12 rules for working two remote jobs at once

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.

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