The Top Seven Retirement Activities, Part 3

We’re continuing our series on the Top Seven Retirement Activities—the key habits and routines that make for a fun, meaningful, and well-rounded life after work.

• #1: Exercise and Staying Healthy
• #2: Building and Maintaining Strong Social Connections

If you missed either of those, be sure to go back and check them out—they lay the foundation for everything that follows.

Now, it’s time to dive into the third essential activity.

This one might come as a surprise to some. There’s a reason it ranks so high on the list, and I’ll walk you through exactly why it matters.

It’s a complex topic, so we’re going to spend two posts on this subject alone (since there are two distinct parts of it).

Here we go…

#3: Some Form of Work

Yes, work—in retirement.

Hahahaha. Someone’s head out there just exploded. Work? In retirement? Seriously?

Trust me for the next few minutes and I think you’ll see why this deserves a spot on the list.

Today’s Definition of Retirement 

Let’s start by clearing up a common myth: that “retirement” and “work” are mutually exclusive.

That may have been true under the old-school version of retirement—when stepping away from your job meant sitting on a porch swing for the last years of your life.

But times have changed. Today’s retirement looks a lot different than it did for your grandparents—or even your parents.

I had a discussion with ChatGPT about the evolving definition of retirement and here’s what it said:

The definition of retirement has evolved significantly over the past 50 years—from a static, one-size-fits-all phase of life into a far more flexible, personalized stage driven by lifestyle choices rather than just age or financial necessity.

Modern retirement is best described as:

A flexible, purpose-driven phase of life where individuals have the freedom to choose how they spend their time, often blending leisure, work (if desired), relationships, and personal growth—supported by financial independence rather than full-time employment.

Key traits of today’s retirement include:

• • Financial independence, not necessarily the end of work
  • Pursuit of meaning, purpose, and engagement
  • Customized structure—some people travel, others volunteer, start businesses, or work part-time
  • Health and lifestyle-focused—with an emphasis on physical fitness, mental well-being, and social connection
  • Nonlinear paths—retirees may cycle between work, leisure, and caregiving over time

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How Retirement Has Changed Over the Last 50 Years

Fifty years ago, the traditional view of retirement was much more rigid and uniform. Most people retired around age 65, stopped working altogether, and lived out their remaining years in a relatively passive way—watching TV, golfing, playing cards, and generally “slowing down.” Retirement was often viewed as a reward for decades of hard work—a chance to finally rest.

Back then, retirement was financially supported by defined-benefit pensions and Social Security. The system was more structured, and the employer often took the lead in providing financial stability. Retirees didn’t typically have to manage their own investments or plan for decades of post-retirement living.

In contrast, today’s retirees often view this life stage as an opportunity to stay active, learn, explore, and even earn. The decline of traditional pensions has placed more responsibility on individuals to fund their own retirement through 401(k)s, IRAs, and other personal savings vehicles. This shift has encouraged many to work longer or engage in some kind of income-generating activity—even after “retirement.”

People are also living longer and healthier lives. Life expectancy has increased significantly, so retirement may now span 25 to 30 years or more. That’s a long time to simply “rest,” which is why many retirees seek ways to stay mentally, physically, and socially engaged.

Additionally, the cultural view of aging and retirement has evolved. Retirement is no longer expected to be passive. Many retirees today pursue entrepreneurship, side hustles, travel, fitness, education, or part-time work. Some even describe retirement as their “second act” or a reinvention phase—a time to pursue long-delayed dreams or make a difference in their communities.

Technological advances have also changed the game. With the rise of remote work, online learning, and social platforms, retirees can stay connected, contribute, and remain mentally active like never before.

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Why This Shift Matters

This evolution in how we define retirement reflects deeper changes in how we view aging, purpose, and quality of life. People don’t want to merely exist after leaving the workforce—they want to thrive.

The phrase “retirement means freedom” is now more accurate than “retirement means rest.” It’s freedom to choose how you spend your time, whom you spend it with, and what you invest your energy into.

So whether you work part-time, volunteer, take up new hobbies, travel, or simply enjoy a slower pace of life, today’s retirement is about living intentionally—on your terms.

Summary

Retirement used to mean “the end of work.” Now it means “the freedom to choose.”

It’s no longer a destination—it’s a phase of life that can be as productive, active, and meaningful as any other.

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I couldn’t have said that better myself! Hahaha.

The part I like the best is the “freedom to choose.”

You have created your own time freedom in becoming financially independent. And you can do whatever in the world you like (within reason, of course.) So why not consider work? There are tons of benefits to it (as we’ll soon cover) and if you can set your own terms, you might just find it enjoyable! 

I’ve written several posts on this subject that dig deeper into it.

