I've been doing the freelance thing for just about two months now and because some people have asked, here's how it's going: Pretty well. Thanks mostly to two big assignments, I'll be able to replace all of the income I would have earned at my job in the last quarter of the year.
When I had my job, I worked at home, but during scheduled hours. My boss was wonderfully flexible, but I still felt guilty if I ran to the grocery store after dropping off the kids and got home late, or spent too much time cycling laundry during the work day. Now I can do that without flinching, plus take a yoga class in the mornings, do my 15-minute school volunteer job twice a week instead of once, and so on.
Still, I am ever conscious of the not-working time. Turns out that in order to be a successful freelancer, you better be really self-motivated. (Imagine that!) I always thought I was--I was never the kid who pulled all-nighters or did her homework on the bus--but man, pushing myself to put in the time can be hard. Especially when one of my jobs has no deadlines or specific assignments. I also stink at self-marketing (hi, I own myname.com and do you think there is anything there? no) and strategic planning. I have no idea where I'm going with this or how or when.
Jo has recently come to appreciate at least some aspects of my work, however. "So people send you stuff. And you write about it. That's a good job." It is. Not as excellent as jellybean caretaker, but it pays the bills.