Successful two remote jobs worker

Traits of Successful Remote Workers With Two Jobs

Search online for traits of successful remote workers, and you’ll find remote work requires self-discipline, good communication (especially written), and compartmentalization. Now try working two remote jobs, and these demands are amplified. Hello, context switching! You’ll want to know if you’ve got what it takes before committing to working two remote jobs at once. So, let’s drill down on each of these traits of the successful remote worker, and see if you’re can handle two remote jobs at once.

Successful Remote Workers Trait #1: Self-Disciplined

Most people think strong willpower equals self-discipline. That’s simply not true. Self-discipline stems from good habits. The good news is almost anyone can develop good habits.

The author James Clear has written the authoritative book on the subject – Atomic Habits. Read and use his strategies to develop micro habits. Identify the habits you’ve now and change them through habit stacking, building one good habit on top of another. Slowly, you’ll crowd out the bad habits and replace them with good ones, changing your life. Before you start, designate your significant other as your accountability buddy.

A fair warning – you’ll face a tug of war between sticking with good habit-forming versus giving into bad habits. Atomic Habits teaches you to design your environment to minimize the use of willpower to crush bad habits. Only count on your willpower in the direst situation as it often fails. In short, self-discipline starts with good habits, and good habit-forming takes time.

How do you know if you’ve got the self-discipline to work two remote jobs?

First, perform a quick Strengths Finder self-assessment. One of your top five strengths should be Achiever. Why? Because as a remote worker you’ll need an internal drive to get stuff done, ya know? No one is going to look over your shoulder. If this does not sound like you, then you might want to think twice about working remotely. And thrice about working remotely for two jobs at once.

White-collar professionals are 50/50 on remote work. The reason? A lack of self-discipline. Having to go into the office actually creates a routine, and that routine is a self-disciplining mechanism. That’s why working from home has been so challenging for some.

Second, check if you’re overweight. This is a common yardstick because over 40% of adults in the US are obese and almost everyone wants to lose weight. Losing weight and keeping it down takes self-discipline. If you can handle controlling your weight, and to an extent, your health, then you’re one step closer to working two remote jobs at once – if only you can listen and communicate well.

Successful Remote Workers Trait #2: Good Communicator

Out of speaking, reading, writing, and listening, listening is probably the toughest skill to master. Our brains aren’t wired for it because it is a simulation machine, always trying to predict the next best move based on past simulations. That’s why we jump in and talk over others, sometimes unintentionally. Over a Zoom meeting, constant interrupting could be perceived at best as eagerness and worst as rudeness. Are you aware of your communication flaws?

Over-index on your communication strengths. Thankfully, God invented emails and Slack. Talkers and listeners can both thrive on Zoom, though my money is on a good listener since they’ve got the most options as they’re usually average on speaking, reading, and writing due to the fact that they actually listen. In my experience, good listeners are very rare.

Minimize exposure to your communication Kryptonite. This is the Overemployed way – if you can’t win, try another way. Now, please be honest with yourself. If your spouse says you’re a poor listener, chances are it’s true. So, try to avoid group Zoom calls or unnecessary one-on-ones. Keep it simple through Slack or emails. Do you.

How do you know if you’ve got the communication skills to work two remote jobs?

First, get 360 feedback from your inner circle, spouse and kids included. You’ll know pretty quickly where you stand on listening, speaking, writing, and reading. Stack up the ratings and if any one of them is below 2.5 out of 5, then you’re out for double remote work. If you’re above average in 3 out of the 4 skills, say low 4’s in writing, reading, and listening, then chances are you’ve passed muster. Also, in my humble opinion, speaking is overvalued in remote work. That’s because prolonged active speaking in virtual meetings is rare. Just record yourself speaking in a virtual presentation and listen back. If you don’t sound like a complete buffoon (bare minimum of 2.5 out of 5), then you’re good for working two remote jobs.

Second, have someone whom you consider a good reader to read your emails. Ask them what do they think about your writing. Your feedback should be warm or close to glowing, else working two remote jobs and sending out emails while in a meeting will be tough. In short, if you can write fast and clean, you probably shouldn’t do two remote jobs. Nowadays, the good news is there’s Grammarly.

