How Employees Get Caught Working Two Jobs 

How Employees Get Caught Working Two Jobs 

Ever wonder how employees get caught working two jobs? We know getting caught can be scary, even when double employment is allowed by company policy. Friends and colleagues will wonder if what you were doing is really ok? If you didn’t follow 12 rules for working two WFH jobs, you risk someone telling on you as suggested by the NYT Ethicist.

Since we don’t know how managers will react, it’s best to keep quiet and avoid tattle-telling on yourself. Working for another boss is likely frowned upon by your current manager. Most bosses will think, “if you have extra bandwidth, then I have some extra work for you”. Also, “we don’t have the budget for that promotion you wanted, even if you totally killed it with the extra work.” As you can see, it quickly devolves into a lose-lose situation.

In this article, we’ll touch on several different situations, but keep in mind your specific situation is unique to you. Only you can determine all the possible outcomes and impacts on your earning potential. You, and only you, can prevent a career forest fire by not talking about two jobs, even with family. Don’t have an ego. Get what you want by giving people what they want. Manage your external perception smartly.

How Do Employees Get Caught

We combed through several situations where employees got caught working two jobs. The common theme is these less-sly employees were caught through unforeseen, shared connections. These common connections are not what you think. They are not always the employers or HR finding out, but rather friends, co-workers, daycare parents, clients, or some third party getting jealous and deciding to notify your employers. 

How Employees Get Caught Working Two Jobs 

For example, a co-worker at your second job, Lisa, was talking to her friend Max about a new restaurant, the exact same restaurant that you recommended to Lisa. Lisa mentioned how you (the double-timing coworker) took your boyfriend, Jefferson, to the restaurant last week and loved it. 

Meanwhile, Max also remembered hearing the exact same restaurant recommendation and a co-worker (yep, that’s you again) that just went this weekend with a boyfriend named Jefferson. Max and Lisa, now intrigued, wondered if this was the same person. They’ll start asking around, and a cascading sequence of events occur where people will ask the same question to confirm their suspicion. Does this sound far-fetched? If so, then you are letting your guard down. 

The Internet has made the world very small

Facebook put out research that shows only three and a half degrees of separation are between us and anyone else. It does not sound like a lot of separation, does it? While those close connections may exist, finding out who they actually are is not that easy. You’d have to friend everyone and actively seek those common links. In our case, we want to minimize those instances that might lead to that common connection discovery.

How To Minimize Chances Of Getting Caught

It sounds like common sense, but to minimize the chances of getting caught, we need to minimize people making common connections that come back to bite you. As humans, we are ego-driven and love to talk about ourselves. Oftentimes, we’re unconsciously oblivious to it. Career networking experts tell us to do so by building rapport with people and tricking them to talk about themselves. We have to act with purpose and keep this natural tendency in check, or risk revealing too much about ourselves. 

Don’t reveal your metadata that can lead back to you

If you’ve ever watched any crime show, you’ll know how profilers connect the dots and build your profile. The school you went to, how many kids you have, where you grew up, the neighborhood you live in, past jobs, or even what you did this weekend. By itself, this information does not tell much about you. But in aggregate, these data points become very revealing and start to pinpoint you. This is what we want to avoid. Check out these two examples. Which one do you think is easier to lead back to you? What can you do to throw someone off the scent?

Sample 1 – Hi I worked the past 5 years in finance and have an MBA at Northeastern. I’m married to my husband Jeff, and we live in Palo Alto with my kids 3 and 8 years old. I also have worked at Intel and HP. In my free time, I like to swim, hike and bike, and now practicing for the half ironman in Kona. 

VS.

Sample 2 – Hi I have experience working in finance and went to a small college out east. I currently live in the Bay Area, South Bay. It’s hard to find time to do anything with my two kids. I wish my kids were old enough to move out for college but they still have a few years to go. Whenever I get some free time, I like doing outdoor activities and spending time with my kids. In the past, I worked at companies that make parts for IoT devices. 

Avoid being caught with passive avoidance 

By passive, we mean to set it and forget it. One thing you can do is hibernate your LinkedIn and control view access to your social networks. Better yet, go to the extreme and get off all social media and erase your online presence. The smaller your surface areas, the fewer chances you can get caught.

