The Story of a Perfect Retirement that

Ended in Tragedy


A Cautionary Tale of Retirement Disaster

Welcome to Retirement Is All On You, where our mission is focused on How to Plan AND Sustain Your Successful Retirement.

While we haven’t met, it’s a safe bet that you’re one of the elite few who are serious about building the secure retirement you deserve.

Maybe you’ve come here to learn specific steps for creating a financially solid retirement.

Perhaps you want to avoid a retirement disaster, and want to learn, from a real-life story, how to steer clear of the sinkholes.

Or maybe you’re already retired, and you want to ensure your retirement is secure for life.

In your quest to learn all you can, you’ve likely read hundreds of books and articles, and visited countless sites that talk about what you should do.

And that’s great.

But what’s missing from nearly all advice is the equally – and sometimes even more – important wisdom on what to avoid.

That’s right, you can do all the right things, but if you don’t avoid the wrong ones, you can still destroy your retirement.

Retirement Is All On You is based on three mandatory pillars of a secure retirement:

1. What you avoid in retirement planning, preparation, and execution is as, or even more important as what you do.

2. When you reach your big day, you cannot not ‘set it and forget it’. To maintain financial security for life, you must embrace your agile retirement.

3. Life can cause us depart from our best intentions The best source of learning on how to avoid departure is to see how others fell off the path. Retirement Is All On You is based on a real-life retirement story.

If you’re New Here, get the most out of our resources by working your way through the links in the three pillars above. Then check out our latest articles at New Articles.

Your time here may be with best investment you ever make for your secure retirement!


With So Much Retirement Info Already Out There, Why Retirement Is All On You?

 We take a different approach. First, we give equal balance between how to plan your successful retirement and how to avoid disaster. Second, what we share is directly related to a real world case of exceptional retirement planning and preparation success, followed by tragic disaster after retirement.

This site is what I learned directly from helping my aunt pick up the pieces from her retirement train wreck after my uncle passed away.

Our purpose at Retirement Is All On You is to share key perspectives to ensure retirement success for the rest of your life instead of tragedy somewhere along the way.

Regrettably, in retirement, there are no do-overs. Once you reach your big day, you’re stuck with whatever financial reality you’ve built.The stakes are simply too high not to learn what to do, what to avoid, and how to remain agile throughout your retirement.

My Aunt & Uncle’s Sad Tale of Retirement Tragedy

It wasn’t supposed to end this way. My aunt and uncle worked exceptionally hard and did what few can. They retired at 55 and 48 respectively, to pursue their passion for boating, travel, and enjoying their two homes and one dog.

My uncle was a skilled tradesman, grabbing every hour of overtime he could in order to bolster their retirement savings. He took an early buyout and received a modest but immediate pension.

My aunt was a nurse who worked loyally for the same doctor for over 30 years. While she didn’t have a pension, she put a respectable percentage of her salary into retirement savings and was better prepared than most.

Decades ahead of retirement, they sought financial advice from a competent financial planner and mapped out their expected income, assets, anticipated expenses, and projected returns. They even bought the land upon which they would build their dream southern winter home.

My uncle’s pre Social Security pension covered 45% of their living expenses, so a solid return on their assets was essential to support their lifestyle, bridge them until they were eligible for Social Security, and ensure annual withdraws wouldn’t undermine their long-term financial health.

Despite this, all seemed to be in balance, given the assumptions for returns, lifespan, and inflation, circa the late 1980s. Most importantly, they had amassed an enviable level of assets, equivalent to $1.1MM in today’s dollars.


Their big day arrived with much excitement and celebration. At their joint retirement party, I remember my uncle grinning ear-to-ear as he handed me a business card that said RETIRED!

As an early twentysomething with many decades of hard work ahead, I was both happy and envious. They had reached a point where they could enjoy life on their terms, no longer subservient to a Monday through Friday 6:00am alarm.

As months added up to the first year, their retirement was off to a great start. They were more relaxed, and enjoyed their wide circle of friends and social activities that came from boating.

Two years after retirement, construction was finished on their southern dream house, far from the pain of the winters they endured during their working years. With their retirement plan complete, summers were spent boating up north, winters fishing down south.

Although both were in good health, they wisely updated their wills, durable powers of attorney, living wills and other documents to ensure their final wishes were known, and their assets would be distributed as they wanted.

As the late 1980s turned into the early 1990s, the stock market was just revving up for its many-year tear, which helped swell their retirement investments above the projections in their original financial plan. Their rewards were well deserved, and life was good.

But then, almost out of nowhere, came the first giant crack in their solid retirement foundation.


Their friends kept bragging about the phenomenal returns their big brokerage full-service broker was earning by ‘trading’ their account. Although my aunt and uncle’s current portfolio reflected their lifelong conservative approach, the temptation became too great.

They signed on with their friends’ broker, moving all of their investible assets over.

The broker convinced them that she could probably (of course no guarantees!) outperform the market, and they signed off on permission for her to trade on their behalf so ‘opportunities could be quickly seized.’

