NYTimes: How to Prepare for a Longer Life

Investing Strategies Retirement Investing
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NYTimes readers share their tips on “How to Prepare for a Longer Life”

https://www.nytimes.com/2026/04/28/your-money/longevity-finances-reader-responses.html

Here’s mine:

1.) Understand the Reagan scam from the 1980’s. Earning wage & salary income is just about
the dumbest thing you can do in America, tax-wise. Trickle-down isn’t helping you. And working uncompensated overtime in the hope of raises and promotions is usually a poor investment – switch jobs instead. I job-hopped through five Fortune 500 companies in the 1980’s before early retiring in 1994 at age 38.

  1. If you’re living off an investment portfolio, you almost have to volunteer to pay any taxes by selling something. Large multi-generational fortunes weren’t created by whatever productive activity the founders were up to. It’s the lack of taxation compounded over decades and generations that creates most of the value. Working would be a better deal if you were paying the same low to 0% tax rates.

  2. Because of the big difference in taxation, you’re really not going to lose anything by retiring early. Wage and salary growth is a small fraction of what you’ll earn with an S&P500 index fund.

Here’s a USA Today article from 2013.

intercst

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Notice that you give up stepped up basis on assets in the trust. Cap gains taxes can be hefty whoever decides to spend some. Of course you can borrow against the assets and pay interest instead.

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How is this thread about trusts? That said - it’s not you who will miss out on the benefit of stepped up basis. You’ll be dead. It’s your beneficiaries who will miss out on the benefit. And if they get some other benefit that they wouldn’t have gotten otherwise, like income from the trust while you’re alive, missing out on that benefit may be a reasonable trade-off.

AJ

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