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Overemployed is a community of professionals looking to work two remote jobs, earn extra income, and achieve financial freedom. Be free from office politics and layoffs. Instead, improve your mental health and negotiate a severance. Join us.

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Why Are You Here? To Learn How to Work Two Remote Jobs At The Same Time

Let’s admit it. You’re intrigued. Why not make more money while having job security? Learn how I got started.

How To Work Two Remote Jobs At The Same Time
Oh, darn those screen savers!

Recommend reading the ideal two-job candidate and why tech before going any further. If you’re already in tech, then you know layoffs, like pooping, happens – you’re gonna get laid off. Why not go on the offensive and work two remote jobs at once? Finally, turn your job search into a team sport, follow our repeatable process which reduces the time required to land high-paying remote jobs. See how your job search meets tech sales – automate your job search while targeting curated top remote companies with the guidance of your own Overemployed sherpa.

But wait there’s more. We offer 24-hour support through our Discord server that includes live salary insights and remote job opportunities. Get the latest news and insights from our Newsletter. Most importantly, we’ve got the Overemployed Guild – our forever promise to create wins for the community. We are here to celebrate your success stories and support your hard-fought victories.

Fear Of The Unknown Holding You Back

I love what this Reddit user has to say about the fear (lighted edited for readability).

Batmanbury – Software Engineer

This topic of working two full-time remote jobs interests me, as I’m sure it also interests others who claim those doing two jobs should be worried. Even though I haven’t managed to swing two full-time remote jobs, I’d be lying if I haven’t thought about it. I mostly do contract work on the side because I’ve some free time. I suspect there’s a mix of opinions for a variety of reasons:

  1. Fear being caught
  2. Think it’s “wrong”
  3. Signed non-competes barring two jobs, so think others shouldn’t try it either
  4. Have a very busy job already and can’t imagine doing two jobs
  5. Want to work two jobs but can’t stomach the risks, so neither should others

I’d really like to learn more about the day-to-day situation:

  1. How did you think about doing two jobs when you first started?
  2. What strategies have you developed to keep things running smoothly on both ends?
  3. Has any coworkers or boss at either of the full-time jobs found out and did they care?
  4. Have you ever considered changing jobs but then decided against a certain role because it’d be too much work and you wouldn’t be able to pull this off anymore?
  5. Are you overestimating tasks so you could manage expectations? Or, is task estimation not a normal part of your workflows?

Are You Still Reading? You’re Ready To Work Two Remote Jobs At Once

It’s OK that these questions are flying through your head. Start planning. Ask the community.

Let me be upfront. Everyone’s situation and risk tolerance are different. For those tired of working under the yoke of layoffs and promises of promotions, the two-job hustle is for you. Having two jobs gives you the income security to take risks and achieve the outcomes you desire. In many ways, Overemployed is a counterculture movement and American Dream, except now globally available and accessible.

In addition to the added financial security, having two jobs will sharpen your technical and professional acumen, making you more valuable in the gig economy later on. All of this is to say, the pros outweigh the cons, especially for inexperienced and mid-career professionals. What’s the worst that could happen? Ok, so you get fired and need to look for another job. Oh wait, you’re already a pro at landing remote jobs!

Pros And Cons To Working Two Remote Jobs

First, make sure you’ve got the self-discipline and communications skills to handle two full-time remote jobs, including being a master in setting low expectations. Else, burnouts will happen. Second, you’ll need to accept average-to-above average performance in one job (the one you consider your primary job) and mediocre-to-subpar performance in the other job. Over the long term, this may have implications for your career and professional network. If you want to sit in the C-suite, then you should focus on one job and be a superstar. But if you don’t care about a potentially unhappy boss or workplace politics, then this path is for you – a double income and early financial freedom.

Working Two Remote Jobs Seasonally For 3-6 Months

For those considering working two jobs in short stints between jobs, you should be fine. There’s a small unknown risk of how your next employer would perceive your hustle – assuming you had to list both employers on your resume or else there would be too much of a gap. The good news is there are many explanations, like being a leave of absence for education or military service. For all we know, you could be on an extended severance package that kept you on the payroll. The list of excuses is endless. If pressed, you can tell the truth – you wanted to tie up some loose ends at the old job before resigning, and there wasn’t any conflict of interests. In the end, I don’t think your next employer would care, not unless you were aiming higher up in the career ladder close to the C-suite.

Working Two Remote Jobs Over 12 Months

For those planning to do two jobs long-term (bless you), such as rotating jobs but constantly have two full-time jobs at any given time, then you should list on your resume only the jobs that were sequential to each other so as to avoid unnecessary scrutiny into your over-employment.

Working Two Remote Jobs To Raise Seed Money

Finally, for those using the two-job hustle as fundraising for your business, then all the power to you. If you’re successful, chances are you won’t go back to being employed again any time soon. But when you do, it’d be so long ago that no one would care you worked two jobs at the same time.

Commit To A New Lifestyle – Forever Work From Home

I’ll say it again, everyone’s situation is different. You need knowledge (often trade secrets) to smartly navigate working two jobs at the same time. Overemployed helps you make clear decisions and accomplish life goals. But more than anything else, we’re building a community to give the man the middle finger for screwing us over when the layoff Grinch shows up. Power to the little people!

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Live long and prosper 🖖