12 Rules for working two remote jobs (WFH)


The concept “x” rules for “y” have been popularized by books for almost any domain niche by now. Here we will introduce our own 12 Rules – for working two remote jobs (WFH). As much as we hate to follow trends, we feel it’s necessary to set up rules and guidelines to operate by.

As with any “x” rules for “y”, we’ve come up with these rules through our community’s collective shared experience working two jobs. Taking notes along the way of what works and what’s important for success down this journey. If you want to dive into the corresponding personality traits, we have an article on that too. Here we go, 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. Yes, even family outside your household. If you can’t keep that secret yourself, how do you expect others to do so that have no skin in the game? This is for your own protection. Most of the people that are found working two jobs are found from connections that share the same network.

2) Don’t fall in love (with your second 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) and don’t rely on others

No one has skin in the game outside of yourself. “Filter out the signal from the noise” and watch out for confirmation biases that only reinforce how you feel. People will give you advice to the best of their experience, and everyone thinks they’re right. This includes what you read on this site. It’s great to have additional input, but you should already have solid research. Only ask around to see if you have missed anything.

4) Have a clear and focused goal

Go into two jobs with a goal, and operate off of that goal. Is it for financial freedom, is it to pay off a house or car? Being indecisive and losing focus of your goal is a recipe for anguish, burnout, and stress. Don’t start on this journey and not know why you are doing it.

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. Have an exit strategy when it doesn’t. It will save you a lot of stress having your exit routes all planned out. Know when to get out, know what you want (goal), and have a plan when things do not go as you planned.

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, 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 preception. 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 cause more 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, 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 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, Time Worked / Salary. 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

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 situations to get you out of a tough scenario. Conflicting meetings, overlapping deadlines, linked in management are all unique challenges you 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 rule #1, bringing it to full circle. Don’t talk about working two remote jobs with anyone outside of your spouse (and even then, think it through the expectations). Remember loose lips sink ships. And people have money scripts that could endanger your new hustle. Unless, of course, it’s on the Overemployed Discord, anonymously.



Work Two Remote Jobs

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