{"id":162,"date":"2026-01-10T01:42:32","date_gmt":"2026-01-10T01:42:32","guid":{"rendered":"https:\/\/whiteoakwealtherie.com\/ideas\/?p=162"},"modified":"2026-01-10T01:42:32","modified_gmt":"2026-01-10T01:42:32","slug":"5-questions-you-need-to-answer-5-years-before-retirement","status":"publish","type":"post","link":"https:\/\/whiteoakwealtherie.com\/ideas\/5-questions-you-need-to-answer-5-years-before-retirement\/","title":{"rendered":"5 Questions You Need to Answer 5 Years Before Retirement"},"content":{"rendered":"<p><i><span style=\"font-weight: 400\">By Michael Nedreski<\/span><\/i><\/p>\n<p><a href=\"https:\/\/whiteoakwealtherie.com\/approach.php\"><span style=\"font-weight: 400\">Retirement<\/span><\/a><span style=\"font-weight: 400\"> 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 <\/span><a href=\"https:\/\/www.bankrate.com\/retirement\/retirement-savings-survey\/\"><span style=\"font-weight: 400\">66% of Baby Boomers<\/span><\/a><span style=\"font-weight: 400\"> (1) feel less prepared for retirement than they\u2019d like to be.<\/span><\/p>\n<p><span style=\"font-weight: 400\">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.<\/span><\/p>\n<h2><span style=\"font-weight: 400\">1. How Will I Maintain a Consistent Cash Flow in Retirement?<\/span><\/h2>\n<p><span style=\"font-weight: 400\">On average, Social Security covers <\/span><a href=\"https:\/\/www.cbpp.org\/sites\/default\/files\/atoms\/files\/8-8-16socsec.pdf\"><span style=\"font-weight: 400\">roughly 39% of one\u2019s income in retirement<\/span><\/a><span style=\"font-weight: 400\">.<\/span><span style=\"font-weight: 400\"> (2) So, where will the other 63% come from? It\u2019s 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\u2019ll want to determine if they\u2019ll cover your needs.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400\">If your projected expenses don\u2019t match your income and savings, you\u2019ll 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.<\/span><\/p>\n<h2><span style=\"font-weight: 400\">2. How Will My Investments Hold Up in Various Market Conditions?<\/span><\/h2>\n<p><span style=\"font-weight: 400\">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 <\/span><a href=\"https:\/\/www.nasdaq.com\/articles\/4-things-retirees-should-know-about-retirement-during-bear-market\"><span style=\"font-weight: 400\">more likely to run out of money<\/span><\/a><span style=\"font-weight: 400\">, (3)<\/span><span style=\"font-weight: 400\"> it is crucial to understand how your investments may react during an economic downturn.<\/span><\/p>\n<p><span style=\"font-weight: 400\">It\u2019s important to regularly analyze your portfolio to ensure that it lines up with your risk level and that you haven\u2019t become too reliant on any one asset category. It may be time to diversify your portfolio (if you haven\u2019t 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.<\/span><\/p>\n<h2><span style=\"font-weight: 400\">3. When Should I Claim Social Security Benefits?<\/span><\/h2>\n<p><span style=\"font-weight: 400\">Social Security benefits can be claimed between the ages of 62 and 70; however, the timing of benefits will impact the total amount received.\u00a0<\/span><\/p>\n<h3><span style=\"font-weight: 400\">Early Retirement<\/span><\/h3>\n<p><span style=\"font-weight: 400\">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 <\/span><a href=\"https:\/\/www.ssa.gov\/oact\/quickcalc\/early_late.html\"><span style=\"font-weight: 400\">reduce your benefit by up to 30%<\/span><\/a><span style=\"font-weight: 400\">. (4)<\/span><\/p>\n<h3><span style=\"font-weight: 400\">Full Retirement Age<\/span><\/h3>\n<p><span style=\"font-weight: 400\">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.<\/span><span style=\"font-weight: 400\">\u00a0<\/span><\/p>\n<h3><span style=\"font-weight: 400\">Delayed Benefits<\/span><\/h3>\n<p><span style=\"font-weight: 400\">If you\u2019re still working or don\u2019t need the money immediately, you can delay receiving your benefits. <\/span><a href=\"https:\/\/www.investopedia.com\/ask\/answers\/102814\/what-maximum-i-can-receive-my-social-security-retirement-benefit.asp\"><span style=\"font-weight: 400\">Your benefit will increase by 8% for each year that you delay<\/span><\/a><span style=\"font-weight: 400\">.<\/span><span style=\"font-weight: 400\"> (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.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400\">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.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400\">In general, <\/span><span style=\"font-weight: 400\">t<\/span><span style=\"font-weight: 400\">he 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.\u00a0<\/span><\/p>\n<h2><span style=\"font-weight: 400\">4. Am I Properly Utilizing Tax-Reduction Strategies?<\/span><\/h2>\n<p><span style=\"font-weight: 400\">As the saying goes: \u201cIt\u2019s not how much you make, but how much you get to keep that matters.\u201d This is especially true as you approach retirement. Once your income sources become fixed, <\/span><a href=\"https:\/\/whiteoakwealtherie.com\/ideas\/tax-efficient-retirement-strategies\/\"><span style=\"font-weight: 400\">managing and minimizing your taxes<\/span><\/a><span style=\"font-weight: 400\"> should be your top priority. If you haven\u2019t already, consider working with a financial advisor to review your potential options, including:<\/span><\/p>\n<ul>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Charitable donations<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Qualified charitable distributions<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Roth conversions<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Health savings accounts<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Tax-loss harvesting<\/span><\/li>\n<\/ul>\n<p><span style=\"font-weight: 400\">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.