With a bull market firmly in place, for the first few years, she initially delivered impressive market-beating returns, and the brightened financial picture made their retirement feel even more secure.

They excitedly shared regular portfolio updates with me, eventually labeling their broker a genius. Despite that I was in the earlier phase of my financial education, I thought that what she had them in was well beyond their risk tolerance and understanding of how those investment instruments can behave.

Then the market began to gyrate, and their monthly statements showed large drops. They started to lose sleep and grow angry. Their broker assured them that everything would be fine, they just needed to sit tight and ride out the ‘paper losses.’

After a many month stretch of consistently negative returns that caused all their gains and half of their hard-earned original principal to evaporate, they finally pulled out and ended their relationship with the genius.

They were smart to preserve at least some of their capital, and regain the peace of mind that comes from not having a pit in their stomach every month when they opened their account statement. But they should have made that move many months sooner.

As much as it was clear their broker didn’t have their best interests in mind, I believe they also needed to accept responsibility for what happened.

Ultimately they had, as many of us do either periodically or consistently, operated on a toxic combination of greed and ignorance.


After closing out their brokerage account, they sought to reinvest their remaining cash at no risk.

Not having much investing experience, and unwilling to invest in a fee-only financial planner, they attended many free dinners that were hosted by commission-based financial salespeople. They went without having a sense of the presenters’ financial background, intentions, or objectives.

They somehow believed they could side step the truth that there is no free dinner.

In avoiding professional paid advice, they committed a common mistake of not investing a little to save a lot. I’m not suggesting that every event they attended was hosted by dishonest salespeople. but my aunt and uncle’s grasp of the how the proposed financial instruments truly worked – the risk, the fees, the restrictions, comparative performance – was limited.

What followed is that they began carving up the remains of their portfolio among multiple life insurance policies, disease specific insurance, annuities, and a few small bank CDs, across more than a dozen institutions and numerous salespeople.

They made their finances unnecessarily complex, with no offsetting benefit.

What was worst amidst a terrible situation is that they put the majority of their liquid assets into one of the worst possible annuities. Terrible terms. High fees. Uncompetitive returns.

Their negative experience with their broker caused them to swing from a very high-risk profile to one of no risk to their principal.


The other significant problem is that although they lost half of their principal, they hadn’t adjusted their spending. They did not update the financial plan that guided them earlier to create a secure retirement, and that should have been immediately updated to reflect their asset collapse.

Had they done this, they may have gotten a wake-up call while there was still time to at least partially address the growing assets-and-income-to-spending gap.

In terms of how to move forward, the right answer, which could only be developed by someone who would review their entire financial position and needs, was to have at least a portion of their assets intelligently exposed to some risk in order to deliver a higher return.

They also would have been advised to significantly cut their spending, to bring it back in line with the reduced asset base and the lower return their risk-free strategy would deliver. At this point they were sustaining two homes, three cars, and the expenses of a large cabin cruiser.

All affordable under their previous plan but certainly not within their new financial reality.

Even just eliminating one of the houses and selling the boat would have gotten them back on track for a secure retirement, but they just pressed ahead in digging a deeper hole by maintaining their current lifestyle.

The severity of their financial challenges would regrettably be eclipsed by a new and more devastating tragedy.


My aunt’s doctor found a lump on her breast, and suggested a routine lumpectomy. Having previously been diagnosed with diabetes, she went to the hospital for what was to be simple outpatient surgery. All seemed to go well and she was released the next day.

Unfortunately testing showed cancer. But before she was able to schedule follow up tests to determine if it had spread, she began having difficulty walking. She was significantly overweight so, at first, her doctor wasn’t too alarmed and just suggested she take it easy at home.

As the pain and swelling grew worse, she was rushed to emergency. It was discovered that she had severe clotting in both legs. Her doctors worked feverishly to dissolve the clots, but to no avail. In order to save her life, first one leg was amputated, and then the other.

Her situation was so dire that her cancer was ignored as her doctor confided that it was unlikely she’d make it out of the hospital because she was still filled with clots, and any one of them could go to her lungs and cause immediate death.

Miraculously, after six weeks of nursing care and post operative rehabilitation, she was ready to come home, now a double amputee. My uncle dutifully committed to do what it took for their lives to remain as unchanged as possible.

Neither of them anticipated exactly what their future would now hold emotionally, physically, or financially.

One complication that made my aunt’s situation extraordinarily difficult, even among double amputees, is that one leg had been taken far above the knee, the other just below it. With poor overall health, she struggled to learn to walk on one artificial leg so that she might be able to get around on crutches, but found it too difficult and resigned herself to life in a wheelchair.

They quickly realized she needed a specialized van to accommodate her permanent mobility limitation. Such new vans can cost $50,000 or more, and insurance provides no reimbursement. This certainly was not in their budget, but a necessity nonetheless.

There were other new and unexpected expenses also not covered by insurance. Many of the biggest were driven by the continual denial that she would never resume her previous life.

