Thanks, all, for the replies so far. Yes, I'm at that precarious point where I could conceivably take the hours at these new jobs and still make pretty much what I'm making now. Of course, these other jobs are predicated upon people wanting/needing those services. Naturally, if the work dried up, so would the cash.

On the other hand, being a home-schooling family, the other jobs would allow at least my older two children to apprentice alongside me and learn more about things they are already interested in.

Yes, this is a really tough decision... I can afford pretty much anything I need and, within reason, lots of what I want, at my current job. I am, on the other hand, clearly losing my joy, finding myself increasingly distanced from any real depth of relationship with my family, and frequently justifying my schedule, fatigue and other issues by talking about how much money I am making. That sucks; everyone who knows me knows that's not what I belong doing or being.

My wife and children and I got by on $400 a week when we were being assisted with our house payment. I'm making nearly three times that much now. I could still be making about 75-80% of my current wage at the other jobs combined with the current job at reduced hours. This doesn't seem like a gamble to me, but I am trying my damndest to care for the feelings and concerns of my wife and best friends who are counseling caution.

My struggle right now is this: do I live like my father and grandfathers did and bust my arse at a boring, frustrating job and leave my children a legacy of nose-to-the-grindstone ennui? Or do I strive to leave them a legacy of following one's passion, damning the torpedoes and sailing on?