Your Essential Guide to Retirement Planning: Key Insights for Near-Retirees in Hawaii

May 18, 2025

By Daniel Masuda Lehrman, CFP®, CSLP®

Are you worried about whether you have enough to retire comfortably? As you approach retirement, the questions can feel overwhelming. With a variety of financial decisions looming, it’s natural to wonder if your savings will last and how to best prepare for this important life transition. In particular, for those in Hawaii, where the cost of living can be high, understanding your financial position is crucial. This blog post will tackle the pressing concerns of near-retirees like you, helping you navigate the complexities of retirement planning while ensuring that you feel confident about your financial future. Retirement is often seen as a time to relax and enjoy the fruits of your labor, but the reality can be quite different if you haven't taken the necessary steps to secure your financial well-being. As a fee-only financial planner in Hawaii, I have worked with many clients who are in their pre-retirement phase, helping them address common concerns such as whether they have enough savings to retire comfortably and how to effectively generate income in retirement. In this article, you will find valuable insights and actionable advice that can empower you to make informed financial decisions as you approach your golden years. Let’s dive deep into some of the most pressing questions that pre-retirees face today. Do I Have Enough to Retire Comfortably? One of the primary concerns for those nearing retirement is whether they have saved enough to enjoy a comfortable lifestyle without the fear of running out of money. The answer to this question is not a straightforward one, as it depends on various factors, including your current savings, expected expenses in retirement, and your desired lifestyle. However, there are practical steps you can take to assess your financial readiness. Start by calculating your expected expenses during retirement. Consider your current living expenses and think about how they may change when you stop working. Will you travel more? Will you downsize your home? It’s essential to create a realistic budget that includes your essential expenses as well as discretionary spending. Once you have a clear picture of your anticipated expenses, you can start to evaluate your savings and income sources. Next, consider your income sources in retirement. This includes Social Security benefits, pensions, and any investment income you may have. Understanding how these income streams will support your expenses is vital. If you find that your income sources do not cover your expected expenses, it may be time to reassess your savings strategy. A common guideline is to have enough savings to replace about 70% to 80% of your pre-retirement income. However, this can vary depending on your lifestyle and needs. Additionally, it’s important to factor in healthcare costs, which can be significant in retirement. According to recent studies, a couple retiring at age 65 can expect to spend around $300,000 on healthcare throughout their retirement years. Having a plan for these expenses is essential to ensure you do not deplete your savings too quickly. How Do I Reduce Risk and Generate Income in Retirement? As you transition into retirement, the focus shifts from growth to income generation. This is where many retirees feel challenged, especially in a fluctuating market. It's crucial to have a diversified investment strategy that balances risk and income generation. Consider creating a well-structured income plan that outlines how and when you will withdraw funds from your retirement accounts. One common strategy is the “4% rule,” which suggests withdrawing 4% of your retirement savings each year. However, depending on market conditions and your personal situation, this may not be the best approach for everyone. A more tailored strategy may involve segmenting your assets into different buckets based on when you will need to access them. For instance, you can have a short-term bucket with cash and bonds to cover your immediate income needs, and a long-term bucket with stocks to provide growth for later years. This strategy can help you minimize risk during market downturns and ensure you have the liquidity you need in the short term. Additionally, consider the importance of annuities as a potential income source. Annuities can provide guaranteed income streams for a specified period or for life, offering peace of mind for retirees concerned about outliving their assets. However, it’s essential to understand the intricacies of annuities, including fees and terms, before committing to this option. Finally, don’t overlook the potential of part-time work or side gigs during retirement. Many retirees find that continuing to work part-time can provide additional income while allowing them to stay engaged and active. How Can I Minimize Taxes on Withdrawals? Tax planning is a critical component of retirement planning that can significantly impact your overall financial health. As you prepare to withdraw funds from your retirement accounts, understanding how taxes will affect your withdrawals is essential. One effective approach to minimizing taxes is to strategically time your withdrawals. For example, if you expect to be in a lower tax bracket in retirement, it may make sense to delay withdrawals from your tax-deferred accounts like traditional IRAs and 401(k)s until you are required to take minimum distributions (RMDs) at age 72. In the meantime, you can withdraw from your taxable accounts or Roth accounts, which can help you manage your taxable income. Roth conversions also present an opportunity for tax management. Consider converting a portion of your traditional IRA to a Roth IRA, especially in years when your income may be lower. This strategy allows your money to grow tax-free and can provide tax-free withdrawals in retirement, reducing your overall tax burden. It’s also wise to consult with a tax professional to create a withdrawal strategy that aligns with your financial situation. By being proactive about your tax planning, you can maximize your retirement income and preserve more of your savings over time. What Happens If the Market Crashes Just Before I Retire? Market volatility can be a significant concern for those nearing retirement, especially if a market crash occurs just as you are about to retire. The fear of losing a substantial portion of your portfolio can lead to anxiety and uncertainty about your financial future. To mitigate the impact of market downturns, it’s crucial to have a well-thought-out investment strategy that includes a diversified portfolio. Diversification across different asset classes can help reduce risk and provide greater stability during turbulent times. Another strategy is to establish a cash reserve that covers your expenses for the first few years of retirement. This cash reserve can act as a buffer during market downturns, allowing you to avoid selling investments at a loss to meet your immediate income needs. Additionally, consider a dynamic withdrawal strategy that adjusts your withdrawals based on market performance. If the market performs well, you can withdraw more, and if it dips, you can reduce your withdrawals. This approach can help you preserve your portfolio during challenging market conditions. Protecting and Transferring Inherited Wealth Efficiently For those who have recently received a significant inheritance, managing and transferring that wealth can be a daunting task. It’s crucial to create a plan that maximizes the benefits of your inherited assets while minimizing taxes and ensuring a smooth transfer to future generations. Start by assessing the inherited assets and determining their value. This includes real estate, investments, and any other financial accounts. Understanding the tax implications of your inheritance is also essential, as certain assets may be subject to estate taxes or capital gains taxes when sold. Consider consulting with a financial planner or estate attorney to develop a comprehensive estate plan that outlines how you wish to manage and transfer your inherited wealth. This plan should consider your long-term financial goals, tax strategies, and how you want to provide for your heirs. By taking proactive steps to manage your inherited wealth, you can ensure that your assets are preserved and passed down according to your wishes. In summary, navigating retirement planning can be a complex process, but it is crucial for ensuring your financial security as you transition into this new phase of life. By addressing key concerns such as whether you have enough to retire comfortably, how to generate income while minimizing risk, and effectively managing taxes, you can create a robust financial plan that meets your needs. Remember, you are not alone in this journey, and seeking the guidance of a fee-only financial planner can provide you with tailored advice that aligns with your unique situation. Are you planning to retire within the next 5 years? If so, start taking proactive steps today to ensure you have the financial security you desire. Would you take the lump sum or the pension if faced with that choice? Curious whether a Roth conversion makes sense for you? Let’s explore these questions together and pave the way for a successful retirement journey!
About Daniel Masuda Lehrman

I am a Fee-Only Fiduciary and Founder of Masuda Lehrman Wealth LLC. Prior to starting my own firm, I was a Vice President Financial Consultant at Charles Schwab in their Downtown Honolulu office. I have worked in financial planning for 10 years at Vanguard, Fidelity, and Schwab. I'm a CERTIFIED FINANCIAL PLANNER™ professional (CFP®) and Certified Student Loan Professional with an Economics degree from the University of Michigan.

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