Bootstrapped to death: why America’s favourite saying is strangling mobility.

JA Westenberg
12 min readJan 21, 2024

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Photo by Documerica on Unsplash

The old saying goes that anyone can pull themselves up by their bootstraps — if they work hard enough. There’s a pervasive and poisonous idea that success or failure rests solely on the individual and their effort. And if you don’t make it, if you don’t lift yourself out of poverty, if you can’t provide for your family (in the middle of a fucking recession, no less), it’s your own damn fault, and yours alone.

Reality check: not everyone starts off on equal footing in our society. Factors like race, disability, gender, socioeconomic status, family background, access to education, networks, and more contribute to differences in opportunities and resources available to people.

Children born into low-income families face obstacles from birth that are mostly unknown to their wealthier peers: food and housing insecurity, underfunded public schools lacking resources, zero access to childcare, healthcare, enrichment activities like summer camps, tutoring and other services that provide development. Those dealing with the daily scramble to simply meet basic needs have less bandwidth for getting ahead in school or work. The extra hurdles delay progress from an early age.

Generational poverty compounds the barriers when there is no family wealth, property or assets to leverage. Accessing traditional routes out of poverty, like higher education, is much more difficult, coming from a background of scarcity rather than privilege. Graduating with massive student loan debt is disempowering rather than liberating.

Research shows that only about 30% of those born into the bottom quintile of income distribution will make it into the middle class. Most people remain stuck in the same economic class as their parents. Meanwhile, about 90% of those born into the top quintile remain there. When the mobility rates are so divergent between economic classes, it points to systemic issues rather than individual effort-determining outcomes.

Money matters

Class intersects with race to further reinforce societal inequalities. Discrimination and institutional racism contribute to economic disadvantage; Black and Hispanic individuals experience some of the lowest rates of upward mobility. For example, Black children born to parents in the bottom quintile have only about a 5–10% chance of making it into the top quintile of income distribution.

At the other end of the spectrum, White children born in the bottom quintile have about a 25–30% chance at the top quintile — still low odds but much higher than other racial groups. Again, this data highlights how critical the starting point — factors outside individual control — shape future outcomes.

Over the last several decades, the gap in both income and wealth between rich and poor has continued expanding. The top 10% of families now control over 70% of the wealth in the U.S. While the owning class accumulates more assets, the bottom half of Americans have no wealth and struggle to get by paycheck-to-paycheck.

Ask anyone struggling to pay bills, afford healthcare, housing or childcare whether money matters when it comes to getting ahead.

The obvious truth is that having disposable income and a financial safety net provides more options for moving up the ladder. Attending an Ivy League school, taking unpaid internships, relocating for work, or having time for career development instead of working two jobs to stay afloat are luxuries out of reach for most without financial resources.

Health hardships

Adding to the monetary shitshow, lack of access to health care inhibits economic mobility in an extreme way. Health issues severely impact education, employment and earnings. Chronic conditions left untreated mean children miss more school and have poorer academic performance. Parents without healthcare take lower-paying jobs just for the health insurance — or rack up generationally crippling medical debt from any and every health crisis, whether it’s giving birth (seriously) or getting cancer.

Over half of personal bankruptcies in the U.S. stem from uninsured medical bills. Financial disasters make it impossible for low-income families to invest in the future — whether saving for retirement, their children’s education or other assets. When basic needs like healthcare remain consistently unmet through generations, it severely restricts upward mobility.

The rungs of the ladder upward are already broken (or missing altogether) for those born without generational wealth or facing systemic discrimination.

Ladders going down

While those at the bottom struggle to climb upwards, the middle and working classes fear falling down the economic ladder. Wages have largely stagnated over the past 40 years while costs continue rising sharply in healthcare, housing and education.

Even before the pandemic, some 50–60% of Americans said they lived paycheck to paycheck, with little savings to handle emergencies or job losses. Most folks have less than $1000 in ready savings, which could quickly disappear due to one crisis. Achieving the American Dream seems like a distant fantasy rather than a near reality for millions of people. The systems are deliberately designed to reinforce class barriers rather than empower people.

With hedge funds and investment groups buying up much of the real estate market, home ownership also feels out of reach to many working-class families as prices skyrocket. The great American dream of a nice home with a white picket fence gets replaced with lifelong rent traps. Precarity and fragile finances again restrict the ability to take career risks, relocate, and pursue entrepreneurship or other avenues for advancement.

Widening opportunity gaps

Access to high-quality education has long been called the great equaliser in society. But even (or perhaps especially) the education system reflects growing divides along racial and socioeconomic lines rather than closing gaps. Well-funded schools in affluent districts continue getting amplified with private donations and enrichment programs, while poorer neighbourhoods suffer teacher shortages, outdated textbooks and crumbling buildings.

