How could one have an arrangement of side contracting work in addition to a seishain job on HSPV (ii) visa?

My seishain job is mind-numbingly dull and is failing to keep my skills fresh. However it pays well and sponsors my Highly Skilled Professional (ii) visa. I would like to do side contract work to help with those issues if it is possible.

Ideally this arrangement would be contract work for a few weeks or months at a time, done in a way so my full-time employer isn’t tipped off by a 3rd party somehow. (If it makes a difference, I’m a software engineer working remotely for my seishain job, and I’m confident I can juggle side work at certain points of the year.)

How could this be achieved as simply as possible, with as minimal paperwork as possible (i.e., avoiding extra tax paperwork, even at the cost of some deductions)? I care less about maximizing deductions and moreso on simplicity, so I can focus my time and energy on getting clients and doing good work. Could I just go straight to finding a client and arranging contract work without much worry? To be clear, I want to file all taxes properly and not violate any visa restrictions. I just want to do some simple contracting side work.

The equivalent I’ve done in USA in the past would be getting a 1099 for contract work in addition to a W-2 for full-time work, and filing them at tax time with TurboTax. Really simple and straightforward with minimal paperwork.

Any other considerations I should be thinking of? For example:

* I understand shakai hoken being deducted by two companies simultaneously would be a problem as it could tip off my seishain job. Could the contracting job be arranged so as to not deduct it?
* Anything else?

by cutelittlecorgis

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