10 Things I Love About Retirement: Reflections After a Decade of Freedom

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 occassion is to write several “10 Things” posts about retirement.

This is the first in the series…covering what I love about being retired.

How Far I’ve Come

When I first walked out of the office in 2016, I knew I was finished with the 9-to-5 grind, the endless meetings, and the pressure of a high-level executive career. But if I’m honest, I didn’t really know what the “other side” would look like a decade in (to be honest, I didn’t know what it would look like a month in. Hahaha.) How could I? Work was all I had known.

Back then, I was focused mostly on the math of retirement. I was checking the “ESI” pillars — making sure the Earn was replaced by assets, the Save had created a sufficient cushion, and the Invest was positioned to weather whatever the market threw at me. I created a budget for the first time in many years and massaged/updated it to make sure things didn’t get off track.

Ten years later, the math has proven itself. But retirement, I’ve discovered, isn’t lived in a spreadsheet. It’s lived in the hours between sunrise and sunset. People often ask me if the “honeymoon phase” ever ends. They wonder if I’m bored, or even if I miss the “prestige” of the corner office.

The short answer is: no. In fact, my appreciation for this lifestyle has only deepened. After 3,650 days of being my own boss, here are the 10 things I love most about retirement (in no specific order).

1. Time Freedom and Total Calendar Autonomy

By FAR the thing I love most about retirement is time freedom! I can do what I want, when I want, with who I want, etc. I can go to the gym, stores, and so many other places at times I select (which is usually when others are at work) and it’s AMAZING!

During my working years my calendar was a Tetris board of colorful blocks representing other people’s priorities (my boss’s, my employees, and so on). I was managed by my appointments, meetings, and conferences. Today, my calendar is a blank canvas.

I still have commitments, of course. I have workouts, I have family time, and I have the work I do here on ESI Money and the Millionaire Money Mentors. But the difference is that I put those blocks there (and they’re written in pencil). If I decide tomorrow that I’d rather go for a long hike than work on a post, I simply do it. I don’t need to check with a boss, a client, or an HR department.

This mirrors the data I’ve seen in the millionaire interviews. When asked about their favorite part of being a millionaire, the word “freedom” appears more than any other word. It’s not freedom from work — many of them still do something — it’s freedom from the imposition of others. This total sovereignty over my time is the “I” in FI that people underestimate. It’s not just about not working (in fact, work itself is fine); it’s about not being scheduled.

I do have calendar commitments now and then — a dentist visit, a car appointment, a worker coming over to do something on the house (we recently had trees trimmed…that was an interesting first experience) — but those are very few and far between these days. Having more than one a week starts to cramp my style and two a week is almost enough to send me into a meltdown. Hahaha.

2. The Death of the Alarm Clock

It sounds like a cliché, but I can’t overstate the profound psychological shift that occurs when you stop living your life according to a mechanical beep.

In my corporate life, the alarm clock was a drill sergeant. It didn’t care if I had slept poorly, if I was in the middle of a great dream, or if my body simply needed another hour of rest. It demanded I stand up and report for duty. Thinking back, it was BRUTAL. How did I survive? lol

Ten years later, I still wake up relatively early (usually around 6 am), but I do so because my body is finished sleeping (not to mention that I’m excited for another day of doing what I want to do), not because a clock told me to.

I’m not alone in this. In many of my Millionaire Interviews, when I ask what the biggest non-financial benefit of wealth is, sleep autonomy is consistently in the top three. One interviewee, a former high-stress attorney, told me that his chronic migraines disappeared within six months of retiring, simply because his circadian rhythm was no longer being assaulted by a 5:30 AM buzzer.

I can also say that my sleep has been so much better in retirement than it was in my working years. This is probably because the reduced stress/anxiety plus the added physical activity (my body is just more tired.)

As for the alarm clock, I’ve probably used it fewer than 20 times in the past decade…and it will probably be even more rare in the next 10 years.

3. The Luxury of Slow

In the corporate world, speed is a virtue. Everything is an urgent request, a tight deadline, or a fast-track project. I spent decades eating lunches over a keyboard and rushing from one commitment to the next. Retirement has allowed me to reclaim the slow version of life.

Now, if a morning walk takes two hours instead of forty minutes because the weather is perfect or I’ve run into a friend, it doesn’t matter. At the pool I often spend more time than even I want chatting with the lifeguards or other swimmers at the YMCA.

I had this mastered in Colorado where I went from getting up to walking to working out to reading over a breakfast sandwich to walking longer (talking to someone on the phone or listening to a book or podcast). I left the house at 7 am and would get home around 10 am. It was heaven.

I got off this schedule a bit in Florida, but here in North Carolina I’m starting to recapture it. I now leave for the Y each morning and swim, walk, and hit the stair master before getting home a couple hours later. So nice!