One expensive example was that my uncle held onto their boat she could no longer board, and that he would therefore no longer use. While after two years he resigned himself to selling it, his reluctance caused him to set the price so high that there were no buyers, and then the Great Recession hit, drying up the market altogether.

He ended up being stuck with the boat for 6 years. The increased carrying costs (annual dockage, storage, winterization, maintenance), and the reduction in sales price versus selling it years earlier, cost them over $40,000.

There were also lifestyle expenses not originally in their retirement budget, like a huge spike in dining out, as my aunt was no longer able to cook, and my uncle had no interest in learning. It sounds like a small thing, but two people eating out all the time even moderately can easily increase food costs by over $8,000 annually, which can have a significant impact on a retirement budget.

After what my aunt had been through, never expecting to leave the hospital, and on medicines to control her diabetes, blood pressure, blot clotting, and other conditions, she understandably had modest expectations for her life span.

It was on this basis they continued to rationalize not adjusting their longer-term plans to accommodate the possibility she would live many more years. Instead, they adopted an avoidance mentality, and who could blame them?

For instance, their primary residence was not adjusted to accommodate her wheelchair. The living room became her bedroom, but she needed daily help getting in and out of bed.

She also could not leave the home unassisted, as there were no built in ramps. Instead, a steep temporary ramp needed to be set in place every time she left.

The cost of modifications was minor, but they just refused to do it. This one thing made her completely dependant on someone every morning, evening and anytime she wanted to simply go outside.

Travel for my aunt was difficult, and she needed to remain close to her team of doctors, so they had a five-year stretch where they visited their southern house only once, staying only a few weeks.

While retaining the southern house wouldn’t make sense to most, it was a compromise because he wanted to sell the northern house and move south, and she wanted the opposite. So this expensive two-house solution somehow made sense to them, but resulted in an unnecessary burden to sustain a residence that was vacant for 99% of over half a decade.

With my aunt’s health challenges and my uncle being seven years younger, she never expected to outlive him. But she did.


My uncle was a rugged football player and valiantly served our country in the Air Force. He was one of those bigger than life guys who we believed would live forever, based just on sheer force of will.

Although he had bypass surgery in his 50s, he reached his 70s with relatively good health and an activity level of someone years younger. One day he noticed abdominal swelling. Assuming it was minor he waited too long to get it checked. Then it got much worse and he was forced to take action.

His doctors concluded he was suffering from liver cancer and cirrhosis, caused by hepatitis C. He’d never been tested for hepatitis C, but his doctor believed he likely contracted it from a transfusion after an injury in the 1970s.

His doctor shared that he needed a transplant, but he was not a candidate due to age. They would do the best they could with various treatments to stabilize him, but there was no cure.

Regrettably, the precious months following his diagnosis were lived in a state of complete denial, just as with my aunt’s medical situation, and just as with their financial situation.

He never shared with my aunt the seriousness of his condition, nor that he was terminal. After his diagnosis, a few months passed between our visits, and when I saw him next I was alarmed and saddened. It was clear just from looking at him that the disease was quickly destroying his body,

He’d lost 70 lbs, his skin was gray, and there was no sparkle left in his eyes as he leaned on a cane to make a short walk that he’d done briskly only months prior. Despite the obvious signs, he kept telling everyone that everything was going to be okay, and he would recover.

During my final visit with him, which was a few weeks before his passing, I asked him some very specific questions about his diagnosis and treatment. Based on the details he shared, there was no question he had little time remaining, but he refused to admit it to me or anyone else.

If you knew him, this would be no surprise, because being the hearty guy he used to be, he simply couldn’t accept his fate. While that’s a personal choice to which he was entitled, he deprived my aunt and us, her eventual caretakers, of the opportunity of preparation.

As his liver completely failed, a form of dementia, caused by the build up of toxins, quickly set in. After a brief hospital stay he was sadly gone.

At first I couldn’t believe it. How could this happen so suddenly? We all expected my aunt would pass first. She was completely unprepared. How would we get her through this? There were so many things to consider. How should the priorities be set?

My aunt was understandably in a complete tailspin. She lost her life partner, her caretaker, and the unsustainable way of life he was able to provide her through his intense daily care. There were no contingency plans. Due to her handicap, she even lost her beloved dog, who was sent to live with a far-away relative because she couldn’t care for him from her wheelchair.

We all immediately pitched in. My mom helped plan the funeral because my aunt was still stunned and my uncle left no final wishes.


The first financial shockwave hit when my aunt didn’t have the cash to pay $7,200 for the funeral. At that point both my mom and aunt asked me to get involved to help “figure things out.”

Our financial discussions in recent years were limited, but I was more than happy to assist as they didn’t have children and had always treated me like a son. Anyhow, I was their executor, so I expected someday to be called upon to help administer financial matters, so this was an opportunity to prepare for that eventual role.

I thought the liquidity issue in covering the funeral to just be my aunt’s distress over losing my uncle, and nothing more. With their prior investments, I thought surely they had enough liquidity to find $7,200. It was probably just a matter of moving some money from one account to another.

