Working two jobs from home at same time

[AZDude]

First, I apologize if this has been discussed in another thread already. I have a vague recollection of talking about this before. Anyway, I am not talking about the traditional two jobs, where you work one 8-5 and then one 6-12, or whatever. I mean two 8-5 type jobs that are remote/virtual at the same time. Has anyone ever done that? I figured if anyone has ever tried it, it would be someone posting here on the MMM forums.

When I previously worked remotely, I considered it. I even applied for, got interviews, and was possibly on the cusp of getting hired when I got cold feet and backed out. Some things I considered:

1) One job would obviously have to be the first priority, since you could potentially get fired from job #2 and still be just fine. However, pissing off both employers could be really bad. So the better paying job, the one you use for health insurance, etc... would always take precedence, right?

2) Scheduling conflicts. I am fairly good at lying to my employer about what I am doing, why I need a day off, etc... Being someone who usually has more time than work needing to get done, I have left work to see movies, play video games, go out with friends, etc... during the middle of the day. I have always have enough lies/excuses to cover for myself if I was ever caught. Plus, I'm a good worker, so the boss cuts me more slack since he knows deep down that I get shit done and he does not want me leaving. However, with two jobs, I suspect you would need George Constanza levels of lies and deceptions in order to keep things from conflicting.

3) Vacation seems to be an issue. Obviously, if I ever needed/wanted a day off, I would have to coordinate with both employers and keep track of two sets of regulations and all that other nonsense.

4) Many employers require you to fly into the corporate office once in a while just to make sure you are a real person(or something). My previous employer made me come in two weeks a year to hang out in the office. Using vacation time to go spend a week in an office would suck, although I suppose you just use unpaid leave, since your 2nd job is just gravy anyway.

5) This would cut in half, at least, the time needed to FIRE, and so it sounds good. Plus, if it doesnt work out, you can just quit one job and be fine.

So, has anyone ever done this? Surely, I am not the only one who has thought about it. How difficult was it in reality? I would love to hear some stories from people who have tried this.

[themagicman]

First, I apologize if this has been discussed in another thread already. I have a vague recollection of talking about this before. Anyway, I am not talking about the traditional two jobs, where you work one 8-5 and then one 6-12, or whatever. I mean two 8-5 type jobs that are remote/virtual at the same time. Has anyone ever done that? I figured if anyone has ever tried it, it would be someone posting here on the MMM forums.

When I previously worked remotely, I considered it. I even applied for, got interviews, and was possibly on the cusp of getting hired when I got cold feet and backed out. Some things I considered:

1) One job would obviously have to be the first priority, since you could potentially get fired from job #2 and still be just fine. However, pissing off both employers could be really bad. So the better paying job, the one you use for health insurance, etc... would always take precedence, right?

2) Scheduling conflicts. I am fairly good at lying to my employer about what I am doing, why I need a day off, etc... Being someone who usually has more time than work needing to get done, I have left work to see movies, play video games, go out with friends, etc... during the middle of the day. I have always have enough lies/excuses to cover for myself if I was ever caught. Plus, I'm a good worker, so the boss cuts me more slack since he knows deep down that I get shit done and he does not want me leaving. However, with two jobs, I suspect you would need George Constanza levels of lies and deceptions in order to keep things from conflicting.

3) Vacation seems to be an issue. Obviously, if I ever needed/wanted a day off, I would have to coordinate with both employers and keep track of two sets of regulations and all that other nonsense.

4) Many employers require you to fly into the corporate office once in a while just to make sure you are a real person(or something). My previous employer made me come in two weeks a year to hang out in the office. Using vacation time to go spend a week in an office would suck, although I suppose you just use unpaid leave, since your 2nd job is just gravy anyway.

5) This would cut in half, at least, the time needed to FIRE, and so it sounds good. Plus, if it doesnt work out, you can just quit one job and be fine.

So, has anyone ever done this? Surely, I am not the only one who has thought about it. How difficult was it in reality? I would love to hear some stories from people who have tried this.

I've thought about it but haven't done it! I would think that it would work out though!

[forummm]

I would think that you'd need at least one of the jobs to be pretty much free from scheduled meetings. Or you'd have to have an acceptable excuse for why you had occasional conflicts. Maybe it's OK for one of the employers that you have a side job and that's your excuse.

[okits]

I think the second job would need to be contract or part-time, and very much results-based (as opposed to "from 8-5 you're mine."

[worms]

Not sure how payroll functions where you are but in some places you would need to explain to one of the employers why they were not doing standard payroll tax etc. deductions as principle employer.  Not a deal breaker, but you might have to have your story well researched in advance.