Funny, Jeff my path was a little similar albeit some differences in career choices and the fact that I was really focused on what I wanted to do in each "career" I choose. I came to the personal truth that I don't really like working, I would prefer my money to work for me.
After I did the self-employed thing for 6 years. I decided I would re-enter the profession that I left six years prior due to a recession (I see a trend here). But I would do it differently, one thing I learned from self-employment and my being let go from my employer in 2000, is that you have to create your own stability.
There is no such thing as job stability. It's this false thing that employers sell to you so you can feel comfortable about making your mortgage payments on a house you bought that is a little bit above what you can afford. I digress, but I realized I need to increase my financial acuity, if I was going to create my own stability.
This meant I was going to get my own financial coach to help me with the finer points of finance and upgrade my tax preparer to a CPA. I knew I would have to use my intelligence and street smarts to not only learn how to work the system, but to make sure that I had health insurance someone else was paying for, which would leave me with covering any other necessary insurances (i.e. rental insurance, travel insurance). It would also mean that I would have to take hold my taxes and related responsibilities, also the sometimes overlooked retirement goals and emergency funds. I got the appropriate books about finance from Dummy books to Rich Dad Poor Dad and things specific to I who I was Talking Dollars and Making Sense a guide to financial well being for African American by Brooke Stephens (who is also my financial coach).
So when I finally left my six year, work for myself gig, and had swallowed my pride and temporarily was on welfare, when I got my first "freelance" gig I deliberately stayed on welfare for six months into my gig so I could focus my goals on saving money for my emergency fund, starting to contribute to my retirement fund, and reducing my debt, while someone else was paying my rent. I would say it was a mildly risky venture, but as someone wise said Welfare was originally set up to give you a hand up, not to be a career choice.
I used it for the essence of what it is and with a year I had over 10k in my emergency fund and 5k in saved in my retirement account, with hardwork and discipline I changed financial habits, and In less then two years I went from Welfare to making a six figure salary, but living so below my means I was literally stacking paper as the rappers like to say.
I say all of this to say I am not one of those people who is bitter about the last decade I did some of the same analysis you did about yourself, and said that I want something different. I learned that "fulltime" can mean a lot of different things and for me it meant "freelance" working for 3-4 months then taking a trip to somewhere exotic.
As of this writing I haven't worked since April of 2008. I started collecting Unemployment in August of 2008 and have been collecting it ever since, but during this time I have traveled to India, Aruba, Belize, Miami, and currently the Dominican Republic. I made choice to do something different and it worked out for me. Notwithstanding I probably need to replenish my coffers but I think I can survive until the economy picks up, where I will continue to live my life on my terms with little to no culpability to no one but myself and my own happiness.