10 Retirement Killers and How I Avoided Them, Part 3

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 articles in this series:

• 10 Things I Love About Retirement: Reflections After a Decade of Freedom
• 10 Things People Hate about Working (That Retirement Fixes)
• 10 Things People Love About Working (That They Want to Keep in Retirement)
• The 10 Best Financial Moves I’ve Made in 10 Years of Retirement
• 10 Retirement Mistakes I Made (And Why They Didn’t Sink Me)
• 10 Strategies for Staying Socially Connected Without an Office: The ESI Guide to Avoiding the “Loneliness Trap”
• 10 Things I Spend More Money on Now Than I Did 10 Years Ago: The ROI of “Value Spending”
• 10 Daily Habits that Make Retirement Great
• A Decade of Freedom: 10 Activities That Have Enriched My Retirement

This is the final part of a series I’m writing on retirement killers.

If you missed either of the first two parts, read 10 Retirement Killers and How I Avoided Them and/or 10 Retirement Killers and How I Avoided Them, Part 2 before you read this post so you’ll be fully up to speed on the complete list.

With that said, let’s get to retirement killer #7…

7. Neglecting Your Health

One of the stranger retirement ironies is that people spend decades trying to save enough money to enjoy freedom, then arrive at freedom with bodies they haven’t taken care of.

That’s a major retirement killer.

Poor health limits everything. It affects mobility, energy, mood, independence, travel, hobbies, relationships, sleep, and spending. In many cases it also changes the emotional tone of retirement. Life becomes smaller, narrower, and more constrained.

In other words, health is not some side issue. It shapes retirement in a huge way.

This is why getting and staying healthy is the #1 retirement activity we all need to pursue.

You do not need to become an elite athlete to benefit. But you do need to respect the compounding power of health habits.

Retirement gives you something many working people wish they had more of: time. Use some of it to protect the body that will carry you through the next few decades. Walk. Lift. Stretch. Swim. Bike. Sleep better. Eat better. Go to the doctor. Handle things early instead of late.

You can’t control everything. Aging is real. Genetics are real. Surprises happen. But ignoring health is one of the easiest ways to damage retirement.

This is perhaps the single biggest non-financial threat that has a catastrophic financial impact. Your health is your primary asset. In retirement, its value only increases. When you’re young and working, you can, to an extent, “borrow” against your health — working long hours, sleeping poorly, eating on the run. The long-term costs seem distant.

In retirement, those bills come due.

Health neglect leads to two massive problems for retirees:

1. Decreased Quality of Life: What good is being financially free if you are too unwell to enjoy it? Early retirement is often pursued to enjoy years of active leisure — travel, hobbies, time with loved ones. Neglecting diet, exercise, and preventative care steals those active years from you.
2. Increased Financial Strain: Healthcare is one of the single largest and most unpredictable expenses in retirement. Fidelity’s annual estimate regularly puts the cost of healthcare for a 65-year-old couple in retirement at over $300,000. And that’s a traditional retirement, not early retirement. An early retiree needs to cover the cost of private insurance for potentially decades before Medicare kicks in, and poor health will only make that insurance more expensive (pre-ACA style) or make out-of-pocket costs balloon. A major illness can devastate even the best-laid financial plan.

How I Avoided It:

Thankfully, I had started a basic exercise plan when we moved to Colorado. When I retired a year later, I had all the elements in place (trainer, gym nearby, time) to ramp things up and get into the best shape of my life.

I treated my physical and mental health with the same deliberate planning I applied to my finances. I made fitness a major priority.

To this day, exercise is not an afterthought for me. It’s part of the foundation. Swimming, running, staying active, maintaining some level of discipline — those things matter. And they are almost always my first activities every day.