Advanced courses, test prep, tutoring, college application guidance and more give wealthier students clear advantages at gaining entry into top universities — essentially buying access to networks and credentials necessary for breaking into lucrative careers.

Cost barriers, discrimination and family pressures also impact who pursues higher education and which fields they enter. Graduating with over $100k in debt compared to no debt severely affects life choices and risk-taking abilities post-college. Critics point out the failure of education to be the tide that lifts all ships — as households with college degrees now concentrate more on wealth and income than in previous eras. Quality education reinforces class divides rather than alleviates them.

The rungs of opportunity from early childhood through higher education are getting further out of grasp for those not winning the birth lottery. A small percentage of elites efficiently transfer status, wealth, and privilege within their inner circles rather than expand meritocracy for others to have a fair shot.

Broken safety nets

Even with all the preceding hurdles, a functioning social safety net, in theory, should still allow for second chances at the American Dream rather than permanent caste status being solidified from birth. Providing transition assistance from job loss, accident, illness, old age, or other challenges gives citizens the room to get back on their feet. But what should be economic trampolines allowing struggling people to bounce back operate more like traps.

Padding poverty wages with government assistance keeps citizens beholden to low-paying work rather than empowered to demand fair wages from corporations reaping record profits. Attempts to transition from benefits to better employment can face a “benefits cliff” where the loss of healthcare, food stamps, and other aid puts the family in a worse financial position than before the wage increase due to the loss of nested subsidies.

Workers wanting more advancement opportunities get penalised. Changing jobs or getting higher pay could mean waiting weeks or months before assistance kicks in during the application cycle. The chronically underfunded and complex bureaucracies of means-tested aid pit citizens against inefficient systems seemingly designed to be frustrating rather than helpful.

Despite expanding needs, budget shortfalls continuously threaten basic assistance programs for the disadvantaged. Curtailing things like unemployment benefits, food stamps, disability benefits, or welfare puts struggling families at immediate risk of homelessness, hunger and utter destitution through no fault of their own when systems fail to provide adequate support. Simply blaming individual choices for landing on hard times overlooks the glaring lack of institutional safety belts for when economies of scale or discrimination crash down.

When governments align benefits more towards corporations than citizens but still smugly claim to put people over profits, they exacerbate the hurdles restricting upward mobility. Social infrastructure crumbles along with the bootstraps myth. Choosing between bankruptcy or begging for charity to afford healthcare, housing, or education becomes the norm hidden under idyllic, blown-up slogans about freedom and opportunity for all.

Systemic social barriers

Social status, discrimination, psychology and the conservative obsession with pushing (and pushing down on) identity politics factor massively into mobility outcomes. Class conditioning begins at a young age. Circumstances create limiting beliefs on what careers or life paths seem feasible. Varied social groups occupy different spheres of influence, which self-perpetuate through generations through shared identities.

Significant identity markers like race, ethnicity, gender, sexual orientation and disability overlay the underlying economic base in complex ways — intersecting to multiply the marginalisation of minorities. These overlapping social barriers block off entire categories of jobs or advancement opportunities, especially in areas dominated by certain majorities (*cough* the GOP.)

Ask most women, people of colour, lgbtq+ individuals or disabled populations about their challenges navigating careers, and you will find abundant stories of biases and harassment stifling growth. Recognising the need for legal protections around equal employment rights acknowledges that marginalised groups face unspoken barriers inside establishments. No law can mandate attitudes, after all. Getting a diversity hire foot in the door proves meaningless if the culture simply tries to sweep them back out. So again, believing anyone and everyone competes on a level playing field ignores social realities.

Psychological barriers, stereotypes and imposter syndrome play a huge role in academic and career trajectories. Children absorb dominant messaging about what roles seem appropriate or expected for people like them. Without ample counterexamples as inspiration overcoming the odds, envisioning certain paths for oneself remains unlikely. “I don’t see people like me doing that” becomes justification enough not to pursue dreams.

Getting educational credentials or job titles as the first of any minority group in an institution comes with immense pressure to represent. Having no safety net or mentorship through uncharted spaces takes courageous risk-taking against unknown odds. Doing so requires ignoring discouraging voices actively trying to preserve status quo inequalities. Critics gladly blame those who fail for aiming too high rather than examining why nobody caught them when they fell.

Every rung climbed on the economic ladder symbolises a major feat for those facing intersecting barriers. Each represents overcoming lifetimes of cultural conditioning, missing role models, direct discrimination, hostile work environments, and institutional roadblocks.

Does making it despite the landmines below prove the mantra that hard work pays off for anyone? Or does it highlight the extensive scaffolding necessary to dismantle such barriers preventing diverse mobility in the first place?

Perception problems

Optimism bias prevents the Haves from acknowledging the lack of upward mobility plaguing the Have-Nots in our economic system. Surveys show Americans consistently overestimate actual odds for economic advancement. But in the zeitgeist, we still contradictorily express dissatisfaction that hard work no longer reliably pays off compared to previous generations.

