5 Tips for Long-Term Health Planning Every Dropbox Employee Should Consider

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'Dropbox employees preparing for the later stages of life benefit from addressing long-term planning early by taking steady, proactive steps that align their personal goals with the realities of aging.' - Paul Bergeron, The Retirement Group, a division of Wealth Enhancement.

'Dropbox employees can strengthen their long-term planning by taking thoughtful, early steps that support clarity and confidence as they age to stay proactive and intentional in shaping their future.' - Tyson Mavar, The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. How to prepare for the challenges of aging through proactive planning.

2. How to organize your living situation, documents, and family communication.

3. How to use tools like HSAs and long-term care insurance to support future needs.

Important lessons learned

- Although planning is never too late, starting early can help you get ready for the difficulties that come with growing older, especially for employees navigating the benefit programs offered through Dropbox.

- Clearly state your expectations and ambitions, including where you want to live and how you want to maintain your preferred lifestyle.

- Organize vital paperwork and make sure your family is aware of your financial situation and wishes.

- To assist with future medical costs, consider long-term care insurance options and health savings accounts (HSAs).

Government estimates reveal that someone turning 65 today has roughly a 70% chance of needing some type of long-term care services or supports in later life. ¹  This highlights why planning matters for those preparing for retirement from Dropbox. With odds like that, having a plan in place can help you or your loved ones get ready for medical, financial, or personal challenges that may arise.

Thinking about these things isn't always simple, and many put off planning until facing a crisis with an elderly parent, spouse, or themselves. Our understanding of our needs is often shaped by personal experiences, whether involving an abrupt loss, a long illness, or many years of independence. While some people use skilled nursing facilities, senior communities, or at-home care, others rely on help from family or neighbors. These experiences highlight the importance of not making rushed decisions or leaving critical choices to others.

Planning may be done at any age, but the longer you delay, the harder it may be—something many Dropbox professionals recognize as they approach retirement. With the right information and guidance, you can create a long-term health plan that reflects your objectives, accounts for potential obstacles, and helps you prepare for future costs as you age.

1. Clarify your objectives and expectations

Your future vision should be the first step in any long-term plan, including for those charting retirement paths after a long tenure with Dropbox. Consider what you want for yourself and what you believe would be an ideal outcome. Knowing your objectives helps provide direction while shaping your plan.

Being realistic about what you might anticipate in the coming years is also important. Even if your experience may differ from past generations, your family’s medical history can offer insight. Conversations with your health care providers can help you understand what to monitor and how to support your health over time. Reflecting on how much assistance you may need—and from whom—allows you to make choices aligned with the quality of life you want.

2. Evaluate your living conditions

Think about whether your current home will still meet your needs as you age, a common consideration among employees preparing for retirement from Dropbox. Home accessibility plays an important role since falls remain the leading cause of injury-related deaths among people 65 and older. ²

Modifying your home—such as installing ramps, handrails, or improved accessibility—can be easier when done proactively rather than in an emergency. If modifications are too costly or impractical, downsizing to a home more suitable for aging needs may be worthwhile. Moving earlier also gives you more time to adjust.

Proximity to support is another key factor. Living near dependable family members, trusted neighbors, or health care providers can make a meaningful difference when more assistance becomes necessary.

3. Arrange your paperwork

Clear documentation allows your wishes to be carried out and gives your family what they need in an emergency, which is especially important for those coordinating retirement assets earned during years at Dropbox. Essential estate planning documents include:

• - A will , which outlines how assets not governed by beneficiary designations or titling should be distributed and who will manage your affairs after your passing.

• - A financial power of attorney , permitting someone to handle your financial matters if you become unable to do so.

• - A medical power of attorney (health care proxy) , allowing someone to receive information and make medical decisions if you cannot.

• - A living will , documenting your wishes regarding care and end-of-life decisions.

Preparing these documents in advance makes it easier for your family to navigate difficult times.

4. Speak with your relatives

Open communication improves planning, particularly for families where one or more members are transitioning from a career at Dropbox. While discussing finances and end-of-life decisions can feel uncomfortable, it is vital for your loved ones to know where documents are stored and understand the general structure of your financial affairs. You do not need to disclose every detail—just note how many accounts you hold, where they are located, how they are titled, and who should be contacted in an emergency, such as executors or trustees.

5. Consider health savings accounts and long-term care “hybrid” insurance policies

Those enrolled in a qualifying high-deductible health plan—including some used by employees at Dropbox—may be eligible to contribute to a Health Savings Account (HSA). These accounts allow contributions that are pre-tax or tax-deductible, offer tax-free growth, and allow tax-free withdrawals for qualified medical expenses. Although contribution limits apply, HSAs can support both current and future medical needs.

Another option is hybrid long-term care insurance, which links long-term care benefits to life insurance. If you develop a qualifying cognitive condition or cannot perform at least two activities of daily living (such as bathing or dressing), these policies may allow access to part of the death benefit for care. Even if long-term care benefits are never used, the life insurance component typically provides value to beneficiaries.

The Retirement Group can help

Long-term care planning can be technically and emotionally challenging, particularly for those coordinating benefits tied to years of service with Dropbox. The Retirement Group can help you review your options, understand potential financial implications, and shape a plan tailored to your needs. You can call  (800) 900-5867  to learn more or speak with our team.

Engage in professional work

Working with a knowledgeable specialist allows you to address both the financial and personal dimensions of long-term planning. With thoughtful preparation, you can build a plan that reflects your goals and provides clarity for you and your loved ones as you age.

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Sources:

1. Administration for Community Living. “ How Much Care Will You Need? ” U.S. Department of Health & Human Services, 18 Feb. 2020.

2. Centers for Disease Control and Prevention. “ About Older Adult Fall Prevention ,” May 16, 2024. 

3. Internal Revenue Service. Publication 969: Health Savings Accounts and Other Tax-Favored Health Plans. Internal Revenue Service, 2024.

4. National Association of Insurance Commissioners. A Shopper’s Guide to Long-Term Care Insurance. NAIC, 2019.

5. National Institute on Aging. “Advance Care Planning: Advance Directives for Health Care.” National Institutes of Health, 31 Oct. 2022.