One Instagram Story Shows Why Retirement Is Such a Toxic Concept

It makes me emotional to bring my 86-year old Dad’s experience to the conversation

Rocco Pendola
Jan 22 · 11 min read
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Photo by Sam 🐷 on Unsplash

My Dad worked his balls off. If it weren’t for the pandemic, he’d still be working part-time. He turned 86 in November.

He didn’t work into old age because of financial reasons. He worked to, as he told me, “keep myself busy.” If I’m able, I’ll be working in 41 years, too. But not to keep myself busy. I’ll do it for financial and attendant lifestyle reasons.

Not surprisingly, my Dad, a member of the silent generation, took a different view on these things, probably less via choice and more because of specific and broad circumstances. He came up in a time — and in a place — where work defines a man. It was his job to provide for his family. He did whatever he needed to do.

You know people like this. Quite possibly your parents. You might not see eye-to-eye with these people, including our folks, but you can — presumably — respect and appreciate why and how they did what they did in life.

My Dad came home covered in soot after long-ass shifts at the carbon plant he worked at — Union Carbide. He took an early retirement from that job, which provided a pension I think he still collects to this day.

When that job ended, he took a gig at the local housing authority, painting and preparing low-income housing units for new tenants. At or around traditional retirement age, he went part-time for a non-profit doing similar work.

Through it all, he moonlighted — in the evening and on weekends — as a painter. I think he painted a house — inside or out — on every block in the city we lived as well as the surrounding towns. He painted for friends, friends of friends, doctors, lawyers, and widows on fixed incomes. He was the kind of guy who would charge someone next to nothing if he knew they didn’t have the means.

Work defined my Dad in the way it did/does a lot of people his age. But I think he saw deeper meaning in what he did, even if he never vocalized it. The way he carried himself and treated others as a worker crafted his character. There’s not a person where I’m from who doesn’t love my Dad. I’ve never heard anyone — to the individual — say a bad thing about my Dad. Quite the opposite.

It’s easy for people like me — liberal, not really working class — to chalk up my Father’s worldview as toxic, mentally unhealthy, and even misogynistic. I mean, my Mom largely stayed home, took care of me and the housework, and received an “allowance” from my Dad to buy whatever we and she needed.

This worked for them. It worked for me.

You might look back on your upbringing and cringe about aspects of it. However, you can also hold the competing view that your parents not only did the best they could, but they actually served you well and set you up for success.

It’s unfair to judge the individual choices people make just because the collective consequences of these decisions don’t make for the best sociocultural outcomes across generations.

This is how we evolve as humans over these generations we assign catchy names to. We respect the choices of those who came before us — particularly our parents (assuming they treated us well and with the best intentions) — and strive to do better.

Isn’t this also part of the ethos that shaped my Father? You want your kids to do better than you did.

In some ways, I’m not doing better than my Dad. I’m biased, but I’ll never be half the man he is. Scratch that — half the person. From a different perspective, I guess I’m objectively doing better. I’m educated. I make more money than he did. I’ve had more experiences. And so on.

But here’s the thing I’ll never lose sight of. I’m only doing “better” than him because of him. So, clearly, he did the work in his own profession and with his son.

It’s important to understand this as we discuss money and, at times, effectively trash the way our parents and previous generations situated themselves. It’s nothing personal. It’s the normal, healthy progression of things. We would not be able to evolve the way we do without having lived, observed, studied, and paid our sincere respect to the way our parents and grandparents lived before us. This process requires honest critiques and hard reflection.

I didn’t think I was going to go on an emotional riff about my Dad when I opened this draft. But it quickly became the ideal lead-in to a discussion of retirement as a toxic concept for those of us under 50. Traditional conceptions of retirement worked for my Father, but they’re sure as hell not going to work for me. And likely not you either.

An Instagram story from a friend prompted this article. I can’t link directly to the story because it expired, but here’s a screenshot. My friend approved using her Instagram account as a source for this article.

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So, unlike my Dad, the man who inspired what originated in a Reddit post did white-collar work, climbing the corporate ladder.

I had multiple opportunities to do just that. I passed.

