Germinating a Business

Why yes, I AM striking out as a freelance illustrator. Officially. As of the month of March. I feel that this would be the most fitting way to start my thirties. I've wanted to start up since graduating college, but never really knew how, and every attempt had been a smashing failure. There are a load of things which have frightened me from becoming a legitimate business of my own. For starters:

• What do I do about taxes?
• How do I handle taxes?!
• Will anyone really hire me?
• What if I strike a bad month?
• What if I can't support myself?
• Do I WANT to be freelance 100%?
• What do I do about insurance?
• What if I get injured or sick? 
• What about a family?
• What about my family?
• OSHA is scary - how do I deal with them?
• Am I going to have time for everything?
• How much is this going to cost me?
• Can I afford to start up?
• Do I have to get a loan?
• How do I determine my budget?

... And many, many, MANY more questions to follow. So there's been a lot of self-doubt. I've thrown all that aside and thought I can't just wish and dream to make it happen. It's time to get to work. So I'm getting a post office box, filing my DBA (Doing Business As) with the NH Secretary of State, and working on my brand as I send out my first batch of postcards. Honestly, what's holding me back today is that I haven't quite settled on my business name - I know it's minor, but it's important to me. 

Kari Chapin's Grow Your Handmade Business has been a helpful tool to get me started. Between this, Holly DeWolf's Breaking Into Freelance Illustration, all literature by Steven Heller, the NH Small Business Development Center, and networking, are helping me get through all the scary parts. As it turns out, there's not so "scary," they're just some things that need to be taken more seriously than others. Chapin's book I grade 4/5 stars.