I have contracted on the side a bit, but only for close friends and family. It's not really for the money, these are people I care about doing things I'm intere

I have contracted on the side a bit, but only for close friends and family. It's not really for the money, these are people I care about doing things I'm interested in, but at some point I found that having a formal paying relationship made everyone behave better, and kept me more interested. I'll admit the family side can be a little fraught- I think one of my relatives is still sore I wouldn't work past a certain point for free, but I think the boundaries are worth it. I'm lucky in that I've been a career generalist and my personal network includes business owners. A lot of small to mid-sized business owners really want a second opinion on whatever the heck it is their full-time IT person is telling them. If you are already serving as that second opinion, its not inappropriate to so "hey, I'm happy to help out here, but I could be a lot more available on this sort of stuff in a formal consulting relationship." If they are interested, you can pursue it, if not, you've established some boundaries.