Retirement planning is not short on information. There are books, calculators, articles, and opinions at every turn. And yet, in my experience, the more people dig into the details, the more they tend to feel confused rather than confident. The topics are interconnected in ways that are not obvious, the rules change frequently, and the stakes are high enough that most people are genuinely afraid of making an expensive mistake.
That combination, complexity plus consequence, is what keeps people up at night. It is also what leads many to either delay planning altogether or make major decisions without a full picture of the tradeoffs. Both paths carry a real cost, not just financially, but in the peace of mind that a well-structured retirement is supposed to provide.
Most of what drives that complexity comes down to five decisions. They are not widely discussed in the way that, say, how much to save in your 401(k) is discussed. But the research is unambiguous: the choices you make in the five to ten years before and after you retire carry more long-term financial weight than almost anything else you will do. Getting them right does not require a finance degree. It requires a clear picture of the tradeoffs.
Here are the five.
Decision 1: When to Claim Social Security
For most people, Social Security is the largest guaranteed income source they will ever have. And yet the decision of when to claim it is often made quickly, based on incomplete information, and without a full understanding of what is at stake.
The numbers are significant. In 2026, the maximum monthly benefit for someone who claims at age 62 is $2,969. For someone who waits until age 70, that figure rises to $5,181.[^1] That is a difference of more than $2,200 per month, or roughly $26,000 per year, for the rest of your life.
For married couples, the decision becomes more complex and more consequential. The higher earner's benefit determines the survivor benefit, which means the claiming decision made today will affect the income of a surviving spouse potentially decades from now. Vanguard's research on Social Security strategies for married couples consistently shows that coordinating claiming ages, rather than both spouses claiming at the same time, can add tens of thousands of dollars in lifetime benefits.[^2]
The claiming decision also affects how long your portfolio lasts. Research published in the Journal of Financial Planning by Meyer and Reichenstein found that for a retiree with $700,000 in savings, delaying Social Security from age 62 to 68 can extend the life of the financial portfolio by more than seven years. Delaying to 70 extended it by more than ten years.[^3] The intuition is straightforward: a larger Social Security check means less pressure on your portfolio every month, which allows the portfolio to last longer.
The break-even analysis that most people use as a starting point ("at what age do I recoup what I gave up by waiting?") is a reasonable first step, but it is not the whole picture. The right answer depends on your income gap in retirement, your health, your spouse's benefit, and how Social Security income interacts with your tax situation in the years before Medicare. We will cover all of this in detail at the May 19th workshop.
Decision 2: How to Bridge Healthcare Before Medicare
Medicare eligibility begins at 65. If you plan to retire before then, you will need to cover your own health insurance for some period of time, and the cost is higher than most people expect.
The average marketplace health insurance premium for an individual at age 62 exceeds $1,072 per month before subsidies.[^4] For a couple, that figure can easily reach $2,000 or more. COBRA coverage, which allows you to stay on your employer's plan for up to 18 months, typically costs $663 to $700 per month per person once you add the 2% administrative fee.[^5a]
Beyond the premium cost, there is a subtler issue: the income you report in the years before Medicare affects your Medicare premiums once you enroll. This is the Income-Related Monthly Adjustment Amount, or IRMAA. In 2026, individuals with modified adjusted gross income above $109,000 (or couples above $218,000) pay surcharges on top of the standard Part B premium of $202.90 per month.[^5] Those surcharges are based on your income from two years prior, which means the tax decisions you make at 63 affect your Medicare costs at 65.
Bridging healthcare before Medicare is not just an insurance question. It is a tax planning question, a cash flow question, and a timing question. Getting it right requires coordinating all three.
Decision 3: How to Organize Your Assets
Most people approaching retirement have accumulated assets in several different places: a 401(k) or 403(b) from work, an IRA or two, perhaps a brokerage account, some cash, maybe a pension or annuity. The question of how to organize those assets, which ones to draw from first, which ones to protect, and which ones to position for growth, is one of the most consequential decisions in retirement planning.
