Are You Ready to Retire? Key Steps to Ensure a Comfortable Retirement

June 14, 2025

By Daniel Masuda Lehrman, CFP®, CSLP®

Do you ever wonder if you have enough savings to retire comfortably? As you approach your retirement years, this question becomes increasingly important. Many pre-retirees aged 55 to 65, especially those with a liquid net worth between $500,000 and $4 million, find themselves at a crossroads, contemplating their financial future. The stakes are high, and the anxiety can be overwhelming. It’s crucial to examine your financial situation and develop a strategy that maximizes your wealth while minimizing risks. In this blog post, we will delve into the often daunting topic of retirement planning, specifically focusing on how to assess whether you have enough savings to retire comfortably. We will explore essential considerations, practical steps you can take, and valuable insights that will help you navigate this significant life transition. If you’re feeling uncertain about your retirement, rest assured, you are not alone. Many individuals share your concerns, and with the right information and guidance, you can find clarity and confidence in your retirement journey. Let’s first address the fundamental question: How do you determine if you have enough to retire comfortably? The answer is not a one-size-fits-all solution. It depends on various factors, including your lifestyle expectations, expenses, and retirement income sources. To begin, it’s essential to have a clear understanding of your current financial situation. This involves assessing your liquid assets, ongoing expenses, and any anticipated changes in your financial landscape. Start by creating a detailed budget that outlines your monthly expenses. Include everything from housing costs and groceries to healthcare and leisure activities. This exercise will give you a clearer picture of your essential and discretionary spending in retirement. You might be surprised at how much you spend in certain categories, allowing you to make more informed decisions about where to cut back if necessary. Next, consider your income sources during retirement. This includes Social Security, pensions, annuities, investments, and any other income streams you may have. It’s crucial to estimate how much income you can expect from these sources and how they align with your anticipated expenses. Understanding the timing of your Social Security benefits and how they fit into your overall retirement income strategy is also vital. You may have the option to start taking benefits at age 62, but waiting until your full retirement age or even age 70 can significantly increase your monthly payments. One common concern among pre-retirees is whether to take a lump sum or an annuity from a pension. Each option has its pros and cons, and the right choice depends on your unique situation. A lump sum provides immediate access to your funds, allowing for potential investment growth, whereas an annuity offers a steady income stream for life, providing peace of mind. Assess your risk tolerance and financial goals when making this decision. Another critical aspect of retirement planning is minimizing taxes on withdrawals. Understanding tax implications can help you strategize your withdrawal plan. For instance, consider the order in which you withdraw funds from your accounts. Traditionally, it may be beneficial to withdraw from taxable accounts first, followed by tax-deferred accounts, and finally tax-free accounts like Roth IRAs. This approach can help you manage your taxable income, potentially keeping you in a lower tax bracket during retirement. Speaking of Roth IRAs, you may be wondering if now is the right time for a Roth conversion. Converting a traditional IRA to a Roth IRA can be advantageous for some individuals, particularly if you anticipate being in a higher tax bracket in the future. However, it’s essential to evaluate your current financial situation and projected income to determine if this strategy aligns with your retirement goals. As you contemplate these financial decisions, it’s also crucial to consider long-term care planning. As life expectancy increases, the likelihood of needing long-term care services rises as well. Addressing this concern early can mitigate potential financial strain down the line. Investigate options such as long-term care insurance or setting aside funds specifically for this purpose. Planning for long-term care is not just a financial decision; it’s about ensuring you maintain your quality of life in your later years. Now, let’s discuss the elephant in the room: market volatility. Many near-retirees worry about what happens if the market crashes just before they retire. The reality is that market fluctuations are inevitable, and while you cannot control the market, you can control your response to it. One way to protect your retirement funds is through diversification. By spreading your investments across various asset classes, you can reduce risk and potentially improve your overall returns. Consider working with a fee-only financial planner in Hawaii to develop a diversified investment strategy that aligns with your risk tolerance and retirement goals. You may also want to explore additional strategies for protecting and transferring inherited wealth efficiently. If you’re navigating a significant inheritance, working with a financial planner can help you understand the tax implications and develop a plan that preserves your wealth for future generations. This may involve setting up trusts or considering charitable contributions to maximize your estate’s value. In summary, as you approach retirement, asking yourself whether you have enough savings is a valid concern. By assessing your current financial situation, understanding your income sources, and considering strategies for minimizing taxes and managing risks, you can gain a clearer picture of your readiness for retirement. Remember, you are not alone in this journey, and seeking guidance from a professional can provide the support you need to navigate these complex decisions. Planning for retirement is not just about the numbers; it’s about creating a lifestyle that fulfills your dreams and aspirations. With careful planning and a proactive approach, you can move forward with confidence and clarity. So, are you planning to retire within the next five years? Have you considered whether a lump sum or annuity makes more sense for you? If you're feeling uncertain about your retirement planning, don’t hesitate to reach out for help.
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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