed. 🙂

    1. I am just leaving my LinkedIn as is (i.e J1 says June 2017-Present). Then I won’t update it for the duration of having 2 jobs. If anyone at J1 or J2 ask I say that I don’t go on there much anymore so it’s not up to date. Hope that helps.

  10. Hey, so I’m thinking of plunging into the 2 full-time job scenario. I just went back to an old insurance job but I also was in the process of interviewing with another new insurance job. If I’m offered a position with the new job, I really would like to take it and still hold onto my old job to see how both go. I’m not in sales and both agencies are in different States and are not really competitors due to the different territories. I feel guilty though even thinking of it. But it’s been a tough year and my $55K income has been stretched to its limit. Anyone else in the insurance world? Did you have any concerns over your licenses and two jobs or running into the same contacts?

  11. Im considering my first foray into this world, Currently I work in an office – work is quiet – I can complete the work within 20 hours – however I am in the Middle East – how do I secure a side gig without
    a) risking main job
    b) hours to suit so long as it is completely remote
    I can bring my personal laptop and work on that for the second gig – meetings I can handle if there are a few hours difference
    Any help and advice would be appreciated

    1. Use other platforms such Indeed.com or Dice.com or Monster.com. They’re, in my experience, not comparable to LinkedIn. All my new two gigs were through LinkedIn and I was not really aggressively looking. Just searched for remote jobs; and submitted to whatever I see matches my skills; and got so many interviews and landed on two of those jobs.

  12. Wondering if anyone experienced the second job happens to use the same retirement management company such as Fidelity? Will that cause any issue?

    1. I’d be very perturbed if Fidelity (or others) let J2 know anything about J1. Privacy concerns aside, Fidelity shouldn’t care enough to point it out and IMHO should keep their mouths shut regardless for fear of being sued (successfully or not).

    2. It’s not just your 401(k) but payroll services (like ADP), Microsoft Office 365, health insurance plans, identity management systems like Duo…

      No one cares, and no one is looking to root out overemployment. Your employers’ relationships with these third parties are separate and distinct, and the couldn’t share information about your relationship with other employers if they wanted to.

  13. I have been on my current assignment for almost 3 years; working as a lead developer making $115/hr on corp-to-corp. Started my second gig making $85/hr on W2; but planning to switch to $100/hr on corp-to-corp.

    I got my third assignment and will start soon; making another $108/hr. You can’t make this thing up. I am happy and I will probably end up cancelling one of them. The 2nd one is a joke and no process/agile in place; so it is kinda messy on their end but good for me 🙂

    I am a happy camper; at $323/hr from 3 gigs… buy a home in 2 years cash; if things go well.

    Thank you everyone for your tips. I must say: I have made stupid mistakes already; where I forgot to mute the mic on job 1 while attending another meeting on 2nd job. I gotta be more careul

  14. This article is so helpful. I’m a GenX in Sr Level Mgmt and I end up doing very little since my boss is a millennial who is determined to make sure I know who is boss, ageism is alive and well in tech. So, I’m turning the tables and starting my side hustle. The nice thing, for my primary gig, I can just delegate work and raise zero suspicion.

  15. I know the IRS wont tell unless you allow them to (its a legal violation for them to disclose anything in your return to an unauthorized party) which even then requires a specific inquiry… but what’s the risk of overlapping payroll processors?

    I logged into new Job #3’s payroll processor the other day on their laptop and had a mild panic attack because I was looking at payroll information for Job #1.

    Since job #1 uses workday as a front end for pay and I never login to the payroll processor directly, I had no idea they use the same payroll processor and I couldnt figure out how they got a hold of paystub info from Job #1. Took me a second to realize what I was seeing and why but it was seriously disconcerting either way to login with my single-sign-on credentials for Job #2 and see information for Job #1.

    Come to think of it, Job #2 uses Trinet and I remember when I first logged into Trinet with Job #2, I saw pay stub history for a long past job that also used Trinet but that was more expected given TriNet’s role (they’re technically the employer).

    1. I’m facing a similar situation with two jobs both using the same outsourced HR, TriNet. My goal is to work two W-2 jobs with them, do you think this would be an issue?

    2. Exact same situation. Just found out job #2 uses Trinet. Job #1 uses Trinet? Anyone know if this will pose an issue?

    3. Old thread here, but the short answer is no one cares.

      That’s also the long answer: your various employers have separate relationships with these third parties, and those third parties can’t disclose that back to anyone. Think about it: you could moonlight as a fitness instructor and they and your primary employer could both be using ADP. Why would they rat you out? To whom? For what?

