What Most People Get Wrong About Retirement Planning

By Tyson Thacker, Co-Founder, B.O.S.S. Retirement Solutions  

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Quick Summary

If you are within five to ten years of retirement, the most important financial decisions you will ever make are still ahead of you. Most people assume that once they have saved enough, the hard work is done. It is not. Retirement success is not determined by how much you saved. It is determined by how you use those savings across income, taxes, Social Security, healthcare, and withdrawals, all working together. In this post, we break down the most common mistakes we see families make in the years leading into retirement, and what a more coordinated approach looks like.

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If you would like to see how these decisions apply to your specific situation, our team at B.O.S.S. offers a complimentary, personalized B.O.S.S. Retirement Blueprint, a one-page plan that covers income, taxes, Social Security, healthcare, and legacy, customized to you.

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Saving for Retirement Is Not the Same as Planning for It

Building a retirement portfolio takes decades of consistency. That effort matters enormously. But retirement outcomes are not determined by how much you saved alone.

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They are determined by how you use those savings.

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Decisions around income, taxes, Social Security, healthcare, and withdrawals are deeply interconnected. Treating them as separate choices leads to inefficiencies that compound quietly over time. A portfolio can be well-funded and still underperform its purpose if those decisions are never coordinated.

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This is the gap we see most often at B.O.S.S., not families who failed to save, but families who saved diligently and then made disconnected decisions that cost them far more than they needed to pay.

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The Retirement Red Zone Changes Everything

The final years before retirement, and the early years after you stop working, carry more weight than most people realize.

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This period is often called the retirement red zone.

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Mistakes here are harder to recover from because time is no longer on your side. A market loss, a poorly timed withdrawal strategy, or an inefficient tax decision in this window can permanently alter your trajectory in ways that are difficult or impossible to reverse.

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Earlier in your career, volatility can be absorbed and recovered. In the red zone, sequencing matters more than almost anything else. The order in which things happen, when you claim Social Security, when you start drawing from which accounts, how you handle a down market in year one, shapes the rest of retirement.

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The Real Risk: Uncoordinated Decisions

Most retirees do not fail because they saved too little. They lose ground because their decisions are disconnected.

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Each of the following areas influences the others:

• Tax strategy affects Social Security taxation and Medicare premiums
• Social Security timing affects income needs and withdrawal strategy
• Withdrawals from IRAs and 401(k)s affect tax exposure and future required distributions
• Required Minimum Distributions influence taxable income and healthcare costs

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One decision rarely stands alone. When handled in isolation, these choices create a ripple effect that can lead to significant, unnecessary tax exposure over time, often tens or hundreds of thousands of dollars that could have been preserved with better coordination.

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Why Taxes Are the Biggest Lever

Taxes are consistently the most overlooked driver of retirement outcomes.

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Most people focus on tax preparation, filing returns each year and moving on. Planning is something different. It requires a forward-looking strategy that considers how income will be taxed across decades, not just the current year.

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The difference is substantial.

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Strategic tax decisions, made in the years immediately before and after retirement, can preserve hundreds of thousands of dollars over the course of retirement. Without that coordination, retirees often pay far more than necessary, simply because withdrawals, Social Security timing, and account structures were never aligned.

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The window to act is not unlimited. The best tax planning opportunities typically exist in the years before Required Minimum Distributions begin and before Social Security triggers higher taxation thresholds. That window is finite, and it closes whether you use it or not.

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For a deeper look at how tax strategy works in retirement, visit our Tax Minimization page.

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Social Security Is Not a Simple Decision

At first glance, Social Security appears straightforward. You can claim early, at full retirement age, or delay to 70. Pick one and move on.

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In practice, the decision is far more complex than that framing suggests.

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The timing of your benefit can increase or reduce the taxation of your Social Security income, trigger higher Medicare premiums through IRMAA income thresholds, and change how and when you need to draw from retirement accounts to fill income gaps.

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Many retirees make this decision in isolation, based on what a sibling did, what a coworker suggested, or a general rule of thumb, without considering the downstream impact on taxes, spousal benefits, or their overall income picture. The result is often a permanent reduction in lifetime income that could have been avoided entirely with better information.

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We have helped more than 6,800 families think through this decision carefully. To learn more about how Social Security timing fits into a complete retirement strategy, visit our Social Security Maximization page.

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Investment Risk Looks Different Near Retirement

Late-stage investors often feel pressure to maximize portfolio growth before they retire. That instinct, while understandable, can create unnecessary risk at exactly the wrong time.

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A significant market downturn just before or just after retirement can be difficult to recover from, especially once withdrawals begin. What was once a manageable fluctuation earlier in your career becomes a structural setback when you are no longer contributing and are instead drawing down.

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At this stage, the question shifts fundamentally.

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It is no longer "How much can I grow this?" It becomes "How do I make this last?"

