worth working two jobs

Worth It? Pros and Cons of Working Two Jobs Remotely

In today’s fully remote world, it’s far riskier to have one job than with two or more. It’s why the Overemployed phenomenon has turned average tech workers into their own Purple Cow– a remarkable Family Inc. with 4-6x income (when both spouses are 2x-ing). TLDR – yes, it’s worth working two jobs at once, because knowledge work can be done in less than 40 hours per week. Try it. I promise it’ll change your life. Just ask our community members.

worth doing two jobs at once
Worth doing two jobs at once.

Pros

1. Make A Lot Of Extra Money

If companies can 2-3x their revenue, they would. It’s a no-brainer. Why then shouldn’t you do the same for your family? With 2-3x income, you can pay down debt quickly and reach financial freedom sooner. You could even afford to take a mini-retirement or sabbatical every couple of years. Nice huh? Run your numbers, and you’ll see why working two or more full-time jobs completely changes the game of FI (financial independence). Also, reality check– your one job’s pay raise won’t ever exceed you having a second job, period. Now you no longer have to overwork and pine for the promotion, nor do you need to despair over how long it’ll take you to get to FI. The game has changed. It’s now rigged in favor of the knowledge workers, and worth working two jobs at once. Now you just have to allow yourself to fly closer to the sun (from The Icarus Deception).

2. Improved Mental Health

With two or more jobs comes financial security and freedom, which in turn make you less prone to overworking. A few of your co-workers that are suffering from pandemic burnouts might be jealous, but staying with only one job was their choice. You, my friend, now get to say no to BS Zoom calls and prioritize your health and family first. You’ll get praised for being efficient and able to get things done without excess meetings. The irony here is you’ll actually end up performing better at both of your jobs by delivering results through OE principles such as slow productivity. Now, what do you say? Worth working two jobs?

3. Rapid Upskilling Through Cross Learnings

Chances are if you’re a backend software engineer using Java on one job and a full-stack engineer using C# in another job, you’re probably leveraging knowledge from one job to perform better in the other. The same could be said for a B2B growth marketer who’s also working as a B2C digital marketer. Again, the unintended side effect of multiple jobs is you actually benefit from the cross-job knowledge sharing, notwithstanding any conflict of interests of course. As knowledge workers, upskilling and learning is constant. It’s how we stay relevant. So why not work two jobs, make more money, while accelerating your upskilling? Who knows what next job you’ll find, or if it finds you first.

Cons

1. Stress From Context Switching

I won’t lie, juggling conflicting meetings, different work personas, and time management isn’t easy. But have confidence that you’re incredibly adaptable. You just have to push yourself a little. Good news is that anyone can do it. Join our community and learn how others are adapting, from color-coded web browsers to using different names for each job.

Working two or more jobs will also drive you to be more disciplined, relying on habits and routines. That includes regular exercise, eating healthy meals, and getting eight or more hours of sleep. This monk-like existence helps protect your biggest asset – your mind. Keep it sharp and ready for context switching and remembering work details on the fly. It’ll pay off in the long run by getting you to financial freedom early.

2. Coordinate Simultaneous Time Off

Even with “unlimited” PTO, coordinating time off across jobs and with a spouse who’s also 2x isn’t going to be easy. But then again, anything good isn’t always easy, right? Again, the good news here is you can pull it off. It’s all about setting the right expectations ahead of time.

However, you can also help yourself by trying to outsource your job internally as much as possible. Basically, have many backups (or direct reports) backfilling your daily tasks while you’re out or get hit by a bus (hopefully not, but if you were then you’ve got your family covered with double life insurance and other benefits).

3. Risks Of Getting Caught

Ah, the big elephant in the room – the fear of getting caught or reputation sullied. First, know what you don’t know, talk to an employment lawyer. Next, to play the OE game, you’ve to be willing to accept the worst case of getting fired from both jobs (highly unlikely based on our community data). Finally, with fully remote, the risks are low and manageable – you’re practically invisible. As our resident lawyer has reminded me once:

“Remember, best block no be there.” 

Mr. Miyagi, The Karate Kid

Let go of the fear. That’s your lizard/monkey brain’s doing what it’s designed to do from evolution. Here’s the kicker: you’re actually not that important. No one will remember you even after you’re fired from both jobs, if that worst case scenario does happen. You simply pick yourself back up and go get new jobs. Oh, by the way, you’ve all the money saved up, so might as well make it a “fired” sabbatical. Put in another way, the risks and returns are correlated.

