Preparing for retirement involves more than calculating your savings. Asking the right retirement readiness questions can help you evaluate if you’re truly prepared—financially, emotionally, and logistically—to transition away from work. From identifying income sources to estimating future healthcare costs, a thoughtful retirement plan begins with clarity around your goals and potential challenges. 

Are Your Income Sources Clearly Defined? 

A core component of retirement readiness is understanding where your income will come from once you stop working. Many retirees draw from a combination of Social Security, retirement accounts like 401(k)s or IRAs, pensions, and taxable investment accounts. Before you leave your job, consider how these sources will be distributed, how they may be taxed, and whether they’re expected to cover your estimated monthly expenses. 

It may also be helpful to evaluate how your income strategy adapts to inflation or market changes. Creating a flexible withdrawal plan that accounts for both steady needs and unexpected expenses can help reduce financial strain down the road. 

Have You Considered Healthcare and Insurance Needs? 

Healthcare often becomes one of the most significant retirement expenses. If you’re retiring before becoming eligible for Medicare at age 65, you’ll need to determine how to obtain health coverage in the interim. Options might include COBRA, private insurance, or spousal coverage. Once you qualify for Medicare, you’ll still want to evaluate supplemental policies and out-of-pocket costs for prescriptions and services not fully covered. 

In addition to general health coverage, long-term care planning is worth considering. The possibility of needing assisted living, home care, or nursing support later in life could impact both your financial and lifestyle plans. 

Is Your Budget Realistic for Your Retirement Lifestyle? 

You may already have a target retirement number in mind, but have you matched it to a realistic post-retirement budget? Start by reviewing current monthly expenses and adjusting for changes—such as paying off a mortgage, travel goals, or reduced commuting costs. Factor in new or rising costs, such as hobbies, insurance, or increased healthcare needs. 

It’s also wise to consider how your spending may shift over the decades. Some retirees spend more in early retirement due to travel and activities, then see a decrease as they age—followed by a possible increase due to health-related costs. 

Have You Planned for Longevity? 

One of the most important retirement readiness questions is: “What if I live longer than expected?” With life expectancies rising, many individuals will spend 20 to 30 years in retirement. Planning for longevity means ensuring that your income strategy is built to last. This may involve evaluating how your portfolio is allocated, identifying income that continues for life, and assessing the potential impact of inflation over time. 

Additionally, consider the needs of a surviving spouse. Will they have adequate income if one Social Security benefit or pension ends? Reviewing survivor income projections and joint asset access is key. 

Have You Addressed Taxes in Retirement? 

Tax planning doesn’t end with retirement. In fact, it often becomes more nuanced. Withdrawals from traditional IRAs and 401(k)s are taxed as income, and required minimum distributions (RMDs) begin at age 73 (as of 2025). Strategic withdrawals or Roth conversions before RMDs start may help manage your taxable income over time. 

You may also want to review which accounts to withdraw from first and how to spread income across tax brackets efficiently. Partnering with a financial advisor who collaborates with a tax professional can help create a withdrawal plan that considers your full financial picture. 

Is Your Estate Plan Up to Date? 

Retirement is a smart time to revisit—or create—your estate plan. This includes reviewing or updating your will, power of attorney documents, healthcare directives, and beneficiary designations. Your estate plan should reflect current goals, relationships, and financial accounts. Clear planning may help reduce potential confusion or conflict later on. 

Even if you’re not planning a major legacy, organizing your financial affairs now can support smoother transitions for loved ones in the future. 

Retirement Readiness Questions to Revisit Regularly 

Retirement is not a one-time event but an ongoing phase of life. As your health, lifestyle, family, and market conditions evolve, the questions you ask yourself should evolve too. Whether you’re a few years from retirement or already navigating this new chapter, it’s helpful to regularly revisit these areas with your financial advisor. 

By returning to these retirement readiness questions and adjusting your strategy as needed, you can build a framework that supports thoughtful decision-making for years to come. 

Take the Next Step with SageGuard Financial Group 

If you’re thinking about retirement, asking the right questions today can help you feel more informed about tomorrow. SageGuard Financial Group is here to support you with personalized planning strategies that align with your life stage and priorities. Reach out to start a conversation about your retirement readiness and how we can help guide you through the process.