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That reframe changes how you think about asset allocation, income sources, and what role your portfolio actually plays in funding your retirement.

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Healthcare Is a Major, Underestimated Cost

Healthcare remains one of the largest expenses in retirement, and one of the least planned for.

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According to research from Fidelity Investments, a 65-year-old couple retiring today can expect to spend approximately $345,000 out of pocket over the course of retirement, even with Medicare coverage. These costs rise faster than general inflation and can significantly impact income needs in ways that are difficult to absorb without a plan.

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Medicare is not free, and it does not cover everything. Dental, vision, hearing, and long-term care are largely excluded. And for anyone retiring before age 65, the gap years before Medicare eligibility add another layer of planning that most people underestimate.

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Without a clear healthcare cost strategy, this single expense category alone can erode long-term financial stability even for families who have saved well.

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Small Adjustments Create Large Outcomes

Retirement planning is not about one large decision. It is about a series of smaller, well-timed adjustments made consistently over time.

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A useful analogy is flight navigation. A plane adjusts its course constantly throughout a trip. A small deviation, left uncorrected, leads to a completely different destination. The same principle applies in retirement planning.

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Minor improvements in tax efficiency, withdrawal sequencing, or income planning can compound into meaningful differences over time, sometimes six figures worth of difference over a 25-year retirement.

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The families who do best are rarely the ones who made one brilliant financial move. They are the ones who made a series of good, coordinated decisions and adjusted when circumstances changed.

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The Three Areas That Drive Retirement Outcomes

At its core, effective retirement planning focuses on three primary areas working in concert.

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Income Planning means creating reliable, repeatable income that replaces your paycheck and adapts over time, whether from Social Security, a structured income strategy, or other sources. The goal is predictability, not just growth.

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Risk Planning means aligning your investments with your time horizon and income needs, not just growth potential. Near retirement, the cost of a significant loss is asymmetric. Protecting what you have built matters more than reaching for additional return.

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Tax Planning means structuring withdrawals and income sources to minimize long-term tax exposure, not just this year, but across the decades of retirement ahead.

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When these three areas are aligned and coordinated, the result is not just a stronger financial outcome. It is genuine confidence in the plan itself.

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Retirement Planning Is Ongoing, Not One-Time

A retirement plan is not something you build once and file away.

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Markets change. Tax laws evolve. Personal circumstances shift. Children grow up, aging parents need support, healthcare costs emerge unexpectedly, and income needs change over time.

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A well-designed plan is reviewed and adjusted regularly to stay aligned with your goals and the environment around you. This is where ongoing coordination becomes essential. The strategy must adapt as conditions change, and those changes happen whether or not you are paying attention to them.

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A More Complete View of Retirement

Retirement planning is not only financial. It is deeply personal.

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It includes how you want to live, what you want to support, and the legacy you want to leave behind. Decisions around family, philanthropy, housing, travel, and lifestyle all connect back to the financial strategy. When done correctly, the plan supports those choices rather than limiting them.

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At B.O.S.S., we build plans that start with the life you want to live, and work backward to the financial structure that makes it possible.

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Retiring successfully does not happen by accident.

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It requires a coordinated approach across income, taxes, investments, Social Security, and healthcare, all working together, reviewed regularly, and built around your specific situation.

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For those approaching retirement, the opportunity is still in front of you. The decisions you make in the next few years will shape the decades ahead. The goal is not simply to retire. It is to do it with clarity, efficiency, and confidence.

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If you are ready to see what a coordinated retirement plan looks like for your specific situation, we would be glad to help.

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👉 Get your complimentary B.O.S.S. Retirement Blueprint

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Or call us directly: (800) 637-1031

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About the Author

Tyson Thacker is Co-Founder and Managing Partner of B.O.S.S. Retirement Solutions and B.O.S.S. Retirement Advisors, a fiduciary RIA based in Lehi, Utah. Alongside his brother Ryan, Tyson has helped more than 6,800 families across Utah, Idaho, and Washington build retirement plans designed to last, addressing income, taxes, Social Security optimization, and long-term financial security. B.O.S.S. currently manages more than $1 billion in retirement assets across 11 office locations.

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Advisory services offered through B.O.S.S. Retirement Advisors, an SEC-Registered Investment Advisor. Insurance products and services offered through B.O.S.S. Retirement Solutions. Information contained in this material is for informational purposes only and is not intended as personalized investment, tax, or legal advice. You should seek advice on legal and tax questions from an independent attorney or tax advisor. Examples and hypothetical scenarios are illustrative only and do not guarantee future results. Actual results may vary. The information is not intended to be used as the sole basis for financial decisions, nor should it be construed as advice designed to meet the particular needs of any individual. 

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Related Resources from B.O.S.S. Retirement Solutions:

• The B.O.S.S. Retirement Blueprint
• Social Security Maximization
• Tax Minimization in Retirement
• Free Retirement Readiness Quiz

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