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.