Confirmation bias sees the “successful” projecting their anecdotal evidence as universally applicable to all. They cling to meritocracy myths because acknowledging luck or privilege accompanying their ascent might diminish their sense of earned status or esteem. If they overcame barriers through fortitude and resilience, why can’t everyone else?

Without direct exposure to the plight of less privileged groups, it remains easy to cling to false notions of fairness and access in society. Wealthier folks growing up in secluded, affluent zip codes are literally unaware of marginalised areas just a few miles away. News and entertainment media outlets largely owned by the same monied interests skew coverage in favour of the status quo.

Personal stories shared in privileged social circles confirm that everyone the wealthy associate with is “doing well.” This availability heuristic creates broad over-generalisations — if no one I know struggles with healthcare bills or college debt, those problems must be exaggerated. Entrenched class divides feeding segregated experiences prevent reality checks on the flawed bootstrap theory. People cannot understand what they never directly see or hear — and the playing field always looks level from the top.

Few of the wealthy fully grasp the expanding mobility gaps driven by inequality and advantage dynamics. Rather than advocating for solutions levelling the field, they purposefully obstruct attempts to widen opportunities for those excluded from their elite circles. They call it unfair for others to receive much-needed assistance that was not previously offered, ignoring the fact that the wealthy of our world have already reaped the benefits of generations of favouritism.

And so, scarcity mentalities abound as people cling tightly to relative status as their measure of self-worth. They perceive expanding access to rights or resources for disadvantaged groups as automatically diminishing their own prerogatives and privileges by comparison. Anything benefiting excluded populations suddenly smacks of reverse discrimination rather than balance.

Until enough people recognise that suppressing entire groups from achieving their full potential harms everyone, real social mobility remains restricted. Hoarding wealth and opportunity is only possible because so many remain denied their fair share. Creating artificial scarcities feeds class conflicts rather than empowering talent to enrich communities everywhere.

Symbiotic solutions

Solving this isn’t rocket science.

If it was, the billionaires might give a shit.

Pragmatic solutions already exist to start transforming restrictive narratives. With targeted policies and individual actions, step-by-step progress can expand possibilities for more people overwhelmed by circumstances outside their control.

Prioritising early childhood education and interventions would significantly expand prospects for disadvantaged children before gaps widen. Likewise, funding quality schools that lift all students together raises boats. Tuition-free college, allowing students to pursue careers based on passion versus paychecks, creates foundations for innovation versus frustration.

Expanded social safety nets would give people room to reskill or transition industries as market needs evolve. Portable benefits delink critical healthcare and caregiving assistance from any one job arrangement. Raising minimum wages and requiring pay transparency pushes back against discrimination swallowing income mobility.

With automation transforming work, shared prosperity models also counterbalance precarious livelihoods. Shorter work weeks or guaranteed basic incomes establish stability so individuals can take career risks. Shared ownership models like employee stock programs build wealth along with wages.

Tax incentives encouraging investments into economically excluded areas stimulate renewed growth, and opportunity zones should be addressed. Justice reforms addressing biased laws and predatory systems disproportionately targeting minorities also open mobility pathways.

At the personal level, those enjoying privileged positions can mentor, highlight and amplify marginalised voices rather than ignore or talk over them. Affluent individuals can pressure peers to stop blocking equity policies, improving access to hoard relative status. And cronyistic insiders must admit when their winning lottery ticket came at the expense of a rigged system.

Frustratingly, these answers get dismissed out of hand as draconian “socialism” by those clinging to bootstrap myths. Cynical critics eagerly paint any solutions as forfeiting personal responsibility to “big government” despite relying heavily on public assistance themselves in the form of favourable tax structures, corporate bailouts, and preferential access. They react allergically to the word “welfare” when applied to assisting struggling individuals, while they gladly embrace it for billion-dollar corporations.

Those standing on third base believing they hit a triple call any attempts at levelling the playing field unfair even as they stack the bases against others. Economic benefits for the disadvantaged are painted as oppression against the privileged precisely because supremacy rests on that engineered inequality. Systemic change is opposed by the fearful, scarcity-mindset ethos of hyper-individualism.

We anchor liberal democracy in the belief that everyone, regardless of race, gender or background, deserves equitable access to opportunity. But that idea is built on a bootstrap lie that can no longer be ignored or forgiven. We have an urgent choice to make. Do we continue perpetuating a broken status quo that has capped human potential and stalled dreams for generations, binding future possibilities to past prejudices? Or do we create a new legacy built on justice and empathy — one that honours courage, effort and ability regardless of the circumstance of birth?

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JA Westenberg
JA Westenberg

Written by JA Westenberg

I write about tech + politics + humans.

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