Conclusion: Crossing The OE to FI Chasm Makes Doing Two Jobs Worth The Risks

I asked myself these questions too when I was considering being Overemployed. Guess what? It wasn’t anything logical that drove me one way or another. It was all emotional (“system 1” or type 1 from Kahneman’s Thinking, Fast and Slow). I got tired of chasing that promotional carrot and living under the threat of layoffs. And then, I worked backward and justified my decision with logical reasoning. I suspect the same will happen to you. Do what feels right to you.

Disagree with working two jobs being worth it? Comment below. I’d like to hear from you.

36 comments

  1. All, i’m based in UK and I’ve received offer for a full time J2 100% homebased, already in full time with J1 which is hybrid working, home based 80% of the time and some site visits required at interval. J1 and J2 are completely 2 separate industry but J2 states in the contract that I am not allowed to work elsewhere or own a business. Is this normal and any advise on this??

    1. Try pushing back on the J2 agreement to modify secondary employment language to a softer as long as it doesn’t interfere with job performance. Or, just do it and stay low-key, though being J1 being hybrid is a bit risky so you might want to find a new J1 that’s fully remote to play OE.

    2. Would be interested to see the precise “not allowed to work elsewhere” language. You can’t moonlight as a yoga instructor or have a personal training business? In what dystopian universe is that enforceable?

  2. I’ve had a 1099 J2 PT gig for several years with a company. They are replacing my gig with a FT position. I need the extra income and don’t want to lose it. The dev I report to encourage me to apply. Not even sure he knows I have a FT gig. Wonder if I should just list my LLC as full-time gig or pretend to resign and go black digitally. I can easily do both jobs since most managers are inept which I why I never sought the c suite.

    1. Not a lot of information to go on, but here’s my process:

      1) Don’t lie
      2) Don’t fill the air (give your answer and STOP TALKING).
      3) Put it back on them.

      For example: “Yes, I have another job.” Then stop talking.

      What are they going to say? Probably nothing. in my experience (and it seems like they like you). The most confrontational thing they can say is “Are you going to resign?”

      Now it’s time put it back on them: “What is your policy on moonlighting?”

      Is the company you’ve been moonlighting with for years suddenly going to prohibit moonlighting when the shoe is on the other foot?

      If they press you on the issue, keep putting it back on them: “I can’t tell you about my arrangements with my other clients any more than I can tell them about my arrangements with you.”

      It sounds like they like you, though, so things probably won’t take this kind of turn. Good luck!

  3. I really enjoy the stories, and am really on the fence on taking the jump to j2. My concern is workday, I remember reading on this site that alot of employers have started to use workday, and some have indicated that by logging into workday they were able to see all the payroll information from both jobs. Is this a concern?

    1. It’s not just workday but your retirement account broker, benefits manager, health insurance… even Office 365.

      Nobody cares. None of those third parties care about rooting out overemployment, and it would be illegal for any of those organizations to talk to your employers about your other jobs. You and your employers have separate and distinct business relationships, and those employers hire a variety of third parties to manage those relationships.

      Imagine you’re a part time yoga instructor for Lifetime Fitness and they and your primary employer use ADP. Is ADP going to rat you out? To whom? For what?

  4. Hi, I am wondering about how can we manage the background check aspects of the application process. When we leave J1 and J2, which one do we report on the resume and background check when we apply for a new job?

    1. This is uncharted territory for me at present, but according to my HR expert office mate 😉 you should be aware of the following:

      1) There are mistakes in background checks all the time.
      2) Background checks are meant to verify what is in your resume–degrees, job titles and companies. They aren’t trying to discover what is NOT in your resume (missing employers, overlaps).
      3) There are a lot of reasons you could still be on the payroll somewhere. My story: I am still doing some work for them on a W2 because they couldn’t find a replacement. If they press for details, tell them you value your clients’ confidentiality. It’s really none of their business.**

      As such, my resume reflects the continuous non-overlapping employment that best suits my job search. If and when I get a J3 offer, then I’ll deal with whatever the background check turns up and let you all know how it turned out.

      **the preceding assumes you aren’t working for competitors simultaneously. THAT would raise eyebrows on a background check.

  5. Hi Isaac, thank you for this context! I’ve enjoyed reading about the overemployed community through your site. Do you have any content or insight into a temporary overemployed situation? For context, I’m leaving my current position for a great opportunity with a competitor; I attempted to time my resignation at my current company with annual bonus payouts based on historical bonus payout dates. My estimation was off by two weeks i.e. one pay cycle. I’m prepared to work the two jobs simultaneously for two weeks so I can receive the bonus in my current position. Any content about winding down one job and starting another at the same time? Balancing meetings etc? My other option is to be candid with my current manager about my situation, I’m fortunate I have a great manager. But when it comes to money, you just never know. Both positions are fully remote

    1. Your “great” manager has bills to pay and mouths to feed. No matter how “great” that person is, they are going to be loyal to themselves and their own needs before they are loyal to you. Don’t say a word.

