As it is, I am acutely aware of my privileges as part of a household with two IT-based incomes and not too many worries, and that the world being what it is right now is giving rise to so many uncertainties that I wouldn't dream of abandoning this unless I had a really big bag of money like the author.
Pretty much everyone says this, but surprisingly few people actually seem to succeed at it when push-comes-to-shove
Ask a wage slave what he'd like to accomplish. Chances are the response will be something like "I'd start every day at the gym and work out for two hours until I was as buff as Brad Pitt. Then I'd practice the piano for three hours. I'd become fluent in Mandarin so that I could be prepared to understand the largest transformation of our time. I'd really learn how to handle a polo pony. I'd learn to fly a helicopter. I'd finish the screenplay that I've been writing and direct a production of it in HDTV."
Why hasn't he accomplished all of those things? "Because I'm chained to this desk 50 hours per week at this horrible [insurance|programming|government|administrative|whatever] job.
So he has no doubt that he would get all these things done if he didn't have to work? "Absolutely none. If I didn't have the job, I would be out there living the dream."
Suppose that the guy cashes in his investments and does retire. What do we find? He is waking up at 9:30 am, surfing the Web, sorting out the cable TV bill, watching DVDs, talking about going to the gym, eating Doritos, and maybe accomplishing one of his stated goals.
Retirement forces you to stop thinking that it is your job that holds you back. For most people the depressing truth is that they aren't that organized, disciplined, or motivated.
I worry that I don't have enough of a life outside of work to make retirement fulfilling, and actually, I don't actually mind working if I'm completely honest. I just never liked the stress of needing a job.
Lack of desires is the first canary in the coal mine of a decrease in mood.
As much as it sounds empty those who are able to distinguish between a 500$ TV and a 5000$ one have a very fine tuned sense of desire which doesn't collapse at the tail end.