10 Things People Love About Working (That They Want to Keep in Retirement)

In 2026 I hit a milestone that seemed like a distant, foggy dream back in my corporate days: the ten-year anniversary of my retirement.

If you want to go to the beginning and get the details on that blessed event, check out I Retired! There are some fond memories for me in that post!

Anyway, my plan to celebrate this momentous occasion is to write several “10 Things” posts about retirement.

So far, here are the posts in this series:

• 10 Things I Love About Retirement: Reflections After a Decade of Freedom
• 10 Things People Hate about Working (That Retirement Fixes)

Work Isn’t that Bad

If you read the last post in this series, you know I’m not shy about calling out the soul-crushing parts of the corporate grind. I’ve spent a decade enjoying the death of the alarm clock, the absence of office politics, and the end of the Sunday Scaries. But as I approach my 10th anniversary of retirement, I have to be honest: if work were all bad, nobody would ever struggle to leave it. (And many wouldn’t want/need to do it in retirement.)

I often see a recurring pattern in the Millionaire Interviews. Even those who have hit their number and have the ESI pillars firmly in place often hesitate to pull the retirement trigger. When I ask them why, they don’t talk about the meetings, the spreadsheets, or the HR manuals. They talk about the things they actually love about their jobs — the hidden benefits that come with many careers. That said, I suspect the issue is more money-related than anything (see below for that discussion).

Retirement shouldn’t be about deleting your old life; it should be about curating your new life. It’s a process of value extraction — keeping the 10% of work that makes you feel alive (or 25% or 50%, you pick the percentage that works for you) while discarding the 90% that drains you. The goal of the ESI framework isn’t just to accumulate enough money to stop working; it’s to accumulate enough freedom to work only on what you love.

In fact, work or work-like activities help to satisfy many/all of the five categories I’ve deemed need to be covered to have a great retirement (the right job can address all five of these):

• Health and Fitness – Keeping your body in good shape so you can enjoy life longer.
• Fun – Activities that are purely for enjoyment and relaxation.
• Work or Work-Like Activities – Either actual work or structured tasks that feel productive.
• Social Interaction – Regular connection with friends, family, or community.
• Mental Stimulation – Keeping your brain sharp and engaged.

So the goal in retirement isn’t to burn the ships and never do anything that brings the same benefits as work, but rather to design a life, with or without work, that meets your particular needs and gives you a great life.

After ten years of freedom and 470+ millionaire interviews, I’ve identified the 10 things (listed in no particular order) people truly love about working, and more importantly, how I’ve managed to keep the ones important to me in my life without the 9-to-5 baggage.

I might even throw in a few bonus items just to make sure everything is covered. 😉

Let’s get started…

1. Keeping Mentally Sharp

Let’s face it, we can have all the money in the world, but if our health fails and our mind goes, it’s all worthless.

We’ve talked about the importance of exercise in a previous post from this series (not to mention many other posts through the years), so for this point I’m going to focus on keeping our minds sharp.

There’s lots of debate and speculation about what actually keeps minds sharp, but ongoing mental stimulation and continual learning appear on most lists. And of course both of these are side benefits of a challenging job/career.

People love the sharpness that comes with a career, and for good reason: your brain is a use it or lose it organ. Work challenges the brain, which helps keep memory sharp and delays cognitive decline.

So when we talk about moving from a work situation where we are challenged mentally and regularly learning to a new environment where those things aren’t part of the default setting, it’s worthy of thought and consideration.

In the working world, you are forced into mental engagement. You are analyzing spreadsheets, managing personalities, and learning new software. This isn’t just work — it’s a high-intensity workout for your gray matter. When you retire, that forced stimulation vanishes. If you don’t replace it with something just as challenging, you risk your mental faculties.