Here are a few for you to review if you’re interested:

1. The Retirement Police and the Definition of Retirement

This article addresses the debate over what it truly means to be “retired.” I emphasize that retirement is a personal concept, varying from person to person. For some, it means ceasing all work activities, while for others, it involves transitioning to work that is more fulfilling or less demanding. The key takeaway is that retirement should be defined by individual goals and desires, rather than societal expectations…and what others might try to force on you.

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2. Defining Retirement

In this piece, I detail different models of retirement beyond the traditional notion. It introduces concepts such as:

• Full Early Retirement: Achieving financial independence and choosing not to work for money again.
• Semiretirement: Working part-time or in a less stressful job, making work optional and on one’s own terms.
• Career Intermissions: Taking extended breaks from work, akin to self-funded sabbaticals, without jeopardizing long-term financial stability. 

The article encourages readers to consider these flexible approaches to retirement, tailoring the concept to fit their personal aspirations and circumstances.

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3. The Retirement Maze: How to Define Retirement and Problems Retirees Face

This article discusses the psychological and emotional challenges that can arise when one’s identity is closely tied to their career. It highlights the importance of preparing for the “life side” of retirement, ensuring that retirees have meaningful activities and connections to maintain a sense of purpose and fulfillment after leaving the workforce.

Finally, here’s a post that’s not mine but which supports a new definition of retirement which includes work:

GOBankingRates recently conducted a survey focused on our readers’ retirement plans. The results show that more than half (58%) of Americans plan to continue working in their retirement. With 66% of Americans worried they’ll run out of money, 50% concerned about unexpected health expenses and 47% preparing for social security to be cut or end completely, it makes sense that people want to keep the paychecks coming.

When over half of people don’t see a disconnect between “working” and “retirement”, I hate to break it to the Retirement Police but the definition of retirement has changed.

Not Just Plain Old “Work”

Now that we’ve spent some time talking about work, let me clarify why I say “some form of work”.

First, because you’ve likely retired from your career—the one you spent decades building—and probably aren’t looking to jump right back into the same grind. Retirement isn’t about replicating your old job. It’s about finding a new form of work—something that fits your lifestyle, interests, and priorities now.

Second, “some form of work” is a broad term on purpose. It can look very different for different people. Here are just a few examples:

• Same field, new setup: Maybe you stay in your old industry, but with fewer hours and less pressure. Consulting or being rehired part-time by your old firm are common options. In many cases, people return with all the stuff they liked—and none of the stuff they hated (bye-bye, office politics and managing teams).
• Part-time gigs for fun (and a little cash): Lots of retirees pick up light work just to get out of the house, stay active, and earn a few bucks. In The Villages, I saw it all the time—retirees working at golf shops, restaurants, and rec centers, just enjoying the interaction.
• Passion projects: You might take on work you love—even if it pays next to nothing. And that’s okay. When money isn’t the main driver, doing something meaningful becomes a powerful motivator.
• Side hustles: These run the gamut—from hobby income to full-blown businesses. Some retirees make a little extra on the side; others bring in serious cash. The point is, it’s on your terms.
• Volunteering: The ultimate form of “work without pay.” While it might not bring in money, the rewards—purpose, fulfillment, and community—are often far greater.

The bottom line: work doesn’t have to mean “job” anymore. In retirement, it can mean anything that gives you structure, purpose, challenge, or joy. The money? Often the least important part.

So when I say “work” in retirement, I mean all these things – potential work situations or volunteer opportunities that deliver work-like benefits.

In this first post, we’ll focus more on work and the general issues surrounding it.

In the next post, I’ll dive deeper into volunteering and why it may be the “work like” solution that works best for many.

Why Work is Good for You

Now let’s focus on why working in retirement is good for you.

Here are the major benefits from work/work-like activities:

• Gets you out of the house and doing things. Keep you active. 
• Can help with social connections and physical activity (both of which are massive positives we’ve already covered in this series).
• Challenges you mentally – helps you learn and grow.
• Gives you a purpose in life. It’s something you look forward to. Also is likely rewarding in some way.
• Makes some extra money. It’s not always needed but is always nice to have.

That’s my list having lived retirement, studied it, and talked to other retirees. But don’t just believe me. Check out what AARP says about working in retirement. They list eight good reasons to keep working after retirement (BTW, that statement alone shows that AARP doesn’t see “working” and “retirement” as opposed) as follows:

1. 1. A cushion for your savings
   2. Exercise for your brain
   3. Overall health
   4. A sense of community
   5. A sense of purpose
   6. A chance to give back
   7. Good times!
   8. Serving the greater good

You can read their thoughts on each one if you want, but I’m going to highlight a few.

Let’s start with what they say about work helping to “exercise your brain”:

The University of Michigan’s Health and Retirement Study (HRS), which has been tracking participants over age 50 for decades, “pretty strongly shows that continuing to work has benefits for cognition,” says Amanda Sonnega, associate research scientist at the University of Michigan’s Institute for Social Research. (This isn’t just because people with better cognitive health are better able to work, she says.) You can get a particular kind of benefit by switching to a different type of job or role: Learning new things—psychologists call it “novelty processing”—may help slow cognitive decline.