      I assume you’re working remotely, so just block out both of your calendars with empty meetings corresponding to the “real” meetings on the other calendar. If an unavoidable conflict comes up, tell them you have a personal commitment (if your manager is so damn great, how could they say no?). I further assume that these are salaried positions, so no one “owns” any particular block of your time. You only need to float this along for two weeks, so use any excuse you want (doctor, dentist, kid’s COVID booster) or none at all (you don’t owe them that information). You could also take vacation if you feel anxious.

      If these companies are competitors, you’ll probably have to pull the plug after your bonus. Then go get another job in a different industry.

      You’d be amazed at how long you can pull this off if you follow the guidelines on this website.

    2. NEVER TELL YOUR MANAGER ANYTHING!!! THEY MAY BE NICE BUT THEY AREN’T _REALLY_ YOUR FRIEND!!!!!

      You gotta do you, boo! Juggle for two weeks… you’re quitting one job anyway so if that one slides, call it a case of “I’m done-itis”. Never, ever, ever, ever, talk about working two jobs, waiting for a bonus, etc… Keep your mouth closed, do what you gotta do then move on.

    3. 100% agree. If you put your manager in a tough spot, they’ll choose to protect their Family Inc. over yours, I’d too. Watch out for your own Family Inc. silence is gold. See nothing, hear nothing, say nothing.

  6. I am working two currently, j2 contract ends in feb then they want me as an fte ( on call, nights and weekends). I will be keeping j1 and looking for another contract gig $ is wonderful.

  7. Hi Isaac, I’m wondering what your thoughts are about whether companies attitudes are changing toward over employment? Do you forsee a future where people would no longer need to hide the second job? While individual companies may not like it, it likely benefits the economy as a whole to have people helping out in 2 companies rather than half-assing 1 job.

    1. Companies and individuals are all subject to the invisible hand and market forces. I do see the Great Resignation and the OE movement of the Great Plugging colliding and forcing the hands of companies who are desperate for tech talent. Trying to monopolize that talent, aka employment contract that says “you cannot have outside employment or work for anyone else,” isn’t going to fly for long. For example, if you’re Google, getting 10 hours of a top talent’s time each week could be worth millions (leverage in software and code), then why wouldn’t you want to capture part of the top talent’s time. Hence why we started this movement to maximize your own Family Inc. and labor, treat yourself just like a logical business machine in terms of cash flows.

    2. Having been at this for a while, I have a more pessimistic view. OF COURSE I would be better at both of my jobs if I only had one. Even if I weren’t stepping up and taking the initiative like I used to, I’d be way less flaky and slow in both roles. But I’m no longer trying to claw my way into middle management, and with a backup job, I’m not really worried about layoffs. I’m just trying to be the middle zebra at J1 and J2 while casually looking for a J3.

      The problem the overemployed community is exploiting is that most managers just delegate and nag people, and most individual contributors’ incentives are out of whack. When we were mostly in the office, those nagging managers could busy themselves with the process and ceremony of work—having meetings, making phone calls, sitting at their desks looking worried. It didn’t matter that they didn’t understand the complexity of their subordinates’ work (or their relative proficiency at it), because in the office, everyone else was busy looking busy, too. The out-of-whack incentives meant that doing twice as much didn’t double your pay (not that I didn’t try anyway). Now that we’re all remote and free from the need to _look_ busy, we can exploit those out-of-whack incentives in the other direction: it turns out that doing half as much doesn’t affect your pay, either. A revolution was born.

      If a substantial fraction of the eligible remote-work population catches on to this gambit, however, corporations will have to take notice. It doesn’t take great prescience to predict that they will not embrace this change. They will want people to get back to chasing carrots and avoiding sticks like they were before, so they’ll double down on strategies some of us have already seen: exclusivity agreements, more monitoring, more nagging, timesheets and other Dickensian tactics. Those of us who longed to be compensated for our efficiency in slaying tickets will grow to rue the day the company obliged us by remanding us to a piecework compensation regime reminiscent of cottage labor.

      So get it while the gettin’s good and before they wise up. Companies know employees want remote work, so they’re hiring for it like mad, but they don’t yet know how to manage remote employees. This golden age of 2x’ing isn’t going to last forever.

  8. You inspire me. I really love the stories. I’m starting a J3 in two weeks. One thing is a new fact for me: I just don’t know when I’ll go back to just J1. I got discolored myself with this routine. Thank you for every single word.