My strategy for good health is:

• Consistent Exercise: This isn’t optional. I have a regular routine I stick to. It’s built into my schedule.
• Healthy Eating: We don’t subscribe to fad diets, but we focus on healthy eating. At least my wife does — and since she makes most of the meals, I do too. Hahaha.
• Preventative Check-ups: We treat regular doctor and dentist visits like mandatory appointments. We don’t skip them. We try to catch things early, when they are manageable and cheap.
• Protecting My Sleep: This is often overlooked, but a solid 7-8 hours of quality sleep is foundational to physical and mental health.

By treating my health as a core component of my retirement plan (not an afterthought), I am protecting my finances and my time.

8. Over-Commitment and the Burden of “Yes”

One of the more overlooked retirement killers is over-commitment.

Most people think retirement risk comes from not having enough to do. And yes, boredom is a real issue. But the opposite problem can be just as damaging. A retiree can fill life so full of obligations, events, favors, meetings, trips, projects, and responsibilities that retirement starts to feel like a job they never meant to take.

That is the burden of “yes.”

This is the sneaky social equivalent of lifestyle creep. Once you retire early, your friends, family, and community suddenly see you as having endless free time. This makes you a prime target. When you retire, your time suddenly looks available to everyone. Friends assume you’re flexible. Family assumes you’re free. Organizations assume you can help. Neighbors assume you can pitch in. You may even make the same assumption yourself. After all, if you’re no longer working, shouldn’t you be able to do more?

Maybe. But not endlessly.

This is where retirees can get themselves into trouble. After years of working under schedules they didn’t fully control, many swing into retirement thinking that every good opportunity should be embraced. Join the committee. Help with the event. Take the trip. Watch the grandkids. Volunteer for the project. Meet for lunch. Attend the gathering. Sign up for the class. Say yes to one more thing because, after all, this is what freedom is supposed to look like.

Saying yes feels good in the moment. You’re being helpful; you feel needed. But soon, your retirement calendar looks just as packed as your work calendar was. The difference is you’re not getting paid for the obligations that are eating your free time. This can lead to resentment, burnout, and the realization that you traded one set of masters (your boss/company) for another (your family/community).

But freedom is not the ability to say yes to everything. It is the ability to say yes to the right things. That distinction matters a lot.

Every “yes” costs something. It costs time, energy, flexibility, and focus. It may also cost peace. A full calendar can look impressive and still produce a life that feels crowded, reactive, and tiring. That is not the point of retirement. The goal is not to re-create the pressure of working life using socially acceptable retirement activities.

Just because I can do something does not mean I should. Just because something is good does not mean it is good for me. Just because someone asks does not mean the answer has to be yes. Retirement has made that lesson even clearer to me. One of the great values of this stage of life is control over my time, and once you hand that away too casually, it’s hard to get back.

There is also a hidden emotional side to over-commitment. Sometimes people say yes because they want to feel needed. Sometimes they say yes because they feel guilty saying no. Sometimes they say yes because retirement has not yet given them a clear internal compass, so they let other people’s priorities fill the vacuum. All of that is understandable. But it can still lead to a life that feels more drained than fulfilling.

In the end, over-commitment is dangerous because it disguises itself as a virtue. Busy retirees are often praised. Involved retirees are often admired. Helpful retirees are often appreciated. And those things can all be good. But when “yes” becomes the default, retirement starts to lose one of its best features: the freedom to live deliberately.

That’s why I think one of the most important retirement skills is learning to decline gracefully.

Not harshly. Not selfishly. Not with the attitude that no one is entitled to anything from you. But calmly and clearly. You can be generous without becoming overextended. You can be involved without being overloaded. You can be helpful without turning retirement into a long list of obligations you secretly resent.

How I Avoided It:

Fortunately my career taught me how to say no. You have to learn how to set priorities in the workplace and say no to some things — or your performance will suffer.

So I had my “no, thanks” response primed and ready. And good thing too because people wanted me to take jobs, create companies with them, do time-consuming projects for them (that I wasn’t interested it), etc.

