10 Things People Hate About Working (That Retirement Fixes)

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.

The first post in the series was 10 Things I Love About Retirement: Reflections After a Decade of Freedom. Check it out if you missed it.

Work and Retirement

Needless to say, I have had a lot of time to think about work, retirement, and the relationship of the two.

Now that I have 28 years of work and 10 years of retirement under my belt, I think I have a pretty good perspective on both.

We’ve been conditioned to believe that trading the best hours of our best years for a paycheck is a fair trade. But once you break the seal on retirement, you realize just how much of the working life is actually a heavy tax on your mental and physical well-being.

And to be clear, I don’t dislike work and my career wasn’t terrible. I just dislike all of the nastiness detailed below that we all have to put up with as part of working.

As I look back on a decade of freedom, I’ve identified (more than) 10 specific things (in no particular order) that people absolutely loathe about working (I couldn’t help myself — I had to go over 10!) — and exactly how retirement fixes them.

1. The Commute: The Unpaid Tax on Life

Let’s start with the most obvious thief of joy: the commute. According to the U.S. Census Bureau, the average one-way commute in the United States is about 27.6 minutes. That’s nearly an hour a day, five days a week. Over a 40-year career, that adds up to roughly 10,000 hours (about three and a half years of 8-hour days) spent sitting in a metal box, breathing exhaust fumes, and staring at brake lights.

And before someone comments that they take the bus/train/whatever — and somehow that makes it fine — let me say that 1) you are in the vast minority of people as 3.7% of people use public transport to get to work (see the link above…it contains that information too) and 2) public transportation does have some advantages but also has its own unique set of horrors (this is coming from someone who once rode the bus and train (two separate jobs) to work). The point is, no matter how you get to work (unless you work from home — 13.3% of the population), most of these points pertain to you (and making work worse).

Now back to our main story: five hours a week…20 hours a month…50 hours a year. That’s just driving to work. Let that sink in.

The commute is the ultimate unpaid work. You aren’t getting paid to sit in traffic, but you certainly can’t use that time for anything meaningful. It’s a transition period of pure stress. Statistics from the University of the West of England found that every extra minute of commuting time reduces job satisfaction and increases strain on mental health. They also found that “Adding 20 minutes more commuting time each day has the same effect on job satisfaction as taking a 19% pay cut, according to a new study using data from Understanding Society.”

In retirement, my commute is the fifteen steps from my bedroom to the coffee maker. Ok, maybe 20 as we now have a bigger home than we did when we lived in The Villages. lol

Retirement fixes the commute by giving you back your most precious asset: Time. Part of those 10,000 hours (whatever you have left…if anything…when you retire) are returned to your account. For me, that’s meant 3,650 mornings over the last decade where I didn’t have to worry about weather, road construction, or the erratic driving of others.

And losing the commute isn’t only saving you an hour a day…it’s saving you a terrible/non-productive/worthless hour every day (and for those of you who live where weather is a factor, you know the “thrill” of a snowstorm turning a 20-minute commute into an hour-long, white-knuckle run for your life).

I was fortunate to never have a really long commute during my career. My longest was 20 minutes one way and my shortest was less than 10 minutes. For the vast majority of my career, I was close enough to come home for lunch if I wanted (which I didn’t as I was working through lunch!)

I also tried to make the most of the time, usually by listening to audiobooks. So it wasn’t a total loss. But is was not the maximum use of time. And it was unpaid…in addition to being costly, of course (just take a cost of 50 cents a mile and add that up). It’s a lose/lose/lose proposition.

It could have been worse. I had friends who lived in New Jersey and commuted into NYC who spent 1.5 to 2 hours per day ONE WAY to get to work. How do you like your high-paying job now? Hahahaha. Ugh.

2. Performative Productivity (The Butts in Seats Cult)

One of the most frustrating aspects of the corporate world is the cult of being seen. In many offices, it doesn’t matter if you finished your work by 2:00 PM; you are expected to stay until 5:00 PM (or later) just to prove your “commitment.”

This is performative productivity. It’s the art of looking busy when you’ve already achieved your goals. It leads to endless busy work, checking emails that don’t need checking, and the slow erosion of the soul.

For most of my career I was among the first in the office and last out of it.

But at my last job, I was done with that. I was already easily financially independent and had a boss who was a piece of work (if you know what I mean).

I still was in early — usually among the first few people in the office every day. But I left shortly after 5 pm. I wasn’t putting in extra time just to be seen. I had finished my work and I was ready to move on with my life. And even with that, I was still in the last third of the company to leave each day.