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400\">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.<\/span><\/p>\n<h2><span style=\"font-weight: 400\">5. How Much Can I Expect to Spend on Healthcare?<\/span><\/h2>\n<p><span style=\"font-weight: 400\">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 <\/span><a href=\"https:\/\/www.fidelity.com\/viewpoints\/personal-finance\/plan-for-rising-health-care-costs\"><span style=\"font-weight: 400\">healthcare costs for a couple is roughly $345,000<\/span><\/a><span style=\"font-weight: 400\"> (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.<\/span><\/p>\n<p><span style=\"font-weight: 400\">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 <\/span><a href=\"https:\/\/www.medicare.gov\/eligibilitypremiumcalc\/\"><span style=\"font-weight: 400\">eligibility and premium estimates<\/span><\/a><span style=\"font-weight: 400\"> (7) to get an idea of what to expect. Thorough research of your supplemental coverage options can help <\/span><a href=\"https:\/\/whiteoakwealtherie.com\/ideas\/am-i-prepared-for-medical-expenses-in-retirement\/\"><span style=\"font-weight: 400\">prevent your healthcare costs<\/span><\/a><span style=\"font-weight: 400\"> from eating into your retirement savings.<\/span><\/p>\n<h2><span style=\"font-weight: 400\">Your Partner for Confident Pre-Retirement Planning<\/span><\/h2>\n<p><span style=\"font-weight: 400\">Planning for retirement doesn\u2019t have to be overwhelming, or something you face alone. At <\/span><a href=\"https:\/\/whiteoakwealtherie.com\/\"><span style=\"font-weight: 400\">White Oak Wealth Partners<\/span><\/a><span style=\"font-weight: 400\">, 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.<\/span><\/p>\n<p><span style=\"font-weight: 400\">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 <\/span><a href=\"mailto:MICHAEL.NEDRESKI@LPL.COM\"><span style=\"font-weight: 400\">MICHAEL.NEDRESKI@LPL.COM<\/span><\/a><span style=\"font-weight: 400\">, or <\/span><a href=\"https:\/\/www.whiteoakwealtherie.com\/contact.php\"><span style=\"font-weight: 400\">scheduling an appointment here<\/span><\/a><span style=\"font-weight: 400\"> and let\u2019s start building a plan that works for you.<\/span><\/p>\n<h3><span style=\"font-weight: 400\">About Michael<\/span><\/h3>\n<p><a href=\"https:\/\/www.whiteoakwealtherie.com\/about.php\"><span style=\"font-weight: 400\">Michael Nedreski<\/span><\/a><span style=\"font-weight: 400\"> is F<\/span><span style=\"font-weight: 400\">ounder &amp; Independent Wealth Coach<\/span><span style=\"font-weight: 400\"> 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.\u00a0<\/span><\/p>\n<p><span style=\"font-weight: 400\">A native of Erie, Pennsylvania, Mike began his career in the financial services industry in 1988. He has earned the Chartered Retirement Planning Counselor<\/span><span style=\"font-weight: 400\">SM<\/span><span style=\"font-weight: 400\"> (CRPC\u00ae) 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).<\/span><\/p>\n<p><span style=\"font-weight: 400\">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\u2019s 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 <\/span><a href=\"https:\/\/www.linkedin.com\/in\/michaelnedreski\/\"><span style=\"font-weight: 400\">LinkedIn<\/span><\/a><span style=\"font-weight: 400\">.<\/span><\/p>\n<p>____________<\/p>\n<p>(1) <span style=\"font-weight: 400\">Bankrate, 2024, September 25<\/span><\/p>\n<p>(2) <span style=\"font-weight: 400\">Center on Budget and Policy Priorities, 2024, May 31<\/span><\/p>\n<p>(3) <span style=\"font-weight: 400\">Nasdaq, 2025, April 5<\/span><\/p>\n<p>(4) <span style=\"font-weight: 400\">Social Security Online<\/span><\/p>\n<p>(5) <span style=\"font-weight: 400\">Investopedia, 2025, November 3<\/span><\/p>\n<p>(6) <span style=\"font-weight: 400\">Fidelity, 2025, September 5<\/span><\/p>\n<p>(7) <a href=\"http:\/\/medicare.gov\"><span style=\"font-weight: 400\">Medicare.gov<\/span><\/a><span style=\"font-weight: 400\">\u00a0<\/span><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Planning for retirement in the next 5 years? Ask yourself these 5 crucial questions to stay confident and in control.<\/p>\n","protected":false},"author":2,"featured_media":163,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-162","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-articles"],"_links":{"self":[{"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/posts\/162","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/comments?post=162"}],"version-history":[{"count":1,"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/posts\/162\/revisions"}],"predecessor-version":[{"id":164,"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/posts\/162\/revisions\/164"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/media\/163"}],"wp:attachment":[{"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/media?parent=162"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/categories?post=162"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/whiteoakwealtherie.com\/ideas\/wp-json\/wp\/v2\/tags?post=162"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}