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15 Post-Retirement Money Habits Of Boomers Who Are Quietly Winning At Life

Kerri Foley

October 26, 2025

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There is a cohort of Baby Boomer retirees who are quietly winning at life. Their victory is not measured in the ostentatious displays of wealth often seen on social media, but in something far more valuable: a state of profound financial resilience.

It is the freedom to travel during the quiet off-season, unconstrained by peak pricing or vacation schedules. It is the deep-seated peace of mind that comes from a robust emergency fund, capable of absorbing life’s unexpected shocks without inducing panic.

It is the quiet confidence to spend with purpose, aligning their resources with what brings them fulfillment, whether that is supporting their grandchildren or pursuing a lifelong hobby. This is the art of a well-funded life—a state of security and contentment built not on luck, but on a foundation of disciplined and intentional habits.

Habit 1: They Master Strategic Debt Management, Not Just Avoidance

The foundational habit of financially successful Boomers is a deeply ingrained aversion to high-interest, non-productive debt. This principle is rooted in a “pay-with-cash” mentality, a disciplined approach where they often delay a purchase until they can afford it in full, rather than financing it. This practice is a cornerstone of their financial stability, preventing the corrosive effect of compounding interest from eating into their fixed retirement income. They understand that avoiding high-interest debt, particularly from credit cards, is one of the most effective ways to protect and preserve the wealth they spent decades building.

However, a closer look at the data reveals a more nuanced picture than simple debt avoidance. While the ideal is to enter retirement with zero liabilities, the reality is that many Boomers still carry some form of debt. In 2025, the average credit card balance for a Baby Boomer was $6,795. What distinguishes the financially astute is not the complete absence of debt, but their active and strategic management of it. An analysis of consumer debt trends shows that the total debt held by the Boomer generation is actively decreasing, having fallen by 1.8% between 2023 and 2024. This stands in stark contrast to younger generations, whose debt levels are rapidly increasing over the same period.

Table 1: Generational Debt Snapshot (2025)

Habit 2: They Create a Flexible Spending Plan, Not a Rigid Budget

In retirement, income streams often become fixed, but expenses remain stubbornly variable. Successful Boomers understand this fundamental asymmetry and build their financial lives around a flexible spending plan rather than a rigid, restrictive budget. They begin by creating a plan based on their core values and priorities, meticulously distinguishing between essential, non-negotiable expenses—such as housing, utilities, and healthcare—and discretionary “flex zones” that include travel, hobbies, and dining out. This clear categorization is not just an accounting exercise; it is a strategic tool that grants them control and adaptability in the face of uncertainty.   

This built-in flexibility is crucial for navigating the primary threats to a retirement portfolio: inflation, which silently erodes purchasing power, and unexpected financial shocks, such as a major home repair or a sudden medical need. For instance, during a significant market downturn, they can consciously and temporarily reduce spending in their “flex zones.” This simple act allows them to avoid the catastrophic mistake of selling investments at a loss to cover living expenses, a key principle of dynamic withdrawal strategies that helps preserve their capital for the long term. Defying the stereotype of being technologically hesitant, many use modern tools like budgeting apps to monitor their spending in real-time, allowing for quick adjustments and maintaining a clear picture of their financial standing. 

Habit 3: They Strategically “Manufacture” Their Own Pension

With the steady decline of traditional defined-benefit pensions, savvy Boomers recognize that the responsibility for creating a reliable, lifelong income stream rests squarely on their shoulders. Instead of lamenting the loss of the old system, they proactively construct a diversified portfolio of income sources, effectively “manufacturing” their own personal pension designed to provide consistent cash flow throughout retirement. This “blended income” strategy is a sophisticated approach that combines the stability of guaranteed income with the growth potential of variable income, creating a resilient financial foundation.   

Their income architecture is typically built on several pillars. For guaranteed and fixed income, they maximize their Social Security benefits and are increasingly turning to annuities, which have seen record sales as Boomers seek to protect their income from market volatility and longevity risk. They also employ traditional fixed-income instruments like bond ladders and certificates of deposit (CDs) to provide predictable cash flow. To generate variable and growth-oriented income, they rely on systematic withdrawals from their 401(k)s and IRAs, rental income from real estate holdings, and a strong emphasis on dividend-paying stocks. They often favor “Dividend Aristocrats”—companies with a proven history of increasing their dividend payouts for 25 consecutive years or more—as a source of reliable, inflation-hedging income.

