Error comments on On not getting a job as an option - Less Wrong Discussion
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Note that you seem to have a huge and invisible to you gender assumption :-)
Have you also thought about the possible connection between your observation and the fact that the US is a very wealthy country?
You certainly can. There are a whole bunch of people in the US who do precisely that. Unfortunately for your argument they don't look to be ultrahip vagabonds who travel the world in between TED talks. On the contrary, they look to be poor, severely constrained in what they can do, unhealthy, stuck in bad neighborhoods with high crime rates, etc. etc.
Life is a series of choices. You can make a choice to drop out and I know people who've done that, both recently and back in the 70s. But there is a price, of course, and for some people the price is worth paying and for some it is not.
There are intermediate stages, too. For example I've met a guy who works for one month per year on an offshore platform and that gives him enough money to travel low-budget in Asia for the rest of the year. He doesn't have a house or an apartment, he is either on the platform or traveling. He stores his stuff at his mom's.
If I may make a generalization, dropping out works much better for people who are young, single, healthy, adaptable, and can quickly find a reasonable job if they need to (aka have sufficiently high IQ and some marketable skills). That's not an iron-clad rule, of course. One somewhat popular way of dropping out is to buy a cruising yacht and go off into the oceans of the world -- and that is occasionally done by full families with kids.
One other point is the uncertainty of the future. Because of it you want to both retain some flexibility and have resources to deal with whatever it throws at you. A vagabond style of life tends to be very flexible but very low on resources.
I am curious just what sort of job he's doing out there, and how he got it, and what kind of real money he's making. That's not a bad way to live.
As far as I remember, he was an engineer, not just a grunt. He also was in his late 30s or early 40s and spent time working (normally) in the industry. I assume that allowed him to build a network of friends and acquaintances who are willing to offer him month-long jobs. It also helps that offshore platforms work on the shift method -- people are flown in for a period of time, they live on the platform for a few weeks working, basically, without weekends, and then they are flown back and have a mini-vacation until the next shift.
I agree, it's not a bad way to live. But there are downsides as well. You literally have no home, for example. Having a long-term partner is problematic, having kids is out of the question. If you are a self-sufficient loner it's a good life. If you want a community to live in, well...