By Michael Nedreski

Retirement is a huge milestone, full of excitement, questions, and uncertainties. For many who are approaching this next chapter, asking the right pre-retirement planning questions can make a world of difference. In fact, a recent survey found that 66% of Baby Boomers (1) feel less prepared for retirement than they’d like to be.

The best way to reduce that uncertainty? Planning ahead. As you get closer to retirement, take the time to consider these 5 essential questions to feel more confident, in control, and ready to embrace the future.

1. How Will I Maintain a Consistent Cash Flow in Retirement?

On average, Social Security covers roughly 39% of one’s income in retirement. (2) So, where will the other 63% come from? It’s essential to have a proper cash flow plan for retirement so you can maintain a consistent income. There are a few potential sources of retirement income, including working part-time, retirement accounts, pensions, fixed annuities, savings, and other investments. Looking at all these income sources, you’ll want to determine if they’ll cover your needs. 

If your projected expenses don’t match your income and savings, you’ll either need to reconsider your expenses or increase your retirement income. Consider working part-time, contributing more to your retirement accounts, and developing a strategy to generate more income from your retirement portfolio. This can be done by ensuring your asset allocation still meets your risk tolerance and time horizon, and investing in assets that will diversify your income stream.

2. How Will My Investments Hold Up in Various Market Conditions?

Market volatility can mean the difference between living comfortably in retirement or just scraping by. Facing a decline in the early years of retirement can be disastrous. Considering those who retire during or near a bear market are more likely to run out of money, (3) it is crucial to understand how your investments may react during an economic downturn.

It’s important to regularly analyze your portfolio to ensure that it lines up with your risk level and that you haven’t become too reliant on any one asset category. It may be time to diversify your portfolio (if you haven’t already), rebalance, and utilize a Monte Carlo simulation to stress test your plan. This can help you see how your portfolio will react to various market conditions.

3. When Should I Claim Social Security Benefits?

Social Security benefits can be claimed between the ages of 62 and 70; however, the timing of benefits will impact the total amount received. 

Early Retirement

You can start receiving benefits as early as 62, but your monthly benefit will be lower than if you waited longer. Your basic benefit is reduced by a fraction of a percent for each month you begin receiving benefits prior to full retirement age. Retiring early can permanently reduce your benefit by up to 30%. (4)

Full Retirement Age

Your full retirement age (FRA) changes based on the year you were born. FRA is 66 for those born between 1943 and 1954 and increases by two months for every year after that you were born until it settles at age 67 for those born in 1960 or later. If you wait until you reach full retirement age to begin collecting your Social Security benefits, you will receive your full benefit amount. 

Delayed Benefits

If you’re still working or don’t need the money immediately, you can delay receiving your benefits. Your benefit will increase by 8% for each year that you delay. (5) You cannot delay and increase your benefit indefinitely, though. Once you reach age 70, the amount of benefits you receive will not increase any further. 

Be sure to reference your Social Security statement in the years leading up to retirement. This important document tells you a lot about your expected benefits, so it can help you in your decision-making process. 

In general, the best time for you to claim your benefits depends on your personal situation and health. If you expect to live longer than average, your overall lifetime benefit will be greater if you delay claiming your benefits to increase your benefit amount. If the opposite is true and you see little chance of making it into your mid-80s, you would likely receive a greater lifetime benefit by taking it sooner, even though it would be a smaller monthly payment. 

4. Am I Properly Utilizing Tax-Reduction Strategies?

As the saying goes: “It’s not how much you make, but how much you get to keep that matters.” This is especially true as you approach retirement. Once your income sources become fixed, managing and minimizing your taxes should be your top priority. If you haven’t already, consider working with a financial advisor to review your potential options, including:

• Charitable donations
• Qualified charitable distributions
• Roth conversions
• Health savings accounts
• Tax-loss harvesting

Your income plan during retirement will also play a major role in how long your money will last and how much will be lost to taxes. 

Each retirement asset has different tax characteristics, whether it be a 401(k), a Roth IRA, an annuity, or some form of equity compensation, and understanding the timing of distributions from each source is a significant part of managing your overall tax bill in retirement.

5. How Much Can I Expect to Spend on Healthcare?

Choosing the appropriate insurance coverage is the first step to take when planning for unexpected healthcare costs in retirement. According to a Fidelity Retiree Health Care Cost Estimate, the amount needed at 65 to cover healthcare costs for a couple is roughly $345,000 (6) after tax. For those who had employer healthcare coverage, retirement may mean paying more for medical insurance (Medicare Parts B and D and Medicare Supplement policies). Even with insurance, some expenses will be paid out of pocket.

Planning for unexpected healthcare costs begins with choosing appropriate insurance. For those aged 65 and above who are eligible for Medicare, it means understanding options under Medicare and choosing insurance to supplement Medicare. Take a look at your eligibility and premium estimates (7) to get an idea of what to expect. Thorough research of your supplemental coverage options can help prevent your healthcare costs from eating into your retirement savings.

Your Partner for Confident Pre-Retirement Planning

Planning for retirement doesn’t have to be overwhelming, or something you face alone. At White Oak Wealth Partners, we provide guidance, tools, and resources to help you navigate your transition with clarity and confidence. From understanding your income needs to evaluating Social Security options and investment strategies, we help you take a proactive approach to your financial future.

Are you ready to see how thoughtful pre-retirement planning can put you in control and give you peace? Schedule a no-obligation introductory meeting today. Reach out at 814-835-4551, emailing MICHAEL.NEDRESKI@LPL.COM, or scheduling an appointment here and let’s start building a plan that works for you.

About Michael

Michael Nedreski is Founder & Independent Wealth Coach at White Oak Wealth Partners, a specialized financial lifestyle and wealth management firm serving entrepreneurs, business owners, executives, and their families. Mike has 30-plus years of experience in the financial services industry and is committed to serving his clients through holistic financial planning, disciplined investment strategies, and proactive personal service. 

A native of Erie, Pennsylvania, Mike began his career in the financial services industry in 1988. He has earned the Chartered Retirement Planning CounselorSM (CRPC®) designation conferred by College for Financial Planning (188-LPL). Mike is also an active member of the Financial Services Institute (FSI) and Financial Planning Association (FPA).

When not working, Mike enjoys spending time with his wife, Amy, and their children. He volunteers in his community and at his church and his children’s schools. An outdoors enthusiast, Mike loves hunting, fishing, golfing, and spending time near or on the water. He also enjoys working out and watching some of his favorite sports teams, the Pittsburgh Pirates and the Cleveland Browns. To learn more about Michael, connect with him on LinkedIn.

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(1) Bankrate, 2024, September 25

(2) Center on Budget and Policy Priorities, 2024, May 31

(3) Nasdaq, 2025, April 5

(4) Social Security Online

(5) Investopedia, 2025, November 3

(6) Fidelity, 2025, September 5

(7) Medicare.gov