How Institutions, the Media, and Money Bloggers Address Working in Retirement

Today we’re concluding our discussion on the Retirement Police.

So far we’ve had two posts in this series:

• Grappling with the Retirement Police
• The Changing Definition of Retirement

You’ll want to read those in case you missed them as they lay the groundwork for today’s post.

Last time we were asking various “experts” in the field of retirement how they think about working in retirement (are they for it, do they see it as two different things, etc.?)

Let’s kick it off with this question from me…

What do leading retirement institutions say about working in retirement?

And here’s ChatGPT’s reply…

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Here’s what leading research institutions say about working during retirement:

Center for Retirement Research at Boston College

• • Researchers at Boston College emphasize that older adults who face late‑career disruptions—like job loss in their 50s and 60s—may take on new work to maintain income and delay drawing Social Security benefits, though often at reduced pay and benefits. Delaying benefit claims can boost overall retirement income, especially when combined with continued labor.

Employee Benefit Research Institute (EBRI)

• • EBRI’s Retirement Confidence Survey shows a gap: while about 70% of workers expect to work during retirement, only ~27% actually do .
  • EBRI highlights that older workers are becoming a larger, more diverse segment of the workforce, underscoring the need for flexible work options and retirement policy support .
  • Its publications explore the impact of working in retirement on Social Security claiming, income, and overall financial security .
  • Urban Institute & Congressional Committee Reports
  • In “Working for a Good Retirement,” the Urban Institute shows that delaying retirement—even by one to five years—boosts personal wealth, improves Social Security solvency, and enhances well‑being, especially among lower-income workers .
  • A Senate Special Committee report (America’s Aging Workforce) finds that many people now transition gradually into retirement—using bridge jobs, part-time roles, or self-employment—not stopping work abruptly .
  • That report also outlines the business case for supporting older workers—citing productivity, experience, and mentoring value—and encourages employers to offer flexible, age-friendly workplaces  .

International & Industry Insight:

Geneva Association

• • The Geneva Association (international insurance sector) promotes a “Fourth Pillar” of retirement: a flexible, phased extension of work life—typically part-time—as a supplement to public pensions, occupational pensions, and personal savings. This model enables retirees to stay active and financially secure .

Main Takeaways

• • Working in retirement is increasing and often necessary, especially when financial shocks occur.
  • While many expect to work during retirement, fewer actually do—due to health, job access, or financial readiness gaps.
  • Continuing work—even part-time or consulting—can boost income, delay benefit claims, and improve well-being.
  • Policy think tanks and employers are being urged to create age-friendly, flexible work environments that accommodate older adults.
  • Globally, retirement is being reframed to include an optional, flexible work phase that enhances security and life purpose.

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I’d say there’s a mixed take on working in retirement…especially if someone needs to work (in any job).

At that point, I think we’ve decided that you may be retired from your original career, but if you must work for financial reasons, you’re not “retired.”

That said, many of the above have no issue with the idea of work being part of a retiree’s life, showing how the concept is gaining broader acceptance.

In my opinion, the thought of working in retirement will become more and more common until they all accept in all conditions that it’s fine to work in retirement. It’s just a matter of time.

I kept pressing this issue, seeing how other sources address the topic, with this question…

What do top news sources say about working in retirement?

Chat’s response…

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Here’s what several well-regarded news organizations—The Washington Post, The Wall Street Journal, and other U.S. media—report about working during retirement. Their coverage supports the view that retirement and continued work are not mutually exclusive, and often overlap with significant benefits and challenges.

Media Perspectives on Working in Retirement

The Washington Post

• • A 2023 feature reports that the percentage of Americans age 65+ working has nearly doubled since the late 1980s, partly because individuals now voluntarily stay in the workforce or need to continue working due to financial pressures.
  • A 2024 wellness article indicates that working past 65 can yield health benefits—those who continue working report better overall health, lower rates of major illnesses, and greater well-being than retirees who fully disengage.
  • Editorial commentary criticizes the outdated notion of forced retirement solely by age and supports the idea that policies should accommodate older adults choosing to remain in the workforce.

