Grappling with the Retirement Police

It’s been over six years since I wrote The Retirement Police and the Definition of Retirement.

Even then the definition of retirement had transitioned to the point where more people than not were comfortable with “working in retirement” and didn’t see “work” and “retirement” as mutually exclusive.

So I figured that by now pretty much everyone in the world would have made the shift. Well, I was wrong.

In the Millionaire Money Mentors (MMM) forums there are a couple lifelong members of the Retirement Police and recently (or should I say “once again”) we had yet another discussion on the topic.

I got comments like this:

“Unless you have a passive source for it, like a defined benefit pension or an oil lease or other source that pays you while you sleep, income ≠ retirement.”

If there are folks among the highly educated MMMers who still think of retirement in this way, there have to be others out there. I’m writing this post for them (and the rest of us too).

Definition of Retirement Police

Let’s start with the definition of Retirement Police so we’re all on the same page.

I asked ChatGPT to give me a definition (to get one from an unbiased source) and received this:

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The term “retirement police” is an informal, often tongue-in-cheek phrase used to describe people who rigidly enforce outdated or narrow views of what retirement “should” look like—usually implying that retirees should completely stop working, disengage from career pursuits, or avoid income-generating activities.

What It Means

“Retirement police” refers to people who say things like:

• • “I thought you were retired! Why are you still working?”
  • “You can’t be retired if you’re still earning money.”
  • “You’re not doing retirement right.”

It also can refer to those who question or criticize retirees who:

• • Work part-time, consult, or freelance
  • Start businesses or side hustles
  • Continue creating, volunteering, or staying active in professional circles

What’s Behind the Phrase

• • Cultural Expectations: Many still equate retirement with total leisure, golf, and no work.
  • Jealousy or Projection: Sometimes it stems from personal frustration (“I wish I could retire, so you shouldn’t be working if you already did.”)
  • Lack of Awareness: They may not understand modern retirement, financial independence, or lifestyle choice.

How It’s Used — Retirees or financial independence bloggers (especially in the FIRE community) often say:

• • “Ignore the retirement police.”
  • “The retirement police will hate this, but I still work a few hours a week—and love it.”
  • “If I’m financially independent, I get to define my retirement—retirement police be damned.”

Why It Matters

• • The phrase pushes back against rigid definitions and defends individual freedom in designing one’s retirement.
  • It underscores the idea that retirement is personal, not prescriptive.
  • It supports the evolving view that retirement can include meaningful work, passion projects, or any activity the retiree finds fulfilling.

Why “Retirement Police” Are Criticized

• • They rely on outdated or overly strict definitions—ignoring the evolving reality of modern retirement.
  • They often fail to account for the psychological, emotional, and practical benefits of purposeful work in retirement.
  • The backlash underlines a broader shift in retirement thinking—from rigid labels to individual freedom.

Summary

The “retirement police” are critics—especially online—who insist you can’t call yourself retired if you earn any income. This view is increasingly at odds with modern definitions of retirement, which focus more on financial independence, autonomy, and fulfilling work, rather than a strict lack of earnings.

Many in the FIRE and broader retirement community now reject those rigid rules and emphasize personal definitions instead.

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Haha! Leave it to ChatGPT to give a college seminar where only a definition asked for! lol

But the above does explain many of the thoughts and issues around the topic…much of which we’ll cover in more detail. For now, let’s move on.

Many Versions of the Retirement Police

My recent conversations are reflective of what’s described by ChatGPT…if you have one penny of earned income, you can’t possibly be “retired” — because income means work and retired means NO work!

Some Retirement Police will waver a bit and say you can earn a small amount, but it can’t be material. But that’s a slippery slope. What’s material? $1,000 a year? $5,000? $10,000? There’s no way to defend that position.

Besides, the mainline denomination of Retirement Police stick to no earned income at all. You can have income, of course, but it just can’t be from an active effort. So interest and dividends are ok as are Social Security payments.

Real estate is somewhat of a gray area. It is an investment (which is ok) but it is also not passive (which is not ok). Again, there are ones who say one thing and ones who say another.

The whole topic is crazy anyway but if we get into this branch versus that branch it gets much crazier. So I’m going to focus on the main point of view among the Retirement Police faithful: any earned income means a person is not retired.

Don’t tell this to the guy who gets a gift card for Christmas for mowing his neighbor’s yard (like my neighbor did in Colorado). It will shock him to learn he’s not retired! lol

Playing Devil’s Advocate

Before we proceed, let me take the Retirement Police’s side and ask, “Ok, if someone can work and be retired, what’s to keep a person from staying in their current job and saying they are retired? That’s crazy, isn’t it?”

