Picture this: You’ve spent decades building wealth, accumulating assets, and preparing for the retirement you’ve always envisioned. But as you stand on the threshold of this next phase, a question lingers—Am I truly prepared?

Many high-net-worth individuals face this uncertainty, not because they lack financial resources but because true retirement readiness extends beyond just savings. It involves strategic tax planning, investment decisions, legacy preservation, and ensuring your lifestyle aligns with your long-term goals.

Retirement planning is not a one-size-fits-all endeavor. It’s a tailored process, much like orchestrating a complex financial symphony. Every component—investment diversification, income distribution strategies, tax efficiency, healthcare considerations, and estate planning—plays a crucial role in crafting a retirement that is not only financially secure but also personally fulfilling.

To help guide this journey, we’ve compiled 22 essential questions that high-net-worth individuals should consider when planning for retirement. These questions are designed to provoke thought, identify potential gaps, and highlight key areas where working with a seasoned financial professional like William Bevins, CFP, CTFA can add value.

Investment & Portfolio Management

1. Is my investment portfolio properly diversified? Concentrated assets—such as company stock or real estate holdings—can create risk. A balanced portfolio with a mix of asset classes can help provide stability and growth.

2. How should my asset allocation evolve as I approach and enter retirement? Retirement requires a shift from accumulation to preservation. The right balance of stocks, bonds, and alternative investments is crucial.

3. How will Required Minimum Distributions (RMDs) impact my financial strategy during retirement? RMDs from tax-deferred accounts begin at age 73. Planning these withdrawals strategically can help minimize unnecessary tax burdens.

Tax Planning for Retirement

4. Am I utilizing the most effective tax strategies for retirement? With the right mix of taxable, tax-deferred, and tax-free accounts, you can optimize tax efficiency. Consulting a financial professional can help you manage withdrawals effectively.
5. Should I consider a Roth IRA conversion? If you anticipate being in a higher tax bracket later, converting funds from a traditional IRA to a Roth IRA could be beneficial, locking in lower tax rates today.
6. How do state income taxes impact my retirement income? Tennessee has no state income tax, which can be an advantage. However, understanding how taxes affect Social Security and other income sources is essential.

Income Planning in Retirement

7. What is my optimal withdrawal strategy during retirement? The sequence of withdrawals from different accounts can significantly impact longevity and tax liability. Planning this strategically ensures long-term sustainability.
8. When should I start claiming Social Security? Claiming Social Security early reduces monthly benefits, while delaying can increase them substantially. A customized plan can determine the best timing.
9. Should annuities play a role in my income strategy? While annuities can provide guaranteed income, they must be carefully evaluated for their costs, benefits, and role within an overall plan.

Healthcare & Long-Term Care Considerations

10. What are my expected healthcare costs in retirement? Medicare alone doesn’t cover all healthcare expenses. Planning for out-of-pocket costs, supplemental insurance, and long-term care is critical.
11. Do I need long-term care insurance? The potential for long-term care expenses can significantly impact retirement assets. Exploring hybrid policies or self-insurance strategies is advisable.

Estate & Legacy Planning

12. How can I reduce estate taxes and maximize my legacy? Without proper planning, estate taxes can erode wealth. Trusts, gifting strategies, and tax-efficient estate planning help protect assets for future generations.
13. What is the best strategy for passing wealth to heirs? Annual gifting, 529 education plans, and structured trusts can help transfer wealth efficiently and according to your wishes.
14. How can I support charitable causes while maximizing tax benefits? Donor-advised funds, charitable remainder trusts, and Qualified Charitable Distributions (QCDs) offer ways to give back while reducing tax exposure.

Lifestyle & Housing Decisions

15. Should I downsize or maintain multiple residences prior to retirement? Balancing housing expenses, tax implications, and lifestyle preferences is key when considering homeownership in retirement.
16. How will my spending habits change in retirement? Identifying discretionary and fixed expenses helps ensure a sustainable lifestyle while preserving wealth for later years.

Market Volatility & Risk Management

17. How should I protect my portfolio against market downturns? Diversification, alternative investments, and a structured income strategy help mitigate volatility risk.
18. What insurance coverage should I maintain as I get older? Reviewing life, liability, and property insurance policies ensures adequate protection in retirement.
19. How do I safeguard against inflation eroding my purchasing power? Investments in growth-oriented assets, inflation-protected securities, and real estate can hedge against rising costs.

Cognitive & Longevity Planning

20. Do I have a plan for cognitive decline in my golden years? Establishing a durable power of attorney, updating estate plans, and appointing trusted advisors provide security.
21. What role does longevity risk play in my retirement strategy? With longer lifespans, ensuring assets last through retirement is critical. A sustainable withdrawal strategy and careful spending habits help mitigate this risk.

Ongoing Financial Review

22. How often should I revisit my retirement plan? Retirement planning isn’t a one-time event. Regular portfolio reviews, tax strategy adjustments, and goal reassessments help maintain alignment with changing circumstances.

Work with a Financial Professional

High-net-worth retirement planning is complex, requiring careful coordination of investments, tax strategies, estate considerations, and personal lifestyle goals. If you’re looking for guidance, William Bevins, CFP, CTFA can provide tailored strategies designed to align with your specific needs.

Visit William Bevins’ website to explore wealth management, retirement planning, and fiduciary services designed to help you navigate your financial future with confidence.