Upper Middle’s “Financial Whoopsies Survey” examines how members of the financial semi-elite mismanage their money. By treating investing mistakes as an inevitability and focusing on the kinds of decision-making that leads to those mistakes and the kind of moral outlook that drives reactions to those mistakes, the survey attempts to understand why we do dumb stuff that loses us money.
Survey respondents had a variety of levels of wealth with the median respondent possessing around $350,000 in investable assets and the average respondent possessing just under $1M. Everyone made mistakes. Some people seemed to struggle admitting it.
WE ALL MAKE MISTAKES
The two most common investing errors across income, wealth, and profession were starting too late and not paying attention1 – forms of avoidance that can lead to underperformance in a rising market.
WEALTH vs. SELF-REPORTED MISTAKES
Other common mistakes – holding losers too long (10.6%), not buying crypto early (10.6%), selling a big winner too soon (7.8%), owning mutual funds instead of ETFs (5.1%), and selling during a crash (2.3%) – track more closely with wealth than with income (r ≈ 0.31 vs 0.22). This is in large part because wealthy investors work with financial advisors and to (rightly or wrongly) trust those advisors. Advisor involvement effectively flattens the relationship between wealth and error frequency, replacing emotional or timing-based mistakes with strategic ones. In other words, income shapes capacity to invest, but wealth – and especially the professionalization that comes with it – shapes how people fuck up and whether they notice. Wealth also leads to a decline in vigilance. Affluent respondents were more likely to report “not paying attention.”
PROFICIENCY vs. SELF-REPORTED INVESTING BEHAVIOR
Still, the most instructive way to understand why members of the financial semi-elite make mistakes is to look at the areas of their life where they don’t make mistakes.
COMPETENCE CREATES INCOMPETENCE
Professions are defined not only by their function and compensation, but by specific relationships to risk. Professionals make the mistakes they are trained to make. Professional trained to avoid risk – doctors, lawyers, educators – hold onto assets too long and avoid volatility. Professionals trained to pursue then mitigate risk – tech and finance bros – sell winners too early (r = 0.30) and dabble in new asset classes (crypto r = 0.24).
In fact, self-reported mistakes line up fairly neatly with professional groups sorted by risk orientation:
Analytical Strategists (finance, consulting): optimize for prediction accuracy
Technical Thinkers (engineers, architects): reduce uncertainty w/ structure
Creative Synthesizers (marketers, designers, media): rely on intuition and taste
Care Professionals (teachers, docs, nurses): prioritize stability and rules
Power Brokers (lawyers, regulators, middle management): act within precedent
Entrepreneurial Operators (founders, high-level execs): iterate constantly
Capital Allocators (investors, bankers): treat risk as an asset
Academic Overthinkers (scientists, professors): verification-driven
Entrepreneurial Operators and Stewards of Capital overtrade – selling winners too early (≈30%) and trying to beat the market (≈24%). Care Professionals and Power Brokers lean defensive, holding losers too long (≈25%) or not paying attention (≈21%), habits of professions built around avoiding blame. Expert Technicians wait for certainty and often start too late (≈18%). Creative Synthesizers feel real bad about not buying crypto. Like… really bad.
PROFESSIONAL GROUP vs. SELF-REPORTED MISTAKES
Professional enculturation has a deep and lasting effect of personal behavior. Most professionals recognize mistakes they’ve made, then continue to make similar mistakes – or at least behave the same way. Entrepreneurial Operators and Capital Allocators were the most likely (≈42%) to have added money to the market this year and the most likely to own non-traditional assets like real estate or crypto (≈38%). Analytical Strategists were still bullish – about a third added capital (≈33%) this year – but also long-term oriented with the highest percentage of respondents maxing out retirement contributions (≈45%) and owning bonds (≈40%). Creative Synthesizers and Academic Thinkers were disengaged2. Many weren’t sure how their investments were performing.
PROFESSIONAL GROUP vs. INVESTING BEHAVIOR
In each case, professionals exercised their specific form of good judgment. Not all forms translated into market success.
