10 Retirement Killers and How I Avoided Them

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:

What Kills Retirement

When people think about retirement risk, they usually think about one thing: money.

That makes sense. If you don’t have enough assets, enough income, or enough margin for surprises, retirement can go sideways in a hurry.

But after being retired for a decade, I’d say that money is only part of the equation. The bigger picture is this: retirement can be “killed” by anything that makes the life you built less enjoyable, less purposeful, less stable, or less sustainable.

That’s why I think most retirement advice is incomplete.

The standard playbook spends almost all its time on the math. How much do you need? What withdrawal rate should you use? Should you claim Social Security at 62, 67, or 70? How much cash should you keep? Those are all important questions, of course. I’ve written about them myself. But if that’s all you solve for, you’re missing half the challenge.

A great retirement needs two things at the same time:

You need enough money to fund the life you want, and you need a life worth funding.

Miss either one and retirement can become a problem. You may have millions and be miserable. Or you may have a great vision for your days but not enough financial margin to support it. The sweet spot is having both.

That’s why I wanted to write this post.

Ten years in, and I’m still here. Ten years of not waking up to an alarm, not driving in rush hour traffic, and not sitting through another pointless meeting. It’s been a decade of freedom, and as I reflect on this milestone on ESI Money, I’m struck not just by what I’ve done, but by what I haven’t done.

Specifically, I haven’t succumbed to the numerous pitfalls that can derail an early retirement.

I often write about how I got to this point – the decades of maximizing my earning power, maintaining an extreme savings rate, and investing early and often. But reaching the finish line is only half the battle. Surviving (and thriving) in retirement is the other, less-talked-about, challenge.

Over the years I’ve seen several retirement killers come up again and again in conversations with retirees, readers, and members of the FIRE community. Some are obvious. Some are sneaky. Some are financial. Some are psychological. A few start small and barely register at first, then become major issues five years later.

Below are ten of the biggest ones I see, along with how I avoided them. (And as now has become my habit, I’m breaking this into three parts — because I couldn’t stop writing! Haha.)

I’m not saying I handled every one of these perfectly. But I did think about them early, take action where needed, and adjust along the way. That has made a big difference.

Here’s my list (in no particular order)…

1. Boredom

This is the retirement killer people laugh off until it hits them.

When someone is in the thick of a career, commuting, raising kids, and squeezing in everything else around work, retirement looks like endless freedom. No schedule. No alarm clock. No meetings. No deadlines. That sounds amazing.

And for a while, it is.

But freedom without direction has a shelf life. The novelty wears off. Then a lot of retirees discover that “not working” is not actually a plan. It’s just the removal of a structure that used to organize their lives.

It’s not that retirees have extra time. Of course they do. The issue is what they do with it.

If you don’t intentionally build a retirement life, that extra time gets absorbed by the path of least resistance. Usually that means too much TV, too much internet, too much aimlessness, too much sitting around waiting for something to happen.

You know who this hits the hardest? People who are so caught up in their careers that they have no life outside of it. It is who they are. It is what they do. It is EVERYTHING to them. They have no hobbies, interests, or outside activities. It was all work all the time.

So when you remove that, they flounder…because they have nothing else in their lives. They sit around for 6-12 months, languishing and miserable, and then guess what they do…they go back to work. Why? Because it’s the only thing they’ve ever had in their lives (or at least such a meaningful part of their lives they can’t live without it.)

But the reason they give for going back is that retirement was “boring.” You can read stories like this all over the mainstream media. They have flashy titles like “He Failed at Retirement.” The points always are 1) he goes back to work because 2) retirement was boring. It doesn’t say that work is the only thing in his life, but that’s the reality of it.

The real reason he went back isn’t because he’s bored but that he has a lack of imagination. He has a lack of curiosity of the world. He has a lack of interest in life.

Of course he can’t admit this, so he says retirement was “boring.” You know what is boring? He is. Hahahaha.

How I Avoided It:

I avoided this killer by making sure I retired to something, not just from something.

While I didn’t have a concrete plan (which I highly recommend everyone have or they risk a crash and burn scenario), I “knew” I had enough interest in life that I would be able to fill up my time.