      This applies to 401(k)s, health insurance, even Microsoft Office 365 (which works surprisingly awesome for multiple organizations on your personal devices).

    4. My J1 is Trinet as well, wondering if logging in with a different email address for J2 would avoid this issue?? Or does it recognize you due to SSN or something similar?

  16. Feel like we need a corollary to Rule #1 and #12.
    Dont talk about it, except with people in your household, you trust implicitly and/or are doing the same thing. As someone else said, build your community of overemployed. After all, these comments in which people are talking about their situation (without details) and encourageing others would seem to be a violation of these rules

    As you note, we’re social beings and generally with that comes the need for support from others. Keeping completely mum seems unrealistic and actually probably works against you since inside you’re probably itching to tell someone… Better to tell someone who cares about you then it is to accidentally blurt it out to someone who doesnt and would rat you out…

  17. I have a pretty relaxed Job and landed another full time job in management . I want to keep both abs want to show second job on my resume because this is management job and can get me next better jobs. How can I manage this ? Because if I shoow both jobs on resume , during the employment verification ( if I switch from second jobs to get better mannenent job) there will be an overlap

    1. I have an overlap on my resume from my side gig. Got laid off from the main (woohoo). Now looking for a new Primary job. Had dozens of interviews, literally no one cares.

  18. How do you handle the application process for a second job? (would love to see an article on this). I can ask that they don’t contact current company in the initial process but most expect to once an offer is made or at least a good reason why not. Options that don’t include outright lying. Any other tips to keep company 2 from contacting company 1? I can’t entirely remove my presence from social media, as it’s a required portion of my primary/original job. How did you list your ‘current’ employer on your resume if you’re looking for a second job where that work experience will be needed to get the job? (ie current employer is my 3rd job since I graduated but the one with the longest work history and most relevant experience. I can’t exclude it entirely or I won’t be eligible for the 2nd position.)

    1. Potential employers do not contact a current employer.

      You want to have things like your current business card, a payroll slip to confirm earnings but basically have the new employer thinking he or she is getting a great person and therefore there will be an alert to the current employer.

      A tip – let the person see the document not to copy it.

  19. An honest question- do none of you ever feel ashamed for this deception? Unless my employers were total dicks I think I would feel too ashamed to do this. I guess if I worked for some mega corporation I would feel significantly less guilty but still a little. Like I’m letting down my co-workers all in the name of greed.

    1. You’re violating rules #2 and 6+7.

      #2 – Dont fall in love with your job, especially your second gig… If you become too emotionally invested and attached, you begin to act emotionally instead of rationally. That feeling of shame and guilt? That’s emotion talking. Your rational brain says I’m being underutilized, I could be doing more and if you’re attached to the employer, your emotional brain kicks in and says that’s right, I am underutilized and getting paid full rate for it so I should be doing more and then goes about creating busy work for you to do so you can feel adequately accomplished.

      #6+7 – Give the people what they want but be Average. You have to accept that what your employer wants from you and pays you for is an average output. If you feel underutilized in the job, that’s not a cue for you to step up and contribute more… That’s a cue for you to step out and find more.

      If you’re sitting there at your job and fulfilling the requirements but still have time on your hands, ask yourself this… If you sit idle during the remaining time of the day, will your employee pay you less? If you use that time to up your production and start producing 2x, will your employer give you what you want and compensate you 2x the salary of your position? Note in 99% of cases the answer to both questions is no, except maybe in sales roles and even there the daily effort involved may not directly corelate to an increase/decrease in pay. You can probably see where I’m going with this… Even if you’re a rockstar, be average in your job so that you have idle time that you can put to use using your rockstar energy to produce 2x but do it for a second employer so you earn 2x.

      As “The Overemployed Way” article on this website puts it, Don’t be the hardworking but naive cart horse from George Orwell’s Animal Farm. The farm’s most dedicated and loyal laborer, he falsely believed that any problem can be solved by him working harder. That’s until he collapsed from overworking and was sent to the slaughterhouse instead of the veterinarian.

  20. Check this out folks. I’m working 5 gigs at a time. 1 FTE role and 4 contracts. I’m a Recruiter for well known organizations hunting technology talent.

    I have 5 different laptops. 2 to laptops in one area with the other sitting near flat screen panels. I make sure to move any meetings I have to other times. All of my roles are 100% remote.

