Navigating Retirement: Key Considerations for Pre-Retirees in Hawaii

June 4, 2025

By Daniel Masuda Lehrman, CFP®, CSLP®

Are you worried about whether you have enough to retire comfortably? As you approach retirement, it’s natural to have questions and concerns about your financial future. With the right guidance, you can navigate these challenges and make informed decisions that support your goals. In this blog post, we’ll delve into the key concerns facing pre-retirees, particularly around retirement planning and wealth management. We will offer actionable insights that can help you feel more secure as you transition into this new phase of life. Retirement planning can often feel overwhelming, especially for those of you who are between the ages of 55 and 65, navigating significant wealth, or perhaps dealing with a recent inheritance. The stakes are high, and the decisions you make now can have lasting consequences for your financial wellbeing in retirement. Whether you are wondering if you have enough saved to retire comfortably, how to reduce risks while generating income, or how to minimize taxes on your withdrawals, this blog will offer clarity and actionable advice. The current economic environment, coupled with the unique challenges of retirement planning, makes it more important than ever to be informed and proactive. The decisions you make today can pave the way for a comfortable and secure retirement, or they can lead to unnecessary stress and financial strain. Let’s explore the vital components of retirement planning and how you can approach them with confidence. When it comes to retirement planning, one of the most pressing questions many people have is, "Do I have enough to retire comfortably?" This question is not just about numbers; it encompasses your lifestyle expectations, healthcare needs, and the longevity of your savings. The general rule of thumb is that you will need around 70-80% of your pre-retirement income to maintain your standard of living in retirement. However, this can vary significantly from person to person. For example, if you plan to travel extensively or pursue expensive hobbies, your retirement income needs may be higher. To determine how much you will need, start by calculating your projected expenses in retirement. Consider factors such as housing, healthcare, food, transportation, and leisure activities. Once you have a clear picture of your expected costs, you can compare that to your anticipated income sources, which may include Social Security benefits, pensions, and personal savings. If there is a gap between your income and expenses, it’s essential to address this gap early on to avoid financial hardship later. Another critical aspect of retirement planning is understanding how to manage risk and generate income once you retire. Transitioning from a growth-focused investment strategy to one that emphasizes income generation and capital preservation is vital. One strategy to consider is creating a diversified portfolio that balances growth investments with more stable income-producing assets. For instance, bonds and dividend-paying stocks can provide a reliable income stream while reducing overall portfolio volatility. Additionally, consider the role of annuities in your retirement income plan. An annuity can provide guaranteed income for a specified period or even for life, which can be particularly appealing if you are concerned about outliving your assets. Tax planning is another crucial component of your retirement strategy. Understanding how withdrawals from your retirement accounts will be taxed can help you devise a plan that minimizes your tax burden. For example, if you are considering whether to take a lump sum or annuity from your pension, it’s essential to evaluate the tax implications of each option. A lump sum may provide immediate access to cash, but it could push you into a higher tax bracket in the year you take the distribution. On the other hand, choosing an annuity can spread out your tax liability over time, potentially keeping you in a lower tax bracket. Additionally, if you are considering a Roth conversion, this could be an effective way to manage taxes in retirement. By converting traditional IRA funds to a Roth IRA, you will pay taxes on the converted amount now, but your withdrawals in retirement will be tax-free. This strategy can be particularly beneficial if you anticipate being in a higher tax bracket later on. As you ponder these decisions, it’s essential to consider long-term care planning as well. One of the biggest concerns for retirees is how to cover the costs of healthcare and long-term care, which can quickly deplete savings. Long-term care insurance can be a valuable tool to help mitigate these costs, ensuring that you have access to necessary care without compromising your financial stability. Additionally, it’s crucial to have a plan in place for transferring any inherited wealth you may receive. Efficiently transferring wealth can help minimize taxes and ensure that your loved ones benefit from your legacy. Consider discussing your estate plan with a fee-only financial planner to ensure that your wishes are honored while maximizing the financial value of your estate. As you approach retirement, it’s essential to remember that you are not alone. Many people share your concerns and challenges, and the good news is that there are well-established strategies and resources available to help you. By taking the time to assess your financial situation and creating a comprehensive retirement plan, you can alleviate uncertainty and set yourself up for a successful retirement. In conclusion, the journey to a comfortable retirement starts with asking the right questions and being proactive about your financial future. Whether you are grappling with whether you have enough saved, how to manage risks, or how to effectively transfer inherited wealth, there is a path forward. By seeking guidance from a fee-only financial planner in Hawaii, you can find the support and expertise you need to navigate the complexities of retirement planning. Are you planning to retire within the next five years? Would you take the lump sum or the pension? Curious whether a Roth conversion makes sense for you? Reach out and let’s explore how we can work together to create a secure and fulfilling retirement plan that aligns with your unique goals and needs.
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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