An in-depth look into why a significant portion of the wealthy population, from high-income earners to millionaires, often report feeling financially insecure or “just getting by,” underscoring that true wealth extends far beyond monetary figures to encompass peace of mind and strategic planning.
The pursuit of financial security is a universal goal, but what happens when you achieve what many would consider “rich,” only to find the feeling of “enough” remains elusive? This isn’t just a philosophical quandary; it’s a surprising reality for a significant portion of affluent Americans.
From high-earning professionals to millionaires, a recurring theme emerges: objective wealth doesn’t always translate into subjective financial contentment. For our community, understanding this paradox is crucial, as it shapes our investment strategies and our definition of long-term success.
The Astonishing Reality: “Just Getting By” at Six Figures
A recent Bloomberg survey of 1,000 Americans earning at least $175,000 a year—roughly the top 10% of tax filers—revealed a shocking sentiment: many feel they are “just getting by,” and some even consider themselves “poor.” This income bracket typically includes individuals who own homes, command six-figure salaries, and hold substantial retirement account balances. Yet, the feeling of financial scarcity persists.
This perspective was echoed by Scott Leonard, CEO of Trovena, a wealth management company. Despite earning over $450,000 annually and living a dream life sailing the world on a 50-foot catamaran with his family, Leonard still identifies as “middle class” or “upper middle class.” He candidly admits to feeling “behind the eight-ball” on critical long-term financial goals like his children’s college education and his own retirement savings. For Leonard, wealth is intensely relative; he compares himself to clients who live off investments and never work a day, making his own substantial earnings seem less significant.
This psychological phenomenon highlights how pervasive the feeling of “not enough” can be, even for those objectively considered highly successful. Billionaires may know they’re rich, and low-wage workers know they aren’t, but the vast swath of America’s “regular rich” exists in a state of perpetual aspiration, as reported by Bloomberg.
What Defines “Enough”? A Shifting Target
The definition of “enough” is inherently subjective and often changes with age and life circumstances. For some, it means reaching a point where passive income covers daily expenses, allowing for leisure like late lunches and waterfront views. Others find “enough” when they can afford all their needs and most wants, even if it doesn’t equate to being “rich.” This self-defined sufficiency is often described as achieving a “rich life” that far surpasses earlier expectations.
Shanli Liu, a finance expert and managing partner of FreedomFolio, articulated that for her, “enough” arrived when her family’s needs, personal lifestyle goals, and future plans were fully funded. However, she quickly realized that wealth without purpose felt incomplete. Liu advocates defining “enough” in terms of security, impact, and fulfillment rather than mere accumulation. She advises mapping out essential expenses, lifestyle aspirations, and philanthropic goals, seeing additional income as a tool for choice rather than a measure of self-worth.
Angelo Crocco, a CPA and owner of AC Accounting, admits that even with significant wealth, the desire for “just a little more” often lingers. He notes that the definition of safety expands: from covering bills to funding college, ensuring early retirement, avoiding medical debt, or shielding against market crashes. Crocco suggests reframing this aim by focusing on sufficiency in small, incremental steps:
- First, covering immediate needs.
- Second, protecting against known risks.
- Third, optional goals like growth, legacy, and philanthropy.
This structured approach helps detach wealth from self-worth, providing stability and allowing individuals to align further pursuits with their core values, as shared with GOBankingRates.
Beyond Dollars: The Millionaire Mindset on True Wealth
Intriguingly, for many millionaires, wealth isn’t solely about the dollar amount. A Northwestern Mutual study revealed that only 32% of millionaires felt wealthy simply by having a million dollars. The majority emphasized that confidence and clarity about the future, often achieved through a robust financial plan, are more significant components of feeling wealthy than being rich in monetary terms.
John Roberts, Chief Field Officer at Northwestern Mutual, highlighted that a comprehensive, custom-built financial plan, guided by an advisor, reduces anxiety and boosts feelings of security. This sentiment is not exclusive to the ultra-rich; it’s accessible to anyone willing to plan. The study found that almost seven in ten millionaire respondents (80% of whom were self-made) work with a financial advisor, significantly higher than the general population. These millionaires are also more disciplined planners, more likely to have a will, plan for outliving savings, and discuss inheritance with family, according to Northwestern Mutual.
This proactive planning extends to retirement questions, with top concerns for millionaires including tax impact, required retirement funds, and the possibility of outliving savings. Their strategies to reduce tax payable on retirement savings include:
- Strategic withdrawals from traditional and Roth accounts.
- Using a mix of traditional and Roth retirement accounts.
- Making strategic charitable donations (e.g., bunching itemized deductions).
- Utilizing Health Savings Accounts (HSAs) or other tax-advantaged healthcare accounts.
- Using products like permanent life insurance or annuities for their tax benefits.
Even inherited wealth requires intentional planning to be sustained, underscoring that without a strategy, money alone does not guarantee lasting security.
The “Out-of-Touch” Gap: When Wealth Becomes Isolation
The disconnect between perceived and actual wealth sometimes leads to “out-of-touch” statements from those who have never experienced financial struggle. These anecdotes, often shared in fan communities, reveal a world far removed from everyday realities. Examples include:
- Complaints about the cleaning costs of multiple houses.
- Statements like, “Why are you so upset? It’s just a car! Just buy another one!”
- Suggestions to “just hire a house manager” to alleviate childcare stress.
- A belief that “poor people are poor because they don’t invest their money right,” coming from someone living off inherited wealth.
- Shock that a $300,000 annual salary might not be “enough to live comfortably” or that a modest income wouldn’t cover an $80,000 purse.
- Assuming everyone can “just ask your parents to pay for it” regarding student loans, or thinking trash collectors come upstairs for collection.
These instances highlight how easy it is for wealth to create an insular environment where basic financial realities are not understood. This “out-of-touch” gap contributes to the societal perception of wealth as inherently disconnected, further complicating the internal feelings of “enough” for those navigating both objective affluence and societal expectations.
Finding True Financial Freedom: A Community Perspective
For investors within our community, the insights from these diverse perspectives are invaluable. The paradox of wealth underscores that raw capital is only one component of financial well-being. True financial freedom is a dynamic state, requiring self-awareness, diligent planning, and a clear definition of what “enough” means for one’s personal journey. It’s about building a robust financial system that provides not just accumulation, but also security, stability, and the freedom to pursue purpose.
The core takeaway is that while high incomes and substantial assets are important milestones, they do not automatically confer a feeling of wealth or security. Instead, actively engaging in financial planning, setting clear boundaries for growth, and intentionally directing resources towards personal fulfillment and impact are the keys to transforming financial gains into lasting peace of mind. As a community, our long-term investment strategies should always be anchored by a personal philosophy of “enough” to truly achieve a rich and fulfilling life.
Redefining Wealth for a Fulfilled Financial Future
The journey to feeling truly wealthy is less about hitting an arbitrary number and more about aligning your financial resources with your life’s purpose and establishing comprehensive plans. It’s about achieving that critical mass where investment gains outpace contributions, and generating wealth provides the freedom to live on your own terms. For the dedicated investor, this means prioritizing not just growth, but also security, clarity, and a conscious decision to define and embrace what “enough” truly means.
