Navigating Retirement: Essential Insights for Pre-Retirees in Hawaii

May 28, 2025

By Daniel Masuda Lehrman, CFP®, CSLP®

Are you worried about whether you have enough to retire comfortably? As you approach retirement, these concerns can feel overwhelming. You’ve worked hard to build your wealth, and now you’re faced with crucial decisions that will impact your financial future. With so many factors to consider—from income generation to tax implications—making the right choices can seem daunting. In this article, we will tackle these pressing questions head-on, providing you with actionable insights and clarity to help you navigate this pivotal stage of your life. We’ll explore how to assess your financial readiness for retirement, strategies to reduce risk, generate income, and much more. The reality is that many near-retirees, especially those with a liquid net worth of $500K to $4M, grapple with uncertainty about their financial future. You may wonder, "Do I have enough saved to maintain my lifestyle?" or "How can I ensure my savings last through retirement?" These questions are valid and deserve careful consideration. In this blog post, we aim to give you the tools you need to make informed decisions and feel confident about your retirement planning journey. Now, let’s delve into the key aspects of retirement planning that will help you find peace of mind as you approach this new chapter of your life. Understanding Your Retirement Needs Before diving into specific strategies, it’s essential to understand your unique retirement needs. Everyone’s situation is different, but there are common factors that can help you assess whether you’re on track for retirement. Start by calculating your anticipated expenses in retirement. Consider the following: - What are your current monthly expenses? - Will those expenses change in retirement? - Have you accounted for healthcare costs, which can significantly impact your budget? - What lifestyle changes do you envision during your retirement years? Once you have a clear picture of your expected expenses, you can begin to estimate how much income you will need to cover those costs. A general rule of thumb is that you may need around 70-80% of your pre-retirement income to maintain your standard of living in retirement. However, this can vary depending on your individual circumstances. Assessing Your Income Sources Next, consider the various income sources you’ll have in retirement. This could include Social Security benefits, pensions, retirement accounts (such as 401(k)s and IRAs), and any additional investments or rental income. If you have a pension, you may be faced with the decision of whether to take a lump sum or an annuity. A lump sum gives you immediate access to a large amount of money, while an annuity provides a steady stream of income for a specified period, or even for life. Each option has its advantages and disadvantages, so it’s crucial to weigh them carefully based on your financial situation and risk tolerance. Generating Income in Retirement One of the most significant concerns for retirees is how to generate income while minimizing risk. As you transition from accumulating wealth to spending it, it’s vital to strike a balance between protecting your assets and ensuring you have enough income to cover your needs. One strategy to consider is creating a diversified income stream. This can include a combination of Social Security, pensions, annuities, and withdrawals from retirement accounts. By diversifying your income sources, you can help mitigate the risks associated with market fluctuations and ensure a more stable financial future. Additionally, consider the possibility of using a portion of your liquid assets to invest in income-generating assets, such as dividend-paying stocks, real estate investment trusts (REITs), or bonds. These investments can provide a steady income stream while still allowing for potential growth. Tax Implications and Withdrawals Tax planning is another critical aspect of retirement planning. As you begin to withdraw funds from your retirement accounts, understanding how those withdrawals will be taxed is crucial. Generally, traditional retirement accounts are taxed as ordinary income when you take distributions, while Roth accounts allow for tax-free withdrawals if certain conditions are met. This brings us to the question of whether a Roth conversion makes sense for you. Converting a traditional retirement account to a Roth IRA can provide long-term tax advantages, particularly if you anticipate being in a higher tax bracket in retirement. However, it’s essential to evaluate your current tax situation and consult with a fee-only financial planner to determine if this strategy aligns with your overall retirement goals. Planning for Long-Term Care As you consider your retirement plan, it’s also essential to think about long-term care. With advances in healthcare, people are living longer, and the possibility of needing long-term care services increases. This can significantly impact your financial plan if not properly addressed. Explore options such as long-term care insurance, which can help cover the costs of assisted living or in-home care. Additionally, consider setting aside a portion of your assets specifically for future healthcare needs. By planning ahead, you can protect your wealth and ensure that you have the resources you need should the need arise. Navigating Market Volatility Another concern that often plagues near-retirees is market volatility. What happens if the market crashes just before you retire? It’s a valid concern, especially given the unpredictable nature of the stock market. One way to mitigate this risk is to have a well-structured withdrawal strategy. Instead of withdrawing a fixed percentage of your investments each year, consider using a strategy that adjusts your withdrawals based on market performance. This can help preserve your investment portfolio during downturns and ensure your savings last throughout retirement. Protecting and Transferring Inherited Wealth If you are navigating a significant inheritance, it’s important to consider how to protect and transfer that wealth efficiently. Inherited assets can have unique tax implications, and it’s crucial to understand how to manage them effectively. Consulting with a fee-only financial planner can help you develop a comprehensive plan that addresses your specific needs and goals. They can provide guidance on tax-efficient strategies, estate planning, and how to integrate your inheritance into your overall financial plan. Summary As you approach retirement, it’s natural to have questions and concerns about your financial future. You’re not alone in feeling uncertain about whether you have enough saved to retire comfortably or how to generate income while minimizing risk. The key takeaway is that with careful planning and the right strategies in place, you can create a retirement plan that aligns with your goals and provides peace of mind. By assessing your retirement needs, understanding your income sources, planning for taxes and long-term care, and navigating market volatility, you can take control of your financial future. Remember, it’s never too late to seek guidance from a fee-only financial planner in Hawaii who understands the unique challenges you face as a pre-retiree. Are you planning to retire within the next 5 years? Would you take a lump sum or the pension? Curious whether a Roth conversion makes sense for you?
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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