I love the advice you are giving people.
If you really want make a splash, you can't just dip your toe in the water and "try it out" you need to jump in. If you jump in and start drowning you have to work with all your might to stay afloat.
Having backup plans is not unwise, but pursuing making sure you pursue your passion with 100% effort is key. Putting too many eggs in one basket is never wise, but that is more from an investment point of view for me.
Instead of trying to be good at a lot of things at once and instead being mediocre at all, dedicating your full effort pays dividends.
I really liked the insight from your friend Olive too. For her there is no other option. She is going to be successful or die trying. The people with that mentality are some of the most driven people I know. They don't blame circumstances or others when things aren't going well for them. They just continue to pour their heart into what they have in front of them.
I see what you are saying @benjmiller222, There are always things outside of your control, so back-up plans A(a), A(aa) etc.... are wise. But like you say, you need to pursue that passion 100%, don't create back-up plans for yourself that ultimately deviate from that passion.