My answer may not be helpful to you. However, here are some advantages and disadvantages, and more detail about my situation.
Advantages
Education: My skill set is almost entirely from on-the-job learning and I’ve learned a great deal about many fields from working side-by-side with medical researchers, lawyers, marketing execs, concert producers, etc. etc.
Networking: By nature, I’m am not particularly social so I have to work at this, but it pays off.
Self-Esteem: When I’m feeling down, I just review the challenges I’ve faced.
Resume: The most time I’ve spent at one job was around five years. This hopping can be a drawback, but most often it allows me to answer any interview questions with specific examples.
Disadvantages
Scheduling: We’re planning a family reunion right now. All of my relatives know exactly where they will be and what they will be doing 11 months from now. I don’t. If you take a second job, you’ll have to think about this.
Taxes: There is no way I could do my own taxes. Sometimes I work on-site, sometimes I work at home, sometimes it’s split, sometimes I have fairly large expenses for work that doesn’t pay well, sometimes I get big bucks for on-site work that cost me nothing. Just add an hour a week for record keeping alone.
Health: Will your family pitch in to make good dinners? Will your family pitch in to do some housework? If you get home at 10:30, and then have to eat PB&J while doing chores… eventually your health will suffer.
Weekends: Ha ha ha. What a weekend?
My situation, in case you were wondering:
I do project based work (like rjung, but more so). Often I will be doing an on-site job which is basically 9-5 (which means 7-7 or worse half the time!) and also do some documentation or analysis or web sites.
There have been times when I was slammed from dawn till midnight for a couple months straight… and there have been times where I did nothing but little art projects (which pay jack) for a month or so.
During those no-life of my own periods, my attitude sinks… but this is usually because my SO, who I support, doesn’t hold up his end of the household chores. The cash disparity doesn’t make me bitter because his industry doesn’t pay well, the idea that I should be both Ward and June Cleaver gets to me, though. This is what leads to those times when I do cheap ass creative crap.
My situation is a little different, though. I take jobs either because I can learn something, or because the offer comes from someone I’ve enjoyed working with in the past - not for extra money.
This lifestyle is not recommended for parents. And I should point out that the opportunities in my second decade in the work world come to me because I paid a lot of dues in my first decade.