Internal assessment of self-worth is one thing. But one thing that I noticed while I was between jobs, was that the rest of the world was also built under the assumption that you "had a job".

Sign up for financial anything, they always ask you, which company you're with? What's your title? What's the range of your income?

I don't know if this is the case in the US, but in my country, I couldn't even open a brokerage account because the automated form required an office job. Entering freelancing or anything of some sort will get auto-rejected.

So it is in your face, all the time. And actually at that time I was fortunate enough not to have to worry about bills etc.