Well, I'm still new to snowmobiling and haven't had too much scare me yet but I haven't done serious mountain riding yet! However, I ride ATV's year round and I can bring some of my "conquer your fears" experience over from there. To a point it really is a matter of "Just do it" but at the same time don't commit to doing something that you flat out don't have the skill to do. ATV's have such a high center of gravity compared to a snowmobile that they actually scare me a lot more- it's much easier to flip them over backward or to roll them, and they weigh (well, mine does) 700+ pounds and the last thing you want is that on top of you. So what I did with ATV's is rode often and challenged myself a little on every ride so that I got better and better without really risking major injury. I now can ride up very steep slopes, ride off-camber, hop logs, all kinds of stuff. Compared to an ATV a sled seems very stable and so a lot of my fears of rolling or flipping over backward are non-existent with a sled. I pretty much go where the guys go. I think the one thing that I would find very scary would be to be coming down a hill out of control. There's one ride that all my friends like to do up to Lost Lake and the favored trail turns into a luge run after a few people have been up and down it. People tell me you're just on the sled for the ride and you have absolutely no control. They said there's this one turn where you're headed straight for a tree but the trail grabs you and pulls you into the turn. I'm sorry, but that sounds terrifying! So that's my big hangup. I only want to go down a big hill if I have a good run-out and no major obstacles (read: tree!) that I'm bound to hit. The other area that I find somewhat scary is how FAST the sleds are-- and therefore how quickly something can go wrong.