There is no such thing as suddenly knowing when you are ready to turn your
passion into your profession. But there is a way of measuring your chances on being
able to get work and eventually sustain a living from it.
Accepting commissions or freelance for low payment won't help you. You can think any penny counts, but it will lower the worth of your work and damage the market.
How to measure that you are ready?
You probably have high goals, but they are usually not your first step. You must search out the clients who can be that first step. Often found in the card game industry, book cover illustrations and smaller game company's.
Look at the artwork shown by a company such as the card game company: Fantasy Flight games. Compare your skills with the average of their artworks. If it matches yours, you will have a chance. However, keep in mind that those artworks had been done in a limited timeframe, usually within 12 hour