The kind of life that everyone is supposed to want- safe, secure, prosperous, no serious worries or upsets, steady employment, 2.5 children- all that sort of thing- is the kind that people are most likely to regret when they look back from the lip of the grave. On the other hand a rackety sort of life, full of changes of scenery and fortune- with slidings up and down the social scale- is the kind they're most likely to be pleased with.
We're not timorous beasties, us humans- we're designed for hardship and adventure. Our brains and bodies are adaptable and resilient. They crave the fullest exercise we can give them. 9 to 5 is not really what we want.
I look back and, by and large, the things I'm proudest of are the risks I took.