I agree with some of the other answers you've received, but I want to add one.
I think there's a kind of impulsive confidence, and unmitigated determination that lets me put on shorts when it's 20 degrees Fahrenheit out, then tells me to stay the course, and accept that I have entirely become cold, rather than merely passing by it.
As for what other people can do to help me feel that feeling, I have no idea. I do those things because of the way that I am. People have already tried encouraging or discouraging me, and it hasn't changed how I prefer to dress (for example).
In my geometry class, there are no angles. In my geometry class, everything is straight lines, parallel to the line between the center of the sun, and the middle of the flat Earth, just like God intended.