Then through the rest of the day there is simply no “late.” If I want to spend three hours researching a single topic for a blog post, I can. This ability to linger — to actually finish a thought or a conversation without checking my watch — is a form of wealth that no salary can replicate.

4. The Death of Stress

In my corporate life, stress wasn’t just an occasional visitor; it was a permanent resident. Even on good days, there was an on-going background hum of cortisol — the stress hormone — driven by deadlines, office politics, and the weight of being responsible for multi-million dollar budgets. I spent decades in a state of heightened activity, reacting to the urgent requests of others (bosses, co-workers, employees, customers, suppliers, etc.)

When I retired, I could literally feel the stress draining out of me. I felt my face begin to relax (it had always been “tight”) and my body felt more calm. It took about six months before the detox was complete and I was back to being a normal person.

Ten years of retirement since then has taught me that the absence of stress is one of the ultimate hidden dividends of retirement.

When you aren’t trading your hours for dollars, you aren’t subject to the manufactured emergencies of a corporation. I no longer have “crises” (that’s in parentheses because they often weren’t a real crisis but someone above me thought they were) that involve slide decks or quarterly projections. My biggest stressor today might be a one-inch snowfall day delaying my swim a few hours (because everything opens late in North Carolina after even one flake falls) or a particularly tricky blog post. But in reality, these are nothing at all.

For me, this transition has been a literal lifesaver. I sleep better, I think more clearly, and I no longer carry that physical tension in my shoulders that was my constant companion for 30 years. You can’t put a price on a resting heart rate that stays resting.

I think we’ve all seen reports of how stress can impact people physically and I am so thankful that I turned that off when I did. I know my mind and body appreciate it.

5. Health as the Primary Investment

When I was working, health was something I tried to fit in around my job. I’d squeeze in a workout when I could (even though I was exhausted and it was rushed). And let’s not even talk about my food choices. Ten years of retirement has taught me that health is the only asset that truly matters.

With the gift of time, I’ve been able to make fitness a cornerstone of my day rather than an afterthought. For most of my retirement, I’ve been in some of the best shape of my life. Even with a recent flare-up in my back from which I’m recovering, I’m still in better shape now than I was during most of my working years. This is because I now have the time to devote to physical fitness that I could never have working 50+ hours a week.

Statistics show that retirees who engage in at least 150 minutes of moderate activity per week (which is easy when you have a completely free day) have a 33% lower risk of all-cause mortality. I love this because between swimming, cardio, and weights I get about 585 minutes a week — and that’s before you count any “extras” like pickleball, taking a walk with my wife, and so on.

We talk a lot about investing on this site, but I’ve realized that the ROI on a daily gym habit is higher than even an index fund could ever offer! Haha! Retirement gave me the time to treat my body the way it should be treated. And if you want a happy retirement, I’d suggest you seriously consider making exercise a regular part of your retirement.

Now, if I can just lay off the ice cream, I’ll be set! lol DTH

6. The Ability to Pick My People

In a career, you don’t always get to choose who you spend your time with. You are forced into proximity with (in some cases) toxic coworkers, difficult bosses, and employees/clients who drain your energy. You spend more time with these people than with your own family.

Ten years ago, that ended. Now, my circle is entirely curated. I spend my time with family, friends, and the community at Millionaire Money Mentors — people who challenge me, support me, and bring joy to my life. If someone is a drain, I simply don’t have them in my life.

Now I’m not saying that I disliked all the people I worked with. In fact, I liked them for the most part. But would I have selected most of them as friends in another context? Probably not. And for some, I certainly would not have picked them for any sort of interaction.

And yes, I’ll occassionally run into someone who’s a bit annoying (generally at the gym where apparently some have no awareness of gym ettiquitte), but those are few and far between these days.

7. Meaningful Work Without the Baggage

A common misconception is that retirement means never earning a penny again. I think we’ve covered that. More than once.

For me, working in retirement has meant doing something that’s meaningful, enjoyable, and challenging — but without all the negatives that often come with “working for the man.” The baggage associated with much of work is gone.

I don’t have to deal with office politics, performance reviews, or budget cuts. I do the parts of work that I love (the creation and the community) and I’ve outsourced or eliminated the parts I hate (or I’m not good at — like the tech stuff. lol).

Roughly 40% of the millionaires I’ve interviewed still engage in some form of income-producing activity. The difference now is they don’t need the income. This “Work Lite” or “Post-FI Work” provides the mental stimulation that human beings need without the cortisol-inducing stress of a career. It turns out that most of us didn’t hate working; we just hated the conditions of modern employment.

Work (or something similar, like volunteering) is actually one of my top retirement activities that I recommend everyone seriously consider. Without it, your retirement could actually be worse than it would be otherwise.