Successful Remote Workers Trait #3: Ability to Compartmentalize Context Switching

Since we’re all working at home, there are literally no boundaries between your personal and work life. Danger Will Robinson, danger. Home is a context-switching, target-rich environment – the cat walking across the keyboard, kids playing “work” and interrupt your meetings. You’ll need super-human abilities to compartmentalize and re-focus quickly.

Remote work creates a lot of context switching if you don’t set boundaries between personal and work life. So, set some predefined boundaries. Create your artificial office walls (not literally, guys).

How do you know if you’ve got the context switching and compartmentalization skills to work two remote jobs?

First, if you’re in roles that require long periods of concentrated work (or by personality prefers to be in-flow ), then you should stay away from working two jobs. This is pretty common sense – software developers and designers usually require periods of concentration to solve complex problems, while operational or strategy roles can make context switching more compartmentalizable. But if you prefer to simply crank out work undisturbed, then the two-job hustle might be a tough fit.

Second, honestly self-assess how well you deal with stress and overwork. Ask yourself how do you react to the feeling of being overwhelmed. Do you resort to unhealthy escapist habits like drinking or shopping online? Or, do you dig in and get good sleep, exercise, and eat the elephant (of the overwhelming inbound tasks) methodically? Our recommendation is to keep a journal before and after starting two remote jobs to make sure you don’t go off the rails. In truth, working two remote jobs can be mentally challenging, requiring self-discipline. If you’re not prepared with red lines for overworking and stress, then you can potentially go down a dangerous abyss.

The Ideal Profile Of A Double Remote Worker

Companies are filled with many different business units, teams, and functional roles – some more demanding than others. Also, when reorg happens, confusion reigns with minimal accountability. There are many factors making a prime two-job candidate, but below are the most common traits:

  1. A person with some moxie and risks taking; willing to be contrarian to the YOLO economy
  2. Has been with one of the companies and role for a couple of years now, and is reasonably competent and efficient with their work; ability to work smarter not harder
  3. Acquired some specialized skills, allowing them to land roles that let them set their own schedule, minimizing inbound meetings in at least one of the two jobs

If this is you, congrats my friend, you’re in a rare position to be able to do two remote jobs at the same time. Now, the next question is what are your time demands and family obligations. Assuming that passes muster, the next gut check is to ask yourself if you’ve got the self-discipline, communication, and compartmentalization skills of a successful remote worker. Now double the demands and ask yourself if you’re willing and able to handle it.

Don’t fret if you aren’t meeting the ideal profile. Rome wasn’t built in a day. Play the long game and get into such a position. But the most important trait of the ideal two-job candidate is that he or she isn’t overly ambitious (therefore willing to take less high-profile roles), can keep a secret (loose lips sink ships), and is overall organized, strategic, and a good communicator. After all, you’ll have to be a master of setting expectations at both jobs!

If you’re at a FAANG, forget about it

I hear from a lot of haw and hem from the mighty FAANGers as if doing two remote jobs is beneath them. That’s fine – I get it that you’re already highly paid. Enjoy yourself and your golden ticket. It is also true that FAANG competes directly and indirectly with each other, and therefore are overzealous in their non-competes and conflict of interest policies. If you’re at a FAANG, for goodness sake, don’t work two jobs. But at the same time, don’t hate and belittle the little people who’re trying to do two jobs in order to play it smart with corporate layoffs. To each, their own, shall we?

Ok, you’re all in on working two remote jobs, now what?

The ideal two-job candidate is also a decent performer and has a good relationship with his or her current boss so that he or she can take a month-long vacation when starting the second job.

Finally, the ideal two-job candidate isn’t hyperconnected to everyone at work and posting every day on LinkedIn. The reason is obvious (you don’t want to accidentally get found) but if you need a step-by-step guide then sign up for the newsletter and ask for the Overemployed checklist.

In closing…

There are many tertiary characteristics of an ideal two-job candidate likely not covered here. But determine early on if you’ve hit some of these prime criteria, and if not then work towards them. Leverage our checklist to determine if you’re two-job ready before making the leap – join us!

Is there a #4 Successful remote workers trait I missed? Share your thoughts in the comments below!

