This week I have a reader question(s), which is essentially about when a writer can quit the day job, and what day jobs are best for writers.
I would say that the answer to both questions is It Depends. For the first question, it depends on your finances, your situation, your personality, your priorities and your goals. I would generally recommend waiting to make that decision until after your first book has been published, you've completed your first contract (if it's a two-book contract, both books have been written and accepted), you've received your first royalty statement and you have a second contract. That doesn't mean that you can quit then, just that then you'll have the information you need to make the decision. You'll know that you're not going to be a one-book wonder, you'll have some sales numbers to tell you how you're doing, you'll know if you're getting foreign sales, and if you've saved most of the writing money you received while still getting a paycheck, you'll have an emergency fund. Remember that book income isn't the same as a paycheck. If you have an agent, the agent gets a commission. You have to pay income taxes and self-employment taxes (the Social Security you pay, plus the part an employer usually pays) and benefits like health insurance, unless you can be covered on someone else's plan. On the other hand, there may be some cost savings from not commuting, eating out less, etc. From there, it depends on what you can comfortably live on. You may be willing to make financial sacrifices to live your dream and really push on your writing career or you may feel more creative without financial worries.
It's not necessarily an either/or thing, depending on your situation. There are ways you can ease into making the leap. I would suggest that if you hope to one day leave the day job, you start preparing now, even if you haven't sold or even written a book. Start saving as much money as you can so that you'll have a financial cushion when the time comes. That allows you to not live from contract to contract. You may be able to work out an arrangement with your employer to cut your hours or telecommute, which frees up extra time. You can look for freelance opportunities either to earn extra money for that nest egg while you're working or so you won't be entirely dependent on your novel writing once you do leave the regular day job. That was the way I did it. I'd sold some books and had been saving money ever since I got out of college, and I already had some freelance work on the side. When I wanted to focus more on my writing, I was ready to quit, but my boss allowed me to cut back to 30 hours a week (and since I was being paid part-time, that meant a firm 30 hours. I'd been working about 60 hours a week before without getting overtime) and telecommute. When I got laid off a couple of years later when my industry took a downturn, the severance pay, my savings and my freelance work allowed me to not look for a new job. The freelance work paid the bills until I got a new novel contract, and then I gradually transitioned to writing fiction full-time.
But should you quit the day job? Again, it depends. You don't necessarily have to if you have a job you enjoy that inspires and energizes you and that allows you time to write, though you may find juggling everything more of a challenge if your writing career really takes off and you have to do things like book tours. I've found in my own experience and heard from others that writing full-time doesn't really mean you spend that much more time writing. I seem to have a certain amount of fiction in me per day. What's nice is the luxury to spend more time if I'm on a roll without worrying about getting up for work the next morning. You may not even see a benefit from writing more, unless you're self-publishing or writing category romances, where frequency is how you build a career. Publishers generally don't want more than one book a year from an author because they can't get more than that slotted, though you may be able to publish more if you write a couple of different things for different audiences or publishers.
Not having a day job mostly allows for all the other stuff that goes with writing once you're selling books, like copy edits, page proofs and publicity. There are blog tours, media interviews, speaking engagements, convention appearances , booksignings, etc. A lot of these are evening and weekend events, but if you're spending evenings and weekends doing this stuff, that eats into your writing time when you have a full-time job. You also have to deal with agents and editors during business hours, and it's nice to be able to schedule conference calls without worrying about how that will look to a boss.
Where I find the real benefits is in the intangibles. For one thing, living according to my body clock makes me a lot more productive. I had a bad mid-afternoon slump when I had a day job, but now I find that's my best writing time, probably because I'm getting the right amount of sleep at night. I may not spend much more time actually writing every day than I did when I had a regular job, but I'm getting about twice the amount written. I'm an extreme introvert, so being around people all day at work drained me. Now that I spend my days at home alone, I have more energy overall and I've developed more of a social life. My life is a lot better balanced, and I have time to do other things I enjoy now that writing is my job instead of my hobby (even when the hobby made money). I can have other hobbies now. I read a lot more, and I think that's important. I think all that helps add up to making me a better writer. The volume of my output hasn't changed drastically, but I think the quality has improved and not just because I have more experience.
As for what day jobs work best, I've heard the advice that you shouldn't have a day job where you write a lot because then you won't want to write when you get home, but it didn't work that way for me because what I wrote at work was so different from fiction. When my job allowed me to hide in my office and write all day, I wrote more when I got home. It was when my job was more about meetings and management and I had to travel a lot that I wrote less. I think that writing as a career made me a better novelist because I had a firm grasp on the mechanics and was used to meeting deadlines. It may not work that way for everyone. I did find that the unhappier I was in my day job, the more I wrote, so maybe you don't want a really awesome day job. But I think that depends on your personality. An introvert will probably benefit more from quitting the day job. An extrovert may not get the same intangible benefits because all that alone time will be draining, and going to Starbucks every day to work gets expensive.
Before you make the leap, I would suggest talking to writers who've already done so. Give it a trial run. Take a week (or more, if you've got the vacation time) of vacation and pretend that you're now a full-time writer, keeping to the schedule and workload you think you'd have. If you're going stir-crazy by Friday, quitting may not be a great idea even if you can afford it. If you dread going back to your day job at the end of the week, then leaving may be something you want to work toward.