It is crazy, IMO.

But let’s let Chat detail why…

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That’s a fair and common reaction—and it hits at the heart of the evolving definition of retirement. Let’s unpack the logic behind it, because while it can sound crazy on the surface, there are some important distinctions.

The Core Issue: Work by Choice vs. Work by Necessity

If someone stays in the exact same job, at the same hours, under the same demands, and just calls themselves “retired,” that does seem absurd. What’s really changed? Probably nothing.

But modern retirement isn’t about the presence or absence of any work—it’s about control.

The key question isn’t “Are you working?” — it’s “Do you have to work?”

If someone stays in a high-stress job they don’t need for income, but continues because they enjoy it, that’s arguably a version of retirement. Not the traditional kind—but one defined by financial independence and freedom of choice.

A Useful Analogy: Retired but Active

Think about retired generals who go on to write books, teach at universities, or serve as consultants. Are they “un-retired”? Not really. Their primary career is over, and they’re no longer financially dependent on a paycheck. They just choose to stay active.

Likewise, a “retired” person might:

• • Step away from their full-time job, but consult in the same field
  • Scale back to part-time hours with full control over when and how they work
  • Shift into an entirely different line of work that’s meaningful or fun

So while staying in the same job and calling it retirement without any change in lifestyle seems disingenuous, staying in the same field or workplace under vastly different terms (e.g., reduced hours, flexible schedule, no financial pressure) is a different story.

Financial Independence Redefines Retirement

In the FIRE (Financial Independence, Retire Early) movement and modern financial planning circles, retirement isn’t the absence of work—it’s the absence of obligation.

This means:

• • You can quit at any time
  • You no longer need to earn money to survive
  • You’re working (if at all) because it brings value to you, not because someone else demands it

So if someone continues their current job but does so without needing the income, and could walk away any time, you could argue they’re functionally retired—even if the optics say otherwise.

But Let’s Be Real…

If someone continues in a full-time, demanding job they don’t enjoy, never changes their workload, and only calls themselves “retired” because they could quit… that’s probably more a mindset shift than an actual lifestyle shift. Technically, sure—they’re financially independent. But calling that “retirement” stretches the word to its limits.

That’s where the retirement police often jump in—and in this case, they might have a point.

Bottom Line

• • If nothing has changed about your work, it’s probably not retirement—just optional employment.
  • If everything has changed—your schedule, mindset, motivation, and financial need—then even if you’re earning money, it may still feel like retirement.
  • Retirement today is less about quitting work and more about reclaiming time, autonomy, and purpose.

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I agree with this.

That’s why when the Retirement Police ask me how I’m retired if I still have earned income (from websites), I sometimes say, “I’m retired from my career.”

I spent 34 years working on my career — six in college/grad school and 28 years working. It was a multi-million dollar asset and still worth a million or two (several million if you count investment returns) when I stepped away from it. I was, after all, in my prime earning years.

I retired from that career doing that type of work for those hours (50+ a week) under someone else’s control.

And when I retired, I actually had nothing but my savings. ESI Money had just started and wasn’t earning much (if anything), Rockstar Finance was in the future, and the Millionaire Money Mentors wasn’t even a thought. I had almost no income (the site was maybe earning a few hundred bucks a year.)

Oh wait! I did have my original financial blog that earned $100 or so a year? Does that count as earned income? I wasn’t actively posting on it but I did have to pay the hosting costs and maybe do a task or two now and then to keep it running. Does that count as work? (See how crazy this gets?)

Anyway, once I no longer had my job, a strange thing happened: I had a ton of free time! lol

I walked a lot, worked out, found pickleball, played a ton of video games, read many books, traveled some, spent significant amounts of time with my family, and I’m sure did a few other things I enjoyed that I can’t remember.

But then a funny thing happened…I wanted more. I wanted an intellectual challenge/pursuit. So I amped up my writing about money at ESI Money — doing something I had enjoyed for over a decade by that time.

And the site took off, completely by accident (other than I did the basics of what it takes to start a good blog). And then the site kept growing. Since I had a lot to say, I kept writing more, which made it grow even more! Hahaha.

The other businesses came in time bit by bit, but there was certainly no plan to create a small business to support my lifestyle — I didn’t need it. And I certainly had no intention of going back to my career (despite offers to do so). I was retired from that.

