➺ January 20, 2026

Hey {{ first_name | Neighbor }}. A black bear broke my bird feeder the other evening, which I found a bit thrilling (it’s nice to see a bear) and more than a bit annoying – at least until a cloud of happy Chickadees descended.

Turns out he didn’t break it so much as make it much more efficient. – AB

➺ Shoutout: Thanks again to Domain Money for sponsoring our big financial planning survey (below). If you haven’t already signed up for a free 30-minute financial planning session with their pros, now (read: before tax season) would be a good time to do it.

➺ Passing Thought: I’ve never seen a popsicle stand, but if I did I’d blow it.

AVOID FINANCIAL HUBRIS

Our data shows that many of you are better at earning money than managing it. No shame there, but if you’re lucky enough to be rocking a six-digit household income you should know how your assets are performing (and when you’ll be able to retire).

Of course, that’s easier said than done. Which is why you need help. That’s where Domain Money comes in. Their Certified Financial Planners specialize in helping high-earners aggressively pursue financial goals that take into consideration:

Ready to turn that complexity into a single, actionable plan? Sign up by the end of the month and Domain will help you get your financial house in order and file your taxes by April 15. Book a free 30-minute strategy session today. It’s a time well invested..

What we’re drinking about while talking.

➽ Natural Enemies
Why does MAGA hate everyone in this Ann Taylor Loft? 
The spread of the term AWFUL – “Affluent White Female Urban Liberal” – among right-wingers has been treated by the Times, the Post, and The Atlantic as further proof of MAGA misogyny. That’s not wrong, but it’s a bit like treating longevity as proof of vampires' protein-heavy diets. What actually makes AWFUL interesting is the word "affluent," a near-synonym for rich acting as a class delimiter. Linguistically, affluent historically a high, steady income derived from professional work. That distinction matters because it maps to the MAGA consensus on legitimate and illegitimate wealth. "Rich" is legitimate because it signals ownership, risk, and "winning." Affluent is illegitimate because it implies someone succeeded inside a corrupt credentialing regime – higher ed, corporate bureaucracy – and must therefore be corrupt themself.

Gender and race are better understood here as intensifiers. "White" and "female" support the implied accusation of corruption because white women are widely understood to have benefited disproportionately from DEI regimes and “woke” corporate governance. That this belief is, at least to some degree, true – numerous studies suggest affirmative action disproportionately helped white ladies¹ – muddies the water a bit, but shouldn't distract from the fact that AWFUL describes a right-wing heuristic for identifying enemies. It's not that just that AWFUL women are successful, it's that they are the wrong sort of successful, which makes them the wrong sort of women.

➽ Intimismo
Why do good books suddenly look so bilious and saturnine?
If you wandered into the new fiction section of your local Barnes & Nobles in five years ago, you saw lots of covers with headless women. Then it was flat color blocks. Then tasteful serifs against beige. Then indistinct, Insta-ready pastel blobs. Now, ambitious new fiction comes wrapped in oil paintings – and not just oil paintings, intimist paintings in the spirit of Pierre Bonnard and Édouard Vuillard, who captured uncanny and alienating scenes of 19th-century domesticity inside and outside bourgeouis homes. You can see it in Daniyal Mueenuddin’s This Is Where the Serpent Lives, with art by Salman Toor, Kirstin King’s A Good Person, with art by Dante Gabriel Rossetti (arguably Pre-Raphaelite, but definitely proto-intimist), and Lidija Hilje’s Slanting Towards the Sea. Even Karl Ove Knausgaard’s The School of Night features a landscape by the (enormously talented) Scandi-intimist Mamma Andersson. The cumulative effect is that bookstores have become moody art galleries papered with old-timey depictions of aestheticized retreat. Talk about understanding your audience.

