When should a journalist go full-time freelance?

I know you wrote about this subject for CJR in 2012, but I'm wondering if there are, like, any specific boxes to check, other than knowing more than 5 editors who will respond to me. 

I'm currently an associate editor at a dead-end print magazine, and I make several thousand a month from freelancing on the side. I feel like I could make more if I quit, but I'm also terrified of losing that security (tried freelancing a few years ago and had to get another job). Financially, I'm stable and don't have too much debt, though I don't have a ton of savings set aside (still waiting for all those checks to come in).

Thanks for any help you're able to offer!

Well, I think the next question is: What are those 5 editors you know able to pay per piece? What kind of savings do you have—and are you willing to eat into it? And how much income do you need? Do some math, and you'll figure out how much you need to write per week/month in order to make it work in the best-case scenario with your existing contacts. If you can't make the math work in even a best-case scenario, you know it's probably too soon to go freelance without a part-time job on the side.