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Unless you're the rare tech entrepreneur getting a lifetime's fortune in a single acquisition event, or the equally rare successful serial entrepreneur, there will be ups and downs and you won't know the outcome until years later. The specifics of what you do today will inevitably become irrelevant even if it's the hottest technology of the moment. Save and continually adapt.

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Also, if that's the plan, live WELL below your means. Note that the OP had in fact saved up $500,000 --- a pretty sizable sum of money by most standards. Downsizing earlier and more aggressively (e.g., selling the house while he still could) might conceivably have stretched it out a bit, but the expenses of eight kids living anything close to a middle-class lifestyle are ferocious no matter what you do about it.

$500000 is inadequate sum of money in his circumstances. He was making at least $300000 per year and he should have planned for at least 15 years of unemployment (50 to 65 when his pension kicks in). His saving rate should have been higher but I would not judge somebody with 8 kids for not saving enough for retirement.

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