I could have followed in my Father’s similar footsteps. Quite easily. I enjoyed working a couple summers with him, his co-workers, and my best friend at the time for the Housing Authority. Even so, I passed.

I was never going to take either of those paths. I was too curious. Curious about experiencing and living in places outside of my hometown. A hometown basically left for dead only to come alive as the perfect stand-in for a classic Springsteen song:

My Dad fueled my curiosity. While he wasn’t the most educated person, I always knew he was smart. The same thing applies to this day. He always asks questions. No matter who’s in the room — no matter what they do — he always asks good questions. Because there’s an intellectual curiosity, I’ve always seen burning inside of him.

So I took the curiosity my Dad handed down and got the hell out of my hometown.

It’s a town full of losers, I’m pulling out of here to win
— Also, Bruce Springsteen, Thunder Road

I crisscrossed the country for a few years, working several careers, jobs, and gigs, before settling in California 21 years ago.

San Francisco, Orange County, Los Angeles, Santa Monica, Los Angeles again.

I have adopted a lifestyle that’s the polar opposite of what I knew as a kid and what my parents have always known. I haven’t stopped job-hopping these last 21 years. And I wouldn’t trade it for the world. It suits me well.

In many ways, my parents and I couldn’t be more different. But this is okay.

Reading about the person’s dad in the screenshot should terrify you. That said, our parents came up during a different time.

If my Dad didn’t do what he did, I’m not sure what he would have done. Frankly, if you didn’t become a hard worker (with equal strokes of luck and relative privilege) in my hometown, you became a deadbeat, drunk, or god awful blend of both. Even with an education, choice isn’t a plenty where I’m from.

To that end, it was much easier to get out as a 20-year old in 1995 than it would have been for my father to get out as a 20-year old in 1954. Two completely different times with distinct and divergent sets of options and possibilities.

At the ripe age of 45, I have settled on a freelance career, writing about money and relationships. I took a hiatus to explore the world of craft cocktail bartending and will likely return to the bar, in some reduced fashion, as soon as the pandemic permits.

We live in a world that not only allows for this, it, in many ways, encourages it. Opportunities to do life differently exist in ways previous generations could have never dreamed of, unless we’re talking about people named Bill Gates or Steve Jobs.

Despite this, many of us still experience a tug of war between the myriad lifestyle options in front of us and the anxieties associated with conventional notions of retirement.

We want to work in a bar. We want to play music. We want to be creative. We want to open our own business. We want the freedom to blow off work for stretches and travel. We relish the chance to clear our schedule for a day and go on a hike or lay on the beach. We want to create content. We want to live the freelance lifestyle. We want to crush the game on Medium, do the digital nomad thing. Whatever.

But we also know we need to money to:

  • execute this modern, non-linear lifestyle,
  • and ensure we don’t end up poor when we’re our parents' age or younger.

This conflict led so many of my friends and others I observe to take the same or a similar route their parents took.

I know some high school friends look at me and think I’m insane. They couldn’t do what I do. They set up shop knee-deep in what they know. They couldn’t get past the legitimately scary thought that something other than standard 9-to-5 type work or doing business in the town they were born would jeopardize their futures. They use their family’s proximity as a security blanket.

This is sad, only because it wreaks of limiting yourself. And it’s personal finance’s fault. It’s the money writers and retirement industry’s fault.

They didn’t do their jobs.

They left us as high and dry as Trump did the nation on the pandemic and his most ardent supporters after they committed sedition in his name.

As the nature of work and our ensuing lifestyles changed, the advice coming from money gurus didn’t change. It barely kept pace. If it weren’t for platforms such as Medium, there’d be a complete and total dearth of relevant personal finance and investing information.

Case in point — I wrote an article the other day inspired by an article Sophie Radvan wrote. Sophie would have never had her incredible article published on a traditional platform because she opened it by brilliantly referring to her “slutty ass wallet.” That would not have gotten past any editor at any platform — digital or otherwise — that covers money.

Granted, I’m nitpicking, but there’s a larger point.