  9. I am working currently working a contract gig and I’m about to take on another. Have not consulted with a lawyer yet tho but the jobs are in two different career fields using my technical skills. I am nervous but I’m also excited. The current gig project work is basically nonexistent so I’m twiddling until something is assigned to me. The new gig is in the profession I am looking to switch to, so this is a perfect time for me. I’m so glad I found this site..

    1. It’s funny when I get asked these questions. Accounting, project management, sales — if you’re asking, chances are someone else is and even more others are already ahead of you doing it. Just join our Discord and join your tribe.

    2. Curious about this as well. Maybe J1 as a PM and J2 as a Scheduler or Projects Control or something?

    3. That’s my plan to work two PM jobs in two different industries. Money talk and bullshit walks. Especially with the high inflation cost now.

  10. This only applies to very specific fields of work where like the author mentioned, leverage the skills in a knowledge based job. I work in industrial design where designers will often compete against each other within the workplace if they want anything of there’s to get chosen for a concept, and subsequently get through to production. Often your reputation as a designer when changing jobs will rely on you having had something manufactured at some point, (but it depends on the work environment as projects can get cancelled easily.) But with certain fields there can only be so much compressing, consolidation, and time management the can be done. Also, companies who rely on styling heavily make you sign NDAs so it’s impossible to work for two companies, also at some companies they even own any artwork you produce outside work hours! So while this might be a great early retirement path for tech workers, for anyone with a more labor oriented or craft job working two full time jobs is untenable. What’s worse is most people then go and do side gigs on the side, fueling the hustle-grindset economy and further dis empowering workers to work themselves into paste just to afford rent or pay some student loans. And the ” just learn to code” mantra doesn’t work because then if everyone learned to code then the same exploitation would happen as all the sudden it’s not a lucrative or coveted skillet. We might all have to go that route anyway like when will the hustle grindset stop or be too rediculus? When we’re all 2.5j -ing, in our pod houses with an augmented reality dog instead of a real one, rent is 4000 for your blackrock pod that you can never own, everyone does remote gig work for Amazon-google-meta’s parent company ‘Giga.’ Everyone’s a contractor and does urban farming on the side and gets paid via an app for the amount of food they pick and get paid via Nft credits.

    1. I’m not sure I completely agree with that. I think 2xing is one way we can shift the limited wealth and resources we have from corporations to individuals.

    2. Im going all in with this plan and I’m confident I can pull it off. The only thing I’m concerned about is what to fill out on my W4 so that neither company knows I have a second job. Any tips on that?

    3. See the FAQ. The bottom line is no one at payroll/HR cares about your tax obligations at either Js. They just process your W4s and do the minimum to comply with the IRS required withholdings, your personal taxes the burden is on YOU to file it correctly from the IRS/government POV.

  11. This is so awesome i thought I was the only one doing it But it has been fruitful and I have been managing. long days at times but Iam paying off debt very fast rate

  12. I particularly like pro #3—just like conventional moonlighting, OE keeps me sharp. I fell into it by accident and have decided it’s going to be my new normal. Slaying debts, maxing out retirement contributions and fixing up the house—none of it would have been possible on one job.

    Regarding con #3, it’s helpful if the jobs are in different industries and based in different locations—not just to avoid conflicts of interest, but so that the professional networks won’t overlap. And while it’s true that only the paranoid survive, the likelihood of getting caught is actually very low. No one is looking to root out overemployment (at least not yet).

    If you’re on the fence, I highly recommend overlapping jobs for a few months to start, and take it from there. If it doesn’t work, you can always drop one. I started out saying things like “I’ll just do this until the bonus pays out” or “I’ll keep two until I pay off XYZ;” now I have a routine and I plan to keep this going as long as I can.

  13. I worked two, six figure professional jobs for one year. It was super stressful at times. The one job, the newest one I never exerted much effort into but because I was a manager, it really didn’t matter. I was able to leverage my team and make solid decisions using their expertise as a guide. Eventually Covid impacts were unavoidable and I was laid off from both within 2 months of each other. But….I grossed almost $200k doing. If only I had been focused enough to capitalize on all that extra dinero.

    I don’t know that I’d try it again, at least not two full time jobs simultaneously but I might.

  14. Love this website and the stories. I am currently on J3 right now and learning to manage my time. May have to go back to just J2, but we will see.

  15. Thanks for keeping your articles very honest. Based on your articles I am trying out a J2 for the last week and earning double the amount have made me more relaxed about my financial security

    1. You’re welcome. We aim to give unvarnished truths about OE. I know I’m biased, simply because this simple idea has transformed my life and countless other Pros in our community. Many OE millionaires coming next door to you. Buckle up inflation!

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