What Centuries of Mistakes Can Teach Us About Saving for Retirement

From hoarding cash to buying stocks, a new book traces 300 years of financial advice and shows why what feels safe keeps changing.

Over the past 35 years, I’ve interviewed hundreds of financial planners, money managers, researchers, academics, benefits consultants and everyday Americans in order to write hundreds of stories about retirement. I’ve learned plenty about smart saving — and the common mistakes people make — and I’ve been lucky enough to apply some of that wisdom to my own investments.

But much of what we think we know about saving and investing today is based on a relatively short span of time. Behavioral scientists call this tendency to overemphasize recent experience and assume tomorrow will resemble today “recency bias.”

In a new book, How to Get Rich in American History (Harper Business, April 28), historian Joseph S. Moore pulls back to examine 300 years of financial advice, showing just how much history and context color our attitudes and beliefs about money and retirement. The book is a timely reminder that a good grasp of financial history is the best antidote to getting caught up in short-term market turmoil — and that many of the most important financial decisions are ultimately personal.

Moore identifies 25 “lessons” from the American history of personal finance and makes himself something of a guinea pig along the way. “Within reason, any interesting idea I found in the past I would try on myself,” he writes. Among his more notable experiments: creating his own crypto coin — “Americans long had self-issued currencies,” he notes — and systematically shorting stocks picked by Jim Cramer of CNBC’s Mad Money. (Net of fees, he lost around $400 on the Cramer trades.) Moore makes plenty of mistakes in the process, but still winds up an early retiree and self-described multimillionaire.

Reading Moore’s book reminded me how lucky I’ve been to live through an era when financial troubles like falling behind on debts didn’t carry draconian consequences like debtor’s prison, as it did in the early 1800s. The US stock market spent much of the period from 1996 to 2026 in a series of bull markets, with a few relatively short notable bear markets mixed in. It’s easy to see why owning stocks has come to seem like the obvious long-term strategy.

But “what is ‘safe’ and ‘sure’ and ‘always worked’ shifts over time,” Moore writes. Looking across a longer span, “the ‘history’ everyone says proves stocks are always good for the long run is less than a century old, which in my line of work is a rounding error.”

The market itself has also changed, with returns shifting from being weighted toward dividends paid out of company profits to being driven by price gains. As a result, Moore argues, “You are no longer buying companies in any real sense. You are buying future buyers of companies,” who (you hope) will continue to drive up prices. (It was in real estate, not the stock market, that Moore made his millions.)

My own worst mistake was keeping too much in cash during a long bull market, missing out on at least $200,000 I’d have made in an S&P 500 index fund — a high price to pay for safety. But in the Civil War era, Moore writes, “hoarding cash, even in banks, invited disaster.” There was no set value for a dollar, and many banks were on the brink of failure. Even though I kept too much money in cashlike instruments, I never had to question whether a dollar would remain worth 100 cents.

Of course, some financial advice hasn’t changed much at all over the course of history. One of the most tried-and-true paths to riches in America has long been joining a wealthy family, by birth or by marriage. After marrying Martha Custis — who was worth more than the equivalent of $8 million today — George Washington became “one of the richest men in America,” Moore writes. “All because he knew the most important piece of financial advice in history: Marry well.”

Moore notes that his wife has a corporate job. While he worked doggedly on his nonprofessorial pursuits — with her support and collaboration — having a solid second income and a committed partner makes taking risks, like his early investments in rental real estate, arguably less risky.

But if “capitalism is a team sport,” as Moore concludes, that doesn’t bode well for younger generations. Pew Research Center data shows that as of 2023 there were about 111 million single adults in the US, up from 70 million in 1990. In 2019 the US marriage rate hit a 140-year low, according to Pew data.

Moore grew up in the South without much money and, as a humanities professor, assigned his students Karl Marx every semester. But he emerged from his financial experiments a committed capitalist, embodying a mindset common among the very wealthy: a belief in abundance and optimism. His money gospel is simple: With hard work, it’s never been easier to get ahead. “Avoid retirement anxiety,” he writes. “You can and will retire.”

I want to believe this. But worrying about retirement is almost a hobby for me — and has led me to save enough that even my risk-averse instincts haven’t sunk me. I have more of a scarcity mindset: I want to keep — and modestly grow — what I’ve earned and saved in order to lead a comfortable life. I don’t want to take big risks.

And to get rich, rather than merely comfortable, you need to focus on the upside and take calculated risks instead of always protecting your flank. Over time, as Moore became an expert in personal finance and real estate, he was able to take bigger and better-calibrated risks until, one day, he made his first million, then his second.

“Our culture swallowed a pessimism pill and it isn’t doing us any good,” Moore writes. I see his point. But it’s hard to rewire your brain if experience has left you anxious about money, and those attitudes often come from our parents. There was a strong undercurrent of money anxiety in my house growing up, even if it was rarely discussed. One of my mother’s main pieces of advice was: “Never go into debt.”

She was wrong about that, as writing about personal finance has taught me. Sometimes taking on the right kind of debt is smart — and sometimes paying it off is not. Perhaps that’s the timeless lesson: Mother does not always know best.