Avoid being caught with active avoidance 

The next step is active avoidance. This includes taking steps to add layers of misdirection and doing some work to protect yourself during every interaction. When asked, don’t voluntarily reveal any identifiable information. You can keep it vague and still answer the question. What school did you go to? “Oh, I went to a small college down South.” We are not lying, just not giving extraneous information that might track back to us. 

Create A Fake Profile Of Yourself Before Entering The “Field”

Take a page from your favorite espionage movie and prepare a profile for yourself. Create a profile that is truthful but also re-directs and does not reveal key data about yourself. The more confident you are in your story and responses, the fewer questions people will ask. If you have to pause to think for an answer, people will start to think twice about your answers. Have well-prepared answers to common questions. This is no different than preparing for an interview. This pre-work will ease your mental strain when answering. Lies are always found out because it’s impossible to keep track of what you’ve said and to whom, so tell the truth but have a solid backup story to misdirect. Additionally, use a different phone number and email when applying to your second job. 

Check out Scientific American’s 18 attributes of highly effective liars. While we never condone lying, you can, however, avoid how other people may perceive liars by avoiding being labeled as one.

Example Profile:

Profile CategoryExample Truth – Job 1 Example Misdirection – Job 2Comments
HometownPalo AltoBay Area – South BayGeneralization 
School / EducationTexas Tech – MBASome small college you may not have heard of.Misdirect and indirectly answer
Job IndustryFinance for 8 yearsI jumped around a bit but am currently in finance. Exact vs. generalization
Family /Relationship StatusSingleIn a serious relationshipUnverifiable, even if you slip up, make up a break-up story that “you rather not talk about”. Good excuse to take a few days off. 
HobbiesSwim, Bike, RunLike to spend time outdoors when you can. Hiking with friends. Answers the question and is generic enough that people won’t ask specifics. 
DreamsMake enough money to not work here anymore. You like baking and want to start a bake shop one day.
These are common attributes that, when combined, reveal who you are.

People like to talk about their family, occupation, recreation, and dreams and often use these talking points to initiate small talk and build rapport. Here’s a great youtube video of this method explained in more detail. Having these questions prepared about yourself can ward off 80% of the most common questions.

Do some research about your “adversaries” and the people you are working with. Do some offensive reconnaissance and see if there are any potential connections to your network with the people you will meet. Ward off any mentions of those connections. How can you use this information to social engineer them to get things to work in your favor?

Takeaways on how employees getting caught working two jobs

Does this sound like a lot of mental gymnastics? To some, yes. To others, this is a fun challenge. There are a lot of ways employees get caught working two jobs. Being Overemployed is not a lifestyle for everyone. But for those who are willing to be a bit mindful and are not afraid to do some pre-work, the upside is getting the two paychecks on payday. A little preparation goes a long way. As with everything, do your own research and know your comfort zone. Comfort and confidence will come with knowledge, research, and preparation. Remember Rule #1: Do not talk about working two jobs. Welcome to the Overemployed spy games.

43 comments

  1. I got an offer from a great tech company. I was wondering if I can take some paid time off from my current employer to start my job at the new company?
    I only need to do that for 2 months, so my restricted stocks will be vested. I have worked very hard for my current employer and I have been very underpaid. Giving up 40% of my yearly compensation as stock and giving it back to my horrible employer for free, is not an easy thing to do.
    Will there be any legal issues in California assuming both companies don’t explicitly allow nor ban moonlighting?

    I really appreciate your input or if you can direct me to somewhere I can read more about it.

  2. I’ve been working two jobs, one part-time and one full-time, for over nine years. I have a masters degree for each field and years of experience in both so the only details shared on my two CVs are my contact details and my BA. I had one job during the Great Recession and lost it and vowed to not live through that again.

    I think one key suggestion I would make would be to work in two different fields so that none of them cross over. For me, it also works mentally as a break from the other. I kept working both during the pandemic while my friends were furloughed or let go. Granted, I work one during the day and the part-time one in the evening, which makes me busy and dull, but I plan my vacations to always be travelling and away from a desk.

