Been free for 14 years, magazine and books. Here's my 10 cents.
Had a SMALL steady gig which helped when I started and still do, but I took my retirement from the previous job that gave me about a 12-18 month window to get above the surface. Made 9 K in year one, steady rise ever since, and money in the bank.
Being good helps, being lucky helps more, didn't have many connections at all. In the first few years take EVERY job offered - you never know who you'll meet and what it will turn into. I was offered one small job that I thought was a one-timer that, over ten years, has turned into a 8-32K annual gig, which really helped.
Hit every deadline, in fact, separate yourself from the crowd by being early, way early when you can.
Be prepared to be turned down. A lot. Be prepared to have a drink and go forward.
Realize that unlike a day job, you never really arrive in a comfortable place where you can kick back and cruise. But then, that's why you quit in the first place.
Some small $ gigs increase your profile, remain worth it, and insureyou don't sit around not using words for too long. I still do a column for less than $100/a month just for that reason.
Insurance is a bench - by far the biggest detriment. Now I'm married.
You might be isolated from peers. That's what the phone is for.
Office use of home is the greatest tax break out there, but be squeaky clean.
You have the great advantage of being able to throw every idea up against the wall to see if it sticks. Don't waste people's time with dumb ship, but do that. Some of it sticks. You'd be surprised.
Couldn't ever work for anyone again. Zero regrets. Home almost every day. Seeing my daughter grow up. Can go to work at 4:00 am and be done by noon, or start at noon. Or work the weekends. Or not. Or go for a walk.
Could you do it the way I did? Probably not. But there are a thousand ways to make this work, probably a million ways to make it fail, but at the end of the day, it's up to you and no one else.
There's a great scene in a Henry Miller novel when he first made the decision to be a writer and walked away from everything he hated. I read that every once in a while.