Whizzard, I make even less than a third of my cash income compared to when I was at the top of my game in a bank, but after you get to a certain point where you have saved enough, the stress of top paying jobs is not worth the money and your health. Right now, I have a 9-5 job in my own office and can disappear at 4pm if I want.

A few ideas which might help you on your quest:

After I quit my job, I went through the same analysis as you i.e., generating passive income > expenditure and trying to ensure that I'm hedging against inflation. I was largely successful, but while your $10m in capital can generate $500K in returns per year, they may not be cash returns unless the $10m excludes equity in the property you live in. I have lower expenditure than you - $200+K per year - and my yield on all my equity and fixed income investments is around 6.5% (helped no doubt by wading into high yield stocks in Mar '09)

About half of my assets (not capital) are in a bungalow that I live in. I have a multi-million dollar loan on the bungalow (currently at around 35% loan to valuation) and the bungalow has more than doubled since I bought it giving me an incredible return. That is the power of Leverage. I think you should lever, but just not too much. For the bungalow, I was able to take what most people would consider a gigantic loan (but still a fraction of my net worth) at around 2% fixed interest rate. In my opinion, its easy to beat 2% in the market. I can pay off the bungalow loan with my capital, but why should I do that if I can easily beat 2% return on cheap leverage from DBS.

I'm already up about 500% off the downpayment on my bungalow, which is like 100 years at 5%. Going forward, I conservatively expect landed property to rise at about 3% pa long-term through the cycle so with a little leverage, I can easily beat inflation and generate an adequate return even without rental income.

However, since I actually live in the bungalow, the return is not cash. So while overall I have been generating waaaay more than a 5% return on my capital for the past few years, my passive cashflow is just around $200K+ and just enough for my family expenses. I've found that working a simple job, you feel better about it and keep busy while seeing your savings continue to pile up, which is a nice feeling. I experimented with retirement, but the boredom drove me nuts. Its better to work a simple easy job at low pay. I wouldn't go back to a difficult job that doesn't pay well. When you have been earning about $1m a year, its fairly easy to convince someone to pay you $200K to do just about anything. I'm fortunate to have found a simple management job in a small unlisted company. Part of the deal is that I get a fair bit of equity instead of cash. I'm prodding them to IPO Whatever you do, don't sit at home and waste away. Once you stop working, the body starts to prepare for death and I've seen so many people who retired and then dropped dead a little later. Keep active by working and you will live longer. Good luck.