I'm ready to advance the learning curve - I think

As I'm reading through the posts of others and following the SWAP thread on sewing world, I often wonder how did you learn that? When did you bite the bullet and decide to go for it? For the most part I'm still hemming my garments with a machine sewn topstitch. Does it scream 'homemade?' Most likely. Is that what I want to be screaming when I wear garments that I created? Definitely not!! So, where and how do you learn about some of these other techniques? What do you use to 'practice' them on? Surely not a piece of your favorite fabric. At what point did you move past the comfort of cutting up cheapy JoAnn fabrics and start purchasing more expensive stuff. When did you overcome the fear of cutting into an expensive piece of fabric. I'm immobilized by fear. I'm afraid that the envisioned creation won't suit the fabric. I'm afraid that the dream garment won't fit right. I'm afraid that I won't know how to pretreat or properly press the fabric. I'm afraid of so many things that I don't purchase fabric over a certain price per yard. I don't purchase fabric of a certain fiber content. And if I should find a great deal on a fabulous piece of a wonderful fabric in the perfect color - it will sit there mocking me for years. Who teaches at this school? How do I advance and quit pulling the learning curve down?