As you approach retirement consider putting much of your new savings into safe government bonds.
This is “safer”, but it introduces new problems. Since your investment has lower expected returns, you need significantly more money saved up. The S&P 500 has historically returned around 10% per year over 25 year periods, and has almost never returned less than 5%[1]. Right now, as far as I can tell, government bonds return 1-2% depending on their length. With 5% expected returns, you need 20x your expenses saved up, but with 2% you need 50x, and with 1% you need 100x. Most of these are probably possible for high income/low expense Lesswrongers to save up, but I’d expect that we have higher value things to do with 30x our expenses than to hold onto it in case of very unlikely personal risks.
It is possible to live for a long time while withdrawing more than you earn. For example, with 5% expenses and 2% returns, you would last about 26 years[2] before running out of money. Considering point #19 though, guessing how long we’re going to live seems like a pretty big risk too.
[1] http://financeandinvestments.blogspot.com/2015/01/historical-annual-returns-for-s-500.html
And what’s the point of making money if everyone hates you?