    Thanks Covid I love you for making America Great Again. F Corporate America and Nail Biting Micromanagers.

    1. I’m in recruiting and want to do this. Any tips here? How do you avoid getting caught? Do you have a Linkedin? The problem is I have a unique name. Wouldn’t want people figuring me out 😜 Also, the contract company does background checks that include wages. Does this ever come up as a problem for you?

  21. I just got hired for 2 Software Project Manager jobs – 1 est and the other cst while also working my full-time cst.

    I’m super excited and up for the challenge. I need the money to change my life. 200k I’m the bank and I can do real estate for forever!

    1. i am also a PM and considering doing the same…… can you please provide insight on how you manage all the meetings?

  22. This was how I was able to escape corp america and become financially free. I first tried 2 jobs in 2009, second was overnight and it was not physically possible for me, both were remote so eventually quit second job.
    A few years later while searching for a job I got hired by the second company I interviewed with, then first company called and made offer and I did not want to leave the other so thats when I real journey started, Then as both became more manageable I got a third and a fourth. 4 jobs was unbearable, then I settled at 3 gig. I always thought 3 was the sweet spot for me as a network engineer.
    I then was able to use the excess income to invest in crypto and stocks, both paid out very handsomely and now in 2021 I was able to quit 2 jobs and will soon left my last one later this year to do my own thing.

    Moral of the story, working 2 or more jobs will provide you with financial freedom.

    1. Hello Scrooge,

      This is great info as I am also a Network Engineer who works as a Sales Engineer for a well-known Vendor. The issue I have is that the ecosystem is small, so I feel I need to find something totally outside of Network engineering. Are all your jobs related to network engineering?

  23. Hi,
    I am glad to know that there are people with similar thinking. On 2020 I had the opportunity get hire for a remote work as a case manager full-time. While working in a totally different position for a different company. The only flaw was that both jobs were getting done at the same time. It was as if I was cheating but I keep my eyes on the price: DOUBLE PAY. I saved a lot of money! I actually followed most of your rules especially DO NOT TALK ABOUT IT. You guys are the first one to know. It is worth it!

  24. I’ve recently read Graeber’s book “BS jobs” and he elaborates on a concept of “being paid for being available”. In other words an employer neither does own your time nor you, it just pays for your availability if needed. This is a progressive view on a job market and the book was written before the pandemic.

    1. On my list to read! Thanks for explaining the concept. It certainly is a much fairer and progressive way of looking at “jobs” for the 21st century.

  25. I am considering getting into this – have got one job which is really flexible and isn’t all that demanding on my time. I thought I’d start out by looking for a 2nd part time, rather than full time role and see how it goes juggling both. If I can get a PT job that asks for about 4-5 hours a day, the reality is it can probably be done in 2-3, so it should be doable all round. I do worry about meetings clashing though!

  26. Question. How do you decide which is a primary job? The one I am in now? Less demanding? This is great, I can’t believe I found this!

    1. To me, every situation is likely different so it would depend on the specifics of yours.

      It’d be nice if things worked out so your first job is your least demanding and thus your primary but it seems rare that it actually happens that way.

      Maslow’s Hierarchy of Needs is probably a good place to start with assessing which job is your “primary.” Your primary job is likely the one that makes up the bulk of your income or at the very least provides sufficient income for you to live on the salary it provides alone. If your jobs have similar pay, then maybe move up the hierarchy. Which of your jobs do you feel provides the better security of employment? This might also extend to which one would help you more in landing the next job (company reputation). Continue to move up the hierarchy and as you do, one of them is undoubtedly likely to fall behind the other. The one that is providing the most fulfillment of needs should probably be your primary.

      Note this assumes you are able to answer questions about the continuity of your resume. There’s a good chance you’ll either have to have periods of unemployment or periods of dual employment listed and if you aren’t prepared to answer the questions that this raises, then your primary should probably be the job that provides you the continuity.

      Again its all situationally dependent.

    1. No anyone in industries that’s friendly to remote and multiple jobs can. I’ve friends who are 2-3x in academia and doctors. Just some examples. Generally, I’d say, 2x-ers are knowledge workers.

  27. I work as a software tester for a company and due to covid, I am allowed to work from home.
    its been 3 months, I feel like I could take a 2nd full time job because I have enough time to handle the tasks.
    After watching some youtube videos about this topics and reading a couple articles, I know im not the only one.
    I have been thinking that on the 2nd job hunt, I would keep a low profile, and express myself as a less experienced candidate so the workload would be also less.
    And yeah, its my logic, dont know if it goes that way in reality.
    Its pretty tempting to me now. Because I have seen plenty of job recruitment memos which offer remote work environment.
    What do you guys think about it?