Sadly, I had absolutely no clue what I was stepping into.

Not the depth. Not the complexity. Not the barriers, or my aunt’s anguish over their financial situation. Nor the uneasy feeling that comes when you take an intimate deep dive into a loved one’s affairs, and unintentionally see how their perception checks up against the awful reality they created.

Or the fact that I would uncover dozens of ugly financial mistakes that were made during the prior decades.

I did, however, have the sense that in the last few years things were starting to slide. My aunt complained that she could barely find the time to pay all their bills, and that two houses were financially draining.

I remember when they remortgaged their primary residence that had been paid off for years, and then remortgaged their southern home at a much higher balance. One was tied directly to needing the first of their two handicap vans, for which they wanted to pay cash because mortgage interest was lower. This move could be rationalized even thought it’s financial insanity to initiate a mortgage so late into retirement.

The remortgage of their southern home was more suspicious, but we assumed they knew what they were doing. And even if they didn’t, they didn’t owe us any answers about their financial affairs, nor did they ask for any perspective from me.

To make matters worse, they both, especially my aunt, had a long-time hoarding problem that got worse after she lost her legs. Their house became so packed with stuff that I was unable to bring dinner over and sit with them because there wasn’t room for even one guest to find a place to eat in their 1200 square foot home with basement.

The clutter was made worse by the non-stop buying they both did on cable shopping channels as a form of entertainment. While TV shopping in itself isn’t necessarily a bad thing, what my aunt bought was not grounded in reality.

As their loved ones, we certainly could see what was happening, but they were adults and had no signs of cognitive impairment. I would ask questions from time-to-time regarding their ‘inventory’ situation, but the response was typically a gentle bud-out. It’s a free country and our hope was that they would stop buying when the space ran out.

After my uncle’s funeral we quickly got down to business. I hoped that focusing on somehow building my aunt a less complex financial future could help her begin to bridge her deep grief.

But before worrying about a will update and elder care plan, both important considerations given her situation, the immediate crisis remained of figuring out why a credit card was needed to pay for the funeral.

The first step was to locate key financial statements in order to pull data on checking, banking and other balances. Knowing their monthly expenses were significant with two houses, I knew that raising immediate liquidity was critical to ensure that she didn’t slip into default.

She handed me stacks of documents, many belonging to accounts that were long closed. Sort them as I may, I couldn’t always ‘follow the bouncing ball.’ Documents like annual privacy notices were neatly arranged and sequenced, whereas the ones that really mattered, like banking and annuity statements, were out of order or missing altogether.

If all the documents were at least in one heap, I would have had a chance at rebuilding the paper trail. Unfortunately, they were spread throughout the house and basement, and the piles of other papers and junk made piecing the puzzle together quickly all but impossible.

I’m not a forensic accountant (or any other type of accountant), but I decided that if I dropped back and started with annual tax returns I could at least identify income sources and then track those back to the institutions.

I located statements for what she believed to be her only currently active bank account, which showed a $2017 balance in checking, and just a few dollars in savings. This is where my real panic set in as her mail box was swelling daily with more bills.

I knew my uncle had some life insurance, but my aunt wasn’t sure how much and, again, gave me a heap of documents. One policy showed the provider changed three times, and then there were no documents for the prior 2 years. Did they redeem it early? Was it cancelled? Did the policy move to another provider? My aunt didn’t know and couldn’t remember.

I researched how I might do a life insurance search myself, but there was an unbelievable void of useful Google results. It looked like there was no easy way. Without the other puzzle pieces yet identified, let alone assembled into a cohesive picture, life insurance was my best chance to raise near-term liquidity, so we continued our focus.

My aunt was certain there was at least one policy in place that she thought was worth $100,000, so I had her begin calling the provider listed on latest paperwork to determine what happened to the policy previously in force.

We quickly found $125,000 total in life insurance, including a $100,000 policy my uncle initiated after my aunt’s health crisis. The near and mid-term liquidity crisis would be solved provided I could get her through the next 2-3 weeks while we waited for payment.

While the bank account was essentially empty, I miraculously found paperwork for an annuity for $54,000 that was purchased from the proceeds of a closed bank account from another institution. Although there was no recent statement, I knew the annuity was active because it showed up as an income source.

After reading through the terms, I couldn’t imagine why they would have purchased such an instrument. I came across their notes, and it looked like they committed to exorbitant expenses and a 7-year tie up period in order to gain a measly 1% extra in annual return over simple bank CDs. Unbelievable.

But as I dug into the contract, I came across the death redemption provision, and noticed that the annuity was wholly in my uncle’s name. Bingo. Immediate liquidity without a redemption penalty.

I called the bank’s ‘financial planner’ who sold them this gem. It took five calls over four days to get him to call me back. No surprise that he didn’t want to hear from me. After explaining the situation, he offered his condolences and said that he had no idea they had liquidity problems.

