6 Retirement Myths Every Overstock.com Employee Should Rethink

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'Overstock.com employees should view retirement planning as an opportunity to enhance long-term clarity and resilience by challenging outdated myths and aligning financial decisions with their personal goals.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'For Overstock.com employees aiming to build financial confidence, it can help to realize that retirement success often comes from balancing disciplined financial management with meaningful life choices.' – Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

1. Common retirement myths that may affect financial decisions.

2. How charitable giving, spending, and debt management can shape retirement strategies.

3. Overlooked risks, such as fraud, that may be more damaging than market downturns.

There are several myths related to retirement finance that have the potential to jeopardize even the most meticulously crafted financial strategies. Last quarter, for instance, we debunked the idea that bond allocations should match your age and that retirees should never touch principal. Misconceptions about retirement planning, however, go far beyond outdated guidelines.

Here, we look at six common myths that can influence retirement decision-making and aim to dispel them before they affect the financial well-being of Overstock.com employees.

Myth 1: Making a Large Splurge Is Not Acceptable

It's commonly believed that spending large amounts of money too soon in retirement is irresponsible and should be strongly discouraged. This isn't always the case, though.

'Enjoying the results of your hard work is what retirement is all about,' says Wealth Enhancement advisor Wesley Boudreaux. 'One well-considered investment won't ruin your future if you've laid a solid foundation.'

Take the case of a person who has saved $3 million and plans to withdraw roughly 4% annually, which comes to about $120,000 a year. The total balance falls to $2.95 million if the person decides to buy a $50,000 recreational vehicle to realize a lifelong goal. The reward of reaching a significant life goal likely outweighs the $2,000 reduction in the sustainable yearly withdrawal that results from this modification. Intentionality is the fundamental difference: a planned, one-time expense is not the same as ongoing discretionary spending that undermines long-term consistency—a lesson relevant for Overstock.com retirees envisioning lifestyle goals.

Myth 2: You Should Only Give Money to Charities After You Die

Many people believe that bequests are the most effective way to give to charities. However, waiting until death is not always the best course of action, even though donating assets to charity through estate planning is a noble goal.

Carlos Hernandez, a Wealth Enhancement financial advisor, observes, 'The estate tax exemption is almost $14 million per individual today.' ¹  This generally exempts many estates from federal estate tax. The upshot? By waiting until death to donate, you might miss advantages you could have right now.

Giving during one’s lifetime has many benefits. It can reduce an estate's size, lower current taxable income, and provide the personal satisfaction of witnessing charitable contributions in action. Donors can feel the direct effects of their gift while they are still alive by establishing a scholarship, setting up a community shelter, or funding a local program. This can create both tax efficiency and emotional gratification for Overstock.com employees interesting in pursuing long-term philanthropic strategies.

Myth 3: You Should Save Everything for Your Heirs and Spend Less

Although modest spending practices are generally recommended, being overly frugal in retirement might result in regrets and lost opportunities.

According to Boudreaux, 'Far too many people undervalue themselves by treating retirement as just another stage of accumulation. A life well-lived is what your savings are supposed to support.'

Decades of financial resources are meant to be used meaningfully in addition to being preserved. Beyond inheritance, thoughtful financial support can offer advantages such as financing family vacations, helping adult children with a down payment on a house, or contributing to grandchildren's education funds. For Overstock.com workers approaching retirement, these investments in opportunities and experiences may yield greater satisfaction than leaving behind a larger inheritance.

Myth 4: Before You Can Retire, You Must Pay Off Your Mortgage

Although it is a compelling goal, it's not always financially advantageous to enter retirement debt-free.

Hernandez says, 'When properly managed, mortgage debt can be a strategic tool.' Low interest rates may compare favorably to investment returns, and interest is frequently tax deductible. Furthermore, paying off a mortgage with tax-advantaged retirement assets may result in needless taxes and possibly place retirees in a higher tax bracket.

The choice should be based on weighing the prospective growth of unaltered investments against the after-tax cost of holding mortgage debt. While putting money into investment accounts may improve long-term financial results, for certain households, ongoing mortgage payments maintain liquidity and flexibility. For Overstock.com families, the right decision depends on evaluating your broader financial picture rather than making a blanket assumption about debt.

Myth 5: You Should Never Take Out a Reverse Mortgage

Despite their reputation for predatory behavior, ²  reverse mortgages are now strictly regulated financial instruments. They can give homeowners 62 years of age or older access to their home equity without necessitating a sale or producing taxable income.

'A reverse mortgage can be helpful for the right retiree—supplementing income, helping cover health care costs, or reducing the need to draw from investments during market downturns,' Boudreaux explains, adding that they are not for everyone.

The proceeds are usually not regarded as taxable income because they are structured as a loan. In some cases, this can result in meaningful tax savings. But careful consideration is essential. Long-term objectives, estate planning factors, and household financial dynamics must all be taken into account when implementing a reverse mortgage. Overstock.com employees should consult trusted advisors before deciding if this tool fits their retirement plan.

Myth 6: Your Greatest Financial Risk Is a Stock Market Crash

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Market downturns frequently make the news, escalating retirement worries. Yet, even though it can be unnerving, volatility isn't always the biggest risk to long-term financial health.

Hernandez says, 'Diversification and careful planning help cushion market downturns. But fraud and scams are among the most underrated threats.'

Con artists commonly use text messages, emails, and phone calls to target older individuals. Scammers take advantage of weaknesses, such as cognitive deterioration, to obtain personal information or money. ³  Financial losses resulting from fraud can quickly damage a retirement fund, frequently more severely than a brief drop in the stock market. Overstock.com retirees should remain cautious by safeguarding personal information, rejecting unverified payment requests, and confirming suspicious communications with trusted advisors.

Retirement Is Individual

Dispelling these six fallacies reveals an important reality: retirement preparation is very personal. Decisions that depend on particular conditions can be oversimplified by general guidelines and recommendations.

Boudreaux highlights that each retiree has distinct objectives, family dynamics, and risk tolerances. 'For this reason, a customized strategy is more important than merely adhering to general myths.'

The objective is to use your savings wisely—to support your lifestyle, your loved ones, and the causes that are most important to you—rather than merely preserving them, Hernandez adds.

Retirement ought to be viewed as a living strategy that is adaptable, flexible, and representative of individual priorities. By moving past outdated beliefs, Overstock.com retirees can approach their financial prospects with clarity, resilience, and the freedom that retirement was intended to offer.

According to recent behavioral finance research, retirees who are financially literate, optimistic, future-oriented, and reward-focused are more proactive in their retirement planning—qualities that can be developed over time. People who possessed these traits were less stressed about money and had a tendency to save more regularly. Even though just about 10% of respondents had all four qualities, the study shows that cultivating them may help enhance retirement results. ⁴

Closing Analogy

Retirement planning is similar to driving across the country. Myths like 'every detour is dangerous,' 'fuel should never be used for a scenic stop,' and 'the journey must end with a perfectly full tank' are examples of out-of-date maps that can lead people astray. Knowing when to share resources along the journey, when to save for unforeseen circumstances, and when to savor a meaningful pause are all essential components of true success. For Overstock.com employees, the path ahead becomes smoother and more rewarding when outdated misconceptions are replaced with well-informed tactics.

Sources:

1. IRS, ' Estate tax ,' October 29, 2024.

2. Bankrate, ' Reverse mortgage scams: What they are and how to avoid them ,' by Kacie Goff, June 9, 2025. 

3. FBI, ' Elder Fraud ,' 2025. 

4. Goldman Sachs Asset Management, ' Retirement Mindset Matters ,' October 2023.