http://www.mrmoneymustache.com/2013/02/22/getting-rich-from-...
http://www.mrmoneymustache.com/2012/01/13/the-shockingly-sim...
With ~$600k in investment assets, you'll generate ~$24k/year in dividends. A family of three traveling the world via sailboat can comfortably live on that (note I mentioned "semi-retired"; I still plan on doing consulting occasionally when I require topping up the freedom chips account).
The rat race is totally opt-in. If you're getting paid as a software engineer in the USA[1] and you're making market rate for where you live, you can easily save >>50% of your salary and retire in 10 years. And really, what you're buying with those savings are options. If you love what you're doing, no one will force you to quit once you've accumulated FU money. For me personally, even money says I keep on working in my same career with little change. But the point is that it then becomes my decision, not something imposed on me. It changes your perspective (and stress level).
[1]: The US is an unusually good place for software engineers from this perspective: by moving from London back to Seattle I was able to nearly double my market rate while modestly lowering my cost of living. But even in London, it was possible to save a substantial fraction of each paycheck.
As a US citizen, perhaps immigrating to a country with universal health care is a necessity.
Come to think of it, the rat race really is a fear driven thing. Fear of not having health care when you need it, fear of not having retirement income, fear of keeping up pretenses of "success" vs your peers and classmates, etc.
I like driving nice, new-ish cars, eating out, using the latest technology, drinking Starbucks or whatever coffee I want and having fun, even if it isn't cheap (when I can afford it). I'm not alone here.
I'm glad you've found a way to enjoy life on little means, but trying to say that it's the best way to live is disingenuous.
$600k in savings and investments means nothing if I'm not doing things I don't like. Money is made to be spent.
But then, I don't feel sorry when someone has to work their entire life to retire; that's their choice too.
Not well in the Bay Area, at least.
Of course, you specified living "well." I believe that we live well -- we're all certainly very happy, don't have any unmet needs, and are able to indulge in little luxuries like eating out once a month and visiting family in Europe once or twice a year. However, if living "well" to you requires having two late-model cars, a big house and eating out a few times a week, then yes, you will have trouble doing that while maintaining a high savings rate in the Bay Area.
To answer the first question, I see myself with a decent paying job that has 401(k) and benefits in 5 years. Sounds average, like a typical college student's goal, but I still feel like a college student in some ways. I graduated at age 25 and 9 years later I am not able to make a living for myself.
I have been burnt out from companies paying so far below the local market rate, going through several periods of time with no work only to get another offer form a company that doesn't pay well, doesn't provide insurance, don't withhold taxes for their workers. And then getting laid off again. I'm spinning my wheels here. I cannot save money with that kind of thing going on indefinitely.
In 5 years I also do not want to be living with my mom. I want to have my own home, being able to set my own rules instead of running errands every day for family. And in 5 years I do not want to use her money to go to a coffee shop almost daily because that is the only way I can get internet access (and thus the only way I can send lots of resumes for a job).
I guess on a sailboat you're on your own as far as health care goes (when making big crossings), but otherwise, living in the US, you're not going to insure a family of 3 for that amount.
Plan B would be spending enough time in another first world country with real healthcare to obtain citizenship.
I'm intimately familiar with engineering around healthcare needs in the US due to my mother being disabled.
Life is too short to live it in fear of "what if".