In one of my favorite freelance writing books, Get a Freelance Life: mediabistro.com's Insider Guide to Freelance Writing, the authors suggest asking yourself 11 questions before taking the freelance plunge:
1. Do you like being alone?
Working from home can be a luxury (sleeping in, working in comfy clothes, taking a walk in the middle of the day), but it can be lonely, too.
Fortunately, there are ways to deal with this. Some examples are going to a coffee shop for a cup of coffee, volunteering a few hours a week or participating in online discussions.
Because you're guaranteed to have some loneliness, make sure you can handle it.
2. Where are you now?
If you've been working at your day job for a while but don't have much writing experience, it may not be the best time to try freelancing full-time. However, that doesn't mean you can't start (you can).
But if you've been getting published pretty regularly and get paid decently, you may be in a good place. If you are unemployed or under-employed, and this is something you really want to do (and writing is your thing), I say make a go at it. The key is knowing where you are, where you want to be and mapping out a reasonable plan to get there.
3. Can you afford it?
If you don't have a few regular, well-paying jobs set up or money saved to last a few months (or a support system), you probably can't afford to just quit your job and start freelancing. So, it's important to analyze your budget and see where you are.
It takes time for freelance work to start coming in, and it might be a minute before you see the money. Take the time to work out a financial plan before making a hasty decision.
4. Are you flexible?
The life of a freelance writer can be quite unpredictable, so you have to create a schedule that works for you and one that permits unexpected changes to it.
5. Can you stick to a budget?
Freelancers rarely have regular paychecks, so you definitely need a budget with a cushion for the slower months and for late checks; you also need to be able to monitor and stick to it.
Stay tuned for part 2!