    1. I did exactly that and it worked.. The the only concern both jobs are processed by ADP.. Not sure if it means any trouble lol

  28. How do you know the job is good for 2x after the interview?
    The vast majority demands everyday meetings in the scrum, and there are always people waiting for results and checking this. It’s really difficult to get this impression this is a good one after the interview.

    1. Look for job 1 in a time zone that’s a couple of hours away from job 2.

      J1 is CST and J2 is PCT. That gives a couple of hours on either side of the day for morning scrums and focus time.

  29. Wow. I literally woke up the other day with this exact “crazy idea”, only to discover in the WSJ no less that all of this existed.

    1. I’m a Project Manager with the same questions. I added 2 contract jobs to my current ft and need some advice on how to manage.

      I control the meeting times, I’m just a bit anxious about training.

  30. One thing I’d like to know – when you apply to the job (and get it) they will presumably do a background check. How do you handle that?

    I’ve been at current job for ~3y and it’s a pretty big one, only one other job after college. I 100% want to make sure the new company does not get in touch with my current employer. What job do I provide as a reference for the checks?


    1. What I did was invent a company, a website, used AI generated imagery, bland auto generated Corp-u-speak content, and a list of 6 Google phone numbers, that all pointed back to a cash only 7-11 burner phone that I only ever used for verification.

    2. A phony employer can be very problematic as it is a false statement, knowingly made with intent to deceive others. If others accept it as true and make decisions based on that information you could have big liability.

    3. Don’t background checks get done BEFORE you start your new role and thus it is expected that you will still be employed by J1 during this process? Employment verification is done by automated HR systems in most big companies. As a manager I never know if one of my employees has gotten their employment verified.

  31. My question is how do you get past the interview process? All a company has to do is look on LinkedIn to see where you work currently and then they’re going to ask questions like “why are you leaving your current position at X company”? Do you just straight up lie (that feels a bit on the nose)? But if you tell them that you’re planning on staying with them there’s almost 0 chance you’re getting a job. Thoughts?

    1. One more question then, what do you generally disclose in the interview when they ask questions like why you’re leaving your current company?

    2. Same as what you say today — growth, learn, blah blah blah. Basically what the other side wants to hear. Play the game, playa! 🙂

    3. I agree with Isaac, yet you can say something like ‘I’m willing to leave X job only if I’m convinced to do so’ – this is true, just not in a way they’d like it 😉

    4. My current role is listed as a consultant.

      I’m in leadership, so I almost never list my current role because then I get hammered by recruiters and vendors all day. Turns out this works well for being Overemployed, too. 😉

  32. Ok so I started one job Wednesday and start another on Monday. However, I’m in setting up/training on both right now. Both require me to be on camera. How do I juggle without being caught ?

    1. If you only need a temp solution for 2 jobs on-camera, tune in to your Monday job on-camera, and tell your other job that your laptop is being fixed and you are using a desktop without camera as a temporary solution. This assumes all equipment is yours. I have multiple laptops, 2 desktops, and a monitor array than can be switched in any combination to any computer, as well as multiple LANs and routers. I watch movies while working 2-4 jobs.

    2. Happens to me a few months ago.
      Place laptops side by side and sit in the middle.
      Have both mics muted, and listen one training on the speakers the other on the headset.
      Made a lot of “brb” and have camera covers.
      I was not really playing attention, just waiting for my name to be called, whenever a I hear my name I said: “sorry, say it again please”.

  33. One rule breaking # 1: Build a community.
    We are 3 friends with 2-3 permanent jobs each and 3-4 temporary, ATM we have 18 jobs (fun fact – some of our positions are in the same company).
    Everyone has 1 major job where we build our careers. Others are basic back-end SWE
    In case, one of them is drowning on first job, others are helping for a fixed rate.
    We apply with nicknames and no-one (except HRs and managers) know our real names.
    LinkedIn profiles have no photo and real name – nicknames are used

    We also land randomly on contract positions (temporary jobs) where we literally do nothing:
    – we go interviews constantly, other folks are backing you app in technical rounds
    – get offer, increase it, do onboarding and then do nothing
    – usually you get paychecks for 3-5 months before they fire you
    – if some position is really easy to manage (taking no more than 5 hours per week) then I consider it as permanent and do tasks

