Navigating Retirement: Do You Have Enough to Retire Comfortably?

June 11, 2025

By Daniel Masuda Lehrman, CFP®, CSLP®

Are you worried about whether you have enough to retire comfortably? If this thought crosses your mind, you are not alone. Many pre-retirees, especially those in the 55 to 65 age bracket, grapple with the uncertainty of their financial future as they approach retirement. With the right planning and insights, you can navigate this critical transition smoothly and confidently. As a fee-only financial planner in Hawaii, I understand the unique challenges you face when it comes to retirement planning. With a liquid net worth ranging from $500,000 to $4 million, you have a solid foundation, but questions about income generation, tax efficiency, and risk management can cloud your path to retirement. In this article, we will explore actionable strategies to help you determine whether you have enough to retire comfortably, manage your investments wisely, and enjoy the retirement you envision. Understanding your retirement needs is crucial in this stage of your life. Many near-retirees wonder, "Do I have enough to retire comfortably?" It’s a valid concern given that retirement is not just about having enough money—it's about ensuring that your lifestyle aligns with your financial reality. The stakes are high; a miscalculation could lead to a lifestyle downgrade, increased stress, or even a return to work after retirement. To start, let’s break down what it means to retire comfortably. For many, it means maintaining their current lifestyle without compromising on essentials or the occasional luxury. It involves planning for healthcare costs, travel, hobbies, and other personal interests that contribute to a fulfilling retirement experience. But how do you arrive at a figure that represents this comfortable retirement? First, identify your anticipated expenses in retirement. Create a detailed budget that includes both fixed expenses, such as housing and utilities, and variable expenses, like travel or dining out. This budget will serve as the foundation for determining how much income you will need. Remember to factor in inflation; the cost of living will likely increase over time. Next, consider your sources of income. Social Security benefits, pensions, and personal savings will all play a role in your retirement income. For those with a pension, a common question is whether to take a lump sum or annuity. Each option has its pros and cons, and the decision should be based on personal circumstances and long-term financial goals. If you have a pension, calculate the present value of the lump sum option and compare it to the lifetime income provided by the annuity. This analysis can give you a clearer picture of which option best meets your financial needs and risk tolerance. Investing wisely is another critical aspect of retirement planning. As you transition into retirement, your focus should shift from growth to income generation. You will want to reduce risk and ensure that your investments can provide steady cash flow. A diversified portfolio that includes a mix of stocks, bonds, and income-generating assets can help achieve this balance. The age-old question of how to minimize taxes on withdrawals is another area to consider. Tax-efficient withdrawal strategies can make a significant difference in your retirement funds. For example, consider withdrawing funds from taxable accounts first, allowing your tax-advantaged accounts to grow longer. Additionally, a Roth conversion may be worth considering, especially if you anticipate being in a higher tax bracket later in retirement. Roth conversions can be beneficial for those who expect to have a higher income during retirement than they do now. However, timing is key. If you choose to convert, do it in years when your income is lower, as the tax impact will be minimized. This strategic approach can lead to substantial tax savings over time. Planning for long-term care is another essential consideration. Many retirees overlook this aspect, assuming they will remain healthy for the duration of their retirement. However, healthcare costs can skyrocket, and planning ahead can save you and your family a lot of stress and financial strain. Consider long-term care insurance or setting aside a dedicated fund for potential healthcare needs. Market volatility is another concern that often plagues pre-retirees. What happens if the market crashes just before you retire? This scenario can be daunting, but having a well-structured withdrawal plan can mitigate some of the risks associated with market downturns. Establishing a cash reserve to cover your expenses for the first few years of retirement can help you avoid selling investments at a loss during a downturn. As we navigate through this complex landscape of retirement planning, it is essential to remember that you are not alone. Many retirees share similar concerns about their financial futures. By equipping yourself with knowledge and seeking the guidance of a fee-only financial planner, you can take control of your retirement planning process. In summary, determining whether you have enough to retire comfortably involves several steps. Start by understanding your expenses and income sources, consider your investment strategy carefully, and think about the tax implications of your withdrawals. Don’t shy away from exploring options like lump sums versus annuities or Roth conversions, as these decisions can significantly impact your retirement experience. Ultimately, the key takeaway is that with the right planning and proactive strategies, you can navigate the retirement landscape with confidence. You have the ability to create a retirement that not only meets your financial needs but also allows you to enjoy the lifestyle you desire. As you contemplate your retirement plans, consider the questions that resonate with you. Are you planning to retire within the next five years? Would you prefer a lump sum or a pension? Curious whether a Roth conversion makes sense for you? These considerations are vital in ensuring your retirement plans align with your financial goals. Remember, a well-thought-out retirement plan can bring peace of mind and a fulfilling future as you embark on this new chapter of your life.
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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