The idea of creating a personal "brand" makes me nearly physically sick I hate the idea so much.
I am very risk averse. I love the predictability of what shows up in my bank account.
"Freelance" for me would just be a euphemism for being unemployed. The situation would just make me depressed and I would end up just getting a new job.
It seems to me the type of person who would thrive at freelancing doesn't need to read this thread or ask these questions to start with.