I had projects. I had writing. I had a business (a small one when I started, then I bought another one — Rockstar Finance). I had exercise. I had reading. I had relationships. I had routines (I had to remake many of these, but I was an organized person and got to the new normal quickly.) I had things I wanted to build and things I wanted to enjoy. Some were productive. Some were recreational. Some were mental. Some were spiritual. But they were real.

That matters.

A good retirement is not one giant vacation. Even people who think they want that usually end up discovering that permanent vacation gets old. Human beings need some mixture of purpose, challenge, rhythm, and enjoyment. Too much idleness is corrosive.

So my approach was simple: I kept my days full/active, but not overloaded. I wanted enough structure to stay engaged, but enough freedom to enjoy being retired.

That balance has worked well for me and is what I continue to use to this day.

2. Drifting without a Plan

Boredom and drifting are related, but they’re not the same thing.

Boredom is about not having enough meaningful activity. Drifting is broader. It’s when retirement loses intentionality.

You wake up. You do whatever seems easiest. Days pass. Weeks pass. Months pass. You’re not in crisis, but you’re also not building much of anything. You’re just floating.

This is one of the most common retirement killers because it doesn’t feel dangerous in the moment. In fact, it can feel pleasant for a while. No pressure. No urgency. No obligations. But over time, drifting creates a dull life. Then a dull life often produces dissatisfaction, even if the retiree can’t quite explain why.

It’s the frog in the pot syndrome…you slowly fade away until it’s too late.

If you ask people what they will do when they retire, many will say, “Whatever I want.” This sounds wonderful, but “whatever I want” often translates to “nothing specific.” Without the structure of a full-time job (40-60 hours a week, including commuting), you suddenly have a massive, yawning chasm of free time.

If you don’t intentionally fill that time, something else will. The great “drift” begins. You start sleeping in later and later. You spend hours aimlessly scrolling on your phone or watching daytime TV. You stop planning activities because, well, you have “all the time in the world.”

This drift almost always leads to boredom, which is a psychological retirement killer. Boredom is corrosive. It breeds dissatisfaction, anxiety, and even depression.

A partial exception to this rule: a little bit of what looks like drifting is ok/fine/recommended at the beginning of retirement, especially if you had a demanding career.

It’s ok to take some time and “do nothing.” I know I had to decompress after 28 years of high-power, high-stress situations. I needed time to just breathe and relax.

I can still remember those early days like they were yesterday. I would get up at the crack of dawn (because I was so excited to not be working — I was FREE!) and spend most of the day (after going to the gym a couple hours after I got up — once it got light out and I walked to the gym) just “being.” I would take long walks, write a bit, and read or play some video games. I would just “chill” as my kids would say.

This is all fine, normal, and even recommended to start out retirement.

But if the time starts to drag on and this habit lasts a few months, which then turns into a year or two, you are off course, drifting, and you need to send out an SOS message. You need to right the ship quickly or you’re headed for a terrible retirement.

How I Avoided It:

The plan here is the same as that for boredom.

My approach was the opposite of drift. As I said above, I retired to something, not just from a job. I knew how I’d spend my time (at least in general). I knew I needed to maintain some structure and purpose, just of my own making.

I had a vision for what I wanted retirement to look like. Not a minute-by-minute master plan, and not some rigid system that had to be followed exactly. But I did have a framework. I knew the kinds of activities I wanted in my days, the priorities I wanted to emphasize, and the lifestyle I wanted to support.

That plan became even more important as the years passed.

My specific framework for avoiding the drift involves several key pillars:

A Solid (But Flexible) Schedule: I don’t micromanage every minute, but my days have a rhythm. I wake up, exercise, then have the rest of my day to do many different things — write, read, connect with friends or family, and/or have designated leisure time. This routine provides the comfort of structure without being rigid.
The Power of Projects: I always have something I’m actively working on or planning. Whether it’s planning a major trip, improving a specific skill, maintaining the Millionaire Money Mentors (MMM) or writing for ESI Money (both of which have bottomless content needs), or taking on a substantial volunteer project, having a “main thing” is vital. These projects replace the sense of achievement and goals I once got from my career.
Active Over Passive Leisure: Reading, hiking, writing, and engaging with communities online (like MMM) are far more rewarding than endless television or social media consumption (though I have times for those as well — usually as end-of-day wind-down times). I prioritize activities that require active engagement.

