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Hoping the Last Check Bounces … and Other Financial Approaches to a Long Life

April 28, 2026
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Hoping the Last Check Bounces … and Other Financial Approaches to a Long Life

Brendan McNamar, a poker dealer who lives in Arizona, doesn’t gamble when it comes to finances.

Mr. McNamar made a living playing poker. But after getting married 10 years ago at 47, he began to reassess his financial situation. At the time, he said, he owned a modest house and his wife had significant student debt. “We looked at everything and decided that we really needed to plug some big holes in our retirement savings.” And that caused him to rethink his career.

“There’s something called variance in playing — it’s the same thing as the variance in stock market returns,” he said in an interview. “You lose for an extended period of time, even though you are doing the right thing. Just like you can invest in stocks but be in a bad market.”

That variance — essentially the fluctuations in outcomes — led Mr. McNamar to switch from playing to dealing poker. He became a casino employee, which gave him income certainty and access, for the first time, to a 401(K) retirement account. “In dealing, while a lot of income comes from tips, I can predictably know what I’m going to make,” he said. “The variance goes away and paying bills becomes less stressful.”

Individuals are now grappling with a financial dilemma: the longevity bonus of an increased life span versus the longevity risk that an individual’s finances won’t cover those extra years, said Mark S. Walton, an executive educator and journalist and the author of “The Longevity Bonus.”

The Stanford Center on Longevity suggests that planning requires a change in analysis. Rather than looking at a life span in three parts — education, career and retirement — the center suggests viewing life in quadrants, a concept proposed by the British professors Lynda Gratton and Andrew J Scott, authors of “The 100-Year Life — Living and Working in an Age of Longevity.”

But financial approaches to planning for a centenarian life vary. Charles Feeney, the billionaire co-founder of Duty Free Shoppers, famously once said “I want my last check to bounce.”

While that view may still ring true for a small group, it’s a sentiment that has not held up with financial turbulence, the pandemic and the unsettled global situation.

Or, as Martha Deevey, the associate director and senior research scholar at the Stanford center, said in an interview, “While I may want my last check to bounce after I have helped my kids — it doesn’t mean I neglect everything else. We need to be more comprehensive planners.”

Erin Sheehan, who works for the State of New York, is well aware of the sentiment of leaving no money at death, but said she has “no such intentions. My plan is to have the money there if I need it, and if I don’t, to further the causes that I care a lot about.” Although she has no children, she anticipates continuing to live a frugal life, leaving a sizable estate, which Ms. Sheehan, 56, and her husband plan to donate to a range of charities.

“Saving means potential freedom — freedom of knowing that there’s always a safety net,” Ms. Sheehan said in an interview. “If the world implodes, we have our savings and we have resilience. We know we’ll be OK. We know how to eke out an existence and enjoy it. I’m not denying myself anything.”

Approaches can be generational.

The Baby Boom generation has an outsized proportion of wealth, which is not surprising since they have had the longest time to amass savings. According to Federal Reserve statistics released in March, Baby Boomers, those born from 1946-64, possess more wealth than older generations (even if adjusting for inflation).

Those in Generation X, born from 1965-1980, have a lower net worth than the Boomer generation had at the same age, Mr. Walton, 75, said.

For example, Corinna Krauskopf, 47, a Seattle resident, said: “As a Gen X-er, my entire professional life has been one of catching up, but on other people’s terms. Job opportunities, career growth, financial resilience, and even personal health have all depended on someone else making the decisions and packaging them as part of the work environment, culture, compensation and benefits.” (Ms. Krauskopf was one of more than 200 readers who answered a questionnaire on The Times’s site about longevity.)

After losing her job in 2024, she decided to start her own business, “Now, I can work on my own terms for as long as I wish. It is my retirement plan on my terms. Is it perfect? No,” she said. While she said it’s difficult to find a suitable health care plan, “overall, I can now set the course of my next chapter on my own terms instead of putting my faith into someone else.”

Ms. Krauskopf, who founded Fearless Philanthropi to help nonprofits, said she hoped to “build out multiple revenue streams, both active and passive, to support and sustain a robust business and a robust life.”

The intention to keep working to some extent — whether for income or on a volunteer basis — reflects the sense that a long stretch of leisure time is not always the goal. Part of that is purely economic. According to research by the Pew Research Center, a sizable and growing share of older adults over 65 continue to work “either out of necessity or according to personal preference.”

(What is not yet reflected in the surveys about working past 65 is the potential impact of artificial intelligence on continued employment. ManpowerGroup, a recruitment and staffing company, recently found that tech confidence among the Baby Boom generation dropped by 35 percent, while that confidence declined by 25 percent among those in Gen X.

The amount individuals need for retirement — especially one where the retiree doesn’t need to watch every penny — is not fixed, of course. But generally, most Americans have far less than is needed.

A recent retirement study from Northwestern Mutual, the life insurance and financial planning firm, found that Americans thought they needed $1.46 million to retire — a $200,000 jump from the 2025 survey. A BlackRock survey of registered voters in 2025 found that people thought they needed $2 million to retire comfortably.

Two million dollars is the amount that Ms. Sheehan hopes to have when she decides to retire. While she initially thought she wanted to live abroad in retirement, her focus has changed. She had traveled extensively in her 20s, but began to work in nonprofits in her 30s, ultimately working for the State of New York. She plans on having sufficient resources to allow her to volunteer for several charitable causes.

But that amount also will cover housing. Ms. Sheehan said she would like to live in “a Life Care community if I choose, or a nice independent living facility.”

Ms. Krauskopf said eventually she might reside in an assisted living or an active adult community. That’s “when I will find my own Golden Girls to support each other.”

The $2 million figure also coincides with the lowest amount Mr. McNamar, who is also a financial planner, intends to have by the time he retires in a few years. With that sum, he and his wife hope to maintain their Phoenix-area home, but, in addition, to lease or buy a second place where they can relocate during the summer.

To ensure this amount, each year he and his wife save a set amount to fund their future lifestyle. Ultimately, Mr. McNamar and his wife “would like to enjoy more leisure and travel and to have some breathing room and to pursue interests that aren’t income-producing.

“We don’t know how long we will live, but don’t want to run out of money,” he said.

The post Hoping the Last Check Bounces … and Other Financial Approaches to a Long Life appeared first on New York Times.

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