Are you looking to do double remote work and reach financial freedom sooner? Let us know!

13 comments

  1. Great Post! Puts things into context for me to know what’s needed to work Two jobs. I’ll need to work on my context switching. Any advice on jugging workload? That’s the one I’m most worried about.

    1. Great question Tyler – workload balancing is highly situational. One of the practical ways to balance is to avoid taking a second remote job with high expectations or workload. Another is to have complimentary or synergistic jobs. For example, the main job could be a Salesforce architect at a Fortune 500, and another is an SFDC admin job at a startup. The main job will likely be high demand and meeting heavy, while the second job is more heads down and responding to inbound tickets. Most of the coping strategies are common sense, but finding the right angles that work for your time demands is highly tailored to your situation. Worse case is an 80-hour work week, but the money you’ll be making still beats investment bankers: https://overemployed.com/100-hour-work-week-versus-working-two-remote-jobs/

      Hope that helps and motivates you to go for it!

  2. I just finished reading every post on your blog and I love what you’ve done here. Thank you so much for sharing it with the world. I’ve been working on pulling this off by doing a commission only sales job on this side with a main development job. It’s really hard with the commission only gig and I’m considering switching to a second job in tech. Any thoughts on doing both sales and development?

    1. Hey thanks Bob! Why not double down on your strengths instead of splitting it between two different job functions? Is your commission only sales in software? If you strengthen is coding then get a second job or contract in that instead. I’ll bet it pays better than commissions only sales which is a horrible compensation structure to begin with. Hope my 2 cents is helpful! You can get more opinions on your question on our Discord — 500+ members on there.

      Again, thanks for reading. Appreciate your comment.

      -Isaac

  3. Worked 3 jobs before. Working 2 now. One is FAANG.

    Glad to know I’m not alone. One job just doesn’t pay enough and the risk of being let go at any time for any reason… I’ll have a backup. FAANG or not, one job is living paycheck to paycheck.

    1. Hi Leetz,

      100% agree. 1 job is the past. With the constant “reorg” and layoffs, it’s high time to be a free agent and look out for yourself and your family first.

      This is the way. And you’re not longer alone.

      Best,
      Isaac

  4. I just came by this post on the verge website and its a great resource. I’ve been working 1 full time remote dev job and a part time remote job for a coding boot camp but the boot camp doesnt pay that much. I’m really intrigued with the idea of working 2 jobs. How man yours should that add up to? I really don’t want to be working 80 hrs a week. Not for the long term anyway.

    1. We don’t work 80 hours a week. Far from it. Skilled professionals with domain knowledge can be a lot more productive now working remotely without commuting and wasting time lining up for lunch.

    2. I’m working two jobs for two Fortune 100 companies in the Data Engineering space. Honestly between the two jobs if I do 15 hours of work a week across both I’d be surprised. It’s the meetings that are more demanding. Juggling two meetings at the same time at least a couple of times a week is stressful. But the workload isn’t anywhere near demanding.

      I’m working 15-20 hours a week, and I have fantastic reviews across both companies.

  5. I’ve been doing one main job and one part time (sometimes full time a few months a year) for 8 years now! I bought a house with no mortgage so I’ll never be homeless. I absolutely love working them both at the same time. One time I had three jobs at the same time. One was online customer service, and other was phone customer service. The third wasn’t customer facing. The two customer facing got stressful quick so I had to let one go. I did 3 at one time back in 2014 so I really think there are a ton of folks doing this, but no one is talking about it I guess for obvious reasons. Thanks for creating the platform for me to share a bit of my story.

  6. Hi! I have loved reading up on working two remote jobs at once. I noticed on this post that ideally, one job will have been under my belt for a while and there would be some ease in adding a second. I’m debating on working 2 wfh customer service jobs at once, but I’d be starting them around the same time. Should I establish myself with one and then go for the other, or should I try both and see what happens?

    1. It truly depends on your role, industry, and work expectations. What I wrote has the context of the tech industry in the background, though that hasn’t precluded others from starting Job 2 and Job 3 simultaneously. All the power to those that can pull it off. For customer service, if I were you, I’d take three jobs and hire someone to help you, especially when it gets busy.

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