LEARNING TO HANDLE RISK
IIt’s unnatural to touch the stove, get burned, and go back to touching the stove. Yet that’s what confident investors do. Confidence is a learned tolerance for loss – an ability to absorb a hit without injury to their sense of self. Now wonder that investors taught by a parent or mentor were far more likely to identify as good investors (r = 0.41), than any other group. Being taught to invest doesn’t result in knowing what to invest in, but it clearly helps people understand how to react to investment returns. It’s a permission structure.
INVESTMENT EDUCATOR vs. REACTION TO OTHERS’ WINDFALLS
(We asked about Nvidia. Suspicious represents people who felt that other people’s profits were somehow suspect.)
Permission varies by gender, culture, and geography. Men were much (≈2.5x) more likely than woman to have been taught to invest and little more than half (23% to 42%) as likely to consider themselves good investors. They were also far more likely (28% to 17%) than men to identify as risk-averse. Black investors were far less likely (5.6% to 17.8%) to have been taught to invest by a parent, slightly more likely (5.9% to 5.6%) to have been taught by a mentor and less than half (47%) less likely to identify as good investors than whites. Hispanics investors followed similar patterns while Asian investors were more likely than whites (20% to 17%) to learn from a parent and only somewhat (20%) less likely to to identify as good than whites.
INVESTMENT EDUCATOR vs. REACTION TO OTHERS’ WINDFALLS
But identity wasn’t everything. Local culture mattered a lot – almost as much as profession. Respondents from California, New York, and Massachusetts (≈35%) were most likely to try to beat the market (r = 0.27) or sell winners too early (r = 0.30), both behaviors that signal belief in second chances. Investors from Midwestern and Southern states were more inclined to start too late (r = 0.25) and hold losers too long (r = 0.18), revealing a more moralized relationship to loss – a deeply internalized expectation of fairness that maps against faith in meritocracy (and Republicanism, FWIW).
LOSER HOLDING vs. INVESTING BEHAVIOR
When it comes to investing, unfairness is the heat. Comfort with unfairness is an advantage..
CONCLUSION
Every investor thinks they’re rational until they lose money. In reality, most mistakes are patterned—products of temperament, training, and moral comfort with risk. These five archetypes capture how the semi-rich succeed, stumble, and self-justify.
INVESTING ARCHETYPE DISTRIBUTION
(Organized by mistakes)
Gameboys (≈22%)
Volatility enthusiasts mostly working in tech and finance. They buy IPOs (r = 0.29), hold crypto (r = 0.24), and chase performance. Their errors – selling winners early (r = 0.30) and trying to beat the market (r = 0.27) – come from overconfidence.
Supersavers (≈29%)
Risk-averse professionals in law, medicine, and education. They max out retirement (r = 0.32), own bonds (r = 0.25), and treat prudence as virtue. Their common mistakes—starting late (r = 0.25) and holding losers (r = 0.19) – reflect caution learned at work. Integrity is their weakness.
Normies (≈15%)
Disciplined, advised, and diversified. They add money yearly (r = 0.39), use advisors (r = 0.30), and keep perspective. Mistakes are minor – selling during crashes (r = 0.17) – but controlled. Risk is procedural, not personal.
Bozos (≈26%)
Late starters who were untaught (r = 0.30) and haunted by missed upside. They regret starting too late (62%) and missing crypto (r = 0.24). Mostly creatives and nonprofit types, they see markets as exclusionary and invest emotionally, which never ends well.
Doubters (≈8%)
Detached and uninitiated. They don’t know returns, hold few risk assets, and rarely had teachers (r = 0.30). They distrust the whole game and refuse to play3.
Top 5 Investing Lessons From Dad
5. Don’t buy English cars even if they seem really cool.
4. Season tickets are worth it even when they aren’t4.
3. Go ahead, get the guacamole.
2. Momentum trade based on last week’s WSJ coverage.
1. Don’t talk about it at dinner.