Keeping your mind sharp is one thing you will certainly want to do in retirement. A little work can help with that.

On to the next item…here’s what they say about work and overall health:

The transition to partial employment or volunteer work unrelated to your prior career also appears to be associated with fewer physical declines and better mental health, Sonnega says. A University of Maryland study of more than 12,000 retirees involved in the HRS research found that having a post-career job was associated with fewer major diseases and functional limitations.

We’ve already talked about the importance of good health in this series. In addition to what I suggested in that post, working provides yet another way to support strong health.

Next, here are their community comments:

The Harvard Study of Adult Development has been tracking generations of families since 1938, and one of its major findings has been how much retirement well-being depends on having good-quality relationships, says Robert J. Waldinger, professor of psychiatry at Harvard Medical School and the current director of the study. Participants who were happiest in retirement replaced their old work relationships with new relationships. Doing any regular work—whether full-time, part-time or as a volunteer—creates an environment for new interactions that can develop into those new relationships.

We covered this last time – social connections are vitally important to having a great retirement.

And finally, the purpose thoughts from AARP:

A job is one motivator to get up in the morning, and one of the major findings of the HRS research was the importance of finding a new sense of purpose after retirement. “That theme of meaning and purpose keeps popping up as a major driver of a healthy retirement,” says Nathan LeBrasseur, professor of physical medicine and rehabilitation at the Mayo Clinic. And continuing to work in some capacity is a great way to achieve that. Research shows that people with a sense of purpose feel younger in retirement.

Now your purpose doesn’t have to be work – it can be many things – but work can serve that purpose if you need it to.

And to round out this section on why work is good for you, ChatGPT offers the following:

Working in retirement—in some form—can be incredibly beneficial. It’s not about staying stuck in the old 9-to-5 grind. It’s about choosing work that fits your life, gives you purpose, and adds value (beyond just money). Here’s why it can be a great move:

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1. Provides Structure and Routine

After decades of having your days structured by work, full retirement can feel unmoored. Working—even part-time or on your own schedule—gives your days shape and purpose, which helps prevent boredom and restlessness.

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2. Supports Mental Health and Cognitive Function

Staying mentally engaged through work challenges your brain, keeps your mind sharp, and helps fight cognitive decline. Many studies link purposeful work to lower risks of depression, dementia, and anxiety in older adults.

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3. Promotes Social Interaction

Work often provides built-in social connections—whether with coworkers, customers, or clients. For retirees who feel isolated or disconnected, this can be a vital source of human interaction and belonging.

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4. Enhances Sense of Purpose and Identity

Many retirees struggle with a loss of identity after leaving a career. Continuing to work—especially in meaningful or passion-driven roles—can restore that sense of purpose, contribution, and relevance.

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5. Keeps You Physically Active

Certain jobs or volunteer roles naturally keep you moving. Physical activity, even in small amounts, contributes to better health, mobility, and longevity.

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6. Allows for Passion Projects

With financial pressure reduced, you can choose to work on what excites you: writing, teaching, consulting, creating art, mentoring, or building something from scratch. The joy of doing what you love—without worrying about the paycheck—can be deeply fulfilling.

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7. Generates Extra Income

Even if you don’t need the money, extra income can:

• • Reduce the drawdown on your retirement savings
  • Provide fun money for travel, hobbies, or gifts
  • Offer peace of mind as a buffer against unexpected expenses

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8. Opens Doors to Volunteering or Service

Work doesn’t have to be paid. Many retirees “work” by volunteering—and research shows that volunteering boosts happiness, reduces stress, and increases life satisfaction, especially when done regularly.

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9. Encourages Lifelong Learning

Whether you’re picking up new skills, staying current in your field, or switching industries entirely, working in retirement often pushes you to learn and grow—keeping life fresh and interesting.

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10. Gives You Control

Perhaps most importantly, modern retirement work is often on your terms. You can choose:

• • How much to work
  • When to work
  • Where to work
  • Who to work with

This autonomy makes work feel like a choice—not an obligation.

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Summary:

Working in retirement is no longer a contradiction—it’s a smart, flexible lifestyle choice. Whether you do it for the challenge, the community, the extra income, or the fun, it can help you stay sharp, engaged, and happy in this next phase of life.

Retirement Work Ideas

So, what sort of work am I talking about specifically?

You’ll need to decide what works best for you. But here are a few to get the ideas flowing for you courtesy of  ChatGPT:

1. Use Your Professional Skills

Leverage your experience from your primary career in a more flexible or low-stress role.