    Some notes:
    – we live in same apartments community, so we can exchange employers’ laptops, actually we work in the community common area
    – webcams are always off, buy webcam cover to protect yourself from camera accidentally being on
    – we are immigrants with pretty strong accent, if there is no choice we actually speak on meetings
    – we are all senior-staff level engineers at our major jobs, our secondary ones are junior-middle positions, don’t take intern positions – there is too much attention

    1. Not that hard actually, you just need to find jobs in the following type of companies:
      – stable and profitable
      – not earning huge amount of money
      – need tech infrastructure but it is a supportive department not money generating

      These companies usually don’t have resources to hire the best and are not able to compete with Tier-1, 2 or even 3 companies on job market. They usually hire engineers on OPT/h1b, pay peanuts (90-120k) and don’t have a lot of work to be done but still need someone. They can’t hire bodyshops as they need to earn money and prefer reacher companies where they can charge x2 to what they pay to engineers.

      In my case – the major job is a public tier-2 company with TC ~230-250k (150 base plus performance bonus and stocks). Takes ~25h/week
      2 other permanent positions are
      – 105k full time crap insurance-related company with almost no work (sometimes you don’t commit to github for weeks). 5 h/week
      – another one is $85/h contract retailer – have been there for a year, 1 meeting per week, it took them 3 months to get VPN working for me, I don’t know why they need me, I spend maximum 5 hours per week actually doing something there

      3 temporary:
      – corp to corp SDET: $75/h – they hired me to build test framework and infrastructure. More than 6 months there, most likely this job will become a permanent as it takes couple of hours per week and I usually spend ~8 hours on work and then can use the results for a month. 2-3 h/week to prepare commits, write documentation, etc
      – back-end engineer for 100k – 2 months there, probably will become a permanent job as well, takes ~10h/week, CRUD operations and basic business logic on back-end
      – back-end engineer for 120k – 2 month there, waiting to be fired, slacking a lot, always ask for syncs and reports
      – recently was fired from an shit-hole accounting firm with $80k salary – put 150 lines of code during 6 months

    2. Can I be part of this circle? Dang lol I have 3 going on right now and building a company as well.

    3. Are you on Discord channel? I need some hints regarding the peanuts jobs you mentioned. I am a Senior Programmer. But being from East Europe, a senior programmer it is still payed 60-70k per year. My ID on Discord is the name here. Some information may help a lot and maybe I can return the favor.

    4. 6Jobs in Pocket – This is next level! Seriously awesome and not for the faint of heart, but it sounds like you are managing it well. I am curious if this can be done outside of the technical vocation, such as sales and or marketing?

  34. (1) Get a good monitor setup. Dual for each role. If you can, use Logitech MX flow to share 1x mouse and keyboard between 2x computers. Stack vertically, and with different color Windows themes. You’ll never miss anything.

    (2) Tell one firm that you’ll “wrap something up next morning,” when in reality you start late at night. RESAVE your files so file modified time stamp is consistent.

    (3) Take sick days at one job when the other job needs focus. Fake a move or family emergency. Fake a marriage, even! Don’t think twice about the ethics and count your extra money. You can bet that 0x companies care about you as a person, so don’t feel bad.

    (4) Use a USB-SWITCHER for your USB headset and/or webcam. Or, buy duplicates of both. Wide-angle webcams make it hard to see if your mouth is moving. Don’t be animated. Two sets of airpods help (one LEFT, one RIGHT for simultaneous meetings).

    (5) Be average

    (6) Don’t stop at 2x. Try a third. ⭐😄

    1. Hi Sebastian:

      You state: “6) Don’t stop at 2x. Try a third. ⭐😄”

      With respect, i disagree.

      Better to be average and employed in two jobs than poor at three and canned from 1 or even 2 positions.

    2. @Numbers Guy,

      Depends on the specifics of your situation. What’s your exit strategy? Where are you at with Job 1? And job 2? Can you be average at all 3?

      Maybe you already have enough cycles to take on a 3rd (or more). Maybe 1 or more of your existing positions is reducing your workload or is going through a re-org where you can get lost in the shuffle.

      Maybe you’re looking to leave 1 of the jobs already. Without absolutely tanking your performance and calling attention to yourself in the process and having them investigate, chances are you could milk that job for a fair stretch before anyone gets too suspicious. Doubly so if you have a ton of un-earned paid time off (the type that isn’t paid out on leaving) and want to burn it down… Take a week or 2 off, start doing 3 days work weeks, etc.