  3. Why do companies not want you ‘daylighting’? Because what you’re doing constitutes time theft. You’re receiving pay for a 8-5 job (for instance) and working another job while getting paid to do the first job. They are paying for your time exclusively for that job. Not for you to double dip.

    Depending on what industry you are in, if you get caught doing this — kiss any future job in that industry goodbye. Weigh your risks and figure out what is ethical to you. Professionally speaking, it’s unethical to daylight an employer in any industry.

    1. Not sure if you play a lawyer on TV, but you’re obviously not one in real life. “Time theft” only applies only to hourly (non-exempt) work.

  4. So, pardon the lame question but won’t my current employer find out about the new job during the background check? How do you get around that?

    1. Just filled out my background check and they asked for my current employer and past information so that they can check start/end dates

  5. If we freeze our info on theworknumber, wouldn’t that be a red flag if job#1 ever checks and doesn’t see themselves listed?

    Are there legitimate reasons (other than hiding a 2nd job) for why someone would ‘hide’ that info on theworknumber that an HR manager wouldn’t think was suspicious?

    1. Yeah, the reason is “nunya.”

      Nunya BUSINESS. You don’t owe anyone an answer about why you want to protect your privacy. Are you supposed to tell every employer you have a stalker ex? Don’t fill the air. If they ask, tell them your privacy is important to you and stop talking.

  6. Why do companies want to keep people from working more than one job?! If the company does not have the means to pay more or are just not willing to pay more, why should they prevent someone from making more money outside the company to bring into their household?

    People should be able to elevate themselves to a new economic status in any way possible and if that means taking a 2nd or 3rd job, so be it!
    I want to do it but we have to sign a form annually and disclose any other jobs… the verbiage is pretty scary.

    Two of my brothers are executives making over 100k and both have other side jobs.
    The side job of one brother is part-time at his friends store. He has 2 kids in college and a added a pool. Some people dont want to go into debt and charge everything on a credit card or dip into a retirement fund to pay for extras like a new pool.
    The other brother likes his side job hustles! Very successful, both he and his wife make over 100k, built a new home, 2 kids in private school, 2 luxury cars, and all the typicals you would see in that economic bracket. His side job is driving for Luxury Uber in a high demand area. He will take an airport run when he needs to also go to the airport, or pick someone up on the way to a meeting, he really makes it work for himself by taking a ride when he is already heading somewhere. He has over the years also worked a high-end valet side job which pays super well especially in tips.

    They both made me realize, there is no shame in a side-hustle no matter what tax bracket you are in! If an Uber side hustle will pay that private school bill, that bill doesn’t have to come out of the main incomes that are brought into the household.

    So, why do some/most companies forbid it and want to hold someone down financially? It shouldn’t be any of their business.
    I think there needs to be some new laws introduced to prohibit companies from this behavior.

    1. Reason 1: Companies don’t want you to work for their competitors.
      Reason 2: Companies are concerned that their job won’t be your primary focus. Most companies will want to give employees who do a stellar job extra work, but they can’t do that if your job is one of many and you aren’t putting maximum effort into it. Companies secretly like to cut costs this way.

  7. Good day all! Kind of glad I stumbled across this.

    I recently had a job opportunity come my way. 4 people quit my current company and went to this other company and now they referred me for a job at this new company. Not much more money pretty much the same. I will say my current company is super stagnant. I am not learning anymore but at the same time I am SUPER comfortable. (I have a schedule I enjoy). Also at my current company they are saying we don’t have much work anymore and if we lose 1 more customer we will have layoffs but they have been saying this for years now. They have pretty much cut as many people as they possibly can and I don’t think they can make to many more cuts. I thought about trying to juggle both jobs but the 4 people that left my current company could say something to my current boss/company and that wouldn’t go very well I don’t believe and could result in termination. I kind of wish I could test the new job without quitting my current to see if I like it. I am super comfortable where I am, the work load is not hard/much and I have a great schedule. I have been losing sleep over this. Please help.

    Should I stay?

    Should I go?

    Should I try to do both?