So what can retirees do to replace the mental sharpness that comes from working? Fortunately, there are many options including:

• Working in retirement. You know I’m a big fan of working in retirement and have named it one of the seven activities of happy retirees. If you can find a post-retirement occupation that you enjoy and doesn’t carry most/all of the baggage many jobs do, you will have found a gem. And you might hit the jackpot and cover the majority of the five categories above in one job. Studies from the Harvard Medical School and the Global Council on Brain Health suggest that continued work — even in a part-time or volunteer capacity — can significantly reduce the risk of conditions like dementia and clinical depression. The cognitive reserve you build through routine problem-solving acts as a buffer against the natural effects of aging.
• Volunteering. See the above Harvard study — volunteering can have the same benefits as working. In fact, if you find the right position, the only difference between volunteering and working is the pay. All the other benefits you get from working, you can get from volunteering. And you get many other side benefits — like helping people directly and knowing you are working to make the world a better place.
• Learn new skills. Now’s the time to get out your wish list. Have you ever wanted to learn Spanish, begin playing the piano, or start a detailed hobby like woodworking? If so, you’re in luck! You now have the time to do those things…AND they will help your mind stay sharp. It’s a win/win!
• Challenge your mind with fun. Try puzzles, read books, and/or play games that require strategy.

Add to these other suggestions we’ve made to help your mind stay sharp including exercise, having good social connections, and eating and sleeping well and you should be in good shape throughout your retirement.

I’ve made this a particular focus in retirement and here are some of the things I do to specifically keep my mind healthy (not including the exercise, eating well, sleeping well, and social connections that are also a part of my life):

• Run ESI Money and Millionaire Money Mentors. I post here twice a week, post there multiple times a day, and run both of them as side hobbies/businesses. Hopefully what I say somewhat makes sense, so I have to think at least a bit to get that accomplished.
• Play several challenging games. Every day these include all the NY Times games (I do all but Pips with my wife, she doesn’t like Pips so I do it alone), two chess puzzles and a speed chess game, Sudoku on Apple Games, and several of the LinkedIn games. These are fun as well as challenging.
• Reading. I read many articles a day online as well as a book now and then.
• Video games. Yes, believe it or not, they can actually help your brain…especially the kind I play where strategy and planning are a major part of the equation.
• Volunteering. I haven’t started this yet but am considering a volunteer position on a town citizen committee.

These seem like more than enough to me…what do you think? And what do you do to keep your mind healthy?

In retirement, your brain shouldn’t be at rest. It should be at play. I’ve realized that the mental sweat of a challenging project is just as rewarding at 60 as it was at 30 — the only difference is that now, I’m the one who decides what problems are worth solving.

2. A Ready-Made Social Circle

The office provides a consistent, low-effort, built-in social network. Work provides a tribe without having to go find one. You show up, and people are there. People love the casual conversations, water cooler talk, inside jokes, shared challenges, and the feeling of being part of a team. For many, their coworkers are their primary community.

The data on social connections is striking. According to the Harvard Study of Adult Development (the longest study on happiness in history), the quality of our relationships is the #1 predictor of health and happiness as we age. Losing that social hub is the biggest fear of some prospective retirees.

Retirement can be isolating, especially for those who are single or whose friends are still working. And even if you aren’t single, it’s highly likely that you’ll see a drop in at least the number of social interactions you have when you retire.

The good news is that having a great social life is not about numbers…at least up to a point. It’s more about having a handful of very close connections. From there you need to scatter some others into the mix, but it’s the close connections that provide the major benefit.

I detailed this in The Top Seven Retirement Activities, Part 2. After sharing lots of data, I made these conclusions:

• You need social connections to have a great retirement. Yes, even if you’re an introvert.
• The research points to needing at least four close connections. Four seems to be the magic number for well-being.
• Good news: Your family counts! You can hit your quota with just your immediate circle.
• Bad news: You still need other social connections beyond your core circle. These don’t have to be deep relationships—casual friendships and acquaintances help too.
• More is better. While there’s no clear research on the “ideal” number beyond your core group, being socially active in general makes a big difference.
• Being disconnected leads to an unhappy retirement. The evidence here is overwhelming—social isolation is a major retirement risk factor.
• The upside: Making connections is easier than you think, and you can do it while pursuing other fun or meaningful activities.

So you need to be intentional in this area to be sure you’re making enough social connections. In the post linked above I give several suggestions for how/where you can do this. Here’s what I’ve done (also from that post):

• Closest relationships: My wife, daughter and son-in-law, son, and dad. I talk to or see all of them regularly—some daily. They’re the heart of my social life.
• Next tier: Extended family (cousins, aunts, uncles) and long-time friends—like a few college buddies I’ve kept in touch with.
• Middle layer: Friends from various circles—former coworkers, neighbors, and yes, online friends from the MMM forums. Some of these have even become in-person friends, especially when we lived in The Villages.
• Acquaintances: Friendly faces I recognize around town—at the gym, church, restaurants, on walks, or during community events.