Despite learning of their situation, he still suggested I consider transferring the annuity to my aunt instead of redemption. Seriously?

While I still had no idea of the true monthly obligations, $145,000 in life insurance and $54,000 from the annuity would give us plenty of breathing space while I figured the rest out. And the rest would be particularly ugly.

Most financial problems are not created overnight, nor are their root causes usually a single factor. I would learn this to be particularly true in my aunt and uncle’s case.

My next focus was on the source and amounts of their monthly expenses. Although I had encouraged my aunt to set up auto debit for years, she insisted on paying nearly all her bills by check. Her resistance to automation was finally a benefit because, while she didn’t have a good handle on most of her financial statements, her checkbook and bills were organized. I began my deep dive.

In addition to the basic living expenses we all experience, the framework of their finances was created by maintaining two complete households, an expensive handicap van, and a layer of incremental expenses (unreimbursed medical, dining out, home services, etc.) directly related to my aunt’s condition. No real surprises there.

However, as I began to fill in the numbers to all their basic living expenses, I quickly became alarmed. I’d had a glimpse of their income from the annual tax return (and hadn’t yet done a deep analysis), but as I added each new living expense I uncovered, it began to swell quickly beyond their annual income.

Given that the liquid assets upon which they could withdraw were zero, how could that be I wondered? Maybe this is just a one-year instance? My digging continued.

In my first high level pass, annual home, car and living expenses totaled $47,245 versus an income of $39,557. The gap of nearly $8,000 was the first big piece of an ugly puzzle.

What I hadn’t looked at yet was the credit card and consumer debt. On top of the $47,245 of annual expenses, they were making over $18,000 annually in credit card payments. On the face of it, this didn’t tell me much, because perhaps they were paying down existing balances that were now paid off.

How I wish that were the case.


I once heard a great quote: “If your upkeep exceeds your income, it will lead to your downfall.” Too many bankruptcies are caused by credit card debt that grows out of control, fueled by persistently living beyond one’s means. Unfortunately this gap-filling dynamic would also be the case with my aunt and uncle.

As I dug into the credit card statements, I discovered 36 active cards, with current balances totaling over $55,000, and a home improvement loan that took total consumer debt to $61,000. Further, the annual $18,000 in payments was mostly going to interest, with minimal principal pay down, and total debt was expanding every month.

The current credit card debt and the home improvement loan represented over a year-and-a-half of their total annual income. At this ratio, it would be impossible to pay off unless radical changes were made to free up some income that was being 100% consumed just to cover part of their living expenses.

Drilling into the source of the ballooning debt revealed a sad truth consistent with the spending-to-earning chasm I discovered: they were filling the gap between their lifestyle and income with their 36 credit cards.

Their addiction to TV shopping and overstocking was adding to their financial burden, but much of the credit card spending fell into 4 categories: groceries, medical, dining out, and home maintenance.

So the terrible truth was that their problems were not caused by binge-spending on frivolous items or taking extravagant vacations, but instead by maintaining a spending level mostly on routine items that was persistently beyond their income level. Their excess frivolous spending like TV shopping just dug the hole a little deeper.

If I deducted the spending mentioned earlier related to my aunt’s health challenges (dining out, medical expenses, wheelchair accessible van), as well as the interest portion of their credit card payments, their annual spending was well within their annual income, as well as close to the annual spending used to develop their financial plan of decades earlier.

With this second major piece of the puzzle in place, the picture became clearer: when their investments were providing higher returns, and my aunt’s health was good, their income and expenses were nicely aligned and assets were growing because withdraws were small. The recipe for an ideal, happily-ever-after retirement.

But when life happened – 50% depletion of their liquid assets due to investment losses, a change in investment strategy leading to lower than anticipated returns, and direct and indirect costs from health problems – they began a two decade slide into the financial abyss.

It happened gradually. At first, the excess spending was caused by a drawdown in assets. Next, they slowly turned to their credit cards, but they did not become alarmed because the unpaid balances grew slowly.

Then, as cards maxed out they simply opened more cards, which were easily granted because they stayed current with the minimum monthly payments. To make matters worse, they didn’t even seek temporary relief by rolling existing balances to new zero interest cards, which would have at least provided a little expense reduction.

Further, there was continued avoidance of reality on the part of both. From my uncle’s perspective, my belief is that he assumed my aunt’s lifespan would be regrettably short, and therefore they wouldn’t have to fill the gap for long. Once she passed he would move south and sell the northern home and handicap van, immediately reducing their expenses by nearly half. I’m certain he did not expect a nine-year period of significant excess spending.

From my aunt’s self-admitted perspective, her expectation was that she would not have to clean up any financial mess because she, too, thought she would pass first.

And from both perspectives, in a desire to ‘keep the peace’, they maintained two households nine years longer than they should have. Even without the benefit of hindsight, they should have sold the southern house and then, if my aunt passed first, my uncle could have easily bought back in without having carried nine years of expenses for a house they rarely visited.