The Wall Street Journal (WSJ)

• • An article titled “Congrats on Your Retirement. Time to Find a New Job” notes that about one-third of adults aged 65–69 are employed, a jump from under one-quarter in 2000, underscoring a shifting reality for late-career individuals.
  • A recent story on late-career job losses shows how individuals laid off in their 60s are transitioning to part-time or consulting roles—which blurs the line between traditional retirement and ongoing work.
  • WSJ also covers how today’s 65-year-olds are redefining traditional milestones—they often remain active, financially savvy, and engaged well beyond past norms.

Although I was unable to access specific NYT articles, the coverage from other reputable outlets suggests that if the NYT addresses working in retirement, it likely aligns with these modern perspectives: that continuing work post-retirement can promote purpose, financial resilience, and well-being.

Other Outlets

• • Kiplinger offers a practical guide to “best side hustles for retirees,” noting that nearly 40% of retirees plan to work during retirement and that monetizing hobbies or freelance skills can deliver flexibility and purpose.
  • Business Insider profiles 90-year-old June Boyd, who continues to work part-time despite financial constraints, highlighting how work can offer both income and community connection in later life.
  • Another BI story features an elderly couple working into their 80s due to financial need—underscoring how many older Americans lack sufficient retirement savings and find work essential to cover costs.

Summary Highlights

• • More seniors are working today—particularly those aged 65–69—motivated by desire, health, finances, or social engagement.
  • Working during retirement can enhance financial resilience, delay drawing down savings, and preserve a sense of purpose and structure.
  • Job market disruptions, such as layoffs in late career, are leading many to take on part-time, consulting, or bridge roles instead of fully exiting the workforce.
  • Media coverage increasingly supports the idea that retirement is not binary: it can include flexible, meaningful work.

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These results are mixed too — at least to me — because they equate being retired with reaching a certain age (usually 65).

These are two separate things. Many retire before 65, and some keep their careers well past 65.

Why is 65 even “the” retirement number anyway? Is it because it was Social Security’s full retirement age for so long? That’s my guess. But it’s not the full retirement age for Social Security these days, so we need to move past that.

That said, the median retirement age in the US is around 62, so more people than not are retired at 65.

Chat followed the above with this question…

Would you like me to show representative quotes from any of these articles or explore specific trends—like how media coverage compares between gender or income groups?

I said I would and got this…

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What Recent Trusted Publications Say

• • A MarketWatch piece titled “Retirement is nonsense” argues that the traditional model of fully withdrawing from work is outdated. It highlights new patterns such as “unretirement” and “rewirement,” with many seniors launching businesses or working part-time well into their 60s and 70s—to stay engaged and financially secure.
  • Time magazine presents stories such as “Why Stop? Meet the 80- and 90-somethings Who Want to Keep Working.” It profiles individuals in their 80s and 90s who continue working by choice, pointing out mental stimulation, social connections, and enjoyment as motivators—aligned with evolving definitions of retirement.
  • Kiplinger’s article “10 Things to Know About Working in Retirement” reports that nearly 19% of people aged 65+ work, often by choice, for both financial and emotional reasons. It notes health benefits, potential for workplace perks, and the importance of job quality in later years.
  • Investopedia’s “How Working in Later Years Can Improve Your Health” highlights research showing that working even one year past traditional retirement age lowers mortality risk by ~10%, improves cognitive function, reduces depression, and enhances social well‑being—though benefits depend on job type and personal choice.
  • The Guardian shares “Why retirees are returning to work,” noting that financial uncertainty and loss of identity often drive retirees back into paid work or volunteering—even part-time—helping restore purpose and engagement.
  • Kiplinger, again, in “The Five Best Side Hustles for Retirees,” reports ~40% of retirees plan to work, emphasizing side gigs that offer flexibility, personal achievement, and supplemental income without compromising retirement goals.

