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Beyond April 15th: What Tax Returns Can Reveal About Your Retirement Readiness

Beyond April 15th: What Tax Returns Can Reveal About Your Retirement Readiness

April 10, 2026

Tax season is winding down here in Iowa, and most of us are ready to put those forms away and not think about them again until next year. But before you file those documents, take a few minutes to review your tax return with an eye towards your retirement planning.

Your tax return isn't just paperwork for the IRS. It's a snapshot of your financial year that can reveal insights about whether your retirement strategy is on track. For those of us approaching retirement in the Midwest, understanding these lessons becomes even more critical as we transition from building wealth to preserving and using it wisely.

At RetireRight, we work with families across Iowa and the Midwest who are serious about retirement planning. We've found that the most successful retirees are the ones who are proactively review their financial picture, including the information hidden in their annual tax filings.

Let's look at some key questions your tax return can help you answer about your retirement readiness.


Question 1: Am I Being Tax-Efficient with My Investments?

Your tax return shows exactly how much investment income you reported last year. This information can reveal whether your investment strategy is as tax-efficient as it should be, especially as you approach retirement.

What to look for:

  • How much did you pay in taxes on dividends and capital gains?
  • Are most of your taxable investments generating ordinary income or qualified dividends?
  • Did you have any significant capital gains from rebalancing or selling investments?

Why this matters for retirement: The investment strategies that work well during your accumulation years might not be optimal as you approach retirement. If you're generating significant taxable income from investments now, imagine what that tax burden might look like when you're retired and potentially in a lower tax bracket.

Consider this: Municipal bonds might not have made sense when you were in your 30s, but for Iowa residents approaching retirement, tax-free municipal income can be particularly valuable. Similarly, investing in tax-managed funds or index funds that generate fewer taxable events might help preserve more of your wealth.


Question 2: Should I Be Contributing to Roth or Traditional Retirement Accounts?

Your tax return shows your current tax situation, which is crucial information for making smart decisions about Roth versus traditional retirement contributions. But here's what many people miss: the real value of Roth contributions isn't what they do for your taxes today, it's what they do for your retirement security tomorrow.

What your return reveals:

  • What tax bracket you're actually in (not just what you think you're in)
  • Whether you're close to the edge of a higher tax bracket
  • How your income might change as you approach retirement

The long-term Roth advantage: While traditional contributions give you an immediate tax deduction, Roth contributions provide something potentially more valuable: tax-free income in retirement. Every dollar you contribute to a Roth account grows tax-free and comes out tax-free, giving you more spending power when you need it most.

Consider the retirement reality: Unlike traditional retirement accounts, Roth accounts don't force you to take required minimum distributions at age 73. This means you maintain control over when and how much you withdraw, which can be crucial for managing your tax bracket in retirement and potentially reducing Medicare premium surcharges.

Finding the right balance: For many near-retirees, the optimal strategy isn't all traditional or all Roth; it's a combination that provides tax diversification in retirement. Having both types of accounts lets you control your taxable income in retirement by choosing which accounts to withdraw from each year based on your tax situation.


Question 3: Am I Saving Enough for Retirement from a Tax Perspective?

Your tax return shows exactly how much you contributed to retirement accounts, but it also reveals something more important: whether you're taking full advantage of tax-deferred savings opportunities.

Beyond the basics:

  • Are you maxing out your 401(k) contributions, including catch-up contributions if you're over 50?
  • If you're eligible for an HSA, are you maximizing those contributions?
  • Are you taking advantage of any other available tax-deferred savings options?

The Midwest reality: Here in Iowa, we don't have some of the high-cost-of-living challenges that force people to choose between current expenses and retirement savings. That's an advantage we should be using to build stronger retirement security.

Consider this perspective: Every dollar you contribute to tax-deferred retirement accounts reduces your current tax bill while building your retirement security. For someone approaching retirement, maximizing these contributions in your final working years can make a significant difference in both your current tax situation and your retirement readiness.


Question 4: What Does My Tax Situation Tell Me About Required Minimum Distributions?

If you're within 10-15 years of retirement, your current tax return can help you prepare for the tax reality of required minimum distributions (RMDs) that begin at age 73.

What to project:

  • Based on your current retirement account balances and contribution patterns, estimate what your accounts might be worth at age 73
  • Consider what your RMDs might look like and how they'll affect your tax bracket in retirement
  • Think about whether your current tax-deferred savings strategy makes sense given your projected RMD situation

Why this matters: Some successful savers discover that their RMDs will push them into higher tax brackets than they expected in retirement. This realization might suggest strategies like Roth conversions during lower-income years or a different balance between Roth and traditional retirement savings.

Click here to learn more about the top things to know about RMDs and your retirement plan


Question 5: Should I Consider Roth Conversions Before I Retire?

Your tax return shows your current tax bracket and income level, but it also helps you evaluate one of the most powerful pre-retirement strategies: Roth conversions.

Why conversions matter: Roth conversions allow you to move money from traditional retirement accounts to Roth accounts by paying taxes now at known rates. Yes, you'll pay taxes on the conversion, but every dollar you convert grows tax-free from that point forward and provides tax-free income in retirement.

The compounding benefit: For someone 10-15 years from retirement, a Roth conversion can provide years of tax-free growth. If you convert $50,000 today and it grows to $100,000 by retirement, that entire $100,000 comes out tax-free. That's potentially thousands of dollars in tax savings during your retirement years.