    1. If the two companies are not competitors or suppliers, this could be a good trial run for you. I’d start with mentally committing to a short overlap, and go from there. Steps:

      1) Get the J2 job offer, and start. Don’t resign from J1 yet. Possibly take vacation for the first week of J2.

      2) Hibernate your LinkedIn. If J2 people want to connect, tell them you had to do a social media purge. None of their business anyway.

      3) See how it goes. Can you stay on top of both roles? Refine your process and setup using the tips in the blog posts here.

      4) Reduce your vulnerabilities. Disconnect as much as possible from people at both jobs, and decide what your “story” is going to be. Need to keep your standing lunch date with your BFF from J1? That’s risky, but remember: your story for that person is that you only work at J1. Never tell anyone you are working at both. You can tell someone you work at J1 or J2 as appropriate, but never both.

      If you decide to cut it short and drop J1, then any overlap turned up by a background check was to finish a project and use unused vacation. I wouldn’t include the overlap on your resume or LinkedIn, but there are other schools of thought on this that you can read about on this site.

      If you decide to keep it going and someone from J2 finds out you are on the rolls at J1 (“so-and-so said you were still in the address book”), then a simple “I’m moonlighting” will do. No need to elaborate. If they press, put it back on them: I am compliant with all company policies, including those related to moonlighting. (This assumes that you ARE compliant with company moonlighting policies, and J1 and J2 are not competitors.)

      I see this is a trial run for you because the situation you describe is NOT ideal for long-term 2x’ing. If you’re serious about 2x’ing, far better to get a remote job based in a geographic area far from your existing professional network and in a different industry. That will make for less cloak-and-dagger stress on your end.

      Good luck! I know this can be stressful, but having two paychecks reduces stress more than the extra work increases it. Think about it: you say you’re comfortable, but how often do you find yourself chasing carrots and avoiding sticks just to be a “good” employee and avoid a potential layoff? Redundant employment takes that threat out of the equation and builds up your financial cushion so you can breathe easy.

    1. Those are typically start-ups who like to do that to show traction and attract talent. And why I don’t recommend OE at start-ups unless they’re very late stage and already giving out RSUs vice options and about to go public.

  8. Has anyone gone so far as to create an alias or use a different name for their second job? I am working two jobs but wanting to replace one of them with a new one. I often wonder if it would add a layer of security to ask to be called by my middle name on whatever new job I would take. Thoughts? Would specifically love an HR professional’s prospective.

    1. Hi Alex,
      You can definitely request to be called by your middle name at a second job. Your full name will be within the HR records and systems but on the company intranet/email you can request IT change your name to your middle name. That way anyone within the company without HR access will only know you by your middle name.

      I work in HR and have had this requested by employees before. It shouldn’t be an issue, just say you have been known by your middle name as long as you can remember.

  9. worknumber can definitely be problematic – but I think the odds are still in your favor. Not every company has their info on there and a lot of companies are verifying against what you tell them in my experience. I have omitted things before and it never came up in the report. I saw that what I told them was verified.

    You can pull your data from theworknumber. It’s a very detailed report of employment history and wage data. I think it is a step too far in my opinion.

    1. Background check data are often wrong, and as James said, the purpose is to verify what is in your resume, not verify what ISN’T in your resume.

  10. I just started a new job in the same field in which both jobs have a partnership with a particular major brand and there’s a person that works for that brand that I interacted with regularly at my first job and just found out that I will be meeting regularly with this same person at my new job. Should I now choose which job to keep or let go or should I see how it plays out?

  11. I don’t understand the issue concerning the work number… An employer MUST have your social, the ID of the other employer, and proof of your written consent to verify employment at that other employer.

    So if you hide the second job, how would they know the ID of the other employer? And even if they guessed the employer ID (or suspected it) at least you’d see it coming because they’d need your written consent, especially in certain states where consent is required for EACH check.

    I suppose you should worry if you live in a state where credit checks can be run repeatedly after obtaining consent the first time AND your contract explicitly states the employer may periodically run background checks without further consent AND they’re pretty sure you’re also working for “company X” down the street.