And if pets count, my cat, Zeus, would add another to the list of the closest relationships. lol

Of course you could continue working in retirement as well…then you get an entire social group thrown in for free.

3. Professional Identity and Status

I’m going to have to write about this one as a total outsider — it is not an issue in any way for me.

That said, I know many who struggle with losing their identity (and the sense of status and significance that comes with it) when they retire.

That’s because our work is vitally important for much of our lives. We live in a society that asks, “What do you do?” before it asks “Who are you?” People love the status that comes with being a “Partner,” a “Director,” or a “Specialist.” That identity provides a sense of place in the social hierarchy and a shorthand for success.

Just think how these hit: “I’m a doctor.” “I’m an engineer.” “I run a company.” “I’m a professor.” “I’m a pastor.”

Titles give clarity and status. Plus there is a profound ego boost in being the person people come to for answers. When you’ve spent 20, 30, or more years mastering a craft, you enjoy being the expert. You love the respect and the sense of importance that comes with a high-level title or a specialized skill set. It feels good to be the go-to person in the room.

Retirement is often seen as a loss of status. You go from “Someone” to “Someone’s Grandpa.” You feel like you’ve lost your rank in the world.

It can also can feel like a demotion to anonymity. Yesterday you were a Senior VP; today you’re just the guy in the grocery store in his gym shorts. (Hahahaha…this was literally me.)

As I said, I get that this is a big issue for many but unfortunately I can’t relate. You see, my job was something I did to create wealth and provision for our family, it was not who I was. As a result, when I lost it, I didn’t lose my identity or sense of significance. I’m as significant now as I was then — at least in my mind. And that’s all that matters to me.

I’m no longer defined by a corporate title; I’m defined by my work at ESI Money, my commitment to my family, and my role in my community. Your status in retirement shouldn’t come from a business card; it should come from the character you’ve built and the value you continue to add to the world. A self-made identity is much more durable than a company-given one anyway. I’d much rather be “The ESI Guy” than “The Executive VP” any day of the week.

But if you’re someone whose personality is wrapped up tightly with your job, you need to think long and hard how to replace that in retirement. Or better yet, make the shift from where you are (career as your identity) to where you want to be (character as your identity) without causing yourself issues.

Continuing to work is an option to help in this area, of course, but volunteering is just as good or better (if you can’t make the shift). You could also start a meaningful side project that also gives you a sense of identity. A few in the Millionaire Money Mentors forums have done this.

But the best option IMO is to throw off that old identity and create a new one as someone who lives their life on their terms. I personally think that’s the best identity you can ever have.

4. The Structure of a Productive Day

Here’s another one where I’m a bit in the dark, but apparently this is a major issue from what I’ve seen and heard.

Humans are, by nature, ritualistic creatures. We love structure, even when we claim to hate it. The 9-to-5 provides a framework for the day. You know when to wake up, when to eat, and when to relax.

Work answers the question, “What am I doing today?” It often dictates a wake up time, what deadlines you need to meet, when meetings are held, and so on.  It provides built-in goals and measurable progress. Work often provides a clear weekly rhythm and reduces decision fatigue (because many of life’s decisions are already made for you).

The structure of work is often what keeps people grounded. Many millionaires in my interviews say they miss the routine as much as the job itself. They miss the gears of the day turning in a predictable way.

Without it, many retirees drift into a state of lethargy that leads to a loss of purpose.

I don’t really get it. Why would I want someone else making decisions for me about what I do and when? And am I really so uninterested in life and so weak at setting and completing plans that if work goes away there’s nothing else that can replace it? Sheesh.

But I guess the point is that we all need/like at least a little structure in our day, so in retirement you’re going to have to address this by creating the amount of routine and structure you want in your life.

