I've seen lots of threads here for how to get children to take on challenges, overcome perfectionism, and 'all that' but today I was struggling with getting my son to do it when I realized I haven't been modeling it.

I never really had to face challenges in school, and even through a lot of university level study it's been a bit so-so, and I RARELY take any real world risks at all. (Especially with money - I get really nervous if someone will be paying me for something confused )

Has anyone had experience learning to take on challenges as an adult? Or had one of those moments when you realize you've been modeling one thing and saying another? How did you overcome it?