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I've been working two remote Java developer jobs for a few years and I'm going to seek future employment in the next year or so.

I've seen objections to this scenario and approach, usually in the form of moral disgust from the perspective of employers. However, in my particular scenario, I have a record of several promotions and multiple raises at both companies throughout my time with them.

In my mind, in order for something to be unethical, there needs to be some form of harm or suffering involved. From the current perspective of both employers, I am a stellar employee who consistently exceeds expectations and has the performance reviews, raises, bonuses, and promotions to back this up in a tangible way. Instead of exceeding expectations at a single job and doing something useless with my spare time* like plenty of other people, I decided to do more work and get paid. I've exchanged value, voluntarily in a mutually beneficial way, and I actually feel quite proud of myself.

When I go out looking for my next role, I don't want to dance around the issue. I want to own my choices and say "Look, I've worked two jobs for over two years, I exceeded expectations at both places, and here's the proof." I assume some interviewers will laugh at me, some may respect the decision. I really won't know until I try this out.

My question is: Does this information belong up front at the very first contact with the recruiter? Or is this best saved for a conversation with a manager or higher-up in the company?

UPDATES:

There is no conflict of interest between the two companies, as they are in entirely different markets.

I don't intend to double or triple dip going forward, I just want one job (with a normal salary, not double) and I'll earn extra income from my investments.

By "spare time", I mean on the clock spare time. Not outside of work.

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    "doing something useless with my spare time like plenty of other people" Your work may be great, but your attitude towards other people isn't. Commented Jun 29, 2022 at 18:00
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    I don't understand your concept of "double-dipping". Are you billing both clients for the same time? So you bill ClientA for 8 hours on Monday from 9 AM to 5 PM and you bill ClientB for 8 hours on Monday from 9 AM to 5 PM? Or do you mean that you work for ClientA and ClientB simultaneously? Like, 4 hours worked and billed to ClientA on Monday from 9 AM to 1 PM and 4 hours worked and billed to ClientB on Monday from 1 PM to 5 PM? If it's the latter, that's not double-dipping. That's how all consultant work. Simply having and working for more than one client isn't a conflict, nor unethical.
    – joeqwerty
    Commented Jun 29, 2022 at 21:58
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    I hope you understand how condescending and arrogant this sounds, even if it's true.
    – Joe
    Commented Jun 29, 2022 at 22:39
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    Are you a freelancer or consultant working for multiple clients at the same time ? Or are you a regular employee for both companies at the same time ? Commented Jun 30, 2022 at 4:06
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    On the clock "spare time" is a strange concept to me. If I'm employed as a full time employee then it is my job to provide value to the company for the x number of hours per week that are stated my contract. If my tasked work runs out it is my job to find more work to do or help out with something else within the company. If there is somehow literally nothing else to do, no place I've ever worked would allow you to do paid work for another company within that time, unless I clock off and leave the office. If I'm working time and materials hourly rate, then "spare time" is not usually billable.
    – rooby
    Commented Jun 30, 2022 at 8:05

3 Answers 3

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It's perfectly fine to disclose this to a new employer, as long as you have disclosed this to both of your previous employers, preferably before starting your 2nd job. To own something is to do a full disclosure, to all the parties involved.

It's OK and a private matter to have a part-time job in addition to your primary one. It requires explicit disclosure when you're on the clock at two places simultaneously.

Job contracts typically specify your working hours and you're expected to be available and dedicated to your employer during these hours. This isn't always possible, but if your hours overlapped, you weren't fulfilling the terms of your contracts. You didn't harm anyone, but you weren't being completely honest.

If you believe this worked due to your high output, without gaming the system, consider working as an independent contractor. If you produce excellent results at 2x the speed, you can earn 4x the money by contracting your services out directly rather than through an employer.

Salaried work has an element of risk pooling: whether you succeed or not, take half the time or twice the time, you get fixed pay. Contract work has a different ethos: only the results matter, and there's a lot of rewards for high performance.

If you want to quit double-dipping, pick the one job you were best at, make it your story on the resume, and don't advertise the rest. If it's necessary to describe the achievements and skills learned in there, say it was a side project. If pressured, do own up to the fact it was a second job, but don't put it forward.

I'm currently hiring. Someone proud of covert double-dipping would be a strong rejection signal to me, because I'd find it difficult to trust them going forward. Someone admitting to it when asked would still be a yellow flag, but it could be resolved.

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  • Love the contracting idea, thank you!
    – Karen34
    Commented Jun 29, 2022 at 20:49
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    @Karen34 Yeah, salaried work has an element of risk pooling: whether you succeed or not, take half the time or twice the time, you get fixed pay. If you deliver results reliably and quickly, there's good money in that.
    – Therac
    Commented Jun 30, 2022 at 8:31
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Imagine going on a date with a prospective romantic partner and they brag about successfully maintaining two romantic relationships at the same time without either partner knowing. They say both partners were happy with the relationships and things ended amicably in both cases. Your gut instinct isn't going to be "well they handled two relationships well, they can handle this one well", it's going to be "how long until they cheat on me and I'm none the wiser?"

Don't disclose this to future employers, even if you're proud of it. Pick aspects of the jobs you can brag about in interviews, but don't specify that they were for different companies.

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When I go out looking for my next role, I don't want to dance around the issue. I want to own my choices and say "Look, I've worked two jobs for over two years, I exceeded expectations at both places, and here's the proof." I assume some interviewers will laugh at me, some may respect the decision. I really won't know until I try this out.

Maybe some will laugh at you. Maybe some will respect your decision.

I suspect most will conclude that a person willing to intentionally deceive their employers and knowingly violate their policies will likely do the same to them. And thus, they will decline your application.

But as you say, you won't know until you try it out.

My question is: Does this information belong up front at the very first contact with the recruiter? Or is this best saved for a conversation with a manager or higher-up in the company?

If you decide to go that route, and since you are quite proud, you might as well be up front about it.

That will save both sides some time, and avoid any sense of trying to hide the facts.

Good luck.

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