Investing & Risk
Having money doesn't mean that you're good with it.
By Andrew Burmon
10.6% not buying crypto early (10
5.1% and selling during a crash (2
2.3% – track more closely with wealth than with
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.
The two most common investing errors across income, wealth, and profession were starting too late and not paying attention 1 1 – forms of avoidance that can lead to underperformance in a rising market.
Other common mistakes – holding losers too long 2 (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 9 (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.” The majority of respondents (59%) admitted they are not confident they can avoid making mistakes, a striking admission from a group that has built careers on competence and precision 3 .
That leaves just 41% who believe they can sidestep errors, which, depending on disposition, reads either as admirable self-assurance or as a concerning blind spot.
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.
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 4 .
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 intuitio