At Two Waters Wealth, we use a framework we call the Fiscal House. It divides your assets into three layers, each with a distinct purpose.
The Foundation is your guaranteed income floor: Social Security, pensions, and any income sources that will arrive regardless of what the market does. The goal is to cover your essential expenses from this layer so that market volatility never threatens your ability to pay your bills.
The Walls are your growth assets: the investments that will fund discretionary spending, travel, gifts, and the things that make retirement worth living. These assets need to grow over a 20 to 30-year retirement, which means they need meaningful equity exposure.
The Roof is your legacy and contingency layer: assets set aside for long-term care, estate transfer, or unexpected needs. These are typically the last assets you would draw from.
The reason this organization matters is sequence of returns risk. T. Rowe Price's research shows that market declines within the first five years of drawing down retirement assets can significantly impair the long-term sustainability of a portfolio, even if the average returns over the full retirement period are positive.[^6] When you are forced to sell investments to cover living expenses during a downturn, you lock in losses and reduce the base available for future recovery. A well-organized Fiscal House creates buffers that allow your growth assets time to recover without forcing liquidation at the wrong moment.
Decision 4: How to Protect What You Have Built
Retirement introduces three risks that most people underestimate until they encounter them directly.
The first is longevity risk: the risk of outliving your money. A 2025 study from the Nationwide Retirement Institute and The American College of Financial Services found that more than one in four healthy, higher-income men and more than one in three healthy women will live to age 95. For a healthy couple retiring at 65, there is a one-in-five chance that at least one partner will live past 100.[^7] A retirement plan that works for 20 years may not work for 30 or 35. The math of a longer retirement is meaningfully different, and most people have not run the numbers for that scenario.
The second is sequence of returns risk, which we touched on above. The order in which returns arrive matters enormously when you are withdrawing from a portfolio. Two retirees with identical average returns over 30 years can end up with dramatically different outcomes depending on whether the bad years came early or late.
The third is spousal loss risk: the financial disruption that occurs when one spouse dies. Social Security income typically drops (you keep the higher of the two benefits, not both). Expenses often do not drop proportionally. And the surviving spouse frequently moves into a higher tax bracket as a single filer. Planning for this scenario is not pessimistic. It is responsible.
Protecting against these three risks requires a combination of guaranteed income sources, appropriate asset allocation, and in some cases insurance products designed specifically for retirement income needs. The right combination depends on your specific situation.
Decision 5: How to Keep More of What You Earn
The years between retirement and age 73 (or 75 if you were born in 1960 or later) represent one of the most valuable tax planning windows most people will ever have. During this period, you may have lower taxable income than at any point in your adult life, which creates an opportunity to pay taxes at lower rates than you will face once Required Minimum Distributions begin.
This is the Roth conversion window. By converting a portion of your traditional IRA or 401(k) to a Roth account each year during this window, you can reduce the size of your future RMDs, lower your lifetime tax burden, and create a pool of tax-free income that benefits both you and your heirs.
The math is compelling. Consider a retiree with $1.5 million in a traditional IRA at age 65. With no conversions, by age 75 that account may have grown to $2 million or more, generating RMDs that push the retiree into a higher bracket, trigger IRMAA surcharges on Medicare premiums, and cause up to 85% of Social Security benefits to become taxable.[^8] This combination is sometimes called the Tax Torpedo, and it is entirely preventable with the right planning in the years before RMDs begin.
There is a related planning blind spot that I see catch people off guard more than almost anything else: the Widow's Cliff. When one spouse dies, the surviving spouse transitions from filing jointly to filing as a single taxpayer. That change cuts the standard deduction roughly in half (from approximately $30,000 for married couples to approximately $15,000 for singles in 2026). It also compresses the tax brackets significantly, with the 22% bracket threshold dropping from approximately $94,000 for married filers to approximately $47,000 for single filers. IRMAA thresholds are cut in half as well, meaning a surviving spouse with the same income can suddenly face Medicare surcharges that did not apply before. And up to 85% of Social Security benefits remain taxable on a much smaller income base. The result is that a surviving spouse can face a dramatically higher effective tax rate in the year after a spouse's death, often with no warning and no preparation. Planning for this scenario while both spouses are alive is one of the most valuable things a coordinated retirement plan can do.
