The Five Biggest Stealth Costs in Retirement for Dropbox Employees

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'Dropbox employees must remain vigilant about hidden costs in retirement, as unexpected expenses like health care, taxes, and inflation can have a real impact on their long-term financial well-being. Proactive planning and budgeting for these stealth expenses can provide much-needed peace of mind as they enter retirement.' – Michael Corgiat, a representative of The Retirement Group, a division of Wealth Enhancement.

'Dropbox retirees often underestimate the impact of inflation and unexpected medical costs on their retirement savings. By planning for these stealth expenses and adjusting their budgets accordingly, they may avoid unnecessary financial strain and maintain a comfortable lifestyle throughout retirement.' – Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. The five most common stealth expenses in retirement, including health care, taxes, emergencies, family-related expenses, and inflation.

2. The impact of inflation and unexpected costs on Dropbox retirees.

3. Strategies to reduce the burden of stealth expenses through proactive planning and saving.

Many Dropbox employees concentrate on budgeting and income management while making retirement plans. While this is crucial, planning for hidden or stealth costs—unexpected expenses that can occur and negatively impact finances—is often overlooked. Even with a well-thought-out budget, retirees may find themselves caught off guard by these expenses, leading to unnecessary stress.

Unexpected expenses are a significant factor in 43% of retirees feeling more financially worried than before retirement, according to a recent study by TheSeniorList.com. ¹  Many Dropbox retirees realize that they are unprepared for the hidden costs that emerge once they leave employment, despite saving substantial amounts for retirement. While $1.26 million is considered an ideal amount to retire comfortably, ²  many Dropbox employees haven’t reached this target, making them vulnerable to unanticipated costs that could derail their financial plans.

“Dropbox retirees and pre-retirees recognize the imperative to plan for unforeseen financial events, but they often struggle to put aside sufficient funds to do so,” says Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement. The current high rate of inflation is making it more challenging for investments and savings to keep up with rising prices, exacerbating the issue. Notably, 20% of retirees and 35% of pre-retirees say they experienced a financial shock that caused them to lose more than 25% of their assets, according to the Retirement Risk Survey conducted by the Society of Actuaries (SOA) Research Institute. ³  This underscores the importance of addressing hidden expenses in retirement.

To help prevent financial strain, Dropbox retirees should prepare for and anticipate the five most common stealth expenses listed below.

Health Care Expenses

Dropbox retirees are often surprised by the full cost of health care, despite it being a known expense. Unexpected medical expenses, especially for serious or chronic conditions, can become a significant financial burden. 'Putting numbers around the potential cost of unexpected medical crisis is notoriously challenging, and even chronic health issues are hard to estimate, especially if they last longer than expected,' says Patrick Ray, a financial advisor at The Retirement Group, a division of Wealth Enhancement. The price of medical care might vary greatly. A hospital stay of two nights could cost about $20,000, but a longer stay or a serious illness could easily exceed $100,000. ⁴

Even for those with insurance, medical bills are a common source of hidden costs. Dropbox retirees may need to cover a significant portion of medical expenses due to escalating insurance premiums, co-pays, and deductibles. By confirming they have adequate insurance coverage, including supplemental insurance for unforeseen medical costs, retirees can manage these expenses more effectively. Home insurance can also provide additional financial support for unexpected costs, such as an injury on the property.

Taxes

Taxes do not disappear in retirement, despite what many retirees may assume. Many Dropbox retirees believe they won’t need to pay taxes once they stop working. However, this is rarely the case, especially for those with multiple income sources. 'Although many retirees no longer earn a salary, they still receive income from an array of sources, such as employer-sponsored plans, savings and investments, and Social Security,' says Kevin Won, a financial advisor with The Retirement Group.

Depending on its source, retirement income may be taxed differently. For example, distributions from retirement accounts like IRAs and 401ks are taxable, and Social Security benefits may be taxed if a retiree's income surpasses certain thresholds. Taxes on investment income can complicate retirement planning. Dropbox retirees can save on taxes by using strategic asset placement and planning. 

Emergencies

Emergencies are an inevitable aspect of life, and their unpredictability makes them especially challenging to prepare for. These emergencies can include anything from car repairs and home maintenance to unanticipated legal or family medical expenses. Neva Bradley, a financial advisor at The Retirement Group, emphasizes the importance of putting money aside for these situations. On a fixed income, she explains, 'retirees who don't put funds aside for emergencies risk facing unexpected expenses that could reduce  their monthly income, making it harder to cover necessary costs.'

Dropbox retirees can manage these unexpected costs by maintaining a separate emergency savings fund. It is important to set aside a percentage of funds specifically for emergencies, so retirees can cover expenses without having to dip into their primary retirement savings or return to work.