      Maybe you’re looking to leave job 1 and have 2 competing job offers and you want to get a lay of the land at both companies before leaving your primary… Honestly, while the advice on this site says to only to take on that 3rd job if you’re stable and confident in your first 2 positions and I can agree its bad to do try and take on 2 new positions simultaneously since you’re pretty much guaranteed to run into meeting conflicts the first few weeks, starting within 2-4 weeks of each other could work well for some. Its just enough time for the dust to start to settle and start making your own schedule at the job you started first and though its a lot to take in, your brain is already in learn mode and building new pathways, might as well harness that and 2x your learning. In addition to that, not only do the first couple weeks at a job not only have some of the lowest performance expectations but its also the time where managers level set their expectation for you for the year. If you set the bar low,

      When you do finally leave job 1, your performance is likely to increase in jobs 2 and 3 and that assumes you continue to work 2x for both companies… Maybe you dont like the boss, the company or the job at one of the 2 companies and you decide to go back to 1x or maybe cycle through to another 3x for a period while finding a replacement for the position you dont like.

  35. Como foi bom ler este artigo . Eu trabalho em um emprego onde sou autônoma e essa insegurança estava me deixando maluca , então procurei outro e iria deixar esse primeiro, mas vi que seria ótimo manter os dois por um tempo financeiramente. Toda segunda é uma loucura , trnho reunião com os dois chefes no mesmo horário 😂😂 Comecei a ser mais organizada para dar conta dos dois . Sempre busquei excelência por obde passei e hoje sofro um pouco com isso , mas é bom em um momento na vida colocar os meus objetivos em primeiro lugar.

    1. Olá, como posso arranjar um emprego a trabalhar por casa, tendo outro emprego em que trabalho no escritório?

      Muito obrigada,

  36. I have two completely separate work areas on two different desks in a ninety degree setup. That way I can easily swivel my chair to work at either job. Each setup has 3 monitors, mouse/keyboard/headset and a white board. In this setup both headsets will reach me for those crazy double meetings where I have different companies barking in each ear and mute buttons in each hand. It’s not for the faint of heart!

    1. We’re doing that at the moment. It is tough because when you’re both juggling, you can’t make plans together – too many time clashes. Even planning a meal becomes stressful!

    2. My husband worked 3 jobs, though one was just a security gig that paid him to sit in his car so he did his other work while in the car, the other 2 remote.

      I work BD&COMM as a consultant for a US University, and in my province for COMM. Both remote. My husband and I work well over 60+ hours a week each. Yet, we have more time then when we had with one job each and commuting. We make each other coffee in the morning, have all our meals together – with our computers always nearby. We are together way more even though we are always working – for us, we love it!

      Tackled all our debt and on track with our goals and we’re not even 25 yet 😉

  37. Don’t forget to adjust your 401k contributions and withholdings at both jobs. I think the max is $59k per year total from you and both employers. Check the limits via IRS.

    1. Is there any way the IRS can notify employers of multiple jobs? Tax withholding strategy? Can employers sue if caught?

    2. the irs wont do that, if you can pay them 2x of 3x taxes they will be happy and lips shut.
      employers can sue but they wont, because the legal cost will be more than what they can gain back if they win the lawsuit.

    3. Better to send the IRS and your state’s tax department additional checks before the year end saying simply please apply to my account That way, as at December 31, you do not have a tax liability that you need to get covered by April 15th.

      With basic tax software you can estimate your 2021 tax bill and compare it to withholdings to date so that you have an idea of what you owe.

      A person who is ahead on his or her taxes will be less likely to have the tax man looking around.

      Given the situation, many CPAs say “pigs get fat, hogs get slaughtered.” It is better to be a happy pig than a slaughtered hog.

      In other words, **do not be an aggressive filer.** Declare every dollar earned. Take the deduction s that are legitimate and nothing more.

      With two jobs, you do not need the stress of a tax audit; that is like a third or 4th job..

    4. So can you explain how this works, if i am working 2 to 3 jobs – whats my max irs contribution so that i dont overpay – lets assume 1 to 2 jobs are full time and one is as a contractor.

  38. I worked at a highly competitive, political company in the pharmaceutical field as a research scientist. With the pandemic, it was all remote and really only required about 15-20 hours a week. I took a second job as an operations manager in the software industry…in the same city. Unbeknown to me, my manager at my pharmaceutical job knows my new manager at the software company and somehow, I came up. Lost both jobs as they cited my “no additional jobs” clause in my employment clause. So two things I learned. One negotiate your employment contracts and two, have job B be located in a different city.

