Essential Retirement Planning Strategies for Pre-Retirees in Hawaii

June 2, 2025

By Daniel Masuda Lehrman, CFP®, CSLP®

Are you worried about having enough savings to retire comfortably? If you are like many pre-retirees, this is a question that keeps you up at night. As you approach retirement age, the stakes feel higher than ever. You want to ensure a secure financial future for yourself and your loved ones. Fortunately, with the right planning and a clear understanding of your financial landscape, you can take control of your retirement journey and make informed decisions that align with your goals. Retirement planning is not just about having enough money in your accounts; it's about having a strategy that fits your lifestyle, priorities, and needs. As a fee-only financial planner based in Hawaii, I specialize in helping individuals aged 55-65 navigate this critical phase of life, particularly those with $500,000 to $4 million in liquid net worth or those facing significant inheritances. In this blog post, we will explore essential considerations for retirement planning, addressing common concerns such as how to generate income during retirement, minimize taxes on withdrawals, and prepare for long-term care. By the end of this article, you will have actionable insights that can help you retire with confidence. As you approach retirement, it’s natural to have concerns about your financial future. You may wonder, “Do I have enough to retire comfortably?” or “How do I reduce risk and generate income in retirement?” These questions are particularly pressing in today’s economic climate, where market fluctuations and rising costs can create uncertainty. This blog is designed to equip you with the knowledge and tools you need to navigate these challenges successfully. Whether you are evaluating your current savings, considering your pension options, or exploring tax strategies, the insights provided here will help you make informed decisions that support your retirement goals. Let’s dive into some of the most common concerns faced by pre-retirees and how you can address them effectively. One of the first questions that often arises when planning for retirement is, “Do I have enough to retire comfortably?” To answer this, you need to assess your current financial situation and future needs. Start by calculating your expected expenses in retirement. Consider housing costs, healthcare, travel, and leisure activities. Many people underestimate their expenses, leading to a shortfall later on. A good rule of thumb is to aim for 70-80% of your pre-retirement income to maintain your lifestyle. Next, evaluate your assets. This includes your savings accounts, retirement accounts, investments, and any other sources of income you expect to receive, such as Social Security or pensions. For those with significant inheritances, understanding how to manage and allocate those funds is crucial. A fee-only financial planner can help you create a comprehensive retirement plan that takes all these factors into account, including your risk tolerance and investment preferences. Once you have a clear picture of your expenses and assets, you can begin to determine whether you have enough saved for retirement. A common strategy is to use the 4% rule, which suggests that you can withdraw 4% of your retirement savings annually without depleting your funds too quickly. However, this rule is not one-size-fits-all and may need to be adjusted based on your circumstances, market conditions, and life expectancy. Another vital concern for pre-retirees is how to generate income in retirement while minimizing risk. It’s essential to strike a balance between growth and safety in your investment portfolio. As you near retirement, you may want to shift your portfolio toward more conservative investments, such as bonds or dividend-paying stocks, to reduce volatility. This shift can help preserve your capital while still providing some income. Consider diversifying your income sources. Relying solely on withdrawals from your retirement accounts can be risky, especially in a down market. Explore options like rental properties, part-time work, or annuities to create additional income streams. Annuities can provide guaranteed income for life, which can be particularly appealing for those concerned about outliving their savings. However, it’s essential to understand the terms and fees associated with any annuity product before committing. Tax planning is another crucial aspect of retirement that can significantly impact your financial well-being. “How can I minimize taxes on withdrawals?” is a common question. One strategy is to consider the timing of your withdrawals. If you can delay taking Social Security benefits, you may receive a higher monthly amount later on. Additionally, be mindful of your tax bracket when withdrawing from your retirement accounts. Strategically withdrawing funds from taxable accounts first can help you manage your tax burden over time. Roth conversions are also worth considering as you prepare for retirement. “Is now the right time for a Roth conversion?” This strategy involves converting a portion of your traditional retirement accounts into Roth accounts, allowing your investments to grow tax-free. This can be particularly beneficial if you expect to be in a higher tax bracket in the future or if you want to leave tax-free inheritance to your heirs. However, it’s essential to consult with a financial planner to determine if this strategy aligns with your overall financial goals. Long-term care is another critical consideration in retirement planning. “How do I plan for long-term care?” As you age, the likelihood of needing assistance with daily activities increases. Without proper planning, the costs of long-term care can quickly deplete your savings. Consider purchasing long-term care insurance or setting aside a dedicated fund for potential care needs. Understanding your options and the associated costs can help you make informed decisions that protect your financial future. Market volatility can also weigh heavily on the minds of pre-retirees. “What happens if the market crashes just before I retire?” It’s essential to have a strategy in place to weather these fluctuations. Maintaining a diversified portfolio and having a cash reserve can provide a buffer during market downturns. Additionally, consider your withdrawal strategy. If you can avoid selling investments during a market dip, you can give your portfolio time to recover. A financial planner can help you develop a plan that accounts for market risks and ensures you can sustain your lifestyle in retirement. For those navigating a significant inheritance, protecting and transferring wealth efficiently is crucial. “How do I protect and transfer inherited wealth efficiently?” Start by understanding the tax implications of your inheritance, including estate taxes and capital gains taxes. Work with a financial advisor to create a strategy for managing your inheritance, whether that involves investing, gifting, or creating a trust. Proper planning can help you maximize the benefits of your inheritance while minimizing tax liabilities. In summary, planning for retirement can feel overwhelming, but you are not alone. By addressing key concerns such as income generation, tax strategies, long-term care, and market volatility, you can create a solid plan that supports your retirement goals. Remember, retirement planning is not a one-time event; it requires ongoing evaluation and adjustments as your life circumstances change. Working with a fee-only financial planner can provide valuable guidance tailored to your unique situation, helping you navigate the complexities of retirement planning with confidence. As you reflect on your retirement journey, I encourage you to consider your own plans. Are you preparing to retire within the next five years? Would you take a lump sum or a pension? Curious whether a Roth conversion makes sense for your situation? The answers to these questions can shape your financial future, and I invite you to reach out for personalized guidance. At www.hawaiiadvisor.com, we are dedicated to helping you achieve your retirement goals through comprehensive planning and expert advice. Let’s work together to build a retirement strategy that brings you peace of mind and financial security.
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.

Schedule a meeting