Habit 4: They Play the Long Game with Social Security

One of the most powerful and readily available financial levers in retirement is the optimization of Social Security benefits, and financially astute Boomers understand its immense value. They treat the decision of when to claim not as a guess, but as a strategic calculation, recognizing that patience can translate into hundreds of thousands of dollars in additional lifetime income. The data is unequivocal: delaying a claim from the earliest possible age of 62 to one’s Full Retirement Age (FRA)—currently 67 for those born in 1960 or later—avoids a permanent benefit reduction of up to 30%.

This strategic patience, however, is remarkably rare. A staggering 90% of working Americans plan to claim their Social Security benefits before reaching age 70, with 44% expecting to file even before they reach their FRA. The primary drivers behind this rush to claim are a pressing need for immediate income and persistent, though largely unfounded, fears about the future solvency of the Social Security system. While the Social Security trust funds are projected to face a shortfall in the 2030s, this would result in a reduction of benefits, not a complete cessation of payments.

Table 2: The Financial Impact of Delaying Social Security

Habit 5: They Withdraw with a Tax-Smart Blueprint

The process of accumulating wealth for retirement receives enormous attention, but the art of withdrawing it is equally, if not more, critical. Getting money out of retirement accounts efficiently can have a profound impact on how long a portfolio lasts. Successful Boomers understand this and do not withdraw funds randomly. They operate with a tax-efficient decumulation strategy, a carefully crafted blueprint designed to minimize their lifetime tax bill and maximize their after-tax income. This involves a deliberate sequencing of withdrawals from their three primary account types, each with a different tax treatment.

The conventional strategy often begins with withdrawals from taxable brokerage accounts. These are typically tapped first because long-term capital gains are taxed at highly favorable rates—0%, 15%, or 20%, depending on income—which are almost always lower than the ordinary income tax rates that apply to retirement account withdrawals. The next source is tax-deferred accounts, such as traditional 401(k)s and IRAs. Withdrawals from these accounts are taxed as ordinary income.

Habit 6: They Confront the Healthcare Cost Head-On

Financially successful Boomers operate with a clear-eyed realism about the cost of healthcare in retirement. They do not underestimate it, nor do they assume it will be fully covered by government programs. Instead, they treat healthcare as a primary, non-discretionary expense that is virtually guaranteed to increase over time, and they build a dedicated funding strategy to address it head-on. This proactive approach stands in stark contrast to the one-in-five Americans who admit to never having considered their healthcare needs during retirement planning.   

The numbers they are planning for are sobering. According to Fidelity’s 24th annual estimate, a 65-year-old individual retiring in 2025 can expect to spend an average of $172,500 in after-tax savings solely on healthcare expenses throughout their retirement. This figure, which has more than doubled since Fidelity’s initial estimate in 2002, critically does not include the potentially catastrophic cost of long-term care. 

Habit 7: They Maintain a “Sleep-Well-at-Night” Emergency Fund

The conventional financial advice to maintain an emergency fund covering three to six months of living expenses is often insufficient for the unique circumstances of retirees. Financially successful Boomers recognize this and adhere to a more robust standard, maintaining a larger cash reserve that provides both a financial safety net and a strategic market buffer. In retirement, an unexpected expense—a new roof, a major car repair, or a surprise medical bill—cannot be covered by working overtime or picking up extra shifts. It must be paid for out of existing assets. A substantial cash reserve, often equivalent to one to three years of living expenses and held in a high-yield savings account, serves two distinct and critical purposes.   

First, it acts as a powerful financial shock absorber. It allows them to handle large, unforeseen costs without derailing their budget, resorting to high-interest debt, or being forced to sell long-term investments prematurely. This provides immense peace of mind. Second, and more strategically, it serves as a market volatility buffer. This is a key component of the “bucket strategy” for retirement income. During a significant stock market downturn, instead of selling equities at depressed prices to cover their living expenses, they can draw from their cash reserve. This simple act of living off their “sleep-well-at-night” fund gives their investment portfolio the crucial time it needs to recover when the market eventually rebounds. 

Habit 8: They Treat Their Home as a Strategic Asset, Not Just a House

For the vast majority of Baby Boomers, their home is not just a place of comfort and memories; it is, by a significant margin, their largest financial asset. Financially savvy retirees understand this dual nature and have a clear, intentional plan for how this massive store of wealth integrates into their overall retirement strategy. Boomers collectively hold an estimated $18 to $19 trillion in real estate wealth, and nearly nine out of ten own their own home. The pivotal decision they face is what to do with this immense equity, a choice that has profound implications for their financial security and legacy.   

