Essential Retirement Planning Strategies for Pre-Retirees in Hawaii

May 31, 2025

By Daniel Masuda Lehrman, CFP®, CSLP®

Are you worried about whether you have enough money saved to retire comfortably? You're not alone. Many pre-retirees find themselves facing this daunting question as they approach retirement age. With the right strategies and insights, you can navigate this challenging phase with confidence. As you find yourself edging closer to retirement, it's normal to have concerns about your financial future. You may be asking yourself, "Do I have enough to retire comfortably?" or "How can I reduce risk and generate income during retirement?" These are valid questions that deserve thoughtful consideration. With the right guidance, you can create a roadmap for a secure financial future that aligns with your lifestyle and aspirations. In this blog post, we will dive deep into some critical aspects of retirement planning, particularly for those aged 55 to 65 with a liquid net worth between $500,000 and $4 million. We'll explore how to assess your readiness for retirement, strategies for generating income, and ways to mitigate tax implications on your withdrawals. By breaking down these concepts, my goal is to equip you with actionable insights that will empower you to make informed decisions as you approach this significant life transition. One of the first steps in preparing for retirement is assessing whether you have enough saved to retire comfortably. This involves not only calculating your current savings but also projecting your future expenses. Many pre-retirees underestimate their expenses in retirement, often overlooking costs such as health care, long-term care, and leisure activities. It's essential to create a comprehensive budget that reflects your expected lifestyle during retirement. Consider consulting with a fee-only financial planner in Hawaii to gain clarity on your financial situation and ensure that you are on track to meet your retirement goals. Once you have an understanding of your expected expenses, the next step is to evaluate your income sources in retirement. This includes Social Security benefits, pensions, retirement accounts, and any other investments. You may be faced with the decision of whether to take a lump sum from your pension or opt for an annuity. Each option has its pros and cons, and the right choice depends on your individual circumstances and retirement goals. A fee-only financial planner can help you weigh these options and develop a strategy that maximizes your income potential while minimizing risks. In today’s financial landscape, market fluctuations can create anxiety for those nearing retirement. Many individuals worry about what might happen if the market crashes just before they retire. To alleviate these concerns, it's vital to have a diversified investment strategy that balances risk and growth. A well-constructed portfolio should reflect your risk tolerance and time horizon, allowing you to weather market volatility while still pursuing growth. Generating income in retirement is another critical aspect of your financial plan. Many retirees rely on a mix of income sources to maintain their lifestyle. Strategies for generating income may include withdrawals from retirement accounts, dividend-paying stocks, or even part-time work. It's crucial to devise a withdrawal strategy that ensures your savings last throughout your retirement. This often involves a careful analysis of how much you can afford to withdraw annually without depleting your savings too quickly. Tax implications are also a significant consideration when planning for retirement. You may be wondering how to minimize taxes on your withdrawals. One effective strategy is to utilize tax-efficient withdrawal methods. For example, withdrawing from taxable accounts first can help you manage tax liabilities more effectively. Additionally, considering a Roth conversion may be beneficial for some individuals, as it allows for tax-free withdrawals in retirement. However, it's essential to consult with a financial planner to determine whether a Roth conversion aligns with your overall financial strategy. Long-term care planning is another aspect that shouldn’t be overlooked. As you age, the likelihood of needing long-term care increases, and these costs can be substantial. It's crucial to factor in potential long-term care expenses when calculating your retirement budget. Options for addressing these needs range from long-term care insurance to self-funding through savings. Understanding the potential costs and planning accordingly can provide peace of mind as you approach retirement. In summary, navigating retirement planning can seem overwhelming, but it doesn’t have to be. By taking a proactive approach to assess your financial readiness, develop a comprehensive strategy for generating income, and plan for potential tax implications, you can build a secure financial future. Remember, you are not alone in this journey, and there are professionals available, such as fee-only financial planners in Hawaii, who can help guide you through the complexities of retirement planning. As you reflect on your own retirement goals, consider how you can implement these strategies to enhance your financial well-being. Are you planning to retire within the next five years? Would you take the lump sum or the pension? Or are you curious whether a Roth conversion makes sense for you? Whatever your concerns may be, taking the time to address them now will set you on the path to a fulfilling and secure retirement.
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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