The gatekeepers — ensconced in the broad machine that dictates what money literature sees the light of day — refused to see the writing on the wall. They stuck with their buttoned-up Wall Street, East Coast approach. They refused to let a little California in. As somebody who tried breaking down these walls at traditional financial media outlets, I can tell you every single day was a fight.

They despised and routinely rejected sexual innuendo, relationship discussions, personal stories, emotion, and anything outside of the playbook they knew and know. If it resonated on a personal level, they didn’t like it. Not much has changed. These seemingly little things are emblematic of the larger issue.

Personal finance is personal. Starting from there, the content you see on Medium is instantly more helpful than what you’ll find in more traditional spaces on and offline. You’re not going to connect with people on a subject such as money unless you make it personal and relatable. Absent this connection, it’s next to impossible to take the next step.

It comes as no surprise we have collectively failed to redefine retirement. To create a more appropriate paradigm to help people use the money they make to live great lives in the present and for the duration. This is what’s terrifying.

It’s not so much that we watch people work the same job for 50 years, retire, get old, and die. It’s that we don’t adapt the way we conceptualize — and execute — retirement planning to fit this relatively new dynamic.

Achieving director level at some corporation. While it might still fly for some of us, it’s fucking soulless for others.

The personal finance, investing, and retirement crowds — for all intents and purposes — pulled a Trump and refused to “govern” for those of us in that latter group. They hung onto the $500 a month invested in an index fund for 40 years to reach $1,000,000 or more because it worked for the constituents who it worked for. They didn’t ask any questions. They didn’t prepare to pivot.

They never paid much mind to the idea of never fully retiring by choice. They only lament the baby boomers and such forced to work into old age to avoid poverty — or make the poverty they experience less bad. They created victims yet offered the same old solutions.

They only discuss financial freedom alongside retirement. They give short shrift to the notion of financial flexibility as a goal today and into advanced age.

This atmosphere has made retirement a legitimately toxic concept.

We’re held to a standard we’re unlikely to meet. To make matters worse, it’s a standard we don’t even have to meet. However, if you know no other way than the traditional path to retirement, what are you supposed to do? Pull something new and brave from a subject you’re already intimidated by out of thin air?

For those of us who do not organize life and ageing the way our parents did, we face an incongruent trajectory. We know it would suck to work 50 years, then realize you have no identity outside of work if you’re a millennial or part of Generation X. But how do you avoid this fate?

Practically, it comes back to crafting an overarching strategy and operationalization of each element within this strategy outside of the confines of our parent’s realization of retirement.

On the ground, this will look different on an individual basis. However, it all functions within the same framework. A way of organizing your personal finance that puts cash and cash flow first. You’re not aiming for $1,000,000. Instead, you’re angling for that sweet spot where you always have cash at the ready to fund periods of temporary retirement and the cash flow necessary to do that until the day you die.

Let’s do away with the old concern of “outliving your money.”

Who thought to phrase it this way in the first place? There’s nothing positive and empowering about those words. They trigger nothing but feelings of anxiety and near-certain failure.

Let’s introduce the notion of your money keeping pace with your lifestyle. You control your money. You don’t let it control you. You earn and allocate it in such a way that you’re always in a position — within reason — to do what you want, when you want to do it, personally and professionally.

This isn’t the style of article I usually write. But I had stuff I wanted to situate in my head. In the next iteration of this thought trajectory, I intend to flesh out this idea of “outliving your money” versus “your money keeping pace with your lifestyle.”

There’s important work we can do in this regard.

This article is for informational purposes only. It should not be considered Financial or Legal Advice. Not all information will be accurate. Consult a financial professional before making any major financial decisions.

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Rocco Pendola

Written by

I write about doing life and personal finance, focusing on the psychology of our relationships with other people and money. I’m anti-guru, pro-empowerment.

Making of a Millionaire

Stories about money, personal finance and the path to financial independence.

Rocco Pendola

Written by

I write about doing life and personal finance, focusing on the psychology of our relationships with other people and money. I’m anti-guru, pro-empowerment.

Making of a Millionaire

Stories about money, personal finance and the path to financial independence.

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