That’s why I’ve tried to carry this rule into retirement: say yes slowly and no more often than feels comfortable.

It’s also yet another reason I like to stay “under the radar” most of the time. I don’t put myself in positions where people ask and ask and ask me to do things.

To me a great retirement is not built by stuffing every open space. It is built by protecting your time well enough that what remains is truly worth doing.

So my answer has been to keep margin in my life.

I want room for the things I care about most. I want time to exercise, write, think, relax, and spend time with the people and projects that matter most to me. I do not want every week packed so tightly that I need retirement to recover from retirement. In fact, I want mostly white space my the calendar — one or two activities outside the normal ones in a week is plenty. It is breathing room. It is flexibility. It is one of the benefits of having worked hard enough to reach this phase in the first place.

I learned the art of the intentional “no.” Before agreeing to anything substantial, I ask myself three questions:

1. Is this truly important to me? Is it a core value, like spending time with close family, or is it a peripheral obligation?
2. Does this genuinely utilize my skills and interest? For example, a community group treasurer position would be a firm “no.” It’s work that uses skills I have but don’t care to deploy for free. Helping a family member build a financial plan might be a “yes.”
3. What am I sacrificing by saying “yes”? Every commitment has an opportunity cost. If I help my neighbor with a project all afternoon, that’s time I’m not doing something else. Is the trade-off worth it?

I am extremely protective of my time, the resource that early retirement was meant to secure. And I learned that saying “no” politely but firmly gets easier with practice. It’s not selfish; it’s self-preservation.

9. Refusing to Adapt

A lot of retirement failure comes from rigidity — from not responding to changes that come along in life as well as refusing to learn new things.

People assume retirement will look one way, then reality comes in at another angle. Markets change. Bodies change. interests change. Family needs change. Housing preferences change. Energy changes. Sometimes your own desires change. All of this is normal (it’s life, after all).

The people who struggle most are often the ones trying to force retirement to match an old script. They expected constant travel, but no longer enjoy the hassle. They expected golf every day, then get bored. They expected grandparenting to fill their time, but family lives elsewhere. They expected to love leisure and discover they need projects.

The world changes fast. This is true financially (new tax laws, new types of accounts, new investment philosophies), but it’s even truer technologically, socially, and professionally. The core of early retirement is often built on skills and habits you spent decades refining. The risk is that you become a dinosaur — refusing to adapt, clinging to “how we’ve always done it,” and becoming increasingly disconnected from the modern world.

More importantly, it robs you of intellectual curiosity. The happiest retirees I know are those who are still learning. The unhappiest are those who stopped, becoming increasingly critical of a world they no longer understand.

This is why I think flexible retirees do better than rigid retirees.

I’ve adjusted over time. That has helped. Some things I thought might matter ended up mattering less (like finances, actually). Some things became more important than expected (like where we live).

How I Avoided It:

I try to stay curious and open to new things. And I try to look at possible solutions when a new challenge presents itself.

I am far from an early adopter (I don’t need to be on the bleeding edge of things), but I’m usually in the next wave once something has a bit of traction.

Using AI is an example of this. I’m not as skilled as some my age, but probably more skilled than most as I’ve spent a significant amount of time using it.

My strategy to intentionally learn new things is as follows:

• Technology as a Tool, Not a Threat: I’m not a tech evangelist, but I force myself to learn the basics of platforms and tools that can make my life (and work on this site) better. I don’t need to master everything, but I need to be competent enough not to be left behind.
• Seeking New Intellectual Frameworks: I read widely, not just in personal finance. This keeps my mind nimble and exposes me to new ideas and ways of processing information.
• The Power of the Site: Maintaining ESI Money and reading hundreds of detailed stories from others forces me to stay connected to a dynamic, evolving financial landscape. The community here (and at Millionaire Money Mentors) helps keep my analytical skills sharp.