    I think the only risk is accessing Company X servers from Company Y’s laptop and/or over their VPN, publications – social media, gossip, or other media published with your name tied to some accomplishment you’ve had with company X. If that happens then good luck my friend…

  12. I had two jobs for about 10 years. One of them was a part-time job offered by a former boss. I was the key contributor in both companies. It was not difficult to handle both and I feel I have the capacity to take another job. My boss in job #1 actually knew my boss in job #2. Fortunately they hated each other and never talked again. I guess I am terrible with most of the things in my life except working.

  13. I am currently working 2 full time freelance jobs and it is incredibly stressful. There are several meetings I have that overlap with other meetings and I need to contribute to both. Any advice on managing this?

    1. This is a good point to be aware of! A dear friend of mine, currently working two 1099-NEC consulting positions, keeps this mantra. Always treat one position as your primary role.

    2. I treat both of my jobs as if they were different projects at the same company.- Even though they are not. This helps me feel confident when skipping meetings and prioritizing each meeting accordingly. Reschedule what you can and skip what you cannot. There are plenty of people not working two jobs who are too busy to attend those same meetings.

  14. I’m a recruiter, I use recruiter to source candidates. From my understanding Linkedin doesn’t allow you to create a second profile. My employers pay for Linkedin recruiter seats, it’s possible to have two recruiter seats but how do you advise getting around posting jobs and connecting with folks?

    1. You can have two Linkedin accounts, just gotta be sly on how you’d go about it. We talk about it inside our private Discord group.

    2. Did you get a second job? How is it going? Contemplating doing the same / creating a new account & using each account for each recruiter seat.

  15. I had a close call once….I had an extra laptop to log into the other Microsoft Teams profile. I had a teams meeting scheduled with a vendor and clicked the calendar link on the wrong computer. It joined the meeting with the wrong teams account…revealing the other email and other company. They asked me about it and my excuse was pretty lame. Imagine if I’d done that with my boss

  16. What would you recommend for that unforeseen shared connection that doesn’t require linkedin or other social media to catch on?

    I find myself in that scenario to a degree. I just started job #2 and I joined our first day orientation to find a previous co-worker… And not just a co-worker as in someone employed by the same company but someone employed by the same team at the same time… and worse they’re on my team at the new company.

    I’ve already worked it out in my head what I’ll say in the event it comes up but it got me thinking in the immediate future but what happens if it doesnt come up and a month or 2 from now that co-worker is talking to a former contact and realizes I’m still there or another person I work with more or less directly goes to leave either company and joins up with my other company?

    I’m also curious about the input others have asked regarding situations such as “theworknumber” and the fact that hiding employment today isn’t as easy as it used to be. I realize getting caught actively working 2 jobs requires someone to take an interest and make that phone call so I think those fears are overblown (assuming you keep the low profile you advocate for) but what do you do when it comes time to move on to the next employer?

  17. You could put a freeze on your employment data with theworknumber.com database
    — employees.theworknumber.com/employee-data-freeze

  18. I’m curious about attempting this however I’m a little nervous. I just came across a site called theworknumber.com by Equifax. It sounds like anyone as long as they have your social and name etc could verify employment with another company thus getting caught leading to getting canned from both jobs! Yikes

    1. Just contact them and ask them about yourself as if you are an employer. See what info they give out

    2. Hi Mike and September 18 anonymous

      In most jurisdictions, you can get your credit report by contacting Equifax or Dun and Bradstreet and asking for it. No extra information. As Sgt. Joe Friday said “just the facts, ma’am”

      Do your research with your state’s “.gov” website to see what your rights are.

      No need to make a false statement that you are an employer. That could be considered ‘wire fraud”.

    3. So I’m curious about what happens if your ever ready to move on? I’ve been thinking about switching from a career in marketing to tech sales but don’t want the pay cut. After a couple years experience in sales I could make way more just doing sales, but what happens down the road when there’s a background check and it shows me employed at two companies?

    4. Yes and no on theworknumber.com. If you were to have two (2) W-2 positions, most likely it would show-up current-state on this database. However, not if you were a 1099-MISC/ 1099-NEC consultant.
      If you did work two W-2 positions at the same time, a future employer’s H.R. department may notice this should the run a theworknumber.com employment verification.

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