Freed by 50

I’ve talked before about my parents influence on my views of money and how I’ve strived to live differently than they have. Today, as many of the older generation of my family are in their mid-70’s, I was reflecting on where they’ve gone with their lives, and how they’ve influenced me. I’m going to look at three couples, my parents, and two sets of aunts and uncles who lived life extremely differently, and how I feel it’s worked for them.

My Parents

My parents were never much for school. Neither graduated a four year college, but my father completed two years of college in order to get his desired job. Both of them started well paying, pension jobs right around 20 years old. They met in their early 20’s and were married in their mid-20’s. Due to medical complications and the ability to travel for free, they decided to put off having kids until their early 30’s when they had their first kid, me, in 1979.

My dad was hurt in the line of duty just before I was born. He took bad advice and opted to receive 3/4 of his pay for life with benefits on medical retirement. This began his string of entrepreneur ventures and get rich quick schemes. My mother continued to work until after my sister was born four years later. She briefly went back to work and she too wound up injured on the job and collects a small disability payment from the company to this day.

The money coming in was never enough to really make ends meet, but we always seemed to have two new cars. When I was three, my parents bought their first house. I’m told the mortgage interest was crippling at the time, but they made it work. When I was seven we somehow had enough to have a custom built 3000+ sq ft home built in a high end neighborhood with a new pool, fancy landscaping, and a massive three level deck. At 13 we moved again to a much smaller home where I’d live with them until I went off to live on my own after college.

It wasn’t until my mid-30’s that I discovered how my parents had lived their lives. They’d borrowed money from family numerous times to cover debts. My father was a wizard at rotating credit card debt. We’d moved so many times because they used home equity like an open checkbook, and would pay off credit cards and unnecessary home improvements with home equity. When the equity ran out, they’d sell and we’d move.

My mother has always seemed to go along with my father’s plans. Whether she’s deluding herself or is complicit I’ll never know. My father has always been quick to call someone “cheap.” Especially one of my uncles who we’ll talk about later. He is savvy, I’ll give him that, and I pity the timeshare salesman my father swindled into a free hotel stay. If they think they’re good at high pressure sales, they don’t know how good my dad is at high intimidation anti-sales. But dad is always ready to get rich quickly, and sees no reason to change from the path he’s been marching down.

My parents, to this day, spend every dime that comes in and then some. They fully retired (from already being mostly retired since the 90’s) in 2004 and live on a golf course in South Carolina where they golf five days a week and mostly spend time with friends in the community. They see my sister often because she lives nearby, but rarely ever see any other family (mine included). Their primary focus is their own way of life and they feel any relationships outside of their day to day will maintain themselves until a time at which they want to be involved.

From a health perspective, I wouldn’t call it the best situation. My father has smoked upwards of 40 cigarettes a day for my entire life and sounds like he has undiagnosed COPD. My mother smokes quite a bit, and drinks about a magnum of wine per day. They walk the golf course a lot, which keeps them in moderate shape, but their habits have taken quite a toll.

Clearly I don’t agree with most of my parents decisions in life. They’ve spent a lifetime remorselessly living above their means and letting others pay the price for it. They continue to ignore glaring issues, like having no savings or insurance, and I assume it’s because my sister and I are expected to pick up the slack next. I will say that I’m envious of their ability to live life to the fullest, consequences be damned. With the exceptions of being a good negotiator, and honestly being overall great parents to their kids for ~20 years, I mostly learned what not to do.

My Fun Uncle

My fun uncle, or drunkle, was the one who introduced me to real music. While my dad was listening to doo-wap and my mom played Barbara Strisand, my uncle was rocking out to The Who. He and my aunt couldn’t have been more opposite and I’m not sure how they ever got together.

My uncle is four years older than his sister, my mother. He volunteered for Vietnam at 18 and came back a changed man. I say today that he died there and someone forgot to tell him.

After returning from war he went into law enforcement where he’d work for 35+ years. He met my aunt, also a pensioner, in his mid-20’s and they had their first kid a few years later. Their second kid and I were born a few months apart. They always lived a few minutes drive from us, and never more than 30 minutes from where they grew up.

My aunt and uncle were always better with money than my parents and lived pretty much your standard American lives. They paid their bills, drove commuter cars, had a nice house, went to work and did their jobs day in and day out. Unfortunately, my uncle’s job and his untreated PTSD from Vietnam never gave him much rest so he self-medicated with alcohol more and more as the years went on.

Around my 14th birthday my aunt and uncle separated. She kept the kids and the house, and he relocated to a shitty apartment near where he worked. My uncle’s lifestyle only got worse, and worse still when he was diagnosed with, and survived, prostate cancer. This continued way into my 20’s until one day he nearly drank himself to death.