• • Consulting – Advise former clients or new businesses in your area of expertise.
  • Freelancing – Offer services like writing, editing, design, coding, or bookkeeping.
  • Teaching or training – Adjunct teaching at colleges, teaching adult education, or corporate training.
  • Board service – Join advisory boards for nonprofits or startups.

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2. Pursue a Passion Project

Do work that aligns with your hobbies or long-held interests, even if the pay is modest.

• • Photography or art – Sell your work at craft fairs or online.
  • Crafting or woodworking – Start an Etsy shop or sell locally.
  • Cooking or baking – Teach classes, cater events, or run a food stall at markets.
  • Writing – Blog, write books, or self-publish your memoirs.

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3. Start a Side Hustle or Small Business

Low-risk entrepreneurship has never been more accessible.

• • E-commerce – Sell products on eBay, Amazon, or Etsy.
  • Property rental – Manage a vacation rental or rent out a room on Airbnb.
  • Pet services – Offer pet sitting, dog walking, or pet transportation.
  • Tutoring – Help students (online or in-person) with academics or test prep.
  • Reselling – Flip garage sale or thrift store finds for profit.

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4. Get a Part-Time or Seasonal Job

Choose work with low commitment but regular engagement.

• • Retail – Work at local shops, bookstores, or garden centers.
  • Hospitality – Serve in cafes, golf clubs, or event venues.
  • Tourism – Work at museums, attractions, or as a local tour guide.
  • Tax preparation – Seasonal work with companies like H&R Block.
  • Delivery or driving – Work for Amazon, Uber, or a local service.

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5. Support a Cause You Believe In

Combine purpose with productivity.

• • Nonprofit work – Manage donor relations, write grants, or assist with operations.
  • Faith-based work – Serve in ministry support, administration, or community outreach.
  • Community development – Help with planning, mentoring, or neighborhood services.

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6. Go Virtual or Remote

Ideal for flexibility and working from home.

• • Remote customer service – Answer calls or chat for companies needing part-time help.
  • Virtual assistant – Support small businesses or entrepreneurs with scheduling, email, etc.
  • Online surveys or user testing – Quick, low-effort tasks that pay small amounts.
  • Sell digital products – Create and sell templates, planners, printables, or online courses.

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7. Help Others Succeed

Use your life wisdom and experience to make a difference.

• • Mentorship – Offer guidance through SCORE, youth programs, or career coaching.
  • Life coaching – Help others navigate retirement, career transitions, or personal goals.
  • Language teaching – Teach English (or another language) online to students abroad.

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Ok, so there are some not-so-great ideas in there (at least for me), but there are also some real winners.

No matter your background or interests, there is something in there for you — either directly or the seed of an idea that you can expand upon to create the work situation that works for you.

My Work in Retirement 

I actually fell into working in retirement. I didn’t plan on doing much of anything work-related when I quit my career, but one thing simply led to another and I ended up working (on my own terms).

It’s been one of the highlights of my retirement and has provided so many benefits that its impact can’t be overstated.

Most of my work in retirement has been because I have an interest in personal finances. Because of this, I began focusing on what I could do with it. This ended up providing me several opportunities:

• Starting ESI Money. I actually began writing it a bit before I retired and it took off. Once I retired I added fuel to that fire by posting more frequently. This effort made the site grow even faster.
• Buying, running, then selling Rockstar Finance. I bought Rockstar because I thought I could make money on the site as well as grow its influence and offerings. I did both, but it started to feel too much like a regular job, which is something I certainly didn’t want, so I sold it.
• Starting and running the Millionaire Money Mentors. People had been encouraging me for years to do something involving millionaires and this seemed like the right thing. It has been tremendously rewarding and I have met some amazing friends through it.

I also had considered other financial products like ebooks, courses, and starting a YouTube channel, but I just never got around to any of those.

Will I ever? Who knows. Financial independence is a blessing and a curse in some ways. I have all the time in the world to do the above but no real need (don’t need the money). Hahaha.

I actually might start allocating less time for work and more for volunteering. You’ll learn more about what I’m thinking along those lines in the next post.

For now, hopefully I’ve convinced you to at least consider working in retirement.

If I haven’t, made I’ll get you into volunteering when I cover that next. lol.

Additional ESI Money posts to read for more on this subject include:

• What Retirees Want: Working in Retirement – Explores why many retirees choose to work after leaving their careers—highlighting purpose, enjoyment, and flexibility over financial need.
• The Retirement Maze: Health, Wealth, Social Activities, and Working in Retirement – Discusses how working in retirement contributes to mental sharpness, structure, and ongoing social engagement.
• What Retirees Want: Retirement Fun and Working in Retirement – Shows how retirees blend fun with meaningful work—whether through part-time jobs, hobbies that pay, or passion projects.
• The New Retirementality: More on What to Do in Retirement Plus Thoughts on Working – Offers a modern take on retirement by emphasizing work as a valuable part of a purposeful, engaging post-career life.