How Will This Past Tax Season Affect My Retirement Plan?

Tax Day has passed (April 15, 2026) and is well behind us, and if you filed an extension, your October 15th deadline is coming up fast. Either way, for a lot of people, getting the return filed feels like the finish line.

But when you are getting close to retirement, like those with 5 to 10 years left, your tax return should be more than just a bunch of papers - it's like a check-up report. As a retirement planner, I look at your tax return as the big picture of the choices you've made, and it can help us, together, to figure out what you need to do to get ready for retirement. Tax season for you is not just about filling out forms; it's about understanding how your decisions affect your taxes and your future after retirement.

Here is what I see when I look at your taxes as a retirement planner:

• What income showed up and where it came from.
• What you paid in taxes.
• What you could have done differently.
• What might impact your Medicare, Social Security, and long-term income later.

Many of our clients at Martello Retirement & Wealth already have a CPA they work with, so when I talk about your taxes, I am not trying to take over your tax preparation. Instead, I want to use the information from your latest tax filing to make improvements to your retirement plan before December 31st, when most of the moves that shape next year’s tax bill get locked in. Really, your tax advisor and your retirement planner should work together on this.

Here’s the lens I want you to use right now when you think about the taxes you just filed: What did this year’s tax return reveal that you should fix before December 31st, 2026?

Step 1: Use your tax return like a retirement planning “x-ray”

Take a look at your 2025 tax return, or even get in touch with your accountant to get an overview, and check for these key points.

1) Was your taxable income higher than you expected?

This can be a warning sign that your retirement tax situation might not get simpler on its own. It may also indicate that required minimum distributions and taxes on your Social Security benefits could add up more quickly than you expect, leading to a bigger tax burden in the future.

2) Did you have a one-time income spike?

A one-time windfall, like a bonus or a big stock sale, might seem like a done deal, but its effects can linger. Medicare sets your premium surcharge using your income from two years earlier, so a spike in 2026 shows up in your 2028 premiums, and a one-time gain or bonus generally isn’t grounds for an appeal.

3) Were your withholdings or estimated taxes off?

If you owed much more than expected, or got a huge refund, you may be flying blind on tax timing. Pre-retirees benefit from predictability, not surprise.

4) Was your tax return more complex than you anticipated?

Stock comp, multiple 1099s, K-1s, charitable gifts, multiple states… when your taxes are complex, it isn’t bad, but it could be a signal that you need better coordination going forward. Start considering how your income or withdrawals could impact your retirement plan.

This is the key takeaway I have for you: Your current tax return tells you what happened. Your updated retirement plan decides what happens next year, on purpose.

Step 2: What did you miss on this year’s taxes, and how do you catch it now?

Even after filing your taxes, there are still plenty of practical steps you can take in the next calendar year to protect your retirement. Consider some of these items you may have missed on your most recently filed taxes and start planning for next year.

Your Missed Item: Incorrect or Incomplete Tax Reporting That Leads to Overpayments

Some issues on your taxes don’t always show up as “errors,” but they can show up as overpaid taxes. It might be best to look closer and ask, “Do I have missing cost basis adjustments, miscategorized distributions, or charitable actions that weren’t documented clearly?”

Here is what you can do now:

• Start by making a special folder for your 2026 tax documents and keep all your important papers in it. You should include your 1099 forms, any letters from charities you donated to, notes about the cost of things you bought and sold, records of home improvements (they add to your home’s cost basis), and any records of transactions or investments that might impact your taxes.
• When you get stock compensation or sell company shares, you’ll want to make sure to keep a record of the basis and how much was withheld for taxes. Don't just assume your brokerage company will get it right every time, take charge and double-check the details yourself. This will help you avoid any potential issues when it's time to file your taxes.

Your Missed Item: You Don’t Have An Intentional Plan For Moving To The Next Tax Bracket

Many people shift into higher tax brackets because income sources start stacking up after retirement, including social security and withdrawals from other accounts. There’s a new wrinkle here too: for 2025 through 2028, taxpayers 65 and older get an extra $6,000 deduction, but it phases out once income passes $75,000 ($150,000 for joint filers). A spike in income can cost you part of that deduction on top of the bracket change.

Here is what you can do now:

• Start by asking your CPA to run a year-to-date projection and see where your income is likely to land for the year.
• Consider asking yourself this question about planning for retirement: "If we remain in this tax bracket for the next 5 to 10 years, will that still be manageable for our lifestyle or goals?"

Your Missed Item: You Don’t Plan For Medicare Premium Surprises Later (IRMAA)

Even if you’re not 65 yet or are waiting to claim Social Security, decisions you make now can impact your future Medicare costs. Medicare’s income-related surcharges (IRMAA) use a two-year lookback, so your 2026 premiums are based on your 2024 return, and the brackets are cliffs: one dollar over a threshold ($109,000 single / $218,000 joint for 2026) triggers the full surcharge for the year.

Here is what you can do now:

• Take note of any big income events you’re considering in the remainder of 2026. Think large conversions, capital gains, business sale, property sale, etc.
• Then implement a simple rule into your planning: no big income moves without first checking how it could impact your retirement plan and tax plan.

Step 3: What You Can Do Between Now and the Next Tax Day

Here is a quick and practical “between-tax-days” roadmap that could support your desired retirement outcomes and even save you some tax surprises come next spring. 