Strategic timing opportunities:

  • Years when your income is temporarily lower (job transitions, market downturns affecting bonuses)
  • The golden window between retirement and age 73 when RMDs begin
  • Years when you can carefully manage your total taxable income

The RMD protection: Perhaps most importantly, Roth conversions can reduce your future required minimum distributions. Smaller RMDs mean more control over your tax bracket in retirement and potentially lower Medicare premiums.


Question 6: Am I Prepared for Healthcare Costs in Retirement?

Your tax return shows your current healthcare-related tax benefits and expenses, which can help you prepare for one of retirement's biggest financial challenges.

What to review:

  • Are you maximizing HSA contributions if you have access to one?
  • How much are you currently spending on healthcare, based on your medical expense deductions?
  • Are you prepared for Medicare premiums and the potential for higher healthcare costs in retirement?

Planning insight: Healthcare costs often increase significantly in retirement, and they're not always predictable. Using tools like HSAs, which offer triple tax advantages, can be crucial for managing these expenses without derailing your retirement security.


The Long-Term Perspective: Taxes in Retirement

Here's something many people don't fully consider: retirement doesn't mean the end of tax planning. In many ways, tax planning becomes more important and more complex in retirement.

You'll be managing RMDs from traditional retirement accounts, potentially paying taxes on Social Security benefits, and trying to control your tax bracket to minimize Medicare premium surcharges. The decisions you make now about retirement savings, investment allocation, and tax planning will significantly impact your financial flexibility in retirement.

The Roth advantage in retirement: In retirement, every dollar of Roth income is a dollar that doesn't count toward determining your tax bracket or Medicare premium surcharges. If you need $80,000 in annual retirement income, would you rather withdraw $80,000 from traditional accounts (all taxable) or $60,000 from traditional accounts plus $20,000 tax-free from Roth accounts? The tax difference can be substantial, especially when you factor in how taxable income affects Medicare premiums.

Tax diversification strategy: The most successful retirees often have what we call "tax diversification", money in traditional accounts, Roth accounts, and taxable investment accounts. This gives them maximum flexibility to manage their tax situation year by year based on their needs, tax law changes, and other factors. In a year when you need extra income for travel or healthcare, you can choose to withdraw more from Roth accounts to avoid pushing yourself into a higher tax bracket.

The control factor: Unlike traditional retirement accounts that force you to take required minimum distributions starting at age 73, Roth accounts let you decide when and how much to withdraw. This control becomes increasingly valuable as you age and face varying income needs. You might want to minimize taxable income in years when you're paying for long-term care, or you might want to leave Roth accounts to grow for your heirs since they also inherit them tax-free.

Future tax rate insurance: No one knows what tax rates will be in 10 or 20 years, but having a substantial portion of your retirement savings in Roth accounts protects against higher future tax rates. You've already paid the taxes at today's rates, so future rate increases won't affect your Roth withdrawals.

For Iowa residents: We have some advantages in retirement tax planning. Iowa doesn't tax Social Security benefits, and our overall tax burden tends to be more reasonable than that of many states. But that doesn't mean we should ignore tax-efficient retirement planning. In fact, our relatively favorable tax environment makes it even more important to think strategically about the balance between current tax savings and future tax-free income.

The estate planning bonus: Roth accounts also provide unique estate planning benefits. Unlike traditional IRAs, you're not forced to deplete Roth accounts during your lifetime through RMDs. This allows you to potentially leave more to your heirs, and they inherit Roth accounts tax-free as well. For families who want to leave a legacy, this can be significantly more valuable than leaving traditional retirement accounts that will generate taxable income for beneficiaries.


Taking Action: What to Do With This Information

Understanding what your tax return reveals about your retirement readiness is just the first step. The key is translating those insights into action.

Consider Taking the Following Next Steps:

  • Adjusting your retirement contribution strategy based on your current and projected tax situation
  • Exploring whether Roth conversions make sense for your situation
  • Maximizing tax-advantaged savings opportunities like HSAs
  • Working with a financial advisor to develop a comprehensive tax-efficient retirement strategy

Remember: Tax planning for retirement isn't just about minimizing taxes this year. It's about optimizing your overall tax situation across your entire retirement. Sometimes paying a little more in taxes now can save you significantly more later.


Getting Professional Guidance

Retirement tax planning can be complex, and the right strategies vary significantly based on your individual situation. What makes sense for your neighbor might not be optimal for your family.

Working with experienced professionals who understand both tax planning and retirement strategies can help you make decisions that optimize your long-term financial security rather than just minimizing this year's tax bill.

At RetireRight, we help families across Iowa and the Midwest navigate these decisions with confidence. We understand that successful retirement planning requires looking beyond the current year to develop strategies that work throughout your retirement years.


The Bottom Line

Your tax return contains valuable information about your retirement readiness, but only if you take the time to look for it. The most successful retirees are those who use every available tool to understand and optimize their financial situation.

Don't just file your taxes and forget about them. Use the information they contain to make better decisions about your retirement planning, your investment strategy, and your long-term financial security.

After all, the goal isn't just to minimize taxes today. It's to build and preserve wealth that will support the retirement you've worked so hard to achieve.

Ready to turn your tax insights into retirement confidence? Let's work together to create a plan that considers both your current tax situation and your long-term retirement goals.