With pieces of the picture becoming clear, I began to understand the mess that I would have to clean up. Like the fact that both homes were mortgaged, one to the degree there was likely zero equity.

Of course while I was sorting all of the finances out, life was still happening. During my uncle’s final few weeks, he fell at home and was bleeding profusely. My aunt called for an ambulance and sadly the crew could not get a stretcher into their double-stuffed house.

As a result, the EMS crew reported her home as an unfit environment for a paraplegic, and she was confronted by Social Services. They informed her they had the authority to remove her from her house, but that she had a window of opportunity to clean it up so that it would be safe enough for outside health care providers to come in to assist her.

When my uncle passed the following week, we went into overdrive to begin removing some of the junk, and she agreed to a self-funded consultation with a hoarding psychologist.

My mom attended the session which provided great insight. The primary take-away was that my aunt had many regrets in life, and the psychologist helped us understand how the things she hoarded provided some form of security and comfort. The items that we viewed as mere scraps of paper and broken appliances were valuable in the memories or intentions they represented.

The insight filled me with empathy and understanding for what I thought was a situation simply solved by renting a few large dumpsters. It helped me see beyond my own frame of reference that was at the opposite end of the clutter spectrum, as I crave zero clutter and open spaces.

During another session with a second psychologist, he asked my aunt point blank, on several occasions and in multiple ways, if her possessions were more important than the people in her life. She consistently said yes.

This helped frame the difficulty of addressing a psychological problem that manifested into a living quarters problem, as well as a contributor to the financial problems.

I’ve tried to reconcile that irony that we have more financial information than ever, yet sound financial management continues to be a persistent challenge for many.

My experiences with my aunt helped me understand firsthand why logical suggestions like “just stop spending so much” don’t always work.

Often, difficult financial situations are simply a symptom of an underlying issue that’s not, at least to begin with, money-related. So unless the underlying issue is addressed, just treating the symptoms will not result in a lasting solution.

In her case, the underlying issues were the dynamic that stuff bought comfort, which drove the hoarding mentality of over-shopping and overbuying. More stuff meant more comfort.

The avoidance approach where they resisted fixing their finances to fit their new reality (for instance they could have easily sold the boat or one of the homes) allowed them to, at least in their own minds, delay accepting a present and future that was very different from a happier past.

I would have thought that the logical argument — that de-contenting was necessary to avoid the prospect of losing her house – would have been a sufficient motivator for my aunt to simply part with items I considered mere trash. But even the reality of being forced from her home did little to overcome the strong emotional pull of keeping her stuff.

With this insight, combined with many discussions with my aunt, I finally had my ‘ah-ha’ moment on the overall situation. The following things came into focus:

– The 36 credit cards provided a level of security that more things could be acquired on a moment’s notice, as well as a means for sustaining an unsustainable lifestyle that had its basis in avoiding acceptance of reality.

– The clutter she buried herself in was tantamount to being continually surrounded by her memories of a better prior life. Taking the stuff away was like ripping the memories away, even though the stuff could cause devastating outcomes like the loss of her home, or even death if there was a fire.

– The resistance to cleaning up her financial situation, as much as the prior situation was stressful for her, was that we were deconstructing the life she and my uncle had created. From my outside perspective, it wasn’t a life that would have brought me comfort, but it was their life, and she wasn’t ready to move forward from it yet, even though not changing would cause continued pain.

– Holding extreme amounts of credit card debt, and thereby paying up to 20% on the balances when she had the means to pay it off, had its essence in her desire for a form of financial security that’s based on faulty mental accounting most of use in some way in managing our finances. In her case, paying off the debt would mean she had less money in the bank and therefore she would feel ‘poorer’, even though it would have given her up to a guaranteed net 17.5% return (she was paying 20% on her credit cards while earning 2.5% on her $54,000 annuity). Also, they purchased a $54,000 annuity only 18 months before my uncle’s death, when credit card debt had already ballooned; they could have otherwise used that cash to pay down debt and been in much better position.

My single biggest takeaway is that we really need to have someone in our lives who can help us see our financial situation more objectively. Some of us are better than others in grasping reality, but I believe it’s true that no human can see their financial life exactly as it really is.

To the degree we have a sense that our objectivity is compromised (and she did understand that, on some level, hers was), getting neutral outside help can be the wisest investment one can make.

For her, I had at least some perspective to help her quickly, and at no cost. For most, however, hiring a fee-only trusted source, who can review and analyze their entire financial position, objectives, needs and hopes, can provide financial payback many times over. Further, outsiders can bring valuable benchmarks, such as “people at your income level typically have X in assets and spend X% on their living expenses.”

Sometimes one’s significant other can help bring partial objectivity to a financial situation. I say partial because with the relationship aspect folded in, along with your partner’s understandable self-interest, 100% objectivity remains impossible.

My aunt and uncle’s case was the worst possible scenario, where each had zero objectivity and their behaviors were additive. Both were jamming the accelerators to financial hell right to the floor, without letting up.

