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.


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.


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.

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