From a financial standpoint, my aunt and uncle’s lives went off the rails when I was 14. Shortly after their divorce, she remarried, then separated again, then just dated for a while. He was spending a small fortune on booze and going out with friends. Yet somehow they both retired with generous pensions that allowed them to pay off their homes in full, and in my aunt’s case, buy a summer home.

Today my uncle’s health is very poor. On top of the drinking he also smoked heavily. In recent years he’s dropped as low as 20% lung capacity and has nearly died twice because of it. He is the definition of what the Harvard Health Study would call “sad and sick.” He lives in poor conditions in a cramped apartment, spending most of his days on a couch he bought in the 80’s. He is unable to drive, let a lone travel, and sees my cousin and her kids at least once a week. He has more money than he can spend, though, and has become a cash cow for my economically dependent cousin. That’s a story for another day though.

My aunt remarried and spends most of her time traveling to see her grandkids. She has also had health issues, but seems to be getting along fine enough.

My Boring Aunt and Uncle

My boring aunt and uncle have lived in the same house for nearly 50 years. My uncle worked out of a detached garage converted to an office all but the last five or so now that he’s retired. This is the uncle my father always called “cheap,” and often with good reason.

If you went to a party at their house, there would never be beer or wine or soda because they forgot to buy it. Every time. My aunt has always been a hell of a cook, and would provide amazing meals cooked in her little, outdated kitchen. They had three kids, but only three bedrooms, so my twin cousins shared a room even into college. This never seemed to bother them.

Growing up they didn’t take nearly as many vacations as we did. They didn’t have video game consoles. Their family drove an old conversion van for half my life.

Curiously, and something that’s just occurred to me, is that this aunt and uncle didn’t work pension/civil service jobs. My uncle had a practice of his own and my aunt was a secretary.

Until my late 30’s this aunt and uncle were completely boring. They were well liked by all, and fun at family parties, but otherwise there wasn’t much to say. Then one day they bought a beachfront plot of land in Georgia and announced plans to retire down there. That was a surprise.

Of course if you want to make God laugh, make a plan. Almost on queue their three kids scattered to three different states and each had three kids of their own. Now my aunt and uncle’s time was spent bouncing from place to place to see their grandkids. And then they got less boring again. They took a trip to the Caribbean, with all three kids, and all nine grandkids, and even a couple people to spare. That summer, they rented a big house in The Hamptons for their family. And then did the Caribbean again that winter. Lather, rinse, repeat.

Turns out while my aunt and uncle were busy being boring, they were hoarding every penny. They host the quintessential family holiday’s with all their kids and grandkids and pets running around the house. They keep their family together by providing the locations and the means to get there.

Although age has taken its toll, and there was no shortage of drinking on their part, my aunt and uncle are in fairly good health. They travel often and have plans to leave a sizeable nest egg for their family.

My Final Thoughs

These are three foundational examples of how I’ve learned about personal finance growing up. I’ve seen hundreds of other families do it differently, but these experiences I lived and they left impressions.

My parents and I have always disagreed on financials. At 18, I told my parents I never wanted to live like they do. They fly by the seat of their pants and run up debts like they’re nothing with no concern about how to pay them back. To this day they tell me that they’re broke every week when they call me from their 2500 sq ft condo on the private golf course where they are members. Although we took trips and had cool cars throughout my life, there’s little to show for it now. Family, as my parents claim, is most important. Except that they’ve alienated most of their family and don’t particularly care to see them.

My poor uncle has caused so much destruction in his life, and has in turn had so much taken from him. He stopped drinking after he nearly died, and stopped smoking after that nearly killed him. His kids resent him not just for their childhood, but now for making them take care of him. He still has strong ties with his extended family, myself included, but he’s a shell of his former self. He whiles away his days in his shitty apartment, and only gets joy from giving his grandkids gifts. His entire existence at this point in his life is to continue to live so his checks keep coming so he can give them to his kids and grandkids.

My boring aunt and uncle are actually quite wonderful to be around. They’re genuinely happy, and quick to spread joy to those around them. Their golden years have been truly golden, and with the exception of a handful of minor health issues, they’ve been in fairly good shape. They raised their kids right, and made sure they were there to help with their grandkids. They were the opposite extreme to my parents, though, and spent far too long hoarding money. Although they’ve lived in the same house for around 50 years it wasn’t until just a couple of years ago that they actually updated it from it’s largely 1950’s state. My aunt LOVES to cook, yet she lived with an outdated, broken down kitchen for most of her life despite having the savings and the income to do something about it. Although they live great lives now, they passed up a lot of opportunities to spend a little more earlier in life without compromising their future.

From these people I’ve learned that I don’t want to be boring, I don’t want to be sickly, and I don’t want to be careless. Said another way, if I’m careful with my money I can find ways to spend it wisely, and if I keep myself in shape and don’t overdo it on vices, I should live a long and happy life.