A lot of people plan hard for the money side of retirement and almost not at all for the life side. They know their asset allocation down to the decimal point, but they have no answer for what they’ll do on a Tuesday in October for the next twenty years.

That’s a problem.

My suggestion is to think about retirement planning in three buckets:

How will I spend my time?
Who will I spend it with?
What will give my days meaning?

Answer those three questions reasonably well and you’ll avoid a lot of drift.

You do not need every answer before you retire. But you need enough direction to keep retirement from dissolving into randomness.

3. Spending Too Much…or Too Little

This one hits both ways.

In some cases, people spend too much in retirement, which is a killer for obvious reasons.

But in other cases (especially among those with great wealth), they spend too little (compared to what they could spend), which is a killer in a whole different way.

Let’s discuss these one at a time starting with spending too much…

Lifestyle creep doesn’t retire when you do.

In some ways it can get worse. After all, retirement gives you more time to spend, more time to browse, more time to compare, more time to convince yourself that you “deserve” upgrades. Better travel. Better cars. Better dining. Better hobbies. Better house. Better everything.

We all know the concept of lifestyle creep when we’re working: you get a raise, you buy a bigger house or a nicer car, and your expenses swell to meet your new income. It’s the enemy of the “Save” part of the ESI framework. But lifestyle creep doesn’t just vanish once you retire. In fact, it can become more dangerous.

When you’re working, your income has a ceiling. When you’re in early retirement (especially if you’re living off a safe withdrawal rate based on assets), there’s a different, potentially more precarious, dynamic. Let’s say your portfolio has a stellar year and is up 20%. The temptation to say, “Hey, we’re rich! Let’s upgrade that trip we were planning to first-class!” is immense.

This is a classic trap. One good year (or even three) doesn’t rewrite your financial plan. A portfolio is supposed to grow to outpace inflation and weather the inevitable down years. Spending a windfall instead of letting it compound is a fast track to a reduced withdrawal rate or, worst case, running out of money.

Some retirees spend too much because they’re trying to “finally live.” Some spend because they fear missing out. Some spend because they feel guilty saying no to adult kids, family requests, or social expectations. Some spend erratically because they never built a clear system for what is safe to spend.

That leads to stress.

There’s also a group that’s oblivious to their situation and spend what they think they are “owed” despite their finances not being able to support this level of spending. Unfortunately, I know people in this group.

The problem is obvious: if your lifestyle expands faster than your assets can comfortably support, you add pressure to the very phase of life that is supposed to be lower stress.

How I Avoided It:

Hahaha. Can I say because I’m cheap? lol.

For us this hasn’t been an issue because we continued to have income sources in retirement and we are relatively frugal (compared to income).

We’re pretty happy folks and don’t need to do extra spending to be happier. In fact, spending for the sake of spending can make us less happy, so we only spend when we think it’s something that will improve our lives.

We have actually had more of a challenge on the other side…

—————–

And this may sound strange in a post about retirement killers, but not spending enough money can absolutely damage retirement.

In fact, I think this is a bigger issue for many financially successful retirees than most people realize.

The reason is simple: the habits that help people become wealthy are often the same habits that make it hard to enjoy wealth later. If you spend decades earning, saving, investing, comparing prices, resisting lifestyle creep, and delaying gratification, those behaviors get deeply ingrained. They become part of your wiring. That discipline is a huge reason many people are able to retire comfortably in the first place.

But once retirement begins, that same strength can become a weakness.

Some retirees keep acting as if every dollar spent is a threat. They monitor expenses too tightly, second-guess purchases they can easily afford, and default to deprivation long after deprivation is unnecessary. They remain in accumulation mode even though the accumulation phase is over. The result is that they end up protecting a lifestyle they no longer need to protect so aggressively.

