Reddit reviews The Freelancer's Bible: Everything You Need to Know to Have the Career of Your Dreams―On Your Terms

I feel like how to figure out how to price your work should be the first thing they talk about in art school. But here's some resources to help you determine your own price. Don't undersell yourself! Artwork is valuable!

Get a copy of the Graphic Artist's Guild Pricing and Ethical Guidelines
handbook. It has a large section on going rates for all kinds of work.

and the Childrens Writers and Illustration Market Guide specifically for children's book work.

and also Check out the Freelancers Bible for all kinds of other freelancing resources.

One more thing. I noticed you are starting at a very low rate for your paintings, which is common when starting out and feeling unsure of your artistic value.

I recommend checking out the Freelancer's Bible and this book on pricing and ethical guidelines. I struggled a lot with figuring out my professional rates, but thanks to these books and fellow professional acquaintances, I managed to sort out rates that were livable and helped me carry my business forward. I hope you can find these useful!

I say go for it. I transitioned from full-time employee to sole proprietor a couple years ago and don't think I'll ever go back to a 9-5. It sounds like you've thought it through and know that there are risks involved, but have planned accordingly.

1. What's the interest rate on your car loan? If it's low, I would definitely not use your savings to pay it off -- that's your cushion should things go south.
   
   
2. You can get health care through the Affordable Care Act. If you're pretty healthy, you could go for a high-deductible health plan, which have the lowest premiums but offer very little coverage. The one upside to them is that many are HSA eligible. If you can get on one of those plans and then open and max out an HSA ($3,350), do so -- it's triple tax-advantaged.
   
   
3. Other advice... Get this book to learn all the things. Know that you are not alone in feeling trapped and tired by corporate life, and that there is nothing wrong with wanting a different life for yourself. Big one -- make sure to set aside plenty of money for tax time, since self-employment taxes are a bitch. I put 30% of every payment I receive into a separate savings account, from which I pay my quarterlies. Also, keep good records of your deductible expenses so that doing your taxes is not a total shitshow at the end. The book goes into much more detail on all of these issues.