The overwhelming preference is to age in place. A 2025 survey found that 61% of Boomer homeowners plan to never sell their homes, a figure that has risen in recent years. The primary reasons for this reluctance to move are a strong desire for independence, the financial security of a paid-off or low-interest mortgage, and a simple aversion to the upheaval of starting over late in life. However, for a significant portion of the generation, downsizing or relocating is a powerful financial strategy.

Habit 9: They Keep Their Investment Portfolio “Boring” and Balanced

As investors transition from their working years to retirement, the primary objective of their portfolio shifts from aggressive wealth accumulation to the more nuanced goals of wealth preservation and sustainable income generation. Successful Boomers embrace this transition by maintaining a “boring,” well-diversified portfolio that is intentionally designed to weather market storms, provide reliable income, and outpace long-term inflation. Their focus is squarely on capital preservation through a balanced and diversified asset allocation, a tried-and-true approach that prioritizes consistency over chasing speculative returns.   

Their portfolio construction typically involves a strategic mix of asset classes. Equities remain a crucial component, providing the long-term growth necessary to protect their purchasing power from inflation. However, their equity holdings often shift towards dividend-paying, blue-chip companies rather than high-risk, high-growth ventures, reflecting a preference for stability and income. Fixed income forms the bedrock of the portfolio, with assets like bonds, CDs, and money market accounts providing predictable income and acting as a crucial buffer against stock market volatility. To achieve further diversification and generate additional income streams, many also include real estate and alternatives, often through liquid vehicles like Real Estate Investment Trusts (REITs).

Habit 10: They Prioritize Experiences Over Possessions

The ultimate goal of “quietly winning at life” transcends mere financial metrics; it is about achieving a state of fulfillment and well-being. This habit reflects a conscious and deliberate shift in spending priorities, moving away from the accumulation of material possessions and toward the creation of memories, the pursuit of passions, and the deepening of relationships. For these retirees, the true return on their decades of saving is not found in a larger house or a fancier car, but in the richness of their life experiences.

This philosophical shift is clearly reflected in their spending patterns. The “retirement spending smile” is a well-documented phenomenon showing that discretionary spending is typically highest in the early, more active years of retirement, before declining in the middle years and rising again later in life due to healthcare costs. Travel consistently ranks at the very top of the list of retirement goals and aspirations. This behavior aligns perfectly with the core tenets of the “Die With Zero” philosophy, which advocates for strategically spending money on experiences while one is still young and healthy enough to fully enjoy them.

Habit 11: They Plan for Long-Term Care Before It’s a Crisis

Among the many financial risks in retirement, the potential need for long-term care (LTC) stands out as one of the most significant and financially devastating. It is also one of the most frequently neglected areas of planning. Financially successful Boomers, however, do not ignore this threat. They proactively confront the massive financial risk posed by LTC, treating it not as a remote possibility but as a probable contingency that requires a concrete and well-funded plan.

The data underscores the wisdom of their foresight. Nearly 70% of individuals over the age of 65 will require some form of long-term care during their lifetime. The costs are staggering and, critically, are not covered by Medicare. As of 2025, the national median cost for a private room in a nursing home facility exceeds $120,000 per year. Even less intensive options are prohibitively expensive, with the median cost for an assisted living facility surpassing $70,000 annually and a home health aide costing upwards of $75,000 per year. Without a plan, these expenses can obliterate a lifetime of savings in a matter of years. To mitigate this risk, savvy Boomers employ several strategies.

Habit 12: They Make Their Estate Plan a Living Document

An estate plan is not a static artifact, created once and then filed away for decades. Financially successful Boomers understand this critical distinction and treat their estate plan as a dynamic, living set of documents that must be reviewed and updated regularly to reflect the realities of their post-retirement lives. They recognize that an outdated plan can be as dangerous as no plan at all, potentially leading to unintended consequences, family conflict, and unnecessary financial hardship for their heirs.

They make it a habit to revisit their plan every two to five years as a matter of course, and more importantly, they trigger an immediate review after any major life event. Common triggers in retirement include relocating to a new state, which brings with it a new set of estate, tax, and healthcare laws ; significant family changes, such as the birth of a grandchild, the death of a spouse or beneficiary, or a divorce within the family ; substantial shifts in their financial situation, like selling a business or experiencing large investment gains ; or changes in their own health or the health of an individual they have designated as a power of attorney or executor. 

Habit 13: They Embrace Lifelong Financial Learning and Adaptation

Retirement does not mark the end of financial decision-making; it signals the beginning of a new and arguably more complex financial phase. The transition from accumulating assets to strategically decumulating them requires a different set of skills and a constant awareness of a changing landscape. “Quietly winning” Boomers embrace this challenge by remaining engaged, committing to lifelong financial learning, and demonstrating a willingness to adapt their strategies as tax laws, market conditions, and their own personal circumstances evolve.

