Hey America, My Middle-Class Bootstraps Are Breaking

American capitalism’s model of personal responsibility takes us too far

Tattered straps and calloused hands

How hard can I pull before the bootstraps are broken, with nothing but a fragment of threadbare worn leather, disintegrating in my palm?

After decades of trying to do the right things in life, I find myself teetering on the edge of anxiety, unsure of what retirement means as a GenXer. I drive by countless tents pitched under freeway overpasses throughout the streets of Los Angeles and wonder if anything more than luck separates me from the fate of holing up residence there.

I have a solid standing in the shrinking middle class, balancing the narrow divide between wealth and poverty, guilt and relief, as a cash-poor property owner. I’m a small business owner, and I own a multi-family income property. I carry the responsibility for the well-being of my employees and my tenants while seeking to provide for my family, and this is far from easy.

The fruits of my labor

I stand on the balcony at the front of our house, soaking in the sunset over the Pacific Ocean in the distance while a plane lands at LAX. It seems like evidence that I’ve “moved on up” to this historically affluent African American neighborhood where Black professionals flocked as soon as racial covenants were deemed illegal.

This was an aspirational neighborhood for me, having grown up in a six-person, two-bedroom/one-bathroom house where for much of my upbringing, I slept on the living room couch.

All of this in the land of opportunity. America: land of the free; home of the brave.

I’ve made it, right? I don’t know. I am tired, and I see no end to the work. I am on the hamster wheel. Can we hold onto the house? Will we pass down a legacy of assets or debt?

The marketing of America

America. Oh, you’re a great marketer. The sky’s the limit for those who want to find it. The engine of capitalism paints a compelling picture of things, experiences, and lifestyles worth acquiring. Homes with picket fences. Family vacations. Weekends with friends.

Americans keep shooting for the bulls-eye in the center of the success dartboard, but at what cost? Are we driving to find the pot of gold at the end of the rainbow? It’s an unreachable target that we can’t ever achieve, yet if we believe the American narrative — we have no one to blame but ourselves.

It’s a narrative that my parents fully bought into and pushed down to my siblings and me. They entered the working world at the height of labor unions and both worked local government jobs with guaranteed pensions. Even though they faced the realities of systemic racism, they landed steady paychecks and pension checks that lasted throughout their lifetimes.

They were hard workers who modeled stability and consistency, both finding careers and sticking with them until retirement.

It’s what they wanted for us too, but the rules of engagement have changed.

Compliance with the rules of bootstrapping

I went to school, earned a degree in accounting, built up my resume, and eventually started my own business. I’ve invested in stocks and real estate and even started an investment club with friends when that was a popular thing to do.

When my parents passed on, I held onto one of their investment properties, buying out my siblings who had no interest in property management.

I have generally worked more hours than most, perhaps all, of the people in my circle. It’s been exhausting, and I feel the effects in my legs after a long day of sitting for far too many hours and taking far too few daily steps.

But retirement savings

Unlike my parents, I’ve never been a member of a labor union nor have I had a pension. Starting with my generation, pensions were replaced with 401(k)s, and the belief that Social Security would be bankrupt by the time I reached retirement age meant that all of the responsibility was on individuals to invest wisely.

Across the board, surveys indicate that GenXers have inadequate retirement savings. According to a survey by Natixis, GenXers have a median retirement savings of $81,000.

If I remember correctly, the retirement calculators said that I would need $2 million at retirement. In true GenX fashion, my solid-middle-class-55-year-old self is nowhere close to this number, and although I am above the median, I can’t imagine how I’ll ever have enough to stop working.

And what about the people that don’t have 401(k)s?

Bootstrapping leaves little room for error

Learning from your mistakes is an essential skill. I don’t want to diminish its value.

But when you make a wrong turn, American capitalism might leave you hanging. From having enough money to retire to keeping a roof over my head, I’ve always felt that I had better have a plan and stick to it, or I’d be destined for poverty.

What happens if you get laid off from work? What about a health crisis? Divorce? Figure it out!

I believe that this level of anxiety produces the productive worker that keeps the exploitative capitalist machine thriving and keeps the American worker tugging away on those bootstraps.

We keep chugging along like The Little Engine That Could exhausting ourselves to get to the top of the hill. But at each turn, the apex sometimes seems further off in the distance.

I think I can. I think I can.

The pursuit of happiness

The American promise of life, liberty, and the pursuit of happiness means that if you want to make a change, you can. You can take risks. Switch careers, start a business, get divorced, whatever you want — all in the spirit of up-leveling your life. Go for it.

But with each change, there’s a risk versus reward equation that must be considered and an underlying assumption that the average Jane is capable of doing so.

This is all in the framework of a capitalist economy, where competition is intended to find equilibrium in a free market, but somewhere the equation has gone awry. It disadvantages people with benevolent hearts, weak boundaries, or discomfort with self-promotion.

As a person who has simply acquired the skills to provide a service and wants to be a productive member of society, navigating the framework of competition and commerce can be daunting.

Plugging along in my lane

I’ve hired a consultant to help grow our business. He repeats this mantra, “I work with business owners who are more afraid of the status quo than they are of change.” It’s intended to incentivize growth-oriented decisions — and to gently persuade business owners to invest in his expertise.

I’ve hired him to help me to build a business that doesn’t require non-stop work or anxiety. Business owners need to learn to transition from working “in the business” to working “on the business” and maintain their original vision.

Finding the best way to deliver value to our clients, while paying our employees well, and supporting my lifestyle is difficult. I’m not crushing it. As a matter of fact, I hesitate to admit that, because it seems that one of the rules of business is that you have to look like you have it all figured out in order to be successful.

Plugging along. It’s what I’ve done, and what I’ll continue to do, but for the betterment of society overall, I’m pretty sure that this isn’t the answer.

Can we all just get along?

While I appreciate the opportunity to chart my own course, and I’m surviving, it never feels like I’m thriving. The weight of the personal responsibility of the bootstraps narrative is becoming too hard to bear.

I want to be of as much help as possible, but I’m finding myself in a space where I have much, yet not enough to make a big difference. Until and unless we course correct, the generations to follow might be doomed.

Capitalism discourages altruism, with its free market competition and Darwinian “survival of the fittest.” Where is the “united” and “indivisible” America that has been promised?

The bootstraps narrative amplifies a culture of individual judgment and blame rather than a collective looking out for the greater good. It is a path toward implosion, and even the willing among us will eventually refuse to participate. I hope we come to our senses before it comes to that.

We must learn to live together as brothers or perish together as fools. — Martin Luther King, Jr.

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Resources:

2023 Natixis Defined Contribution Plan Participant Survey, May 2023