The 2017 Tax Cuts and Jobs Act created historically favorable tax brackets that are currently scheduled to expire after 2025. Whether those rates are extended or not, the principle remains: the years between retirement and your first RMD are a window for strategic tax reduction that will not come again.
Why These Five Decisions Are Connected
The reason these decisions carry so much weight is not just that each one is important individually. It is that they interact with each other in ways that can either compound your advantage or compound your exposure.
Your Social Security claiming age affects your income gap, which affects your healthcare subsidy eligibility, which affects your IRMAA exposure, which affects your Medicare costs, which affects how much you need to draw from your portfolio. Your Roth conversion strategy affects your taxable income, as well as your future RMD picture, which also affects future Medicare premiums.
Pull one thread and the whole thing moves.
The goal of good retirement planning is not to optimize each decision in isolation. It is to understand how they fit together and make choices that work as a coordinated system. That is what the SMART Retirement Blueprint is designed to do.
The Bottom Line
In my experience, the further people go down the rabbit hole on these topics, the more they find themselves confused and, in many cases, overwhelmed. They do not want to make expensive mistakes, and they are not sure who to trust or where to start.
If you are within five to ten years of retirement and you have not worked through these five decisions with a clear picture of the tradeoffs, the May 19th workshop is designed specifically for you. It is free, it is practical, and it covers all five decisions with real numbers and time for your questions.
References
[^1]: Social Security Administration. "What is the maximum Social Security retirement benefit?" January 2026. https://www.ssa.gov/faqs/en/questions/KA-01897.html
[^2]: Vanguard. "Social Security Strategies for Married Couples." https://investor.vanguard.com/investor-resources-education/social-security/strategies-for-married-couples
[^3]: Meyer, William and Reichenstein, William. "How the Social Security Claiming Decision Affects Portfolio Longevity." Journal of Financial Planning, April 2012. https://www.financialplanningassociation.org/article/how-social-security-claiming-decision-affects-portfolio-longevity
[^4]: SmartAsset. "Average Cost of Retirement Health Insurance for Ages 62-65." March 2026. https://smartasset.com/insurance/health-insurance-age-62-to-65-average-cost
[^5a]: COBRA Insurance. "How Much Does COBRA Insurance Cost?" January 2026. https://www.cobrainsurance.com/kb/how-much-does-cobra-insurance-cost/
[^5]: Centers for Medicare and Medicaid Services. "2026 Medicare Parts A and B Premiums and Deductibles." November 2025. https://www.cms.gov/newsroom/fact-sheets/2026-medicare-parts-b-premiums-deductibles
[^6]: T. Rowe Price. "Retiring into a Down Market: How to Make Your Savings Last." https://www.troweprice.com/personal-investing/resources/insights/how-to-make-your-savings-last-when-retiring-into-a-down-market.html
[^7]: Nationwide Retirement Institute and The American College of Financial Services. "Joining the Century Club: The New Retirement Risk Americans Aren't Ready For." May 2025. https://www.theamericancollege.edu/knowledge-hub/press/joining-the-century-club-research
[^8]: Internal Revenue Service. "Publication 915: Social Security and Equivalent Railroad Retirement Benefits." https://www.irs.gov/publications/p915
Jason Rindskopf is the founder of Two Waters Wealth Management and creator of the SMART Retirement Blueprint®. He works with high-achieving professionals and couples in the Charlotte, NC area who are within 10 years of retirement or recently retired. If you'd like to talk through your retirement planning and the five decisions that matter most, book a complimentary consultation here.
