I started thinking about retirement about 42 years ago when I opened my first IRA at 23. Since then, I have had some good years and lean years. I am now within a year of retiring at 66. It strikes me that the "rule" of needing 80% of your income replaced by asset withdrawals doesn't necessarily apply for high earners.

For the last six years, I have earned $1 million to $1.4 million annually, but have no ongoing need to spend even a quarter of that. I have $1.1 million in IRA/401(k) assets. I will also have $2.5 million expected from liquidating my business interests and $2.1 million in real-estate net equity ($550,000 in 4% mortgages on both of them), $275,000 of emergency cash and no debt.

My wife has about $350,000 in 401(k)/IRA assets and $250,000 in taxable investments. We anticipate between $1 million and $1.5 million in additional inheritance within five years. In 2028 and 2029, I will have no earned income or Social Security. Social Security could kick in at 70, starting at $58,000 annually; my wife's Social Security could start at 62 with $30,000.

Yes, I consider myself pretty lucky.

I will be comfortable spending $250,000 annually on more than $4 million in investments plus Social Security. Homes, insurance, travel, cars, taxes, and healthcare are the biggest anticipated expenses. I imagine between 40% and 70% equity allocation would be appropriate. I am considering a dual-life annuity for a fixed income substitute.

I also have other questions: 1) Do I pay off my 4% mortgages instead of investing my cash? 2) Do I play it safe and buy an annuity for maximum income (especially if Social Security is diminished)? 3) Do I defer 401(k) withdrawals to age 73 and hit my taxable accounts harder until then? Maybe I should start Social Security at 68 instead of 70? I hope to ensure sufficient income, inflation protection and a legacy for my children.

Somewhat Confident

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By investing in your 20s, you have earned riches without the embarrassment.

The answers to your questions -- do you pay off your mortgage, get an annuity and defer 401(k) withdrawals until you're 73? -- lie in the laps of the gods. You're asking the impossible. You are assuming that there is one answer that will suit your needs. The answers are based on your risk tolerance and needs. If in doubt, split the difference on your various options.