Sometimes the "duh" moments are right in front of us but it's too hard to see.
As for number 12 — I still deal with it as well. I am a blogger supplementing my income and working/striving to make my life better as well as a blossoming community of doers, thinkers, creatives and general badasses looking for freedom in their lives. I still need to wait tables in fine dining establishments, however.
The stigma of being a server waned over my head for a long time. I was college educated and now I'm serving (I was fired from Corporate America, hehe and it was the best thing ever) but you know what? I'm happy and reaching fulfilment.
What are you working on? I'd love to hear it!