But my boss wasn’t satisfied. He told me that me leaving early was setting a bad example for the employees. I asked him where he was when I got in at 7 am and if his getting in at 9:30 am each day was setting a bad example for employees. He didn’t appreciate those questions. lol. But what did I care? I was already contemplating leaving by this time and this sort of questioning and comments pushed me over the edge. It was a clear message that my time to go was now.

Retirement fixes this issue by shifting the focus from inputs to outcomes. In my retired life, I still do things. I write for this site, I manage my investments, I work out.

But if I finish a task in thirty minutes, I’m done. There is no manager peering over my shoulder wondering why I’m not typing. My productivity is now measured by my own satisfaction and the value I provide, not by an arbitrary clock. When you own your time, you realize that efficiency is the ultimate luxury.

3. The Sunday Scaries: The Psychological Weight of the Looming Week

There is a specific type of dread that sets in around 4:00 PM every Sunday for many workers. It’s a low-level anxiety, a tightening in the chest as you realize the freedom of the weekend is evaporating and the grind is about to resume.

It actually started about noon on Sunday for me…right after church. There was a realization that the weekend was almost over and it was time to start gearing up for another week of battles.

Even if you like your job, the Sunday Scaries (or Sunday Blues if you prefer) are real. They represent a lack of control. You are anticipating five days of someone else’s priorities, someone else’s schedule, and someone else’s demands. (BTW, I’m being generous saying “five days.” For much of my career I worked six or even seven days a week…at least some on the weekends.)

Retirement fixes this by eliminating Sundays. I don’t mean the day disappears, but the feeling of Sunday does. In my ten years of retirement, I haven’t felt the Sunday Scaries once. Why? Because Monday is just as good as Sunday. In fact, it’s better because everyone else goes to work and the stores, gyms, theaters, etc. are pretty clear.

When every day is a “Saturday” (or a “Tuesday,” depending on how you view it), the calendar loses its power to inflict dread. I wake up on Monday morning with the same sense of autonomy that I have on a lazy Saturday afternoon. This psychological relief is worth more than any bonus I ever received in my career.

4. Office Politics and the Toxic Coworker

You can choose your friends, but you cannot choose your coworkers. In every job I ever had, there was at least one person who was a drain — a gossip, a credit-taker, a micromanager, or someone who simply thrived on drama.

Office politics is a game of survival that has nothing to do with the ESI framework. You spend hours navigating egos and trying to stay out of the line of fire. Research from the American Psychological Association shows that difficult coworkers are one of the leading causes of workplace stress and burnout.

Here are a few of the office politics I’m talking about — see if any of these ring a bell: favoritism, power struggles, inter-department struggles, gossip, ego battles, and so on.

And if the toxic person is your boss, hold on for dear life! Have fun dealing with their micromanaging, poor communication, lack of appreciation, and inconsistent expectations.

In retirement, my colleagues are the people I choose to associate with. If someone is toxic or draining, I simply don’t spend time with them. I have replaced forced proximity with intentional community. I spend my time with people who challenge me intellectually and support me emotionally. The freedom to fire anyone from your social circle is one of the most underrated benefits of being financially independent.

By the way, even if there’s no drama-inducing person at a specific company…there are people. And people in their own right, thrown together from a variety of backgrounds, perspectives, and life experiences, carry their own burden (which they are happy to transfer to you).

Who are these people? Bosses. Boss’s bosses. Co-workers. Employees. Suppliers. Customers. Business partners. And on and on and on.

I’m getting PTSD flashbacks just thinking of it…

5. The 40-Hour Work Week Myth

The 40-hour work week is a relic of the industrial age. It’s an arbitrary block of time that assumes every job requires exactly 2,080 hours a year to complete. In reality, most knowledge work is performed in bursts. We have periods of high creativity and periods where we just need to rest.

But the corporate world demands the grind. You are expected to be on from 9:00 am to 5:00 pm, regardless of whether your brain is actually functioning at peak capacity. And in reality, that’s just the entry price for a well-paying job. Generally it’s more like 7 am to 6 pm with additional work at nights and the weekends. As I’m sure you can imagine, this feeling of always being “on” can easily lead to burnout.

Over the years we’ve talked a lot about making the most of your career to maximize your earning potential. If you get to a high-paying job, I can tell you they don’t hand those out to 9-to-5ers. Just ask the vast majority of millionaire interviewees who make a great salary — 40 hours to them would seem like a vacation week.

Retirement eliminates this feeling of never-ending demand.