Summary of the Media Perspective

These respected publications consistently frame retirement not as the end of work, but as a choice:

• • Many retirees strive for continued engagement and flexibility through part‑time roles, consulting, or side gigs.
  • Health and mental benefits of working later in life are widely recognized.
  • Financial concerns—longer lifespans, inflation, and Social Security uncertainties—lead many older adults to maintain earnings.
  • Overall, retirement is increasingly viewed as a phase that can—and often does—include meaningful work.

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We’re seeing a pattern here. The definition of retirement either has changed (for most of these) or is changing (for some) to include working in retirement. It’s pretty clear to me.

It also makes sense that we’d see it first with publications who are constantly updating their content. They are on the frontlines of changing trends, definitions, etc. so they should be (and are) the ones who are most likely to accept working in retirement.

There’s also another group (probably even more advanced in thinking about and living retirement) that Chat itself asked me about as follows…

Would you like a few real-world examples of people who define retirement this way—either from millionaire interviews, FIRE blogs, or mainstream retirees? I can include 2–3 brief profiles to bring this concept to life.

I said I would and got this…

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Here are three real-world examples of people who are “retired”—by financial independence standards—but still choose to work in ways that bring them joy, structure, or income. These stories highlight how retirement today is more about freedom than finality.

Mike Piper – Financial Author and CPA

Mike Piper, widely known as the author of the Oblivious Investor blog and a series of “Plain English” investing books, technically retired from full-time CPA work years ago. But instead of quitting completely, he transitioned into writing and speaking—on his own terms. He continues to earn income through books and courses, but does so from a place of financial security.

He doesn’t have to work. He just enjoys sharing financial wisdom with others. For Mike, retirement means freedom from obligation, not freedom from activity.

“Mrs. Frugalwoods” – Blogger and Homesteader

Liz Thames, better known as Mrs. Frugalwoods, and her husband reached financial independence in their 30s and “retired” from city life to live on a rural homestead. But Liz still blogs, writes books, and runs financial consults from time to time.

She considers herself retired because she no longer needs the income—and chooses only work that aligns with her values and lifestyle. Her version of retirement is about living deliberately, not sitting still.

Millionaire Interview #132 from ESI Money

This interviewee retired at 55 with a $3 million net worth and immediately started consulting in his previous field—on a limited, part-time basis. He now earns extra income, keeps his mind engaged, and gets to pick and choose projects.

He says, “I’m technically retired, but I still enjoy working… just not 50 hours a week.” His story reflects a common pattern among retirees: keep what you enjoy, drop what you don’t.

Bottom Line

These examples show that modern retirement isn’t about quitting everything—it’s about reclaiming control over your time and energy. Whether you write, volunteer, consult, or build something new, if you’re working because you want to, not because you have to, the retirement police don’t get a say.

Would you like a few more profiles—maybe a mix of FIRE folks, traditional retirees, or even people who “unretired”?

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I said, “Sure.”

The response…

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Here are four more real-world examples of people who blend work and retirement in creative, flexible, and financially independent ways—further illustrating that modern retirement can include purposeful work without contradicting the idea of being retired.

Bill Bengen – Creator of the 4% Rule

You might expect the man who created the famous 4% safe withdrawal rule to quietly fade into retirement. But Bill Bengen has stayed actively engaged in the retirement research community—speaking at conferences, giving interviews, and even re-evaluating his own 4% guidance in recent years.

Despite technically being retired, he continues to contribute thought leadership because he enjoys it and feels a responsibility to share what he’s learned.

Tanja Hester – Author of Work Optional

Tanja Hester retired from her full-time public relations career in her late 30s after achieving financial independence. But she didn’t stop working—she began blogging, writing books, and speaking on financial literacy, inclusion, and ethics in the FIRE movement.

She considers herself retired because she has full autonomy over how and when she works, and she chooses only meaningful, mission-driven projects.

Wes Moss – Financial Advisor & Author

Wes Moss, known for his book You Can Retire Sooner Than You Think, is a retirement expert who often profiles clients who “retire happy”—and many of them still work in some capacity.