I don’t have a boss in retirement, but I have a schedule. It’s not set in stone (you can easily go too far the other way and over-schedule yourself), but it’s roughly this:

• Up by 6:15 am
• Feed the cat, drink a glass of water, and have a cup of coffee
• Sit in my recliner, listen to light music, and play a few challenging games on my iPad
• Get ready (brush teeth, pack up, etc.) and head to the pool for a swim
• Shower and change after swimming and head to the main YMCA building (next door to the pool) to walk/run and use the stair master
• Head home, eat something, and settle in for the day

These are the things that are rather fixed in my life (I do them every week day) and that set my day up for success. From here, I can add anything to the day as I like. Potential add-ons are:

• Checking in at the Millionaire Money Mentors
• Writing for ESI Money
• Playing pickleball
• Reading
• Watching YouTube
• Shopping with the kids (we hit Costco together at least every other week and have dinner of a rotisserie chicken afterwards)
• House chores (including outside stuff)
• Dumbbell weight-lifting session (3 times a week)
• Video games
• Watching a show with my wife
• Taking a long walk

Basically, the mornings are mostly set/routine for me and the afternoons are where I can be flexible/creative. It’s just enough structure to provide a routine but not so much that it’s stifling. Plus it gets the most important stuff done early in the day, which I love.

By keeping the rhythm of a workday without the stress of a workday, I’ve maintained the productivity I love without the burnout. Structure isn’t the enemy of freedom; it’s the skeleton that allows freedom to stand up. If you don’t schedule your time, the world will schedule it for you.

5. The MONEY!

Should I have listed this first? Hahahaha.

Remember, this list is in no particular order (primarily because that order would be completely different for so many folks). But if it was, this would probably be at the top of the list. It certainly is for many folks.

Why is that? Because retirement is scary:

• You are making a multi-million dollar decision (You are giving up a HUGE financial asset)
• You are leaving a 30, 40, or 50-year career/life
• You are making what is often a no-way-back decision
• You are doing something you have little to no experience with — it’s a one-time event
• You are giving up regular cash flow

These all combine to make retirement a nerve-wracking move for many. It’s why One More Year Syndrome is real…then it turns into two more years, then three, then…

But the last point above is the one that really gets people. Let’s be honest: people love making money. Even after they have enough, the act of earning is a game that many find incredibly fun. It’s a tangible way to measure progress and winning. In our society, money is the ultimate yardstick for value.

Plus a nice income cures many financial ills. What if something was to go wrong financially and you didn’t have it? It could be very painful.

A paycheck brings financial security. Even if someone has assets/investments, a paycheck provides predictability, confidence, and optionality. Earned income feels stable.

Many people fear that retirement means the end of the Earn pillar — that they will forevermore just be consumers of their past efforts, watching their pile slowly shrink.

And for some, this is what happens. If they have an asset withdrawal retirement strategy, they are (likely) going to see their assets decline. And this is scary…especially if there’s no income being brought in.

That’s just one reason I prefer (and advocate for) at least some income in retirement. Work has so many intangible benefits (as we’re highlighting here and I’ve done in other posts) but earning a paycheck, even if it is a small one, is a very tangible reward.

Besides, an income can make up for a massive amount of savings. Even if you only make $20k a year in retirement, that’s half a million dollars (at 4%) you didn’t have to save up like those using the asset withdrawal method only.

As I’ve shown in my own life, the Earn pillar doesn’t have to die in retirement. I still earn money through this site and the Millionaire Money Mentors (not to mention through investments). For me this is bonus money as I don’t need it. But it sure is nice to not have to make asset withdrawals and instead let your investments continue to compound. This alone has meant several million dollars to our net worth.

6. Having a Meaningful Challenge

There is a specific psychological high that comes from being “in the zone.” Whether it’s solving a complex engineering problem, closing a difficult deal, or writing a perfect piece of code, the flow state is one of the most satisfying human experiences. It’s the feeling of your skills meeting a high-level challenge where time seems to disappear.

Many people fear that retirement will be a long, boring flatline of easy living. They love the feeling of being stretched intellectually. They worry that without a job, their brain will turn to mush.

Retirement doesn’t fix the need for challenge; it just allows you to choose the mountain you climb. For some, this is taking a hobby to a new level (I had a friend who went all-out on pickleball and is now a very highly rated player). For others, it’s traveling and learning about new people and places. And for many, it’s working. Only this time they pick challenging jobs that give them what they want and eliminate much of the junk that goes along with working a career.

