Hi Kevin,
Dont' worry! You're not alone. I haven't done much offroading and only started in 2009 and even then it was quite sporadic.
First, I did BMW Offroad School Level 1 course - money well spent! Learnt some basics and gave me a starting modicum of confidence (despite shoulder barging a tree on second day when believing I could leap a large stone sitting in the rut I was riding in).
Then in 2010 4 days in Spanish mountains with Touratrail - awesome fun and more confidence gained (no trees hit but a couple of small offs).
I bought offroading bike last December after joining TRF. Didn't get around to doing anything until about May then checked the OS and Surrey Interactive maps, and the current ByWays / Restrictions list, and made first gentle foray into Surrey - Bockets to Leith Hill and back.
Then a couple of Enduro practice days (Blue Light at Bagshot and Kent Enduro) which told ne that I'm not an Enduro rider
Then a couple of trips on the Ridgeway over near Marlborough and a gentle 2 day event in Wales in October (WTRF Cambrian Rally).
Now I'm planning (once leg injury resolved) to try to go out regularly with Surrey TRF in rideouts suited to my ability. I know I will be far slower than most but from what I read on the site these are a decent bunch of guys who are happy to accommodate all levels of rider so that all members maximize their enjoyment of the common interest.
Hope to see you on a ride soon.
NJ