Minidust posted:

Thanks guys, I'll try and give more details for clarification. Old employer is probably shutting down soon (business was drying up), so yeah, this is just me getting the final trickle of their projects done in my off hours. There's only 4 full-time employees and the work is highly specialized, so hiring/training a replacement would be far more trouble than it's worth at this point.

The old company (and by extension, this arrangement) could conceivably last through the year or indefinitely, if more business comes through than expected. Either way I don't plan on taking this "business" on the road or anything.

What my current boss suggested was a daily rate derived from my current salary (i.e., [X/52]/5 ), increased by 15%. So I'd bill the company for that amount on any day I do work for them. So it seems like a pretty favorable arrangement for me, especially on days where the work amounts to just an hour or two.

From skimming various articles on Legal Zoom and such, it sounds like I could just be a sole proprietorship under my own name, and the only major formality would be reporting the income by April (or perhaps 4x/year like someone mentioned?). As I understand it, sole proprietorship doesn't really entail any setup process, it's just kind of what you are if you're billing somebody for your services.

If it turns out the LLC thing makes sense I could go that route, but since I'm basically just continuing a relationship with my employer of 15 years, I'm not really concerned about any litigation. Also I want to reiterate that this might only last for 2 months, as the status of the old company remains up in the air.

I've been on a health plan through my spouse's job this whole time so that's a non-issue. Other benefits will all go through my new full-time job.

Thanks again goons!