As for flexibility, we’ve had to adjust to things like a couple moves, buying and then selling a business, selling our rental properties, getting a cat, and many other “curve balls” we’ve been thrown (or thrown ourselves) in the last decade.

A good retirement plan is not a frozen document. It’s a living framework. You review it. You revise it. You make smarter decisions as new information arrives.

That’s how you stay on offense.

Intellectual rigor isn’t just about managing your portfolio; it’s about managing your life so you remain interesting, relevant, and engaged.

10. Forgetting that Retirement is a Life Stage, Not a Finish Line

This is the big one that ties all the others together.

Too many people think of retirement as the end of the race. Work hard, save hard, invest hard, get to the number, cross the line, and then…you’re done.

But retirement is not an ending. It’s actually a new beginning. It’s also a phase of life. For many people it is a very long phase of life.

That means you still need direction, discipline, relationships, health, financial stewardship, emotional maturity, and purpose. You still need to manage your days. You still need to grow. You still need to make decisions. You still need to avoid self-destructive patterns.

The upside is that retirement can be very good…if you take the right steps — like have your finances in order and have a plan for how you’ll spend your time in retirement (and on the latter I’ve even provided a cheat sheet for the best activities to have a great retirement.) Also see A Decade of Freedom: 10 Activities That Have Enriched My Retirement for some helpful hints.

I think retirement is fantastic. It’s been amazing for me personally!

But it does not become fantastic automatically. You have to build it.

That’s really what this post is about (and the other posts in this series for that matter). The biggest retirement killers are not mysterious. They are usually some version of aimlessness, excess, neglect, isolation, rigidity, or confusion. They are the things that erode quality of life slowly until you wake up one day and realize retirement is not what you hoped it would be.

I’ve avoided those outcomes mostly by doing a few simple things consistently:

• I kept structure in my days.
• I made health a priority.
• I stayed engaged mentally.
• I maintained purpose.
• I watched my finances.
• I remained flexible.
• I treated retirement as something to manage well, not just something to arrive at.

Plus I’ve added in these 10 effective habits.

None of it is flashy. None of it would make for a dramatic headline. But that’s usually how good lives are built — through steady decisions and small daily actions, not heroic moments.

Guard Yourself

If I had to summarize retirement success in one sentence, it would be this:

Retirement works best when you have enough money and enough meaning.

That’s the formula.

Money without meaning produces emptiness. Meaning without money produces stress. You need both. That is why the ESI framework has always made so much sense to me. Earn, save, and invest are not just about getting rich. They are about building a life with options. And once retirement arrives, those options need to be used wisely.

That means guarding against the killers…

Guard against boredom by staying engaged.

Guard against drifting by having a plan.

Guard against lifestyle creep by knowing what is enough.

Guard against money obsession by remembering what money is for.

Guard against purposelessness by finding ways to matter.

Guard against isolation by investing in relationships.

Guard against health decline by respecting your body.

Guard against over commitment by learning to say no.

Guard against rigidity by adapting.

Guard against passivity by remembering that retirement is still real life.

After ten years of retirement, my conclusion is that the best retirement is not the one with the fewest obligations. It’s the one with the right ones.

It’s not the one with the most leisure. It’s the one with the right mix of leisure, purpose, relationships, and freedom.

It’s not the one that looks best on paper. It’s the one that actually works day after day, year after year.

That’s the retirement I’ve tried to build. Yes, I’m still working on making it better, but I’ve lived most of my retirement life at an 8 or higher on a scale of 1-10, so that’s pretty good. 😉

And a big key in this success has been avoiding these killers.

Ten years later, my retirement isn’t just an enduring success because I maximized my income or optimized my savings rate. It’s because I’ve spent as much energy managing my time, purpose, social life, and mental flexibility as I have my investments. The numbers are necessary, but they are not sufficient.

Avoiding these ten killers required more than a spreadsheet; it required intention, discipline, and the willingness to realize that reaching the peak is only the first step. The real journey begins when you start to live there.