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
Upper Middle is a member-supported publication. Want access to the data and analysis that has helped 5,300+ anxious professionals re-negotiate their relationship with status, taste, and money?
Already a member? Sign In.
➺ Weekly research-focused "Class Notes" essays looking at learned behaviors, cultural/social biases, and internalized expectations.
➺ Biweekly survey data-driven "Status Report" teardowns of why people like us act like this. (Future state: Access to raw data via AI portals.)
➺ Invitations to "Zero-Martini Lunch" live Q+As with scholars, authors, experts and minor celebrities with insight into the Upper Middle lifestyle.
➺ Other stuff. Access to deals. Introductions…. We're always trying shit.
