8 Questions That Could Shape Your 2026 Tax Outcome

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For most people, tax filing feels like a necessary administrative task. You gather your documents, plug numbers into software, submit the return, and move on.
But for retirees, pre-retirees, business owners, and high-income households, tax filing is rarely that simple, or that inconsequential. The way your tax return is prepared can influence far more than just this year’s refund or balance due; it can make a big difference in your retirement income, investment strategy, estate planning outcomes, and long-term wealth preservation.

As the 2025 calendar year tax filing season approaches, it’s worth stepping back and asking a more important question: Is your tax return simply compliant, or is it aligned with your broader financial strategy?

Below are several key considerations that can help ensure your 2025 tax return supports not only what happened last year, but where you want to go next.

Does Your Tax Return Match What the IRS Already Knows?

The IRS no longer relies solely on what taxpayers report. Today, it operates on data matching.
Before you file, the IRS already has copies of your:

W-2 wages
1099 income
Interest, dividends, and certain digital transactions, even in a brokerage account
Brokerage transactions

When your return doesn’t align with that data, the issue is often not if the IRS will follow up, but when.
That said, matching totals alone isn’t enough. One of the most common issues arises from how income is categorized and reported, not whether it exists. Income that is reported correctly in total can still be classified incorrectly, timed improperly, or taxed differently than expected.

These issues can quietly increase your tax liability or trigger unnecessary IRS correspondence. A thoughtful review before filing helps ensure your return reflects not just the numbers, but the correct tax treatment of those numbers.

Are You Paying Attention to Cost Basis on Investment Sales?

If you sold investments in 2025, such as stocks, mutual funds, or ETFs, your brokerage Form 1099-B plays a major role in determining how much tax you owe.
Cost basis represents what you originally paid for an investment. If that information is missing or incorrect, your taxable capital gain can appear significantly higher than it actually is.

This issue commonly affects:

Investments purchased many years ago
Assets transferred between brokerage firms
Inherited investments
Accounts with dividend reinvestment plans

Even though brokerage reporting has improved over time, gaps still occur, and those gaps often result in overpaying taxes.
Before filing, it’s important to confirm:

That cost basis information is present and accurate
That inherited assets reflect the proper stepped-up basis
That long-term and short-term gains are correctly classified

Once a return is filed, correcting cost basis errors can be time-consuming and frustrating. Catching them early can prevent unnecessary tax costs altogether.

Are You Filing for Accuracy, or for Optimization?

A tax return can be technically correct and still financially inefficient.
One of the most common misconceptions about tax filing is that deductions and credits automatically “work themselves out.” In reality, timing, sequencing, and coordination matter, especially for households with multiple income streams.

Before filing, consider questions such as:

Does itemizing deductions still make sense in a given year, considering changes in income or state and local tax exposure?
Were charitable contributions structured in the most tax-efficient way?

For example, strategic charitable giving, income smoothing, and retirement distribution planning can significantly affect your overall tax burden, but only if those decisions are made intentionally.
Tax planning is not about bending rules. It’s about understanding how the rules interact with your financial situation and using that knowledge to make informed decisions before deadlines pass.

Are You Looking Beyond Income Taxes?

For many taxpayers, income tax is only part of the equation.

Additional taxes and penalties can quietly increase your effective tax rate, including:

Net Investment Income Tax (NIIT)
Additional Medicare Tax
With interest rates remaining elevated, underpayment penalties and interest charges are more expensive than they’ve been in years. A small miscalculation in withholding or tax advice regarding estimated payments can result in meaningful costs down the line.
Phaseouts of deductions and credits

These costs often don’t stand out on the first page of a tax return, but they can materially impact your financial picture.

With interest rates remaining elevated, underpayment penalties and interest charges are more expensive than they’ve been in years. A small miscalculation in withholding or estimated payments can result in meaningful costs down the line.

A well-prepared tax return doesn’t just answer the question, “What do I owe?”
It also answers, “Why do I owe it, and could it have been reduced with better planning?”

Are You Using Retirement Contributions to Reduce Your Tax Bill?

Retirement planning and tax planning are deeply connected.

Even as the filing deadline approaches, you may still have opportunities to reduce your 2025 tax liability by contributing to retirement accounts such as:

Traditional IRAs
SEP IRAs for self-employed individuals and business owners

These contributions can lower taxable income while strengthening long-term retirement security.

For individuals nearing or already in retirement, contribution and distribution strategies become even more critical. Decisions about when to draw income, how much to convert to Roth accounts, or how to coordinate Social Security income benefits can significantly affect lifetime tax exposure.

Retirement accounts are not just savings vehicles; they are powerful tax management tools when used thoughtfully.

Have You Accounted for State Tax Changes?

State tax rules change frequently, and those changes don’t always make headlines.
Relocation, remote work, or income earned in multiple states can introduce unexpected complexity.
Even without moving, changes in state-level deductions, credits, or tax rates can affect your outcome.
Before filing, it’s important to review:

Any changes in residency
Out-of-state income or withholding
Recent state tax law updates

Ignoring these details can lead to surprises months or even years after filing, often in the form of state notices or unexpected tax bills.

Have You Reviewed Your Withholding and Estimated Payments?

If your income changed in 2025, due to bonuses, investment income, retirement, or a new job, now is the right time to review your withholding and estimated tax payments.

A proactive review allows you to:

Adjust withholding for 2026
Avoid underpayment penalties
Create more predictable cash flow

Small adjustments made now can prevent unpleasant surprises next April.

Does This Tax Return Set You Up Well for 2026 and Beyond?

Perhaps the most overlooked aspect of tax filing is its forward impact.

Elections made on a 2025 return, including depreciation methods, carryforwards, basis reporting, and even filing status decisions, can shape your planning options for years to come. Many of these choices are difficult or impossible to reverse.

This is especially important if you are:

Transitioning into retirement
Selling a business or significant asset
Adjusting your investment strategy
Navigating changes in family or household structure

A return that minimizes this year’s tax bill but limits future flexibility may not be the optimal outcome.

Thoughtful tax filing considers not just what closes the books on last year, but what keeps doors open for the future.

A Final Thought: Tax Filing Is a Financial Decision

Filing a tax return is easy. Filing a good tax return takes intention.

Taxes are not just a calculation; they are a reflection of timing, decisions, and long-term priorities. When tax planning is integrated with investment management, retirement planning, and estate considerations, it becomes a powerful tool rather than a recurring stressor.

At Goldstone Financial Group, tax planning is never viewed in isolation. It’s part of a comprehensive financial strategy designed to help clients preserve wealth, manage risk, and plan confidently for the future.

Whether you’re approaching retirement, already retired, or navigating complex financial decisions, working with an experienced financial advisor can help ensure your tax strategy aligns with your broader goals.

Before you file your 2025 tax return, consider speaking with the team at Goldstone Financial Group to review your strategy, identify potential opportunities, and make sure your financial plan is working as hard as you are.

Disclosure:

Goldstone Financial Group, LLC (“GFG”) is a registered investment advisor with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or qualification. This material is provided for informational purposes only. Opinions expressed herein are solely those of GFG. None of the information presented in this material is intended to offer personalized investment advice and does not constitute an offer to sell or solicit any offer to buy a security or any insurance product and 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 an individual’s situation. This materials is not intended to provide, and should not be relied on for, tax, legal or accounting advice. You should consult your own tax, legal and accounting advisors before engaging in any transaction.