I started my first real mini-business in 1994 when I was still in high school. It was called Paradigm Interactive Media (pimedia.com) and we were a web site development company. Since I didn't know anything about developing websites, my job was to go out and sell the websites to local business; jewelery shops, hair salons, restaurants, etc.
Every time I entered one of those businesses looking for a sale, I was terrified.
Right after high school, my family went through some financial setbacks and I wanted to do what I could to help, so I got my real estate license and started to sell houses.
Every listing appointment and each time I met with a buyer, I was terrified.
After some time I got less terrified being a real estate agent and actually got kind of good at it, so I decided it was time to push myself one-step further and I recruited a group of my peers and created a real estate brokerage.
I bootstrapped the brokerage and grew it while being incredibly underfunded. Because I didn't has sufficient credit, capital, or experience to license a franchise, I created the company as an independent; without any sort of support infrastructure I had no idea what I was supposed to do. Every day going into the office I was terrified, but I went in anyways.
One thing led to another and now I find myself running a business that is blazing a trail of innovation and yet at the same time foraging for survival. Everyday I am charged to do at least one thing that is well beyond my knowledge level, skill level, talent level, or experience level; often times it is beyond my level on all four fronts. But I do that thing anyways. I put myself into the position that I have no choice but show up and do my best. Calling in sick is not an option.
I show up to work and don't know what the day will bring. I try things where the outcome is unknown. I am terrified everyday, but I would have it no other way.