Core Memo

Memorandum

To
Anyone who needs the day in one page
Date
August 27, 2026

Memorandum

From
Connor Quincy via Fortune | FORTUNE
Date
Filed
Business·6 min to read
Re

The ‘upper-middle-class trap’: why $300,000 a year no longer feels like winning

ReThe ‘upper-middle-class trap’: why $300,000 a year no longer feels like winning

A growing body of analysis argues that households earning $200,000 to $400,000 are stuck in a financial arms race, working harder for goods of declining quality. The cost of the American Dream now exceeds $5 million, while economists debate whether the middle class is truly shrinking or simply moving up.

Households earning $200,000 to $400,000 a year are increasingly caught in what analysts call the “upper-middle-class trap”: working more, relaxing less, and spending heavily on products and services whose quality is declining. The concept, developed by Nick Maggiulli, chief operating officer of Ritholtz Wealth Management, describes a financial arms race in which individually rational decisions collectively drain bank accounts without improving quality of life.

Maggiulli’s evidence spans housing, education, and travel. New single-family homes shrank by 12% in average size between 2014 and 2024, even as the price per square foot surged 74%, according to LendingTree data. A home near a top-rated public elementary school costs 78.6% more than a comparable home in the surrounding county. Homebuyers who win bidding wars fare worse: one study found their purchases produced 6.9% lower annualized returns than homes bought without competition.

Higher education shows a similar pattern. The number of college applicants has jumped 78% since 2015, while acceptance rates at elite schools have collapsed, driving tuition and private-school costs up roughly twice as fast as overall inflation. Maggiulli argues that competition for the same scarce positional goods — homes in good school districts, prestigious degrees, premium experiences — lowers everyone’s quality of life while raising costs.

One accelerant is nearly impossible to opt out of. Citing Brookings Institution data from November 2025, Maggiulli notes AI usage rises from 9% among earners below $30,000 to 34% among those earning $100,000 or more. High earners, worried AI threatens their careers, adopt it just to defend their position — a “Red Queen” dynamic in which everyone runs faster just to stay in place. “If AI doubled everyone’s productivity overnight,” he writes, “suddenly someone with half your skill would be able to compete with you just by using AI.”

His prescribed exit is blunt: stop competing for positional goods that don’t materially improve your life. Send kids to good public schools, fly economy, buy a smaller affordable house. His test for any big purchase: “Am I buying this to improve my quality of life, or merely because other people are buying it?”

The trap helps explain a number that has circulated for the past year. The cost of achieving the American Dream surpassed $5 million in 2025, according to an Investopedia analysis drawing on government data, industry statistics, and survey responses from more than 1,200 U.S. adults. The cumulative lifetime cost of eight pillars of middle-class aspiration — retirement at $1.6 million, homeownership at $957,594, new cars every five years at $900,346, raising two children and paying for their college at $876,092, health care at $414,208, annual vacations at $180,621, pet ownership at $39,381, and a wedding at $38,200 — came in nearly $600,000 higher than the year before.

The average American with a bachelor’s degree earns about $2.8 million over a career, less than half of what’s required. Two college-educated earners are functionally a prerequisite for “living the dream.” Homeownership remains the most commonly cited obstacle: 58% of respondents named high home prices as their top barrier, followed by rising living costs (51%) and elevated mortgage rates (47%).

Maggiulli’s framework has run into a countervailing, income-based analysis. A January report from the American Enterprise Institute, authored by economists Stephen Rose and Scott Winship, argues the “hollowing out” narrative is only half-true. Their data shows the share of American families earning between roughly $133,000 and $400,000 — their definition of the upper-middle class — tripled from 10% in 1979 to 31% in 2024. For the first time in U.S. history, more families sit above the traditional middle-class income threshold than below it. Median family income, adjusted for inflation and family size, rose 52% between 1979 and 2024.

“It is simply inaccurate to characterize the ‘shrinking’ middle class as reflecting diminished economic security rather than material progress,” Rose and Winship wrote. Winship previously acknowledged the limits of an income-only lens: two people with identical lifetime earnings can end up with very different wealth if one saves and the other spends. AEI is reportedly preparing a follow-up using wealth data, with preliminary results showing a similar pattern: the middle class shrinks mainly because the upper-middle class booms.

Maggiulli’s counter reframes the debate around wealth rather than income. The share of U.S. households with $1 million to $10 million in net worth more than doubled, from 7% in 1989 to 18% in 2022-23. “There’s a good portion of them that feel like they don’t have enough,” he previously told Fortune. “They feel like they’re just getting by.” A $1 million net worth placed someone in the top 5% of Americans in the late 1990s; today, that same number puts you in a far less exclusive bracket.

Connor Quincy

Author

Technology Reporter

Connor Quincy covers public affairs, politics, business, culture and daily news for Core Memo. The role focuses on verification, context, and clear explanations for readers.

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