I lucked out in this regard. Shortly after I retired, I started writing more on ESI Money and it took off. This then led me to Rockstar Finance and then the Millionaire Money Mentors. I have had ten years of challenging, interesting, stimulating work that I can do on my time schedule from anywhere in the world. Oh, and it earns a nice paycheck to boot!

When you retire you don’t want to retire from challenge; you want to retire from irrelevant challenge.

7. The Thrill of the Win

Whether it’s hitting a sales target, launching a product, or finishing a project on time, people love the hit of dopamine that comes from a win. Work provides a constant stream of measurable victories (hopefully).

Work gives built-in achievements, wins, and milestones like promotions, completed projects, performance bonuses, and various forms of recognition. It also provides external validation like feedback, praise, metrics, and awards. Work often gives clearer validation than retirement does.

Many people love the simple validation of a job well done. There is a deep, primal satisfaction in completing a task and receiving a thank you or a positive result. It’s the closing of the loop on effort. In retirement, the loops are often longer and less obvious. You don’t get a “Great job!” from a boss at the end of the day.

I must admit that this was my favorite part of working — the competition for sales, market share, profitability, etc. You got a steady stream of quantifiable data to tell you how you were doing. It was thrilling to set goals and see them hit in real time. I saw it as one big game…but with lots of money. Haha.

In retirement, winning becomes more subjective. There are no quarterly reviews, promotions, or bonus checks to tell you that you’re doing a good job. This can leave people feeling like they are just marking time.

Personally I feel like a winner every day when I see people my age and older going to work (or talking about it). Hahahaha. Losers! lol. I have FREEEEEEDOM!!!!! Nothing makes you feel more like a winner than that!

When I was a decade younger it was even more thrilling to tell people I was retired because it almost caused them to melt down (how could anyone retire so young????!!!) Now that I’m older and at the age where the average American retires, it’s not as impressive (though it is a bit as I’ve been told by many that I look ten years younger than I actually am.)

In addition to this, I’ve replaced corporate wins with other wins. I track my fitness metrics (steps, weight, gym PRs), my blog growth, and my financial progress (mainly net worth via Quicken).

When I see my net worth increase despite ten years of no formal job, that’s a win. When a reader emails me to say they’ve hit their own FI number because of something I wrote, that’s a massive win (same goes with someone helped in the MMM forums). When I crush someone at pickleball…well, you get the idea. Hahaha.

You can still play to win; you just change the scoreboard. The stakes are lower, but the satisfaction is higher because the win belongs entirely to you.

8. The Feeling of Being Needed

One of the deepest human needs is the need to be useful. Work provides that in spades. Your team needs you to lead; your clients need you to solve their problems; your company needs you to stay profitable. Being needed is a powerful motivator that gets you out of bed.

People often lose this feeling in retirement. And if nobody needs you to show up on Monday morning, it can lead to a crisis of identity.

I’ve kept this by shifting from functional usefulness to mentorship. I am needed by the community I’ve built here and at Millionaire Money Mentors. I am needed by my family as a present husband and father. I am needed by myself to design and live a fulfilling life.

The secret is to realize that while your company doesn’t need you anymore, the world still does. You just have to find a better way to give of yourself. Significance doesn’t require a salary.

I know I’ve already mentioned volunteering a few times in this post, but it bears repeating here as it really addresses the feeling of being needed. Who could need you more than people who have no food, clothing, or shelter? If you really want to feel needed, volunteer for an organization that helps those less fortunate to meet their basic needs.

Much of my “volunteering” these days is done with money as I know I can have a much larger impact with what I can give than any amount of time I could spend with an organization. And it’s pretty great feeling to know that we just fed 10,000 people and we “literally saved lives” (a note from one charity we support said this) with our donations.

9. Being Forced to Grow

Jobs often force you to learn new things. Whether it’s a new software, a new regulation, or a new management style, work provides a forced environment for growth. New problems to solve. New skills to master. New technologies to adapt to. People love the fact that they are constantly being pushed to evolve, even if they complain about it at the time.

In retirement, growth is optional. And because it’s optional, many people stop doing it. They stop learning, stop growing, and eventually, they start fading.

The vast majority of people I know have read fewer than five books since they left high school. Let’s face it, growth is difficult. It requires effort. And while people “like” to grow (or at least say they do), they lack willpower. So a job that forces growth has that as a built-in feature.

This is another one I don’t have an issue with as I’ve always been curious and self-motivated.