Your TO-DOs for October 2026: Clean up and set your baseline

• Compare this year’s tax return to last year’s. Ask “what changed and why?”
• Identify repeatable income vs one-time income events that could impact your retirement tax plan
• Confirm your withholding settings and estimated-tax approach with your tax advisor, and share the result with your retirement planner so the plan reflects it.

Here is your goal for October: Reduce surprises and avoid preventable tax stress.

Your TO-DOs for November 2026: Do a mid-year retirement tax check

This is the point where people who are planning for retirement ahead of time set themselves apart from others.

• Ask your accountant or financial advisor to give you a quick forecast. Try asking this question: "What's our expected financial situation going to be like by the end of the year?" They can help you figure out where you'll stand and plan accordingly.
• Review your retirement plan assumptions and ask your retirement planner, “Is this the income pattern we want?”

Here is your goal for November: Catch issues while there’s still time to change course.

Your TO-DOs for December 2026: Use the planning window

December is the season when pre-retirees can make high-impact moves before the year ends. Consider doing these things before the end of the year:

• Evaluate whether a partial Roth conversion fits your long-term tax plan. Conversions add to this year’s taxable income, can’t be undone, and count toward Medicare’s IRMAA calculation two years out, which is why they belong in a plan, not an impulse. This is exactly the kind of decision we work through with clients.
• Decide whether harvesting gains or losses supports your retirement plan (mind the wash-sale rule, and remember a harvested loss only helps if there’s a gain or income to offset).
• Review your charitable strategy, because the rules changed for 2026. Itemizers can now only deduct gifts above 0.5% of adjusted gross income, and non-itemizers can deduct up to $1,000 ($2,000 joint) in cash gifts to public charities. Bunching, donor-advised-fund timing, and qualified charitable distributions all look a little different than they did last December.
• Confirm your retirement contributions and cash flow strategy with your retirement planner.

Here is your goal for December: Make deliberate tax and retirement moves, not last-minute ones.

Your TO-DOs for January through April 15th, 2027:

Now it's time to get your tax files in order. By this point, most of your decisions that impact taxes are already locked in, so your goal during this time becomes:

• Accurate reporting
• No missing documentation
• No rushed decisions

One window is still open, though: IRA, HSA, and SEP contributions for 2026 can be made right up to April 15th, 2027.

Ultimately, you should look to treat your tax filing as confirmation of the tax plan you put in place with your retirement planner, rather than a scramble to see how your retirement plan has been affected by the choices you made over the past year.

The Retirement Planning Point Most People Miss

Tax season can be a real wake-up call for people, making them think about their finances in terms of a single year. But when it comes to planning for retirement, you need to think in much bigger blocks of time - we're talking 10, 20, or even 30 years. The thing is, tax season can actually have a pretty big impact on your retirement plan, and it's really quite simple:

The way you create income today shapes your taxes, benefits, and flexibility later.

When you're just 5 to 10 years away from retiring, you're at a point where making a few smart, well-thought-out decisions can really make a big difference in how your retirement turns out,  and that impact can last for decades to come.

Here Is Your Thoughtful Next Step Toward Better Tax Planning

If you were surprised by your tax return this year, that's actually a good thing for you or your retirement planner to know. At least you know that your retirement plan and tax situation might not be perfectly in sync. At Martello, I am not doing your taxes, although I can work with your CPA or accountant to make informed retirement decisions. My goal as a retirement planner is to help you use your tax situation to create a plan that works for you.

We want to help you design a retirement that takes into account your tax picture, so you can make the most of your money. By understanding how taxes fit into your overall retirement plan, you can make smarter decisions and reduce surprises down the line. Our approach is all about helping you align your retirement goals with your tax reality, so you can achieve the future you want.

• More predictable retirement income
• Fewer tax surprises
• Smarter coordination with Medicare and Social Security
• A plan that supports your lifestyle and legacy goals

If you're within 5 to 10 years of retirement and want a second set of eyes on your 2025 return, I’d be glad to walk through it with you, and with your CPA, before the year-end planning window closes. We’ll look at what your return is telling you and which changes are still available for

Martello Retirement and Wealth, LLC is a registered investment adviser. Registration does not imply a certain level of skill or training. This article is for informational and educational purposes only and does not constitute tax, legal, or investment advice or a recommendation of any particular strategy. Martello Retirement and Wealth does not prepare tax returns or provide tax advice; consult your CPA or tax professional about your specific situation. Tax figures cited are as of the publication date and are subject to change.

Disclaimers:
Martello Retirement and Wealth, LLC is a Registered Investment Adviser. For more information about our firm, including our services, fees, and conflicts of interest, please refer to our Form ADV Part 2A, available on our website at https://www.martelloretirement.com/l/adv.

This content is for informational and educational purposes only and is not intended to provide specific tax, legal, or investment advice. Tax laws are complex and subject to change. Always consult with a qualified tax professional or attorney regarding your specific situation before making any tax-related or estate-planning-related decisions.

Past performance or hypothetical scenarios are not indicative of future results.

There are no guarantees that any tax or estate planning strategies discussed will achieve specific outcomes or avoid future tax liabilities.

The information provided is general in nature and does not consider your individual circumstances, financial goals, or needs. Personalized financial or tax advice can only be provided after a comprehensive understanding of your personal situation.

Unless expressly stated otherwise, any tax advice contained in this communication is not intended or written to be used, and cannot be used, for the purpose of avoiding penalties under the Internal Revenue Code.