➽ Fart of the Deal
Why don’t Americans haggle?
Americans don’t want to negotiate. New Indiana University data drawn from five studies shows that 95 percent of respondents chose not to haggle when given the opportunity, even in contexts where negotiation has traditionally been normal—car lots, garage sales, and other secondhand or discretionary purchases. On average, participants required savings of 21 to 36 percent before they considered bargaining worth the effort. There are obvious explanations: fixed pricing, limited employee discretion, widespread discomfort with face-to-face interaction, and even algorithmic demoralization. But there’s also a less obvious one. According to BLS data, those in the top income quintile spent on average $150,342 in 2024, almost 5x those in the bottom quintile. Historically, wealthier shoppers have been more reluctant to negotiate. As economic sociologist Viviana Zelizer has argued, higher-status consumers are more constrained by social norms than their poorer cousins and more likely to avoid anything so undignified as haggling. Seen this way, the end of negotiation isn't a surprise, just a downstream effect of the economy being rebuilt to serve the privileged.

Want to earn up to $200-an-hour for your insights, get three free months of Upper Middle member-only content, and get half off our (pretty cheap, tbh) $50 annual membership? Join Upper Middle Research, our professional research platform.

Travel Like You Mean It

In professional offices where travel is normalized and honesty is not, everyone from the receptionist at the front desk to the CEO not in his office implicitly understands that where an employee goes on vacation is shaped by what they’re trying to get away from – meetings, coworkers, responsibilities, or existential malaise². As such, travel plans are read like tea leaves by managers comfortable with their employees leaving for a week or two – PTO being contractual and all – just not in a way that suggests they wanted to.

What suggests that they wanted to? Their destination. No one infers more from a plane ticket than a thin-passported manager who spent the last corporate offsite showing off pics of him and his MBA class in Hong Kong. He may not say anything. He will, however, draw conclusions about his absentee report's state of mind and future at his company...

1. Tulum/Costa Rica: Demonstrates a well-honed ability to follow and the tendency to manage stress through spending. Assign more work.
2. Paris: Indicates a daydreamer's inability to spot the difference between what is promised and what is delivered. No need for a bonus.
3. Mexico City: Signals curiosity, risk-aversion, and a Monocle-reader's mental map of the world as an archipelago of coffee shops. Nothing to worry about.
4. Hawaii: Shows a willingness to expend enormous energy seeking out relaxation, likely in reactionary to burnout. Probably looks at job ads on Linkedin. 
5. Iceland: Reflects a deep desire for adventure and deep ambivalence about actually going on an adventure. Wants a promotion, not a new gig. 
6. London: Suggests a desire to live elsewhere and the inability to figure out how to pull it off. Probably whining in private Slacks, but not going anywhere. 
7. Southern France: Demonstrates interest in the three-hour lunch lifestyle as well as a willingness to be culturally uncomfortable in order to enjoy a better quality of life. Probably unhappy. Definitely open to offers. 
8. Thailand/India: Points to the sort of crisis of meaning that inevitably leads to meditation and the purchase of a small sculpture of the Buddha Siddhartha Gautama. Start getting documentation together. 
9. Berlin: Implies an interest in art, chaos, espionage, and public club sex. Will stay just long enough to pay for the penicillin prescription with HSA money. Block Slack access immediately.
10. Miami: Fire – for cause.

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Upper Middle’s “Financial Planning” Survey examined how members of the financial semi-elite set financial goals and pursue them over time. By decoupling goal setting from goal-pursuing behaviors, the survey sought to understand which behaviors are habitual or performative and which are associated with confidence in long-term results.

While the vast majority of survey respondents engaged in goal-setting behavior, significantly fewer demonstrated belief that their actions would leave to them achieving those goals. This “conviction gap” is best explained as a lack of hope, which psychologist Martin Seligman defined as the ability to see problems as temporary and specific. Organized planners – whether self-directed or assisted by certified financial planners – didn’t do more, but did act more hopeful.

1. Desire

Taken together, the survey data suggests a group that is hard-working, numerate, and goal-oriented, but facing in the wrong direction. The highest ranked financial goal was “Making More” (composite score of 4.7 out of 5), followed by “Investing Smarter” (4.2), “Spending Less” (4.1), and “Retirement Planning” (3.9). Those focused on “Making More” not only did not report higher incomes, they reported lower levels of financial diligence and were less likely to report both living below their means having organized their financial data.