So there is something about retiring from your career which involves leaving a long-term, full-time employment commitment to be fully retired. But that’s not what the Retirement Police focus on anyway. They focus on a guy who was a CFO who left that and now has his own YouTube channel on training for marathons, which earns $1,000 a year. He’s not retired (they shout)! Give me a break!

Deep Dive into Retirement Work

To cover the subject of working in retirement (hopefully once and for all), I wanted to dive deep into the issue. That’s why I started a conversation with ChatGPT…who is (in theory) neutral on the subject…to see what it had to say.

ChatGPT is generally pretty agreeable, so to be more than fair to the Retirement Police I tried to get Chat to agree with me while making it think I was a member of the Retirement Police. I began with this question:

Tell me about earning income through work while in retirement. Doesn’t retirement mean not working?

It came back with this…

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Great question — and one that’s often misunderstood. Here’s a clear explanation of what it means to earn income through work in retirement, and why it’s not a contradiction.

Doesn’t Retirement Mean Not Working?

Traditionally, retirement meant you stopped working entirely, usually around age 65, and lived off a pension, Social Security, or savings. But that definition is outdated for many modern retirees.

Today, retirement is more about freedom of choice than never working again.

• • You’re financially independent (or mostly so).
  • You choose how to spend your time — and many people choose to work, but on their own terms.

Why Retirees Choose to Work

Many retirees return to or continue working for reasons such as:

• • Supplemental Income: To reduce the drawdown from retirement savings.
  • Purpose and Fulfillment: Work can provide structure, identity, and social interaction.
  • Lifestyle Upgrades: Extra income can pay for travel, hobbies, or gifts to family.
  • Mental Engagement: Staying sharp and active is easier when you’re solving problems or helping others.
  • Health Insurance: Some work part-time jobs that provide coverage before Medicare eligibility.

Ways Retirees Earn Income Through Work

Here are common, flexible income options for retirees:

1. Part-Time Jobs

• • Retail, hospitality, tutoring, or office work
  • Low commitment, social interaction, and some benefits

2. Consulting or Freelancing

• • Leverage your career expertise on a flexible schedule
  • Often higher pay with full control over your workload

3. Self-Employment or Small Business

• • Start a side hustle (e.g. Etsy, eBay, coaching)
  • Turn hobbies into income: woodworking, baking, pet sitting

4. Seasonal Work

• • Tax prep, tourism, parks, or holiday retail
  • Perfect for those who want work only part of the year

5. Online Work

• • Blogging, YouTube, surveys, virtual assistant roles
  • Fully remote and flexible — great for travel-friendly retirees

Examples of Working Retirees

• • A retired engineer consults 10 hours/week for $100/hour.
  • A former teacher tutors students online from home.
  • A retiree with a passion for photography sells prints on Etsy.
  • A couple works part-time at a national park in exchange for RV site rental and income.
  • A retiree joins a local golf course as a ranger, enjoying the outdoors while getting paid.

Conclusion: Retirement Is What You Make It

You’re retired if you don’t have to work for money — even if you choose to work because you enjoy it or want extra cash. In fact, earning income in retirement can be part of a smart financial plan and a fulfilling lifestyle.

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Some thoughts on all this:

• “That definition is outdated for many modern retirees.” My point precisely! I don’t want to get into the history and process of how the English language evolves over time, but we all know it changes tremendously. Consider what “cloud”, “spam”, “troll”, “woke”, “gay”, and many other words meant 40 years ago and what they mean (or can mean) these days.
• “You choose how to spend your time — and many people choose to work, but on their own terms.” This is part of it —you have the freedom to do what you want and one thing you want to do is work (for one or many reasons). I could quit working tomorrow but my life would be worse off, not better. So why would I? And yet I am retired.
• “To reduce the drawdown from retirement savings.” This is a big one. Even for a person not planning to work in retirement, some work in the early years can dampen or eliminate sequence of returns risk. For me, working allowed my investments to keep compounding and now I have 2x+ higher net worth than I did when I retired despite high spending and giving levels. If a person is working to reduce their drawdown, are they retired? I think it goes back to whether they must work (not retired) or not (are retired).
• “Work can provide structure, identity, and social interaction,” and “Staying sharp and active is easier when you’re solving problems or helping others.” These are some of the benefits of working in retirement that I pointed out in The Top Seven Retirement Activities, Part 3 (FYI, I also covered the Retirement Police in that post.)
• “Earning income in retirement can be part of a smart financial plan and a fulfilling lifestyle.” Stated above already but I just wanted to call attention to it one more time — so everyone gets the point. lol

What about Semi-Retirement?

