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I'm going to leave my current job as a part time IT Assistant/Web developer soon and move to another state. When I resign, I want to bring up the possibility of continuing employment working remotely either as an independent contractor or a regular employee. Though I've never worked as a contractor before, I'm the co-owner of my father's company, so I wouldn't have to go through the process of creating my own in order to be a contractor.

My question is, which option would not get me a "no goodbye" right away as a response? Which option would an employer be more receptive to? Should I even bring up the contracting suggestion without a contract to show them? Or should I simply ask to continue my current responsibilities remotely as a regular employee? There is no policy for remote work in my employee handbook but there is also no immediate person who could continue my job so I feel they would be more inclined to consider remote work.

I've never done this before and it's a lot of variables that I don't know how to best utilize.

closed as off-topic by Xavier J, mcknz, Chris E, IDrinkandIKnowThings, gnat Aug 10 '17 at 18:56

This question appears to be off-topic. The users who voted to close gave this specific reason:

  • "Questions asking for advice on a specific choice, such as what job to take or what skills to learn, are difficult to answer objectively and are rarely useful for anyone else. Instead of asking which decision to make, try asking how to make the decision, or for more specific details about one element of the decision. (More information)" – IDrinkandIKnowThings, gnat
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    It will be hard to answer as it greatly depends on your employer's openness to remote work and/or contractor work. My advice would be to discuss that directly with your employer like "Although I'm leaving for another State, I really love working for you so is there any possibility, as an employee or as a contractor, to continue our collaboration remotely?" – Laurent S. Aug 9 '17 at 14:51
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The path of least resistance is to tell your boss "I'm moving to another state in xx weeks, and would be willing to continue my work here as a remote employee" (assuming you can do your job online and don't have to pull cable).

Have your resignation in hand and be prepared for the possibility that you may be let go. That shouldn't be a big deal, since you're moving anyway.

If you want to switch to a contracting relationship, see Leave full time job and work as Contractor and Becoming a I.T Contractor - Need Advice & Tips as well as many others.

Becoming a contractor can be expensive. People converting from full time to contract employment often undervalue themselves. Insurance and taxes take an enormous bite, and you never get as many hours as you think you will.

Be sure to talk to your father if you're planning on contracting through the company you two own. He may have concerns or suggestions that would be helpful to you.

  • +1 for highlighting the potential complications of being a contractor. Remaining an employee might not be quite as lucrative in the long run, but it sure would be a lot simpler. – trpt4him Aug 9 '17 at 15:08
  • I don't think the OP searches for advice on contractor Vs employee, but rather on how to continue to work for the same company, but remotely because switching state. – Laurent S. Aug 9 '17 at 15:33

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