Their commitment to financial literacy, honed over decades in the workforce, extends into their retirement years. They stay informed on topics that directly impact their financial well-being, such as changes to Medicare regulations, shifts in Required Minimum Distribution (RMD) rules, evolving estate tax laws, and the introduction of new financial products designed for retirees. This continuous learning empowers them to make informed decisions and to work more effectively with their financial advisors. 

Habit 14: They Build a “Personal Board of Directors”

The financial challenges of retirement—from creating a sustainable withdrawal strategy to navigating the labyrinth of Medicare and tax law—are extraordinarily complex. Recognizing that no single person can be an expert in all of these areas, savvy Boomers do not attempt to go it alone. Instead, they assemble a “personal board of directors,” a team of trusted, credentialed professionals to provide expert guidance and act as a sounding board for critical decisions.

This team typically includes three key members: a Certified Financial Planner (CFP) to oversee the holistic retirement plan, a tax professional (CPA) to manage tax-efficient withdrawal strategies and compliance, and an estate planning attorney to ensure their legacy goals are legally sound and up-to-date. They understand the wisdom of a Nobel prize-winning economist who described the decumulation phase of retirement as one of the “nastiest, hardest problems in finance,” and they view the cost of professional advice not as an expense, but as a crucial investment in their long-term security.   

Data on advisor usage supports this approach. Boomers are more likely than younger, more DIY-oriented generations to seek out a “do-it-for-me” relationship with financial professionals. Their selection process is telling; when choosing an advisor, they overwhelmingly prioritize trust and personal referrals above all other factors, including investment performance. The demand is shifting away from simple investment management and toward holistic advice that addresses their entire financial life, from cash flow management to long-term care planning. 

Habit 15: They Give with Intention and Tax-Efficiency

For many financially successful retirees, “winning at life” extends beyond personal financial security to include making a meaningful and positive impact on their communities and the causes they care about. Their philanthropy is not a random or impulsive act, but rather a thoughtful and integrated component of their overall financial and legacy plan. They approach giving with the same strategic mindset they apply to their investments and spending.

Boomers are a formidable force in the world of philanthropy. As a demographic, they exhibit high rates of charitable giving, and the average charitable donor in the U.S. is 64 years old. Individual giving continues to be the largest source of charitable contributions in the United States, totaling over $392 billion in 2024, and this cohort is a major driver of that generosity. Their giving, however, is often highly strategic and designed to be as tax-efficient as possible, allowing them to maximize their impact while minimizing their tax liability.   

They employ several sophisticated giving vehicles to achieve this. For those over the age of 70.5, Qualified Charitable Distributions (QCDs) are a powerful tool. This strategy allows them to donate up to $100,000 annually directly from their IRA to a qualified charity. This distribution counts toward their Required Minimum Distribution (RMD) but is excluded from their adjusted gross income. This not only provides a significant tax benefit but can also help them manage their income to avoid higher Medicare premiums. Another popular strategy is the use of Donor-Advised Funds (DAFs).

Conclusion: The Compounding Power of Good Habits

The financial security and quiet contentment enjoyed by this cohort of successful Boomer retirees are not the product of a single, brilliant investment or a fortuitous stroke of luck. They are the cumulative, compounding result of decades of disciplined, intentional, and often unglamorous habits. Just as small, consistent contributions to a 401(k) grow into a substantial nest egg over time, these consistent financial behaviors build upon one another to create a fortress of financial resilience.

The power of these habits lies in their interconnectedness. A flexible spending plan (Habit 2) is not just about budgeting; it is the critical enabler that allows a balanced investment portfolio (Habit 9) to weather market storms without forced selling. The decision to delay Social Security until age 70 (Habit 4) is made financially viable by the prior work of creating a diverse set of “manufactured pension” income streams (Habit 3). A sophisticated, tax-efficient withdrawal strategy (Habit 5) is not devised in isolation; it is crafted and refined with the guidance of a trusted “personal board of directors” (Habit 14). Each habit reinforces the others, creating a cohesive and robust financial ecosystem that is far stronger than the sum of its parts.

For those looking toward their own retirement, the list of 15 habits should not be a source of intimidation, but of inspiration and empowerment. The path to financial independence is not about achieving perfection overnight. It is about taking the first, deliberate step. The journey to “quietly winning” begins with a single, well-chosen habit. Whether it is finally building an adequate emergency fund, meticulously tracking expenses to create a true spending plan, or scheduling that long-overdue first meeting with a financial advisor, the most important action is the one taken today. The future self will be profoundly grateful for it.