    1. Sorry about your bad experience, this is a good one though – check if your 2nd job has LI connections to your first! Pure gold over here. Did you land on your feet and find another Pharma job Christy, or did you end up going into software perhaps? Wishing you the best of luck

      – Finance

    2. Thanks, Finance! I ended up shifting my mindset around “career” to focus on what I wanted in life. Rather than “career-building”, I am focusing on my personal core values and my personal goals as my Northstar. It changed how I look at employment as a “means to an end” rather than focusing on my employment as my core engine for personal growth and value. What I did was secure one FT role outside of pharma in software and then have secured 3 contract ‘gigs’. The one FT role is taking me about 20 hours per week to complete and then the side gigs are all based on specific completion of tasks, not time.

  39. Has anyone actually hired some help, Im thinking of hiring an “intern”. someone young in the field and trying to build some experience.

    1. Hire an “apprentice”. This communicates that you are going to actually invest in their life and they will gain work experience in that given trade / vocation. Set clear terms that are mutually beneficial. Pay a fair wage for not only you but the other person.

    2. I have recently hired a freelancer apprentice straight out of Uni to help me with my side hustle. He saved me about 5 days worth of work for a fraction of my expected income. He gained lots of valuable experience which will help him land his first job, or I could keep paying him to do mine. Best decision ever.

    3. I have used my brother and others from upwork to help me with simple/repetitive tasks. Its a must for when you work over 2, 2 is easy for me now, but when I had 3-4 it was very stressful.

    4. I am. I just picked up a second job and I’m a bit worried about the work load. if you’re capable of doing network engineering, cloud. Linux, or python work – I could use you. Hit me up on here.

  40. I will add:
    – Have separate computers for each job.
    (I know a case that a guy was sharing screen in a meeting and accidentally switch windows and code and slack from the other job showed in the meeting.
    So, invest on another computer if you want to avoid silly mistakes.)
    – Take notes of all your action items
    – Track your meetings
    – If you have a meeting on one project that you cannot miss or move, create a “lunch” schedule in the other job so no one assigns you a meeting at that time.
    – Do not update you LinkedIn, if possible delete it.

    1. I have an L-shaped desk with separate computers on opposite ends for both of my jobs. Both jobs are just a pivot of my chair away. With what I do, it would be literally impossible for me to do my job accurately if they shared. I keep a calendar of all meetings and events and one job has my actual cell number while another has my google voice number. I don’t use LinkedIn at all and never speak about even having another job. My companies are technically competitors but my roles use two completely different skill sets.

    2. Most operating systems let you have multiple desktops these days – that should probably suffice. Just make sure you keep your file system well organized and separated. No disks with obvious names. No messy folders with multiple work projects together. Etc

    3. I strongly disagree! Have 2 computers or notebooks separate from each other and color code or put the name of the company in huge letters clearly visible above each. REMEMBER: 1 mistake and it could be over.

    4. All good advice. Different computers, delete LinkedIn (I haven’t updated mine in about 10 years). I also don’t use social media. Since I work for banks, I even have different banks so that there’s no overlap there. Paranoid? Maybe but better safe than sorry. Keep your head down, keep a low profile and keep banking those extra paychecks for as long as possible.

  41. I’d add;
    – Record EVERY conference call
    – Manage your calendar like your life depended on it
    – Take vacation from all jobs at the same time (so you don’t get burned out)
    – Hire help (an assistant)
    – Invest and pay off ALL debt (don’t squander the $)

    1. Recording all calls is useful but I am curious if you have time to check back and review the calls.

    2. -I record every call.
      – each job has its own calendar but I have a third one that combines the 2.
      – create separate profiles so things don’t get confusing

    3. I’ve been over-employed for nearly 6 years now. In Academia, the biggest challenge is using J1’s network you do not manage to do J2’s online tasks. Simply using 2 computers doesn’t solve the issue of a nosey IT tech. Covid has made this easier since I am now fully at home and on a network that I own. This morning I received a job offer, similar industry-but no overlap/competition issues. I’ll be taking it so that I can ditch J2 which has turned out to be more of a hassle than anything else. I concur that the #1 key to making this work is to manage your calendar like an Olympian. You cannot afford to screw up too many meetings or provide too many issues. From time to time, I take PTO from one job to cover something essential at the other. This is extremely doable—and has made a real difference in my financial reality.