Some days, I’m in the flow and I’ll write for six hours straight. Other days, I might spend no time at all on work because I’m headed to the outlet mall for a fun shopping spree. I listen to my body and my mind. If I’m tired, I nap. If I’m energized, I create. This alignment with my natural rhythms has made me more productive (in the ways that matter) than I ever was when I was forced to sit in a cubicle for “forty” hours a week.

6. The Performance Review Charade

Is there anything more demoralizing than the annual performance review? You spend months doing great work, only to sit across from a manager who has to find “areas for improvement” so they can justify a 3% raise that barely keeps up with inflation.

And writing them is even worse…ugh.

The review process is often a theater of the absurd. It’s based on subjective metrics, 360-degree feedback from people who don’t understand your role, and the constant pressure to “exceed expectations” just to stay in the same place.

But that’s just during one time of the year. The rest of the year you’re still being judged, measured, ranked, or compared throughout the year. It’s a nice feeling, right? Hahahaha.

In retirement, I am the only judge of my performance. I don’t need an HR department to tell me if I’m succeeding. I know I’m succeeding because my net worth is growing, my health is improving, and my relationships are thriving. My review happens every morning when I look in the mirror and ask, “Am I living the life I want to live?” If the answer is yes, I’ve exceeded expectations.

Spoiler: 10 years going the answer has been “yes.” 😉

7. The Conflict Between Career and Health

In the corporate world, your health is often treated as a secondary concern to the company’s goals. We eat catered lunches of processed junk, we skip the gym to make a deadline, and we sacrifice sleep to grind through a project.

And don’t get me started on how long we sit each day and how terrible that is for your health.

Or how stress eats people up from the inside. The data is clear: long-term corporate stress leads to higher rates of heart disease, obesity, and mental health struggles.

We trade our health for wealth, only to spend our wealth later in life trying to buy back our health. It’s a bad trade.

Retirement fixes this by making health the primary business. In my ten years of freedom, I’ve realized that I am the CEO of my own body. My daily board meetings happen at the gym. My research and development happens in the kitchen with fresh, whole foods. Because I no longer have the office stress of managing people and budgets, my cortisol levels have dropped, my sleep has improved, and I am in better physical condition at 60+ than I was at 45.

Retirement gives you the time to treat your body like the high-value asset it is.

8. Missing Real Life: The Opportunity Cost of the Office

There’s an opportunity cost associated with working. Every hour you spend in a windowless office is an hour you aren’t spending with your spouse, your children, your aging parents, or your hobbies. You are missing the small moments that actually make up a meaningful life. I remember being at work and realizing I had missed the first snowfall of the year because I was in a windowless conference room discussing a marketing plan.

In retirement I don’t have to choose between making a living and living. I am present for the random Tuesday lunches with my wife. I am available for my adult children when they need advice. I can watch the seasons change from my own porch. Retirement isn’t about doing nothing; it’s about being there for the things that actually matter.

I was luckier than most in my career as I was able to attend most of my kids’ activities, often being intimately involved with them (like being their coach on a sports team). That said, I know so many people who missed so much because of office demands, travel, and other work-related activities.

9. Artificial Urgency (The Death of the Fire Drill)

I still remember it clear as day. I was at my first job after graduate school. I was greener than an Irish hillside — a country bumpkin from Iowa with a freshly minted MBA.

One of my co-workers rushed in and said, “We’ve got a fire drill!”

I wondered why I hadn’t heard the alarm, but I believed him and started getting ready to leave the building. Then he laugh and explained to me that a “fire drill” at work was an urgent request that needed to be completed immediately.

Google is less politically correct in its definition: “A ‘fire drill’ in slang refers to a chaotic, high-pressure, or disorganized situation where everyone must urgently drop their current work to handle a sudden, often unnecessary crisis. It implies a state of frantic, inefficient panic rather than a planned, productive response.”

Hahahaha. Yep, that’s what they were!

And they often seemed to land at around 5 pm as we all were beginning to get a glimpse of freedom for the day…

In the corporate world, a lot of things qualify as a fire drill. Managers use urgency as a tool to drive productivity, often when none is actually required. You are expected to treat a slide deck or a spreadsheet as if it were a life-or-death situation. This constant state of high alert keeps your cortisol levels spiked and your nervous system on edge. I spent decades answering urgent calls/emails at dinner, only to realize the emergency could have easily waited until the next day or Monday.

Retirement fixes this by restoring perspective. Ten years in, I’ve realized that almost nothing in life is actually urgent. If I don’t finish a blog post today, the world doesn’t stop. If I delay a rebalance of my portfolio by forty-eight hours, the market doesn’t care.

