El Pilot,

You may not realize this now, but single pilot flying in small airplanes in threatening environments (ice, night, high winds, battling fatigue) is MUCH more difficult than multi pilot 121 or 135 ops. When I was a 200 hour commercial pilot I knew nothing. Sure, I could fly an airplane safely, but all I knew was the training environment. You absolutely do not have to CFI as others have said. BUT, you need to somehow fine tune your limited flying skills and gain experience in more controlled environments before you can safely fly freight in small airplanes. As a former CFI I can tell you that no one cares if you are goofy or a little shy, they just want to understand what you are talking about and feel like they are learning something useful. My advice? Man up and get your CFI then teach primary students for a while. Then, once comfortable, get your CFII and get comfortable with other people trying to stall your airplane in the clouds. Then, once comfortable with that, get your MEI and watch people try to hit the wrong rudder near VMC. You'll soon realize how little you actually knew before you started teaching. Chances are you'll get over your shyness along the way pretty quickly. Probably about the time your first student pukes or when you cut the back of your first solo's T-shirt after he or she solos. Good luck