His interviews and surveys show that the happiest retirees often stay engaged with work, hobbies, or projects, especially if they involve helping others or using their skills in new ways.

Doug Nordman – Military Retiree & FIRE Blogger

Doug retired from the U.S. Navy at age 41 with a pension. He could have coasted, but instead he started a blog (The Military Guide), wrote a book, and continues to speak on financial independence and military retirement.

He earns some income but considers himself retired because his lifestyle is entirely funded by passive income and military benefits—any work he does is purely optional.

Pattern Across These Stories

Across all these examples—whether high-profile or everyday folks—the same themes appear:

• • They reached financial independence, which gave them the freedom to walk away from traditional work.
  • They chose to keep working in some capacity, but only on their terms.
  • Their work brings purpose, identity, and connection, not stress or necessity.
  • They openly reject the “retirement police” mentality and redefine retirement as a life of freedom and intention.

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Hahaha! Chat found Nords!

He’s one of the top mentors in the Millionaire Money Mentors (MMM) forums! I LOVE reading his sea stories, and he has unique and insightful views on money too. He’s a fan favorite!

Overall, you can see how these folks are even more comfortable with the notion of working in retirement.

Basically, what we’ve seen throughout this series is the more “institutionalized” or rooted in tradition/bureaucracy an organization or person is, the more likely they are to side with the Retirement Police.

And the more an individual or group is attuned to what’s currently going on in the culture, the more they are willing to accept working in retirement as a valid concept.

So if you’re rating these at home, here’s the listing of organizations and people who are most likely to be fine with working in retirement, listed from most open to least open:

• Financial bloggers and early retirees
• Money publications
• Retirement researchers and institutions
• Financial organizations like AARP
• Government entities (who can’t seem to agree on what they think)
• Dictionaries

Before we wrap up, let me share one more instance of an “expert” (actually a few of them) who totally agree that working in retirement is not only fine, but something that’s generally good.

While I was working on this post, I was also reading How to Retire by Christine Benz (which is an excellent book I’ll be covering sometime in the future). Here are a few times the book talks about working in retirement that either imply working in retirement is valid or say it outright:

• In the foreword, Jonathan Clements says (when discussing what to do in retirement): “Should I work longer or work part-time in retirement?”
• On page 9, retirement researcher Michael Finke says, “One idea that is ingrained in us socially is that we just step away from the workforce at a certain age. That’s what retirement means. In the future, I hope that we will increasingly see retirement as the ability to control one’s own schedule. It doesn’t necessarily mean that we stop working forever.”
• On page 28, blogger and retirement expert Fritz Gilbert says, “If you think you’re going to keep working when you retire…”
• On page 176, Vanguard’s Maria Bruno asks about a retiree and says, “Do you want to work part-time or volunteer?”
• On page 189, Jamie Hopkins says, “Retirement is very different for some people. You can choose to continue to work, you can take a different career, you can start a business, you can volunteer more of your time.”

Ok, I think we’ve beaten this dead horse long enough.

But I wanted to show a broad spectrum of organizations, media outlets, and prominent individuals who consider “working” and “retirement” go together and are not in conflict in any way.

To me, everything we’ve covered shows that the tide has turned and the majority (more than 50% of the people) are fine with some type of work in retirement.

I know some will disagree and hold onto their Retirement Police status forever, but once a few organizations flip (which they are close to doing), and especially when the dictionaries change their definitions, the Retirement Police won’t have much left to hold onto. Haha!

I’ll leave you with some wise words on this subject from my friend Doug Nordman, who said the following in the MMM forums:

“As ESIMoney wrote, if this definition was locked in discrete quantitative terms, then the Perpetual Internet Debates would have terminated decades ago and the Internet Retirement Police would have… retired.

Dictionary definitions and etymology: meh.

Language was never static and these days it’s evolving even faster with the Web. One end of the bell curve is anchored (for now) by the Oxford English Dictionary & Merriam-Webster, while the other end is anchored by the Urban Dictionary & subReddits.”

Well said!