The "when" is such a personal decision. I took a HUGE risk leaving when I did, it was downright irresponsible. I was involved in a project that got funded and I thought would really work out (HardFork Series) but it fizzled and I walked away with nothing but more screenwriting experience. I would recommend to anyone that can take a sabbatical from their job (without repercussions) to get a taste of what retirement is really like to do so. Like everything in life, there are pros and cons.
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Yeah, that is a good point. You can have all kinds of plans, but until you actually live it day to day, you aren't going to know if it will work. I kind of don't think it would be fair to retire five to six years before my wife!