If you have a sense of unease, then maybe your gut is trying to tell you something.

How reliable is this person? How long is the work guaranteed for? What backing is there for the guarantee? Have you done due diligence on their business? What would happen if it doesn't work out? How does your work add value to their business? What happens after you sort out the current problems? or complete the scope of work?

Whatever you decide upon, make sure you document everything! The very act of minuting every decision, seems to improve the quality of decision making. Of course, you want to make sure there are unambiguous, signed-off specs for all work to be done.

All very good points indeed.

I've been working for this person for over three years with side-business, we have a solid understanding of each other and I understand their brands and projects because of this. I also know that the work is steady enough that the company is still going and growing after those three years.

The scope of work luckily is an ongoing thing, basically the position is technical lead for one of their largest clients and also technical lead on a lot of new business as well.

I'll admit, there is a large degree of impulse in my decision here (turned in resignation today ack!), but also I've been working towards this goal for years now and have built a solid relationship and understanding with them, if nothing else it will be a lot of new and exciting experience and I think the next logical step in my career. I just can't see myself moving any further/faster with my current company.

There is always a contract though (I have one with them right now already for the projects I'm working on).

We'll see how it goes, hopefully it turns out alright and I won't have to go out in search of another job in the near future haha!

Thanks for your input, very well thought out.

In general it sounds like a great deal -- freelance-type hours but with a regular paycheck and health benefits.

I had a similar position once and it was great for my family. I never had to miss anything important and had no commute. The only con was lack of face-time with peers.

What are your concerns? It sounds like you are looking for some hidden gotcha.

EDIT: I posted my comment prior to your edit. So, here's my counter-edit :-)

I suggest talking to an accountant. He/She will be able to tell you what costs to keep track of and how to put aside enough for taxes -- and possibly if you're getting a good deal.

Thanks, and yes, I am looking for some kind of hidden gotcha, because it sounds a little too good to be true. Maybe I'm just skeptical as it will be my first job outside of a corporation in this field.

Thanks for the input, the lack of face-time I can handle, right now my "peers" at work are all uninterested COBOL programmers aside from the one other .NET guy, so I won't be missing much haah.