In fact, my aunt relayed instances of one-upmanship, saying: “The more he spent on dumb stuff, the more I spent because I deserved it.”

Just as in marital counseling, an outside financial coach or counseling may have given them a source of objectivity to see where all this was headed. Maybe my aunt could have gotten the help she needed before things got to this point. Maybe an outsider could have helped them recognize the avoidance mentality that we saw so clearly, for so long.


With short-term liquidity in place to cover the bills, and the house 20% de-contented, I was eager to press to get to the goal of a cleaner house and finances completely in order. The psychological insights gave me the perspective to proceed more gradually, however, as my aunt needed to process the many things that had happened in the four months following my uncle’s death.

I recognized that my aunt was starting to make the following realizations:

– The clear understanding they’d ruined their financial lives and because of it, her future financial reality would be significantly different.

– Our financial clean-up would eventually result in zero debt but little cash or investments, undermining her previous false sense of security that came from higher balances.

– The need to permanently align spending with her income, which would now be lower due to the partial loss of my uncle’s pension, but offset by the cost reduction of selling the southern home and eliminating the credit card interest

– The loss of her caretaker meant a permanent change in her way of life as we and her part-time help could not fully compensate for all my uncle did for her.

– The loss of someone else to blame for her financial circumstances. Her future was now all on her.

– A shift in being surrounded by all her stuff (and therefore the memories and security it brought), to an environment that was a bit more tidy.

– The need to come to terms with the reality that she needed to plan for future contingencies if her health deteriorated further.

– Becoming comfortable with the accountability and intrusion of me overseeing her financial decisions, at her request

The last point was one that had a much bigger and more immediate positive impact on my aunt’s finances than I expected.

When I uncovered the 36 credit cards, my aunt was grounded in enough reality to be deeply embarrassed. I told her that I wasn’t there to judge, but only to make things better for her future. I asked for her commitment that she would stop using all but two credit cards, and to use them only for essentials, and remarkably she complied immediately.

Next I asked, with the life insurance payout funds, she pay down every single outstanding balance as each statement came in, and then close out and cut up the credit card. She complied.

She was also fortunate that one of the biggest balance cards, at over $18,000, was solely in my uncle’s name, and the credit card company miraculously agreed to forgive the balance. This immediately reduced her total credit card debt by nearly a third.

Things were finally starting to look up!


Things were now sorted out to the degree that we could enter the next and final phase of financial clean-up which included:

– A revised will

– Consideration of an elder care financial plan

– Liquidation of unneeded assets, including the southern house, to increase cash and decrease non-credit card debt

– A long-term budget

– Paying off all remaining debt, including the mortgage on her full-time home and her handicap van

– Contingencies for assisted living if her health required

While I had expected to be at this point about a month after my uncle’s passing, it was now six months in, but it was still encouraging to see the light at the end of the tunnel.

During clean up, one complication was that there was both a will and a trust. The will came first, and the trust was written later, without my aunt’s full recollection. The distribution of property changed from the will to the trust, and my aunt didn’t realize that either.

Further, after my deep dive, which included meeting with the salesperson who was part of developing the trust (the attorney had since died), it became clear the trust was essentially no more powerful than the will as they’d never moved their assets (homes, car, etc.) into the trust.

The date of the trust coincided with my aunt’s near death hospital stay, and therefore it made sense her recall was poor. Unfortunately, the trust also contained an annuity that was purchased concurrently.

This annuity represented about half of their liquid wealth at the time, and my observation was that it was an extraordinarily poor choice as there was no death benefit, and they were now entering year 10 of the stream of payouts, yet my aunt was still over five years away from even recapturing the principal. What a horrible financial instrument for someone in their 80s to be holding.

As I was sorting things out, my aunt received notice she that was part of a class action as a buyer of the annuity because the company behind it was being sued for unfair sales practices. Based on the quality of this annuity, and suitability for their needs, it was likely she was indeed a ‘textbook’ victim.

In fact, one new attorney I would later consult believed that it’s likely the trust was sold-in with the primary purpose of packaging the unsuitable annuity. I’ll never know the whole story, as the two primary parties – my uncle and the trust’s attorney – were deceased. One thing that was sure was that my aunt and uncle had met the attorney / salesperson duo at a ‘free’ dinner. Damn that spaghetti dinner advice!

I next sought a financial elder care attorney to help us update the will to reflect some changes I knew my aunt had in mind, as well as update critical provisions where my uncle had to be replaced. I also wanted to understand if she would benefit from specifically an elder care financial strategy, as it was likely she would eventually need some form of living assistance beyond just periodic visits from an in-home helper.

Over the space of two months, I talked to eight potential attorneys. After briefly explaining our overall situation, I was consistently given estimates of $5-10,000 for an updated trust and elder care plan. Even those estimates were hard to come by as some attorneys required five or more calls before I could even engage them in a live conversation. Perhaps business was so good they didn’t need more clients.

I was eventually fortunate enough to find the legal expert via referral from an attorney who believed we needed more expertise than she could provide. He was later in his career, well- spoken, and widely published on the topic of elder care.