Priorities did not affect tracking behavior and the findings don’t suggest that ambition is irrational. Rather, they underscore the hazards of focussing on the least controllable financial input³, an attitude particularly common among those in sales and business development roles. This gap between goals and agency produces a familiar psychological disconnect between behavior and belief. When the primary goal is the least controllable input, even responsible financial behavior starts to feel beside the point.

2. Delegation

Roughly one half of survey respondents reported working with a financial professional: 37.27% reported working with a financial planner and 31.37% self-reported working with an accountant. Planner usage was strongly correlated with net worth, not income; 43.6% of respondents with $1M-$2.5M in net worth and 56.4% of those with $2.5M+ reported planner use. Accountant usage was more closely correlated with income. Both planner (87.25%) and accountant (85.06%) relationships were widely characterized as “helpful.”

Planning-frequency data helps clarify why. Planner users self-reported engaging in planning less frequently than non-users. Nearly two-thirds of respondents planning annually (63.33%) worked with a planner, compared with half of those planning quarterly (50%) and a third of those planning monthly (34.40%). This explains why planner use was correlated with self-reported discipline, but not necessarily confidence in a retirement timeline. Planners and accountants don’t change the financial picture. They make problems temporary and specific.

3. Vigilance

Almost all survey respondents engage in near-constant financial vigilance. The vast majority of respondents reported monitoring their checking and savings accounts (86.45%) as well as their credit card balances (86.08%). Far fewer tracked total spending (55.68%) or discretionary spending (33.33%), and fewer still tracked state or federal taxes (22.71%).

Income and wealth shape what people monitor, not whether they monitor. Wealthier respondents – particularly high earners with company equity – were more focused on equity performance (62.64%) and less focused on discretionary spending.

The meaningful distinction here is not between “checkers” and “non-checkers,” but between respondents with systems and those without. Among respondents who tracked total or discretionary spending, roughly 62% also reported having consolidated and organized financial data. These organized respondents were more likely to report working with financial planners (40.6%) and more likely to self-report being financially disciplined (50.0%).

The implication is that tracking behaviors are nearly universal, but without systems they become performative. 

4. Confidence

Survey respondents asked how certain they were that they would be able to retire at 50, 60, or 70 indirectly provided a measure of confidence in the efficacy of their financial plans. Most respondents anticipate retiring in their 60s, but the variation in confidence reveals something more important: long-term financial confidence is most correlated to professional and personal predictability, not to planning frequency or professional help.

Respondents in optimization- and compliance-oriented professions – finance, accounting, law, and medicine – reported higher confidence about retiring earlier than those focused on sales, business development, or operations, even at similar income levels. This suggests that confidence is shaped less by upside than downside potential.

As professional predictability erodes across the economy, personal predictability becomes more valuable. Respondents who reported having consolidated and legible financial systems were more confident about retirement at every age, regardless of profession. These respondents focus on what they can control—and on the tools, including planners and accountants, that help keep uncertainty bounded.

Conclusion

The results of Upper Middle’s “Financial Planning Survey” suggest that effective financial planning is less about diligence or “grindset” thinking than about maintaining hope by maintaining plausible, predictable systems. Many respondents engage in financial planning frequently but without conviction, mistaking activity for control. The data suggests that lower-touch, higher conviction planning – particularly when paired with strong systems – produces similar or better outcomes with less stress.

This makes the case not only for financial planners, but for financial dashboards: tools that clarify relationships rather than overwhelm with detail. The key is not simply knowing what the numbers are, but understanding how they interact—and how to work efficiently and deliberately toward goals that remain within reach.

Upper Middle’s Top 5 Financial Planning Tips

5. Don’t plan around higher future earnings.
4. Don’t plan around higher future earnings.
3. Don’t plan around higher future earnings.
2. Don’t plan around higher future earnings.⁴
1. Be born rich.

[2] A key indicator here is whether the employee openly considers going to Burning Man.

[3] This output feeeeeels controllable if you believe that raises are meritocratic. If you do, please email me about this bridge I’d love to sell you.

[4] Don’t plan around higher future earnings.