Great analogy with the bike - the context is all that matters. As long as you can do things for fun, they rarely will become stressful for you. But if your (financial) well being depends on it, things are going to stress you out even if you'd normally enjoy it.
I've realized that especially when I started to manage funds for @alexandrabauer. It's just play money for her, but the moment I had to make decisions concerning a friend's money, things I love to do stressed me all of a sudden and I was a lot more anxious to make wrong decisions than what I am with my own money.
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Ooh I wouldn't want to be investing other people's money, even if they say 'it's fine if you lose it all; - there's still stress with that!