Once people leave this high-stress environment, great things start to happen — like their blood pressure drops and their perceived stress levels fall. You stop living in a state of manufactured panic and start living in a state of deliberate action. You reclaim your heart rate. You learn the difference between an actual crisis and a manager’s lack of planning.

10. The Meeting Mirage (The “Could Have Been an Email” Tax)

If there is a single ritual that symbolizes the inefficiency of the corporate grind, it is the unnecessary meeting. Or is it simply the meeting? Do we need to add unnecessary? You can decide.

I spent a massive portion of my career sitting in windowless conference rooms, watching a laser pointer dance across a PowerPoint slide, while mentally calculating the opportunity cost of the time being wasted.

I spent years in meetings where the primary goal was to justify the existence of the meeting itself. Not to mention the company blowhards pontificating on whatever was their pet subject of the day.

We spend hours in meetings to “touch base” on “deliverables.” This linguistic gymnastics is a symptom of a larger problem: the disconnection between work and reality. Much of corporate life is spent talking about doing things rather than actually doing them.

In the corporate world, meetings are often used as a crutch for poor management. They are the default setting for anyone who wants to feel productive without actually producing anything.

Retirement has permanently cured me of this frustration. Here is why the Meeting Mirage is one of the things I hate most about work — and how retirement provides the ultimate fix:

• The Massive Time Sink: Statistics show that the average middle manager spends 35% of their week in meetings, and for upper management, that number jumps to 50% or more. That is half of your working life spent talking about work instead of doing it. In retirement, my meetings are spontaneous conversations with friends or family that actually have meaning.
• The Productivity Black Hole: A study by researchers at the University of North Carolina found that 71% of meetings are considered unproductive by the people attending them. They are often circular, lack a clear agenda, and serve only to “align” people who were already aligned. In my ten years of freedom, I’ve realized that the majority of the meetings I attended could have been handled with a three-sentence email.
• The Obligatory Theater: Meetings are often less about information and more about face time. You are required to be there to show you are a “team player,” even if you have nothing to contribute. It is performative professionalism at its worst. And you know how I feel about that.

Retirement fixes this by giving you Total Calendar Sovereignty. Today, my agenda is mine alone. If I want to discuss something, I pick up the phone or send a text. There are no standing meetings, no status updates, and no syncs. I’ve traded the conference room table for the hiking trail, and I can tell you, the air is much better out here.

Bonus Four

I couldn’t limit myself to just 10 things people hate about work, so here are four bonuses…

11. Geographic Tethering (The Location Prison)

In the Earn phase of life, most people are tethered to a specific zip code. You live where the jobs are, which usually means high-cost-of-living (HCOL) areas with high taxes, high traffic, and high stress. You are essentially paying a location tax just to have access to your paycheck.

Thankfully, I was able to have high paying jobs in low cost-of-living locations (which really helped to build wealth), but many do not have that option. They are forced to live in higher cost areas to make the salaries they want to make, but living in those areas eats up much of their extra earnings. It’s a brutal system.

Retirement fixes this by unlocking geo-arbitrage (yes, I know that some have this option at work these days, but this is still a small percentage of workers). Once the Earn pillar is decoupled from a physical office, you are free to live anywhere.

Maybe this is a problem for me as it allowed a move to a place I didn’t enjoy (Florida)…so perhaps I’m out of my depth on this one. lol

That said, ten years ago, I realized that I no longer had to live within a 30-minute radius of a corporate headquarters. I could choose my location based on lifestyle, proximity to family, or tax favorability — not because a CEO decided where the building should be. Thankfully I lived in a great area of a great state, so we stayed there for another six years before taking the ill-advised Florida plunge.

When you retire, stop being a geographic prisoner to your job, and can live wherever you want, your net worth can go further, and your quality of life skyrockets. You stop paying for the privilege of working and start choosing the environment that serves your soul.

12. The Vacation Debt (The Catch-Up Penalty)

Now let’s talk about not working. That’s what happens on vacations, right? Haha.

Working people don’t actually get vacations — they get deferred work. For every week you spend on a beach, you spend two weeks prior working double-time to prep, and two weeks after working double-time to catch up. This is what I call Vacation Debt. The stress of leaving and the anxiety of returning often negate the benefits of the time off.

I went to a seminar once where the speaker talked about “working like the day before vacation” as a way to say a person was working especially hard. A co-worker friend of mine who went to that seminar with me used to joke now and then saying we were working like the day before vacation. lol.

But as for vacation, has anyone reading ever checked email, taken a call, or done any work on vacation? Is it really a vacation if you do that?

I can remember checking email from a cruise ship…before they had good wi-fi.