    4. YEs! Omg I’m so happy other people understand this. My friends think I’m fucking stupid for “putting myself through so much stress” but hey! I’m bout to buy my first house AND that Tesla I want 🤣🤣🤣. Debt is paid off!

    5. Other people will judge. Even family. People get jealous. Best to keep your 2x-info to yourself and of course you’ve the Overemployed community to support you!

    6. Hi Anon –

      Perhaps there should be a Rule 11A – “Never have a nicer car than your boss; better to have a clean 4-year old Toyota in top mechanical condition than a Tesla that flashes too much money” and is a red flag…

      Furthermore, cars are depreciating assets. As they say “buy land – they aren’t making any more of it.”

      PS: Your friends should not know of your separate gig. As they said in WWII “loose lips sink ships!”

  42. Luckily for me, my 1st job won’t promote me, they said this job is what it is and needs to stay that way. And this job is easy to do and doesn’t take up a 40-hour workweek. It’s why I interviewed fir another job in a completely different field I have ever worked. As I was thinking about turning in my notice at job A, I thought, since I worked D.C. hours for them and job B will be PST time why don’t I work both. I know job A will be required to return to the office while job B is strictly remote. My plan is to keep job A until we are told to return and then I will quit. Having both will help tremendously financially to pay off debt.

    1. Same here brother! I have kept both since Oct 2020 and paid off my car and have a full salary already saved! Keep it going, don’t feel bad.

    2. Mostly same here, Sally. Except job 1 keeps expanding responsibilities and raising the bar of their expectations with no promise of promotion or raise (rather a be happy you’re still employed). With job 2 PST, hours don’t overlap. But it has taken and will continue to require juggling now that job 1 is no longer WFH. Now to figure out my exit plan – if I want or need one.

    3. In my experience, the really valuable job is not the one that pays most or that offers the most satisfaction. No. Its the one that is easiest and least demanding of your time. That enables you to work a 2nd job with no stress or even a 3rd if you’re motivated. If one of your jobs or contracts is too demanding, drop it.

  43. how about you do your job so other people that rely one you to do your job don’t get pissed off at you all the time and commit suicide because they have to work with useless people

    1. lol – are we working on a production line here? Sorry, old thinking. The moment you don’t perform, you get shown the door. Now better question is why do managers keep low performers around? Hmmm. Let that stew for a little bit.

    2. I have a low performer the company won’t let me fire so they can remain in the graces of good press.

    3. Couldn’t keep the job if we’re not doing it…. Why are you even here if none of this applies to you? Go do your job reading articles about how to keep your one mediocre job

    4. @The real truth…
      Working multiple jobs and performing well in any/all of them are not mutually exclusive events.
      Conversely, you should recognize that none of the occurrences mentioned are necessarily dependent events.

      That is to say person 1 could do their job and do it well but still be useless.
      Person 2 could fail in their job and still not have people pissed off at them.
      Person 3 could do their job and do it well and still have people pissed off at them.
      Person 4 could still convince themselves everyone they work with is uselessly aggravating and commit suicide when they reach their breaking point whether its true or not.

      Bullets 6-10 basically amount to “be mediocre” so the criticism by @the real truth is isn’t exactly unfounded, just misdirected.

  44. I agree with 13-15 posted above. I would add the following.
    16- Be an aggressive note taker. I have to take notes of everything I have said or committed to doing or else things just get lost in the shuffle. .

    1. I work one job remotely in a call center what do you guys think it would fit for me as a second job?

  45. 13. No Conferences
    14. Avoid jobs in overlapping sectors
    15. Pay off debt aggressively or Invest extra income.

    1. It’s so refreshing to realize I am not alone! I could have written this rules myself!! I had to figure out myself!

      It’s hard to be average. I have found out my productivity has increased aggressively. Unintentional side effect of time over management.

      It’s not for the faint of heart which makes rule 4 so important. What do you want? “Pay all debts” “down payment for a home” “increase savings in 100k” .. have a goal, reach it and reassess. Rinse and repeat.

    2. I have this challenge as well. Especially when those around you are less than mediocre

    3. I’ve found that trying to be average still has me miles ahead of peers. And I just can’t bring myself to lower the quality. Rather, I have put it on a clock. And struggle more with reining in myself and trying to retrain others (and myself) that I’m not going to [continue to] be available 24/7/365.

Leave a Reply

Your email address will not be published.