After the comments above from Chat, I wondered whether we were describing retirement or semi-retirement — and what the difference was anyway!

So I asked…

What is semi-retirement?

This is what I got…

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Semi-retirement is a modern approach to retirement where a person reduces their workload or professional commitments without fully withdrawing from the workforce. Instead of quitting work entirely, semi-retirees shift to a more flexible, less demanding, or more fulfilling form of work—often part-time, freelance, seasonal, or self-directed.

Key Features of Semi-Retirement

• • Reduced Hours: Working fewer hours than a standard full-time job (e.g. 10–25 hours/week)
  • Optional Work: Work is often by choice, not necessity
  • Flexible Schedule: Semi-retirees may control when, where, and how much they work
  • Supplemental Income: Earnings may support lifestyle, reduce withdrawals from retirement savings, or fund specific goals (like travel)
  • Phased Exit: Often used as a transition into full retirement, rather than an abrupt stop

Why People Choose Semi-Retirement

• • Stay Mentally and Socially Engaged
  • Maintain a Sense of Purpose or Identity
  • Reduce Stress Without Stopping Work Entirely
  • Gradually Adjust to Retirement Lifestyle
  • Stretch Retirement Savings

Examples of Semi-Retirement

• • A former executive now works two days a week as a consultant.
  • A teacher retires from the classroom but tutors students privately.
  • A retiree opens an Etsy shop to sell handmade crafts.
  • A nurse leaves full-time work but picks up occasional shifts at a local clinic.
  • A business owner sells the company but stays on in an advisory role.

Summary

Semi-retirement allows people to enjoy the benefits of retirement—like more free time and lower stress—while still maintaining the mental stimulation, social connection, and income that work provides. It’s a highly flexible model that aligns with how many people view modern retirement: not the end of work, but the beginning of freedom and choice.

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Ok, now I was really confused because Chat seemed to be talking about semi-retirement in the same way it was talking about retirement.

So what’s the difference anyway?

I called Chat on its mixed messages and asked…

You just described semi-retirement by citing an example of a former executive who now works two days a week as a consultant. But you also used the consultant example to show someone who is retired and keeps working. So is this person semi-retired or retired?

Chat’s response…

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You’re absolutely right to notice that the same example—a former executive working two days a week as a consultant—could describe either a semi-retired person or someone who is fully retired but still doing some work. So which is it?

The answer depends on the person’s financial situation, motivation, and mindset. In other words, it’s not what the person is doing that defines whether they’re semi-retired or retired—it’s why they’re doing it and how they view it.

Here’s the distinction:

A semi-retired person has intentionally scaled back from full-time work but hasn’t fully exited the workforce. They may still rely on some income from work to support their lifestyle or stretch their savings. Semi-retirement is often used as a transitional phase—a way to ease into full retirement over time. These people usually still think of themselves as being “in the workforce,” just in a reduced capacity.

A retired person who still works, on the other hand, has usually reached financial independence and has already stepped away from their primary career. Any work they do now—whether consulting, part-time, or project-based—is done by choice, not necessity. They could walk away from it at any time and still be financially fine. In this case, the person typically identifies as fully retired, even though they might earn occasional income.

So, going back to the example: If the former executive is consulting two days a week because they need the money, they’re probably semi-retired.

If they’re doing it purely for enjoyment, stimulation, or personal fulfillment—and could stop at any time without financial consequence—they’re more accurately retired (but still working).

That’s the nuance.

Key takeaway:

Semi-retirement is usually a step toward full retirement, where a person still depends partially on work.

Working in retirement, by contrast, means a person is already financially independent and working purely because they want to—not because they have to.

It’s the same activity on the surface—but the context behind it makes all the difference.

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Ok, so if you’re working because you have to, you’re not retired (though you might be semi-retired), you’re just working in a different way.

If you’re working because you want to (though you don’t need to because you are financially independent), then you are retired.

I can live with that distinction. It also matches what we discussed above.

That said, if you don’t need to work and yet you still keep your same exact job with the same exact hours, pay, etc., are you retired? I would say no because you’re still in your career. So yet again, saying you are “retired from your career” has meaning in the discussion.

At this point we’ve barely gotten started, and we already have a long post.

We’ve got a lot of territory to cover! To read more, check out part 2 here.