Replying to How does one decide when to ski harder terrain?

Curious what your process, if any, is for approaching trails you've never done and ones that are definitely higher in technical difficulty than you've done before?

For example, how does one decide, "hmmmmm I think I'm gonna huck this giant cliff today"

Is there any good reasoning, other than growing a pair, behind when you actually decide to pull the chain and finally send it down that line you've been eyeing all year? Obviously you need to be confident in your skills, but just curious.

I pretty much just try to push myself a little more each day I'm out and go a little more out of my comfort zone each time. Some days more than others. That seems to have a good impact on my progression. The only downside is usually the people I'm skiing with say fuck that I'll meet you at the bottom, which sucks cuz it's so much easier if you have another person saying hell yeah let's do this.