My main form of growth is learning, and I’m consistently learning…be it by reading (articles and books), listening (podcasts or audiobooks), watching (you can learn a ton from YouTube), or by doing (mainly writing these days).

I treat my personal growth with the same discipline I once gave to professional development. If you aren’t growing, you’re dying. Other than making life more interesting, this also has the side benefit of helping your brain by constantly feeding it new challenges.

If you’re looking for ways to grow in retirement, I have a couple options for you:

• Start a business. This can have all the benefits of a job that are contained in this post. So what’s not to love?
• Become a mentor. Teaching others is a GREAT way to learn and grow yourself. Need a place where you can mentor? Here’s an idea.

10. The “Big Stage” (The Scale of Impact)

In a high-level job, you often have the chance to work on projects that impact thousands or even millions of people. You love the scale of your work. Whether it’s managing a $100 million budget or launching a national campaign, there is a thrill in operating on a “big stage.”

Retirement can feel small. You go from managing a department to managing a lawn. The reduction in scale can feel like a reduction in life itself.

Not a big issue for me, but I’ve kept the big stage by building a digital platform. Through ESI Money, I have a reach that rivals many of the corporate projects I worked on. I can influence the financial futures of thousands of people across the globe. The stage is different — it’s a digital one — but the impact is real.

If you love scale, you can use your retirement to build something that reaches beyond your backyard. The internet is the ultimate force multiplier for the retired expert. (If I had to start over today, I’d probably begin with YouTube FWIW.)

Two Bonuses

And because I simply couldn’t contain myself to 10 things, here are two bonuses:

11. The Variety of the Human Circus

Despite the toxic coworkers you may run into, many people genuinely love the variety of people they encounter at work. The office is a cross-section of humanity — different ages, backgrounds, and perspectives. It keeps you plugged in to the world and exposes you to ideas you wouldn’t find in your own bubble.

Retirement can lead to a silo effect, where you only interact with people who are exactly like you (usually other retirees).

I’ve avoided this by broadening my horizons — mainly by my mentoring work here at ESI Money and at the Millionaire Money Mentors (where we often disagree with each other). In addition, I make a point to stay curious about how the world is changing (though I limit my news intake as I find too much news is not good for the soul).

I’ve kept the human circus in my life, but I’ve moved from being a performer in the ring to being a curator of the show. You have to be intentional about staying connected to the real world so you don’t become a relic.

12. Mentorship and Developing Others

One of the most rewarding parts of a career is watching someone you’ve mentored succeed. People love passing the torch and helping the next generation grow. It provides a sense of legacy that transcends a paycheck.

When you retire, you lose your “disciples.” There is no more junior staff to guide, no more proteges to develop.

I’ve replaced this with community mentorship. I get to mentor through every post I write and every comment I respond to. I also mentor in my personal life, sharing what I’ve learned about the ESI pillars with those who are still in the grind.

Statistics show that “generativity” — the concern for establishing and guiding the next generation — is a key marker of successful aging. You don’t need an HR department to be a mentor; you just need someone who is willing to learn and a heart willing to teach.

Again, a retirement job or volunteering can fit the bill here. Consulting, teaching, mentoring, or volunteering through paid or unpaid roles allows retirees to share their wisdom with others. It’s a way to “pay it forward” while staying engaged — and often, retirees find deep satisfaction in being seen as a guide or expert.

Retirement is an Upgrade, Not a Delete

The list above is made up completely of human needs: challenge, community, significance, and growth. The mistake we make is thinking that a job is the only way to satisfy those needs. We have been conditioned to believe that the grind is the only theater where these virtues can be performed.

Ten years into retirement, I can tell you that I haven’t lost a single one of these loves. In fact, I’ve enhanced them. I’ve stripped away the junk — the commutes, the politics, the jargon — and kept the core. I have the challenges without the deadlines. I have the community without the forced social functions. I have the Earn without the boss.

If you are afraid to retire because you love some part of your job, don’t be. The ESI framework isn’t just about building a portfolio; it’s about building a life where you have the resources to keep the best and fire the rest. You aren’t giving up your loves; you’re just giving them a better environment to thrive in.

What about you? What are the things about your job that you actually love and are afraid to lose in retirement? And for the retirees, how did you re-create that love in your new life?