re: Working 2 jobs at once - is this wrong?

If you could do 2 full time jobs at the same time, then neither is actually a full time job.

The problem will be when contemporaries in the industry start talking and they figure it out or worse the new company puts out a media release announcing the new hire

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It’s not necessarily unethical, because the jobs support different markets within the country,

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What kind of mental gymnastics do you have to do to convince yourself of this? Let's just look at the fact that the two companies are competitors, the fact that the markets do not overlap today mean nothing in terms of what may happen tomorrow.

Throw in that both companies have policies which disallow this as stated in

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However, the companies are competitors and would never allow this.

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and clearly the industry as a whole frowns upon this as evidenced by

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but job #1 and job #2 can’t find out about each other, or he’d surely be blackballed.

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the the very act of doing thid in spite of the company policies and industry standards is unethical.

Add to that he is already calculating how he can use his flexible hours for Job #1 to put them off to make sure he can cover Job #2.

My advice would be to pick one job, either, if you want to be ethical. Pick both if you want a nightmare of possibilities ending in unemployment and a damaged reputation hoping you can make it 2 years and figure out a way to quietly disentangle yourself from the mess you've created. .

Everyone is assuming the companies would not allow this. That is not an established fact.

Even if it were - I'm not sure it's a COI. Different markets means they have no possibility of competing with each other, thanks to Obamacare.

If the jobs are as high paying as suggested, then he should visit an attorney and get some legal advice. If the attorney thinks he's in the clear then he should go for it. For that much extra salary, it would be worth the attorney costs. Would also allow him to provide quick service of a pending suit if one of them fires him.

Go for it.

What do you put on LinkedIn? Lol

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Everyone is assuming the companies would not allow this. That is not an established fact.

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OP said the companies would never allow it.

Other than the fact that hecould lose both jobs? I am guessing there is a clause in the contract regarding this issue.

Lots of insurance salesman set up side gigs with different carriers. They often work for well established insurance companies with many customers that do not qualify for insurance with that company for whatever reason. They set up a side gig to funnel those people to their own company. The thought is that the large insurance company they work for will not insure the person, so there is not conflict. If that is the case, why are they so secretive about it?

I was fine with everything until:

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However, the companies are competitors

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Pick one, or lose both...

A lot of insurance companies run certain employees credit every year. He is going to get caught and fired and possibly blackballed if word gets around

I personally would not give any advice. If you tell him go for it and it blows up, he can say you told him to do it. If you tell him to forget it he will think of all the money he could have made except for you.

No win situation.