Planning for retirement is one of the most important financial steps a person can take, yet many individuals enter the process without asking the right questions. Thoughtful retirement planning requires clarity, realistic expectations, and a strong partnership with an experienced advisor. Knowing what to ask your retirement planner can help you feel more confident about your future and better prepared for unexpected challenges.

1. What Will My Income Look Like in Retirement?

One of the first questions to ask during retirement planning is how your income will be structured once you stop working. A retirement planner should help you understand all potential income sources, including Social Security, pensions, personal savings, and investments. It’s important to discuss how long your savings are expected to last and whether your income will keep up with inflation. This conversation can also reveal gaps in your current plan and give you time to adjust your strategy before retirement begins.

2. How Should I Prepare for Unexpected Expenses?

Even the most carefully designed retirement planning strategy can be disrupted by unforeseen expenses. Medical bills, home repairs, or economic downturns can quickly impact your financial stability. According to EBRI, when asked if they have enough emergency savings to cover three months of costs, only 59% of retirees said yes, highlighting a common vulnerability. Asking your planner how to build and maintain an emergency fund during retirement can help you avoid relying too heavily on long-term investments or taking on debt when surprises arise.

3. What Risks Could Impact My Retirement Plan?

Every retirement plan comes with risks, and understanding them is key to long-term success. A knowledgeable planner should explain potential risks such as market volatility, inflation, longevity, and healthcare costs. More importantly, they should outline strategies to manage these risks, such as diversifying investments or adjusting withdrawal rates over time. By addressing these concerns early in the retirement planning process, you can make informed decisions that protect your financial future.

Asking the right questions allows you to take an active role in your retirement planning journey. With clear answers and a solid strategy in place, you can move forward with greater peace of mind and a stronger sense of financial security. Ready to get started working with a retirement planning firm you can rely on? Contact O’Keefe Stevens Advisory, Inc today.