I flew for 10 years before trying online with VATSIM. I was too timid to try.
It just seemed overwhelming, what with practicing ATC, dealing with FMCs, handling Squawkbox etc.
A year ago I took the plunge and flew online. On the first time, I'll never forget how nervous I was when asking the Gatwick controller for clearance. He was patient with me, and if you make mistakes he helps you out.
Whenever there's a VATSIM scheduled event I try to join in. The more you fly online, the more confidence you get!
I managed to convince my brother in law, who was too scared to fly online, to give it a try.
We met online using Skype. I acted as controller and coached him how to speak correctly. We both used FS Commander so I could see him realtime on a moving map. It was great fun, and tomorrow he will go solo on VATSIM. I'll be there with him on Skype to help if things get hectic.
If anyone wants to be trained I wouldn't mind helping.