You couldn't pay me enough to have a boring 9-5 job where you clock in every day and do the same thing for 20 years that you're not really that great at. Some people have a built in character for taking these kinds of risks. I actively turn down investment money to fight my away from lifestyles that you have described. Everybody dies, even the guy safe in his treehouse, next to the water cooler from a heart attack built up of years of pointless stress worrying over someone else's dream.
So I'm an entrepreneur and I think this is a negative and unhealthy attitude. It also just doesn't make sense. If you're an entrepreneur, is everyone that helps you build your company a loser?
It comes down to risk tolerance. Some people can tolerate more risk and desire more automony. For me, I view my company as a combination of many dreams. I don't make all the decisions or come up with all of the ideas. I actually find encouraging autonomy and mastery, my employees are more productive and happier.
It also seems wrong to morally judge people for living a life they want to live. For too many people simply having a stable job is a dream.
You can't escape judgement, as the parent post shows in his own judgement of other's risk taking behaviour. Some people think it's an 'impossible risk' some people thinks it gives life, a difference of values. The risk is a side thing. The focus is on creating what has value in my world view and somebody else's dream is not it.
I don't make any bones for or against a moral 'argument' in terms of other peoples lives, just a stalwart defense of my own and others like it. I don't think any boss gets far hobbling their employees in any capacity. I have a great respect for the work people do and getting in their way is a waste of everybody's time. For those that dream of a stable job I would encourage them to dream bigger, if they are focused on work and not on some social or personal journey in life.
If everybody was aiming at the same thing I did and valued the same things I did, then yeah they would be losers for copping out on what they want. But not everyone is me and I barely have an opinion beyond passing interest about people who live with different values and goals, but are happy to see them succeed. A rising tide lifts all boats.
