Many readers write in asking about quitting their day job in order to write. They want to know how I did it, if I regret it, and if it is advisable to quit your day job.
Many many writers want to know if they should transition full time into freelance writing. While I can't make such huge life decisions on your part, I can tell you about my experience, and give you some pointers.
First, those who are the primary or only wage earners in the family will have a much more difficult time in making this transition. Let's be honest: choosing to take your passion to a full time business is much easier if you're not carrying the brunt of the mortgage, not to mention the whole health insurance issue. This demographic will have to engage in a long, detailed process that specifically plans for the financial transition, the health insurance issue, and so on. There are any number of variables that need to be dealt with, before quitting the day job, and many estimates put this planning process at about 6 months to one year.
Those who are a secondary or extra wage-earner will fare a little better, although this is dependent on several personal factors. The secondary wage is less of an amount to make up, and insurances, retirement and other benefit issues can be shifted to the first wage earner in these families.
So, should you? I can't say. I can tell you that, when I get asked this question, the rest of the conversation takes place from this leading question: What exactly do you already contribute to your family, income and benefits? And then we go from there.
When I made the shift, I was a secondary wage earner, which eased the process. However, many freelance writers are the primary income in the family, and have also made the shift successfully. It's all in the planning process.