Family Emergencies

Financial emergencies involving family members can also be a significant hidden expense in retirement. Many retirees, including those at Dropbox, want to help their adult children or grandchildren during difficult times. Helping adult children in a crisis or contributing to grandchildren’s college tuition could cost up to $20,000 per year or more for tuition alone.

Major family events, such as the death of a spouse, can also create high expenses. For instance, typical funerals cost between $7,000 and $12,000, ⁵  and there may also be legal fees to settle the estate, which can range from $5,000 to $10,000 or more. ⁶  Financial advisor Kevin Won stresses the importance of planning for these expenses. “Retirees who want to help family members through tough times should think through how they plan to cover those costs,” he says.

Costs Associated with Inflation

Inflation is one of the most common and unpredictable expenses in retirement. Many Dropbox retirees aren’t prepared for their purchasing power to slowly decrease. Inflation can significantly erode the value of retirement funds, making it harder to maintain your desired lifestyle. 'Inflation isn't something you can control, but it is something you can plan for,' says Kevin Won. This begins by understanding how inflation could erode your purchasing power over time. For instance, investments of $50,000 annually today would notionally need to grow to $90,000 in 20 years to maintain the same purchasing power.

Inflation impacts every aspect of life, from housing and health care to food and transportation. Inflation and the cost of living were cited by 28% of retirees as the most unexpected aspect of their retirement planning, slightly surpassing the 27% who mentioned medical and health care costs, according to the SeniorList survey. Dropbox retirees living in older homes or regions susceptible to natural disasters may also face additional costs for repairs or insurance.

Three Strategies to Reduce Retirement Stealth Expenses

Fortunately, Dropbox retirees can take steps to prepare for and reduce the burden of these hidden costs.

Create a 'Stealth' Annual Budget

One practical approach is to create an annual budget specifically for stealth expenses. By planning in advance, Dropbox retirees can minimize the stress of dealing with unforeseen bills, which many mistakenly treat as emergencies. Neva Bradley advises, 'Budget for these expenses annually.' Regular retirement budgeting should include costs such as car updates or appliance replacements.

Delay Retirement

Delaying retirement by even a few months or years can help enhance a retiree's financial situation. Continuing to work allows retirees to save more, avoid early withdrawals from retirement accounts, and let investments grow. Neva Bradley recommends that Dropbox retirees 'push back retirement for as long as practical' to strengthen their financial position.

Put the Money Away Early

One of the most effective ways to prepare for unforeseen expenses is to start saving for retirement as early as possible. Paul Bergeron from The Retirement Group suggests using health savings accounts (HSAs) to save for future medical costs. 'Health care costs are on the rise and often exceed what retirees anticipate. An HSA can help,' he notes. Even without an HSA, Dropbox retirees should prioritize saving for medical expenses to cover co-pays, co-insurance, and uncovered health care costs that can quickly add up.

In Conclusion

Hidden costs, such as health care, taxes, emergencies, family-related expenses, and inflation, can significantly affect Dropbox retirees’ financial well-being. While these expenses are often unforeseen, retirees can take proactive steps to plan for them. By budgeting for unexpected costs annually, delaying retirement, and saving strategically, Dropbox retirees can alleviate the financial strain brought on by stealth expenses and craft a comfortable retirement.

The soaring expense of long-term care, often not fully covered by health insurance, is a major concern for retirees. Those who are currently 65 have almost a 70% chance of needing some type of long-term care services in the future. ⁷  Planning ahead for these costs, whether through insurance or savings, is crucial for safeguarding retirement income.

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Sources:

1. TheSeniorList. ' Surprise Retirement Costs: What Seniors Need to Know To Protect Their Savings ,' by Amie Clark. 8 Oct. 2024.

2. CNBC. ' The 'magic number' to retire comfortably fell to $1.26 million--but people are less confident they can reach it ,' by Jessica Dickler. 21 Apr. 2025. 

3. Society of Actuaries. “ Retirement Risk Survey Finds Financial Shocks .” Society of Actuaries, 19 Dec. 2024.

4. International Citizens Insurance. ' How Must Does Healthcare Cost in the U.S.? ' 2025.

5. Trust & Will. ' Funeral Costs 101 .' 2025.

6. Trustate. ' Estate Expenses - Who Pays What? ' 2025.

7. Administration for Community Living. ' How Much Care Will You Need? ' 18 Feb. 2020.

Other Resources:

Kiplinger. “The Five Biggest Stealth Costs in Retirement.” Kiplinger, 26 May 2025.