During our initial conversation, for which there was no charge, he helped me sort out our situation and offered that we could simply dispose of the trust and update the prior will. Additionally, given her current status, he believed that a full elder care plan was unnecessary. His quote for what we needed: a comparative mere $1200. It was the rare combination of getting the voice of experience, and the opinion to keep things simple, that led to a great outcome for her at a much lower cost that any of the other attorneys had discussed.

He quickly put together the needed revisions, and we discussed the triggers that would cause us to pursue a full elder care plan.

I had also been reluctant to start selling off assets until I understood the sequence that would be most advantageous for my aunt. With his counsel, I now felt comfortable selling the southern house and all its contents as he confirmed there was no strategic reason to retain it.

My objective of this final phase was to eliminate all her debt and excess assets, thereby substantially reducing the intensity of managing all the monthly bills. Further, for the first time in over 20 years, I wanted to give her a clear picture of her net worth, and where everything was. And finally, I wanted to simplify her remaining assets to support an assisted living situation as I believed living in her home alone represented an unsafe situation, and she’d eventually agree.

At month eight I reached that point and breathed the figurative sigh of relief as we had a clear financial path forward, and expenses were coming in line with income, meaning debt should not return.

While my aunt’s net worth was just around a quarter of what their original financial plan had projected, the outcome was much better than I’d anticipated during the early part of my clean-up efforts.

The factor that made the difference was the life insurance that my uncle carried. While it’s not typically the right financial move to carry such a high level of life insurance so late in life, given all the other financial challenges, it worked out because it represented a part of their financial mix that they couldn’t touch. The life insurance was also helpful as my aunt’s living expenses would be higher than my uncle’s if he passed first.

Without the life insurance payouts, instead of my aunt’s remaining net worth being a quarter of what was originally planned, it would have been just above 10%. The life insurance proceeds represented the difference between her being able to transition to assisted living (assuming a realistic remaining lifespan) and instead having to move to a nursing home setting supported by government assistance.

As we closed out the 12 months that had passed since my uncle’s death, we successfully sold the southern house and contents. Sadly, the house sold for about $110,000 less than if it had been sold near the housing peak 9 years earlier. The contents were sold for pennies on the dollar because much of it was ‘mementos’, meaning they had overpaid for knick-knacks that had little value to buyers. And my uncle’s prized vehicle had to be donated to charity, as it was stored improperly and the cost of the significant repairs to make it drivable would have well exceeded its value.

All in all, the 9 year delay likely cost my aunt a total loss on the house, car, and contents of approximately $130,000. Had they sold the house when they should have, and put the $130,000 in a 4% no-risk investment, it would have grown to $179,000.

What’s worse, had they avoided the 9 years of carrying costs (property taxes, mortgage interest, significant upkeep and improvement repairs, general upkeep, utilities, standard maintenance) they would have saved an additional $210,000.

All together, my aunt could have been in a financial position that was $389,000 better had they simply recognized the reality of their new life and sold the house when she became ill. On a dollars basis, the delayed sale ended up being a mistake on the scale (inflation adjusted) of their stock market loss of the 1990s. Very painful indeed.


Shortly after we had my aunt’s finances in order she became ill. What started as routine minor surgery spiraled into significant deterioration in her remaining health. While in rehab, it became clear she could no longer sustain living on her own. Although she’d previously fought the idea of leaving her home of 51 years, her doctors convinced her there was no choice.

I went shopping on her behalf and found several attractive assisted living alternatives. Had I not gotten her finances in order, there was no way that assisted living could have even been a consideration.

Even so, I spoke with her primary care doctor, putting him in the uncomfortable position of playing actuary, because it was possible my aunt could outlive her assets. If she did, it would force her to move down from assisted living to a nursing home covered by government financial aid, which we certainly wanted to avoid.

He agreed that there was probably only a 25% chance of that risk, so I proceeded. We were relieved that she had this opportunity to transition to a living arrangement that would further remove the stress of worrying about maintenance and home upkeep.

She could afford an individual apartment with 3 meals a day included, without being a nursing home setting. When she was up to it, there were also great daily activities and weekly field trips. And we would have peace of mind knowing she had access to 24 hour help.

Sadly, just as I was ready to take her out of rehab for an afternoon to tour the finalists, she became critically ill and passed away after three days in ICU and a few hours in hospice.

I’ll never know what role the stress of her finances played in her overall health and enjoyment of her retirement years. I will, however, never forget the anguish she expressed when she couldn’t pay for my uncle’s funeral. She finally came to the full and painful realization of the reality that she and my uncle created with their decisions after entering retirement.

As hard as it was to witness a loved one feel that pain, it was very gratifying to see the relief she experienced after I got all her bills paid and finances in order.

In sharing this story I have honored a commitment I made to her as we sorted through her financial debacle: to tell her story, with all the painful details, so that maybe at least one other person might avoid the pain and anguish of a self-inflicted retirement disaster.



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