How Employees Get Caught Working Two Jobs 

Getting caught working two jobs has a negative connotation to it. Even if it’s allowed by your employment contracts, people will still question “is what you are doing really ok?”. Since we don’t know how your bosses will react, it’s best to keep things quiet while working two jobs. It’s usually not looked upon favorably by your manager. Most bosses will think, “if you have extra bandwidth, well, I have extra work that I can give you.” Also, “we don’t have a budget for a promotion even if you do well”. 

We touch upon different situations in this article but your specific situation is unique to you. Only you can determine all the possible outcomes in your scenario and only you can prevent your career forest fires. 

Tying this back to our 12 rules, Rule1, rule 9, and rule 6. Don’t talk about two jobs, Don’t have an ego, and get what you want by giving people what they want (manage your external perception).

How do employees get caught working two jobs?

We combed through different situations where employees are caught working two jobs. There was one thing in common when we take a look at all the stories. Those employees that were “caught” were all discovered working two jobs through shared connections. These common connections are not what you think. They are not always the employers, but friends, co-workers, daycare, clients, or some third party notifying your employers. 

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

Meanwhile, Max also remembered hearing the exact same restaurant recommendation and a co-worker (you) that just went this weekend with a boyfriend named Jefferson. Max and Lisa, now intrigued if this was the same person will ask around and start a cascading event 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. 

How Employees Get Caught Working Two Jobs 

It’s truly a small world 

Facebook put out research that shows only three and a half degrees of separation 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’d 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 you. As humans, we are ego-driven and love to talk about ourselves and oftentimes are unconscious of it. Experts even tell us to network by building comfort with people in tricking them to talk about themselves. We have to act with purpose and keep this in check from revealing too much about ourselves. 

How you reveal youreslf with metadata

If you’ve ever watched any crime show you’ll know how profilers connect the dots and build a profile of you. The school you went to, how many kids you have, where you grew up, the neighborhood you live in now, past jobs, or even what you did this weekend by itself does not tell much about you. It’s the combination of these data points that will build a very specific profile of you. This is what we want to avoid others from building. Check out these two examples, which one is easier to lead back to you? What can you do to throw someone off the tracks?

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 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. 


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. How old? I wish my kids were old enough to move out for college but they have a few years to go. Whenever I squeeze out some free time, I like outdoor activities and spending time outside 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 to hibernate your LinkedIn and control view access to your social networks. The smaller the visible footprint you have on social media, the fewer chances you can be found out.

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 reveal any identifiable information. You can keep it vague, but still, answer the question. What school did you go to? “oh a small college down south”. We are not lying, just not giving any information that might track back to us. 

Create a fake profile of yourself before you enter 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 think twice about your answer. Have well-prepared answers for common questions. This is no different than preparing for an interview. This prework would ease your mental strain when answering. Lies are always found out because it’s impossible to keep track of what you said to who, so tell the truth and have a story solid. In addition, use Google Voice for a different phone and Email to apply to your second job. 

Check out Scientific American’s 18 attributes of highly effective liars. We never condone lying, but there are some takeaways here. Knowing how other people may perceive liars, you can avoid becoming labeled as one. 

Example Profile:

Profile Category Example Truth – Job 1  Example Misdirect – Job 2 Comments
Hometown Palo Alto Bay Area – South Bay Generalization 
School / Education Texas Tech – MBA Some small college you may not have heard of. Misdirect and indirectly answer
Job Industry Finance for 8 years I jumped around a bit but am currently in finance.  Exact vs. generalization
Family /Relationship Status Single In a serious relationship Unverifiable, 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. 
Hobbies Swim, Bike, Run Like to spend time outdoors when you can. Hiking with friends.  Answers the question and is generic enough that people won’t ask specifics. 
Dreams Make enough money to not work here anymore.  You like baking and want to start a bake shop one day.
These are common attributes that 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. Have these questions prepared about yourself to ward off 80% of the most common questions.

Do some research about your “adversaries” and do research on 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 work and mental gymnastics? To some, yes. To some, this is a fun challenge. There are a lot of ways employees get caught working two jobs. This lifestyle is not for everyone. For those who are willing to be a bit mindful and are not afraid to do a bit of pre-work, the trade-off is the two paychecks. A little preparation work goes a long way to your ultimate goal, keeping the two paychecks going. As with everything, do your own research and know the limits of your comfort zone. Comfort and confidence come with knowledge, research, and preparation. Rule number 1: Do not talk about working two jobs.

Work Two Remote Jobs

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