That is not always wisdom. Sometimes it is just fear. And fear can quietly shrink retirement.

It can keep people from traveling when they want to travel, helping family when they want to help family, improving their home when it would make daily life better, or paying for conveniences and experiences that would add real enjoyment. In extreme cases, retirees become caretakers of money they never meaningfully use. They worked hard to build freedom, but then they refuse to cash in any of that freedom because spending still feels wrong.

And if you don’t spend it then it’s certainly true that you didn’t need it and thus worked longer than you needed to (i.e. retired too late.) Ugh.

This is actually more common among the group I hang out with. Many retirees do not have a spending problem. They have a permission problem.

They know how to save. They know how to invest. What they do not know is how to shift gears and say, “We have enough. We planned well. We can use some of this money now to improve our lives.”

That is a critical transition.

Of course, I am not suggesting reckless spending or the kind of emotional consumption that often passes for “living your best life.” I am not talking about blowing up a sound retirement plan because you suddenly decide you deserve every luxury you skipped in your working years. That is foolish. But being too stingy can be foolish too. There is a middle ground between waste and needless restraint, and a good retirement usually lives there.

How I Avoided It:

I wouldn’t say I have “avoided” this. I would say that I’m working on avoiding it (or at least lessening it.) Haha.

We’ll start with the fact that I absolutely saved too much for retirement and I could have retired 5-10 years earlier than I did. So there is that.

Then on top of that I took one good income source into retirement (rental real estate) and created more (ESI Money, Rockstar Finance, MMM, dividend stocks, and more). Not a bad thing, of course, but if I had known I could do that, I could have retired even earlier (maybe into my 30’s).

We have spent at least $100k for most of the years we’ve been retired. It’s just that we’ve earned more than that. So our assets have grown dramatically.

Even at $100k spending, we still were too frugal in areas and the MMM mentors have really helped us open up the purse strings a bit. I knew we needed to spend more and so we have — mostly by giving more money to charity. We don’t need much more and giving brings us joy, so why not?

The purpose of wealth is not to sit untouched in an account simply so people can admire it (at least for most people). The purpose of wealth is to fund a good life. That includes security, of course. It includes margin. It includes protection against surprises. But it also includes enjoyment, convenience, generosity, comfort, and the ability to do things that matter to us.

If spending supports those goals and fits within the broader plan, then it is not a failure of discipline. It is the successful use of discipline.

A lot of people need to hear that once retirement begins, there is a time to loosen the grip a bit. Not abandon prudence. Not throw away the spreadsheet. Not stop paying attention. But loosen the grip. You can spend intentionally and still be wise. You can enjoy your assets and still be responsible. You can improve your lifestyle in meaningful ways without falling into lifestyle creep.

This is especially true when the spending improves daily life, not just status. A more comfortable home, a better mattress, easier travel arrangements, a helpful service, a hobby you love, time with family, or giving more generously can all be excellent uses of money. They are not just expenses. They are ways of converting financial resources into a better life.

That, after all, is the point.

One of the saddest retirement outcomes is when someone has done all the hard parts successfully, built substantial assets, and then lives as if they are still one bad month away from financial ruin. That mindset may feel safe, but over time it can create a smaller and narrower retirement than necessary. The person has enough money, but never quite lets themselves enjoy what that money can do.

So yes, not spending enough can be a retirement killer.

It kills experiences. It kills flexibility. It kills generosity. It kills comfort. And sometimes it kills gratitude, because the retiree becomes so focused on preserving wealth that he forgets wealth was meant to be used in service of life.

The balance I think works is this: save aggressively when you need to, spend thoughtfully when you can, and never confuse hoarding with wisdom.

In retirement, money should be managed carefully. But it should also be put to work making life better. If you have truly planned well and have the assets to support it, then one of the smartest things you can do is learn how to spend with confidence.

Part of good retirement finance is giving yourself permission to spend appropriately on what matters. Another part is having the discipline not to let every emotion turn into an expense.

That combination is underrated.

That’s it for this post!

Stay tuned for the next part soon.

What Kills Retirement

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