Priority one is playing bills. I started freelancing in 1982 while painting apartments by day to pay bills. Four years and 40–50 published articles later and I had a strong enough portfolio to get a writing job. This led to an advertising career, but also 35 years of moonlighting. I never quit my day jobs to do freelancing, but never stopped freelancing and in two years of retirement have enjoyed steady freelance income at a leisurely pace.
MY OPINION regarding quitting a job to do freelancing is: don’t. Unless you have nerves of steel, the pressure to produce and pressure to keep getting more assignments will be very distracting. I myself did not feel I had the internal fortitude to depend on freelancing for a living, not with a family to provide for.
Each person has to make their own choices. I took the route I did, but you might be able to take a different route that works for you.
Thanks, Lindy, for putting this out there as an antidote to the other messages so prevalent today.