8. The Joy of Mid-Week Living

There is a specific kind of pleasure in doing things when the rest of the world is at work. Going to the grocery store on a Tuesday morning, hitting the gym at 10:00 AM, or traveling when the crowds are thin and the prices are lower.

The weekend is a social construct designed for the workforce. When you retire, every day is a Saturday, but without the crowds. This ability to out-cycle the general population makes life significantly smoother. You don’t wait in lines, you don’t sit in traffic, and you don’t have to fight for a reservation.

Of course the benefit of this retirement reward has been tempered a bit since Covid kicked off the work from home craze (I regularly see younger people at the gym in the middle of the day), but enough people still commute to work to make it a satisfyingly awesome thing about retirement.

One of my favorite interviewees, a retired civil servant, told me his favorite retirement perk was going to the movies at 1:00 PM on a Wednesday and having the whole theater to himself. It’s a subtle benefit, but after ten years, I still get a little kick out of realizing it’s Wednesday and I have absolutely nowhere I have to be.

BTW, the opposite is true too. I’ll often say, “Tomorrow is Saturday. I’m not going antwhere (because there are people out and about).” Hahaha.

9. The Uniform of Freedom

One of the most liberating — and underrated — perks of the last decade is the total reclamation of my wardrobe. For thirty years, I played the costume game. Initially I wore suits, starched shirts, ties (!), and the long pants required by the corporate dress code. Things loosened up a bit over the years, but there still was a work dress code that needed to be followed. It was a daily tax on my comfort.

Today, I have a very simple rule: If it requires long pants, I’m probably not going.

My uniform of freedom consists almost exclusively of shorts and athletic clothes. It’s practical, comfortable, and fits my active lifestyle. Besides, it’s much easier to have stealth wealth when you look the part. lol

And yes, I’m serious about the shorts part. I don’t even like wearing long athletic pants. One great thing about North Carolina (plus having grown up in colder climates — I am able to handle cold weather) is that there are only about five days a year I need to wear long pants — and then it’s just for a short time — like for a walk outside. There have been several times this winter where I am the only person in Costco who’s wearing shorts. Hahahaha.

In retirement, my status comes from my autonomy, not my attire. I’ve reached a point of wardrobe sovereignty where my comfort is non-negotiable. If an event or a venue has a dress code that requires me to sacrifice my comfort, I simply decline the invitation. This isn’t about being difficult; it’s about the fact that after three decades of suiting up for the grind, I’ve earned the right to never wear a pair of slacks again.

We recently got an invitation to attend one of those “free” dinners where they talk about financial planning. Not that I was going anyway, I’ve been to far too many of them, but when I saw it said “business casual dress suggested” I knew it was a certain “no” from me. I don’t need that sort of negativity in my life. Hahaha.

10. The Peace of Enough

Finally, among the things I love most after a decade of retirement is the profound sense of peace that comes from knowing I have enough.

In the accumulation phase of life, there is a constant underlying anxiety. Do I have enough? Am I saving enough? What if the market crashes? What if I lose my job? Then when you retire, the questions get even worse…DO I HAVE ENOUGH? And as I’ve said, you don’t want to trade work stress for money stress.

But ten years of retirement later, things are very peaceful in the money-stress arena. And while I’ve seen market dips, inflation, and the world seem to ebb and flow — I’m still here. And not just here, but thriving and content. And certainly not worried.

One thing that has helped big-time in this process (in addition to saving a bundle and knowing I had several margins of safety): income. By making more than we spend (sort of by accident, and despite buying and doing everything we want), it’s allowed us to let our assets keep compounding. Anyone have any idea what the stock market has done the last ten years? I think it’s gone up a bit, right? Haha.

In fact, our net worth is now well over double what we retired with despite spending on whatever we want and implementing our five-year giving plan.

That initial money anxiety (which was really only a few weeks at most) has been replaced by a deep-seated security. I no longer feel the need to win or to more my way into happiness. Once your net worth clears a certain threshold (usually between $3M and $5M from what I can tell from the interviews), the marginal utility of more money drops to zero, but the marginal utility of peace goes through the roof.

Ten years in, the greatest gift of retirement isn’t the money in the bank; it’s the quiet confidence that I am truly free.

The Next Decade

If the first ten years are any indication, the second decade of retirement will be even better. I’ve moved past the figuring it out stage and into the thriving stage (I actually spent very little time in the former, thankfully).

If you are still in the grind, keep going. The ESI pillars aren’t just theoretical concepts I write about for fun; they are the keys to a life that is richer than you can currently imagine. And if you’re already retired, I hope you’re finding your own “ten things.”

What about you? For those who have already crossed the finish line, what do you love most about your freedom? And for those still working, which of these ten things are you most looking forward to (or maybe something else)?