You often hear the advice "do what you love" when starting your own micro-business.
Im not sure this is the best advice. My advice would be-- do something you enjoy AND are good at.
That's probably not going to be your favorite passion or hobby. In fact, I think its generally a bad idea to create a business that involves something you truly and fanatically love doing. For example, I love to travel. I also like writing and am decent at it when I put my mind to it. So its obvious-- I should do travel writing, right?! Wrong.
I did a bit of freelance writing while living in Thailand. It was alright, but in general I found I didnt like turning two passions/hobbies into work. Writing is great when Im doing little haiku in my journal or blog posts... not so much fun when I feel the need to make money doing it. This is even more true with travel.
I did some thought experiments on this topic. I imagined various travel based businesses and realized theyd all destroy my love of spontaneous wandering. I thought of being a tour guide but as I imagined the details of ferrying tourists around, the thought lost its appeal.
Finally I settled on English teaching... an excellent choice it turns out. This is something I like doing... but as a job. Also, Im good at it. Though I really have fun teaching English, I have always thought of it as work and so Im happy to work at it.
When thinking of what to do for your own business, I recommend you set aside your true loves and passions-- dont base a business on those. Instead, think about what you've already done (or are doing) to make money. Could any of those jobs-tasks be turned into a micro-business? What about items you know a lot about (clothes, computers, etc.)... could you find a manufacturer and sell one of those?
Remember, we're not trying to become rich here... you don't need something that will make millions. You just need enough to support your simple Hobopoet lifestyle. Think hard-- there's definitely something you can do.
As for the details of running your project, start with The 4-Hour Workweek... its got some good practical suggestions.
The scariest part is starting. You don't need to choose the perfect thing... just choose something and try it. Try, test, evaluate, modify... then repeat. Thats the basic process for micro-business success. You can do it.. you can free yourself from wage slavery and be free.