Obviously retirement fixes this problem because there is no work prep for a trip, and there is no re-entry nightmare. When I travel now, I don’t check my email with a sense of looming dread. And I don’t have 100 unread messages waiting to ambush me on Monday morning.

Statistics from the U.S. Travel Association show that Americans leave millions of vacation days on the table every year, largely due to the fear of the workload upon return. In retirement, you leave for vacation when you want, stay as long as you want, and return to the same peaceful routine you left behind. It turns travel from a stress-relief tactic into a lifestyle choice. It’s no longer an escape; it’s an exploration.

That said, I’m a big fan of creating the life you love at home so you don’t need or want to travel…because traveling has its own set of horrors these days.

13. The Professional Costume

Most workers have two wardrobes: the one they actually like, and the one they wear to signal professionalism. Whether it’s suits, dry-clean-only dresses, or high-end business casual, the cost of the professional costume is a significant drain on the Save pillar. Between the initial purchase price and the ongoing maintenance (dry cleaning, tailoring), you are spending thousands of dollars just to look the part.

Retirement fixes this with the Uniform of Comfort. For me, that transition was simple: I moved from dress shoes to Brooks Ghost 15s. My work attire now consists of shorts and athletic clothing. Sooooooooo comfy!

The Save implications here are subtle but real. In ten years of retirement, my clothing budget has plummeted. I no longer pay for dry cleaning, I don’t need to replace worn-out dress shirts every year, and I don’t have to keep up with dress code of a corporate office. It’s a return to authenticity. You stop dressing for others and start dressing for yourself.

14. The Mandatory Fun Tax

Finally, there is the “Mandatory Fun” — the office holiday parties, the team-building retreats, and the after-work happy hours that you attend only because you fear the political consequences of staying home. These events are an imposition on your time liberty. They are work disguised as play, and they are exhausting. You are essentially paying a tax with your personal time to maintain professional appearances.

I thought about creating a top ten list of the worst retreats, parties, and other events I had to attend for work. But that list would probably grow to 20 or more, so I’ll pass. Hahahaha.

That said, the “best” one was probably the sales conference where we flew all our store managers into a “great” location where we had to have many of the meetings outside (because the venue didn’t have enough meeting places for everything we needed to do). We got an awesome deal on the place…because it was in Phoenix in the summer! No, I am not making this up.

In the corporate world, social interaction is often transactional. You are constantly assessing who can help your career (or at least do something for you). In retirement, it is purely relational. This shift removes the mask you have to wear at any functions — or whether you even want to go to any functions (which I generally don’t). You don’t have to laugh at the boss’s bad jokes or pretend to be interested in a colleague’s fantasy football team just to maintain alignment. You spend your social capital on the people who actually matter to you.

After ten years, I can tell you that the deep, authentic friendships I’ve formed in retirement are far more valuable than any professional network I ever built.

Ok, I need to stop for now. But let me just mention two others:

• The feeling of always being replaceable — Do you think your company is loyal to you? They are…until they aren’t. Many workers know that loyalty isn’t reciprocated, layoffs happen quickly, and contributions are forgotten. You have to remain on your toes while working and look out for yourself (and your most valuable asset — your career).
• Limited meaning or impact — Ever feel like what you do doesn’t matter? You’re not alone. Many roles feel transactional, repetitive, and detached from purpose. This can be soul-sucking for those who hold these positions.

The Exit is Worth the Effort

Many of the things people don’t like about work boil down to one thing: they don’t have control of their time. They have fixed schedules, required presence, limited vacation, and have to ask permission to leave.

A friend of mine used to say that “Someone in the family has to go out and trade their life for money so that the family can survive/thrive.” And that’s the deal with work — you are literally trading your life for money. Saving for retirement (and becoming FI) therefore is buying your life back. And when you retire, you get it all back (what’s left of it, of course).

If you are still in the Earn, Save, and Invest phases of your journey, keep your eyes on the prize. The corporate world will try to convince you that the grind is necessary and that retirement is a scary void of inactivity.

Don’t believe them.

The things you hate about working — the commute, the politics, the lack of control, the manufactured urgency — are not facts of life. They are the price of admission for a system you are working to outgrow. Ten years of retirement has taught me that life on the other side is richer, calmer, and infinitely more meaningful.

The ESI pillars are your ladder out of the pit. Every dollar you Save and Invest is a minute of your future life you are buying back from a system that doesn’t care about your well-being. Keep climbing. The view from the ten-year mark is better than I ever imagined.

What about you? What is the one thing about your current job that you “hate” the most? And for the retirees in the room, what was the biggest “work burden” you were happiest to drop once you retired?